Luxury Vacation Rentals in Chatham

(195 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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3 BR | 2 BA | Sleeps 6 | Quick View

1
owner special
Owner special: Owner Special - Discount applied on 2-week or longer rentals.

Distance to beach: 0.6 miles to Ridgevale

$369

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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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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2 BR | 1 BA | Sleeps 4 | Quick View

$228

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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$1000

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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4 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 60 miles to Pleasant Bay

$929

avg/night

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Key Amenities

  • Kid friendly

About this property

WATERFRONT on Pleasant Bay! This charming 4-bedroom, 3-bath summer home with central A/C offers the perfect coastal getaway for up to 8 guests. A newly renovated kitchen with an expansive island and adjacent dining area offer panoramic views of the bay. The spacious living room (with working fireplace) ...

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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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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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5 BR | 3.5 BA | Sleeps 11 | Quick View

Distance to beach: 1 miles to Nauset

$850

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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Key Amenities

  • Kid friendly
  • Oceanfront

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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3 BR | 2 BA | Sleeps 7 | Quick View

1

Distance to beach: 1 miles to Coast Guard

$808

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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3 BR | 2 BA | Sleeps 6 | Quick View

$800

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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$796

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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4 BR | 2.5 BA | Sleeps 10 | Quick View

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

$777

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 | 2 BA | Sleeps 10 | Quick View

Distance to beach: 0.0 miles to Atlantic Ocean

$770

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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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

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Key Amenities

  • Rentals by owner

About this property

Enjoy spectacular water views from almost every room of this 3 Bedroom, home that sleeps 7. Minutes from town, wake up to the calm, crystal smooth waters with sightings of seals, launch your kayak right from the property...wind down after a great day on the beach to cocktails on the expansive deck complete ...

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Property Type

Orleans 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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4 BR | 3 BA | Sleeps 10 | Quick View

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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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Key Amenities

  • Oceanfront

About this property

Owner Special for weeks of 6/29,7/6,7/13, and 8/24 if you book before 5/31/24-reduced rate $5850 (plus fees and taxes) Welcome to Gray Haven, a rambling ocean front home on Lewis Bay with lots of Olde Cape Cod Charm! Enjoy beautiful views from every room, feel the breeze off the bay, and watch the ferries ...

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Property Type

Yarmouth House

"Great location!"

Location can’t be beat. Gorgeous views from every room. Great neighborhood, close to everything. House has everything you need. Wonderful, grassy yard as well.

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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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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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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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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

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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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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5 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 2 miles to Nauset Beach

$625

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

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3 BR | 4 BA | Sleeps 8 | Quick View

Distance to beach: 0.0 miles to Bakers Pond

$614

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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$605

avg/night

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Key Amenities

  • Beachfront
  • Kid friendly

About this property

Sweet beach house tucked on a sandy lane, just minutes to both Priscilla Landing inlet and Nauset Beach. The home offers three bedrooms with one king and two others each with a queen bed. There is also one and a half baths. There are window A/C's throughout the house for your comfort and electric ...

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Property Type

Orleans House

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3 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 500 miles to S. Sunken Meadow

$600

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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3 BR | 2 BA | Sleeps 6 | Quick View

3
last minute deal
LAST MINUTE DