Luxury Vacation Rentals in Chatham

(196 rentals)
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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Please call for pictures and more info- owners are private and appreciate screening first to see if a fit large gorgeous newly renovated home sleeps 11 3 floors with finished walkout basement with games and sitting and playing including air hockey 5 bdr 3 full baths; a queen and twin on first floor ...

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Property Type

Chatham House

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Key Amenities

  • Kid friendly

About this property

This classic 2 bedroom and 1 full bath Cape beach cottage only a 10-minute walk to Forest Beach. Amenities include wifi, dishwasher, washer/dryer, central air conditioning unit, cable TV, DVD, skylight, microwave, blender, two types of coffee makers, board games, DVD Library, large deck with ample seating, ...

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Property Type

Chatham Cottage

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3 BR | 2 BA | Sleeps 6 | Quick View

1
last minute deal
LAST MINUTE DEAL 8/17 - 9/4: August Rate Reduction for weeks: 08/17 to 08/24; 08/24 to 08/31; 08/31 to 09/07.

Distance to beach: 0.6 miles to Ridgevale

$319

avg/night

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Key Amenities

  • Beachfront
  • Kid friendly
  • Rentals by owner

About this property

Only 6/10 mile to family favorite warm water Ridgevale Beach on Nantucket Sound, our custom home is located on a private cul-de-sac in a quiet residential area near the South and West Chatham line. Our area is comprised exclusively of private single-family homes with paved roads and underground telephone, ...

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Property Type

Chatham House

"Lovely Chatham Home"

This lovely Chatham home ticked all the boxes for what we were looking for when vacationing on Cape Cod - located in a quiet neighborhood with a scenic backyard, walking distance to the beach, close to ...

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DEAL

2 BR | 1 BA | Sleeps 4 | Quick View

$231

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Lovely two bedroom cottage located off Cockle Cove Road in South Chatham and 0.8 mile to Cockle Cove Beach. It is located on a non paved quiet road with many other homes . This home is suitable for young family or a couple , or parties of four . It has a newly renovated kitchen and bathroom. There is ...

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Property Type

Chatham Cottage

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4 BR | 3 BA | Sleeps 10 | Quick View

1

Distance to beach: 0.1 miles to Nauset Beach

$998

avg/night

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Key Amenities

  • Kid friendly
  • Pool
  • Private pool

About this property

Smell the sea air and listen to the soothing rhythm of the ocean at Sea Mist!  A short 2/10ths of a mile from one of the most beautiful beaches on Cape Cod, this property brings together easy access to Nauset Beach with the luxury of a salt-water heated pool that includes a hot tub and sun shelf.  ...

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Property Type

Orleans House

"Beautiful House, Would Move in if We Could"

This home was absolutely gorgeous from top to bottom, and we would move here if we could. The larger bedroom on the second floor has fantastic sunrise views, and I can’t think of a better way to wake ...

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Key Amenities

  • Kid friendly
  • Private pool

About this property

This new rental was purchased with your family get together in mind. The owners wanted to give you an opportunity to have a place to gather with friends and family and either host a special event or just social distance with loved ones in a beautiful serene atmosphere. Whether its in the spacious house ...

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Property Type

Dennis House

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5 BR | 2.5 BA | Sleeps 12 | Quick View

1

Distance to beach: 2 miles to Coast Guard Beach National Seashore

$969

avg/night

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Key Amenities

  • Kid friendly
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Spend the day at the National Seashore then come home for an evening swim in a heated pool. This home is perfect for a multi-family summer retreat. There are plenty of private living spaces for Mom, Dad, kids & grandparents to spread out after checking out all of the wonders that Cape Cod offers. ...

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Property Type

Eastham House

"Great House!"

Very close to Coast Guard Beach. Grandkids biked each day, while the "elders" stayed poolside. Lots of room for everyone, including our two dogs. The welcome package was a nice touch.

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5 BR | 3.5 BA | Sleeps 10 | Quick View

Distance to beach: 1 miles to Nauset

$952

avg/night

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Key Amenities

  • Kid friendly

About this property

Let nature surround you in this sprawling contemporary where an artists touch and peeks of the Atlantic Ocean are present throughout. Enter this home into the large living, dining space with vaulted ceilings & large sliders all around. Down the hall from the living area you will find a full bath with ...

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Property Type

Orleans House

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4 BR | 4.5 BA | Sleeps 8 | Quick View

Distance to beach: 5 miles to Nauset Beach

$929

avg/night

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Key Amenities

  • Kid friendly

About this property

Enjoy your own private SALTWATER POOL! Pristine Contemporary Cape with central A/C and enclosed saltwater pool. This 4-bedroom, 4.5 bath home is designed for today's living with an inviting open floor plan and great vacation feel throughout. Wonderful updated kitchen with island, spacious living ...

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Property Type

Orleans House

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4 BR | 2.5 BA | Sleeps 11 | Quick View

Distance to beach: 10 miles to Many many beaches

$929

avg/night

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Key Amenities

  • Beachfront
  • Kid friendly
  • Oceanfront
  • Rentals by owner

About this property

Large 4 bedroom colonial on a private salt water beach with walkout basement, outdoor shower and lower level play rooms for the youngsters. Morden kitchen with big center island. Formal dining room, huge living room, large family room, pantry & private office.Mordern baths with an outdoor shower. ...

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Property Type

Dennis House

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3 BR | 2 BA | Sleeps 7 | Quick View

1

Distance to beach: 1 miles to Coast Guard

$829

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Our home has three spacious bedrooms, all on one main floor. The primary bedroom has a king-sized bed and a gorgeous waterfront view. The second bedroom has a queen and twin-sized bed, and the third bedroom has a queen-size bed and water view with access to an outside deck and outdoor shower. All beds ...

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Property Type

Eastham House

"Can't wait to come back!"

What can I say? This house, and the location is to die for. Truly, one of the best views on the Cape overlooking the marsh and outer beaches. We brought our paddle boards and had a great time exploring ...

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5 BR | 3.5 BA | Sleeps 11 | Quick View

Distance to beach: 1 miles to Nauset

$803

avg/night

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Key Amenities

  • Kid friendly

About this property

Cape Cod elegance describes this expansive, fully air-conditioned home sitting peacefully on 2.4 acres in the desirable Pochet area of East Orleans. Beautifully renovated in 2022 with new furnishings throughout makes this 5 bedroom, 3.5 bath home ideal for the larger gathering. The open kitchen/dining/living ...

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Property Type

Orleans House

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About this property

This 3,000 sq ft. plus rental is equipped like a home with quality furniture, appliances, finishes and every amenity you could think of to make your vacation complete. Our home boasts an open floor plan, with 4 bedrooms - one downstairs (queen bed), two upstairs (one with two twin beds and another with ...

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Property Type

Wellfleet House

"Stunning home, great location and wonderful stay in Wellfleet!"

This home is clean, well-appointed and a fantastic layout for groups or multigenerational families. Located in a quiet neighborhood with views of the marsh, this home truly has it all. Beautiful sunsets ...

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$746

avg/night

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Key Amenities

  • Beachfront
  • Kid friendly
  • Oceanfront
  • Pet friendly

About this property

Set within the trees and surrounded by the neighborhood wildlife, this charming 4 bedroom, 3.5 bath home has everything one would need for the perfect Cape Cod vacation, including stunning sunset views across the Wellfleet Bay and a gorgeous stretch of private beach that is just a minute walk from the ...

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Property Type

Wellfleet House

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$742

avg/night

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Key Amenities

  • Kid friendly

About this property

Location, Location, Location! Desirables south side Nantucket Sound resort area with your choice of beaches. Just steps away from Middle Beach and a short walk to Smugglers, Seaview and Parkers River Beach. 4 bedroom, 2 bath with central A/C and hi speed Wi-Fi. Linens Included!Former Red Jacket ...

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Property Type

Yarmouth Cottage

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5 BR | 2 BA | Sleeps 10 | Quick View

Distance to beach: 0.0 miles to Atlantic Ocean

$723

avg/night

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Key Amenities

  • Kid friendly

About this property

Incredible spot! Expansive Cape cottage on a bluff in Nauset Heights overlooking Nauset Inlet and the Atlantic with upper level deck and a private stairway down to the beach. Casual Old Cape Cod with pine panelling throughout. The main floor bedrooms consist of a large bedroom with queen bed and a second ...

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Property Type

Orleans House

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4 BR | 2.5 BA | Sleeps 10 | Quick View

Distance to beach: 50 feet to Property Private Beach on Long Pond & Black Pond

$717

avg/night

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Key Amenities

  • Kid friendly

About this property

Enjoy spectacular water views from almost every room of this 4 Bedroom, 2.5 bath waterfront home with large private beach and docks on both Long Pond and Black Pond in Harwich. Take a gradually descending path down to the home's private, sandy beach where you have use of the house pedal boat, kayak, ...

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Property Type

Harwich House

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5 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 1 miles to Boatmeadow

$700

avg/night

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Key Amenities

  • Kid friendly

About this property

Wonderful and spacious 5-bedroom home located in a lovely Boat Meadow neighborhood offering its own heated in-ground pool and association tennis courts. Two of the bedrooms have queen beds, one on the ground floor, the other upstairs; the other bedrooms (all upstairs) have twins. Features a large familyyroom ...

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Property Type

Eastham House

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3 BR | 2 BA | Sleeps 6 | Quick View

$672

avg/night

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Key Amenities

  • Kid friendly

About this property

This beautiful 3 bedroom 2.5 bathroom Crystal Lake home has high end finishes throughout and a location that can't be beat! Crystal Lake Haven has peeks of Crystal Lake and direct access to the lake via the property in front of it. The main level offers a large eat in kitchen/living area with ...

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Property Type

Orleans House

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3 BR | 1 BA | Sleeps 7 | Quick View

$644

avg/night

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Key Amenities

  • Beachfront
  • Kid friendly

About this property

West Dennis - Renovated cottage new to the rental inventory for 2020 this 3 bedroom 1 bath cottage is located about 100 yards from the private beach on Nantucket Sound! Open floor plan on first floor is perfect for entertaining. First floor has one bedroom, 2 additional bedrooms are located on the second ...

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Property Type

Dennis Cottage

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Key Amenities

  • Kid friendly

About this property

**New Listing** This spacious 3BR/2.5BA Cape-style home (1936 sq/ft) has central A/C, a lovely screened porch, an enclosed outside shower, and is within walking distance of a private association beach on Herring Pond (less than 1/4 mile). First Encounter (2 miles) and Coast Guard Beaches (3.6 miles) are ...

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Property Type

Eastham House

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Key Amenities

  • Kid friendly

About this property

Spacious, modern cottage in a fantastic location 4BR/2Bath open concept w/ fully fenced yard, outdoor shower & patio for outdoor entertaining. short walk to deeded access on Long Pond, a 716 acre freshwater pond for swimming, kayaking or fishing. Walk the bike path to Pleasant Lake General Store ...

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Property Type

Harwich House

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4 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.0 miles to Town Cove

$629

avg/night

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Key Amenities

  • Kid friendly

About this property

'Westwinds' is a wonderful, classic expansive ranch located on beautiful Town Cove. Set far off the road, this very special property is surrounded by meadows, woodlands, and lovely waterfront views. Enjoy direct saltwater access from the property-- ideal for kayaking, canoeing, fishing and sailing ...

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Property Type

Orleans House

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4 BR | 3 BA | Sleeps 10 | Quick View

$622

avg/night

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Key Amenities

  • Kid friendly

About this property

Lovely family home in South Yarmouth, short 4 minute walk to private beach.Updated open kitchen dining and living area.Four bedrooms, Master Bedroom with King Bed; additional bedroom on first floor with a queen bed, and a twin bed and full bath. Second floor consists of a king bedroom and another ...

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Property Type

Yarmouth House

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Key Amenities

  • Kid friendly
  • Pet friendly
  • Rentals by owner

About this property

Young, like new ''million dollar'' 3500 sq. ft. colonial style home in a quiet, private hillside setting set back from Route 6A in the very sought after area of East Dennis. Water views of Cape Cod Bay and Northside Marina. One mile to the nearby 18 hole golf course, Northside Marina, ...

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Property Type

Dennis House

"So much room!!"

We were so happy to have found this rental. There was so much space and the house offered everything and more that you could expect for a wonderful stay!! Very clean and offered all sheets and towels, beach ...

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4 BR | 2.5 BA | Sleeps 10 | Quick View

Distance to beach: 0.2 miles to Herring Pond

$607

avg/night

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Key Amenities

  • Kid friendly

About this property

Beautiful four bedroom home on a quiet sandy lane. Enjoy summer evenings on the screened porch or walk down to Herring Pond. Located near the bike trail and equipped with high speed internet. This is a great central location with many great amenities nearby.

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Property Type

Eastham House

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Key Amenities

  • Kid friendly

About this property

Enjoy your summer vacation in this beautifully renovated spacious home with central air! Less than 3 miles to Corporation Beach, and under 4 miles to Mayflower beach! Just a quarter of a mile to Lost Dog Pub, ice cream and markets. Wonderful layout with 3 levels. The first floor has a dining room, ...

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Property Type

Dennis House

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5 BR | 3 BA | Sleeps 10 | Quick View

1

Distance to beach: 2 miles to Nauset Beach

$598

avg/night

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Key Amenities

  • Kid friendly

About this property

Beautiful FIVE-bedroom home with A/C and full amenities only minutes from Nauset Beach and East Orleans village! Ideal for larger gatherings and/or extended families, this meticulous, well-appointed, and beautifully decorated home offers two separate gathering spaces, two separate bedroom wings, air-conditioning, ...

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Property Type

Orleans House

"The Perfect Vacation Rental"

We have been visiting the Cape for many years , decades. Always renting a new location.I know now that we never found the right house until I came across this treasure, 2 yrs ago. This home is well constructed, ...

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3 BR | 4 BA | Sleeps 8 | Quick View

Distance to beach: 0.0 miles to Bakers Pond

$597

avg/night

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Key Amenities

  • Kid friendly

About this property

Contemporary 3-level home with water views from every room and a private path to the pond only 75 feet away. Set on a cul-de-sac on a private lane only .5 mile to Nickerson Park biking and hiking paths and 3 miles to Skaket Beach on the Bay. Relax in air-conditioned comfort in this 2800 sq. ft. open-concept ...

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Property Type

Orleans House

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Important note..... Please do not use the " Book it now" option here.We are very careful with our home and take great pride in making sure it is a good fit for your family and visa versa. It's important for both and for ensuring you have a great vacation.Simply use the " ...

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Property Type

Yarmouth House

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Key Amenities

  • Kid friendly

About this property

A condo brand new in 2013 with spectacular ocean view and private ocean beach on Nantucket Sound! You wake up to the sound of the ocean wave and gorgeous view every morning! Just steps away from the private ocean beach! Master bedroom and kitchen facing ocean directly! Large sliding glass doors opening ...

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Property Type

Dennis Condo

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$573

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Escape to your dream vacation at this charming 3-bedroom home nestled along a private road adorned with vibrant hydrangeas and fragrant roses, mere steps from a shared private beach.The home boasts modern amenities including central AC, ensuring your comfort throughout your stay. With three cozy bedrooms ...

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Property Type

Dennis Cottage

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4 BR | 4 BA | Sleeps 8 | Quick View

Distance to beach: 1000 yards to Crowell Beach

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

This classic Cape Cod cottage is newly renovated! A 4BR/4BA duplex allows for couples, multi-generational families and friends to rent together but retain some privacy. Tasteful furnishings, modern amenities, and air conditioning combine to make this an ideal vacation home. The kitchen is well stocked ...

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Property Type

Yarmouth Cottage

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Key Amenities

  • Kid friendly

About this property

Location, location, location! 60 steps to a sandy ocean beach (Haigis) right across the street. No need to pack the car for the beach, you just have to walk a minute, and you are there! The property consists of 2 separate 3-bedroom homes located on one lot directly across from Haigis Beach. It's ...

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Property Type

Dennis House

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3 BR | 2.5 BA | Sleeps 10 | Quick View

Distance to beach: 0.2 miles to Mill Pond

$564

avg/night

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Key Amenities

  • Kid friendly

About this property

Salt waterfront home located in the Ocean Harbor Association in East Orleans. This home is set on over an acre of beautiful multi-level grounds with frontage and views of Little Cove. Enjoy kayaking right from your backyard, access to the association tennis courts or deepwater boating access and swimming ...

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Property Type

Orleans House

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3 BR | 2 BA | Sleeps 6 | Quick View

4
owner special
Owner special: August 28-31, 3 nights $2000 includes cleaning

Distance to beach: 0.0 miles to Bay

$558

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Coastal gem! Surrounded by conservation land on 3 sides, our professionally designed home has 3 bedrooms 2 full bathrooms. 2 bedrooms have queen size beds and the other bedroom has a full size bed. Plus there is a queen sleeper sofa in den. Walk to bay beach with calm waters for swimming, kayaking, ...

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Property Type

Eastham House

"Fabulous! Best July 4th at best house!"

Fantastic house, everything we need, loved the grill, pristine kitchen. Beautiful back yard, kids loved the basketball court. Walked to fireworks up the road at the beach, gorgeous night. We took in the ...

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4 BR | 3 BA | Sleeps 11 | Quick View

Distance to beach: 3 miles to Nauset Beach

$555

avg/night

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Key Amenities

  • Kid friendly

About this property

Wonderful East Orleans property with newer furnishings and central A/C, perfect for family and friends of all ages. Enjoy this terrific 4 bedroom home that affords space for everyone. The main house has a spacious king bedroom on the 1st floor with a full bath and walk-in shower. The 2nd floor features ...

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Property Type

Orleans House

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Key Amenities

  • Kid friendly
  • Oceanfront
  • Pet friendly
  • Rentals by owner

About this property

This beautiful, sunny farmhouse located near the heart of Orleans is an antique home that has modern updates inside and a gorgeous surrounding yard. Very private with ample parking. Walking path to Gould Pond for birdwatching and nature walks.The house is open, airy, very clean and well cared for. ...

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Property Type

Orleans House

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Key Amenities

  • Kid friendly

About this property

This beautiful East Dennis House has Central Air and everything you need for a wonderful relaxing vacation on the Cape. Enjoy the beautiful north side beaches: Sea St., Corporation, and Mayflower. After enjoying a sun-filled day at the beach, wash the sand off in the outdoor shower and kick back on ...

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Property Type

Dennis House

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Key Amenities

  • Pet friendly

About this property

Owner special! July 20-27th. $2000 for the week (plus taxes and fees)Central air! Renovated and ready for your summer vacation! Room for the whole group in this 3 bedroom home with two additional guest rooms, new kitchen, dining area with large table, living room with comfy couches. Large deck with outdoor ...

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Property Type

Yarmouth House

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Key Amenities

  • Kid friendly
  • Pool

About this property

Swimming Pool & 300 Yards to the beach - This roomy & Clean Cape style home is a free standing property within a small complex of seven other townhouse properties with use of a beautiful 20 x 40 swimming pool. Walk 300 yards to the ocean beach at the end of the street. (you can see the water ...

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Property Type

Dennis House

"Great vacation"

Great location, walk to the beach and swimming pool. The kids liked the park across the street. We arrived to a nice clean house, very comfortable and everything we needed was there. We plan on coming ...

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3 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 500 miles to S. Sunken Meadow

$525

avg/night

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Key Amenities

  • Kid friendly

About this property

Completely renovated, updated home with waterviews! This spacious house will give your whole family room to spread out. Walk to a private beach and located on a quiet side road this is the perfect vacation location. This home has the living area, kitchen and dining area (as well as one bedroom) on the ...

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Property Type

Eastham House

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4 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 0.1 miles to Atlantic Street Beach

$521

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Last available week thus summer is week of August 24 to August 31st. Dates also available from September 21st through October.Highly sought after vacation home in walkable, historic “Campgrounds” on quiet, private dead end street. Stroll to Nantucket Sound beaches (without crossing Rt. ...

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Property Type

Harwich House

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Key Amenities

  • Pet friendly

About this property

CENTRAL AIR! -This beautifully renovated 4 bedroom home, just .5 mile to the beach has everything you'll need to enjoy summer on the Cape. Pretty Cape decor with plenty of room inside and out! South Middle and Bass River beaches so close by! 2 bedrooms on each side plus upstairs room available for ...

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Property Type

Yarmouth House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 1 miles to Nauset Light Beach

$503

avg/night

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Key Amenities

  • Kid friendly

About this property

HEATED POOL, HOT TUB and A/C! Swim in comfort and privacy, surrounded by lovely landscaping and a koi pond, then soak in the hot tub under the stars. This lovely house with brand new kitchen for 2023 offers central A/C, a large primary bedroom with king bed and sitting room, living area, den with tv, ...

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Property Type

Eastham House

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3 BR | 1.5 BA | Sleeps 6 | Quick View

Distance to beach: 0.0 miles to Cooks Brook

$501

avg/night

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Key Amenities

  • Kid friendly

About this property

Beachfront Home! Located on Cape Cod Bay at Silver Spring Beach in Eastham!! Here's your opportunity to rent a beachfront home with fabulous views! Watch the sunsets over Cape Cod Bay, swim, fish, kayak, walk the beach, its all right there in front of you. The home has 3 bedrooms, 1.5 baths, fireplace, ...

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Property Type

Eastham House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.1 miles to Boat Meadow / First Encounter

$500

avg/night

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Key Amenities

  • Kid friendly

About this property

FANTASTIC beach home just a short walk to Cape Cod Bay! Beautifully finished Cape cottage with all the high end amenities for an enjoyable vacation. This home has been totally renovated from the ground up and features custom kitchen with induction range (enjoy your morning coffee over looking the marsh!), ...

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Property Type

Eastham House

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3 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 3 miles to Mayflower

$500

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

This charming ranch, located on the historic 6A side of the Cape is close to quaint villages, shopping, dining and beautiful beaches!The house is located in a quiet neighborhood, right off of 6A, with easy access to the highway. Stylish and contemporary, it provides one floor living. The home's ...

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Property Type

Yarmouth House

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About this property

Saturday-Saturday Rental. Former Sea Captain's home between the Village and the beach. Great location in desirable Harwich port. Spacious, well maintained home in a beautiful park like setting. Central air! Plenty of parking and privacy. It has 3 bedrooms, 2 1/2 baths, very spacious eat in kitchen, ...

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Property Type

Harwich House

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Welcome to our Beach Retreat, “After Dune Delight”. Our home was purchased and completely renovated in 2021. Tastefully decorated in classic Cape Cod style and appointed with all your beach vacation needs, the house is located in Colonial Acres, a very quiet and safe neighborhood. We are ...

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Property Type

Yarmouth House

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Chatham Vacation Rentals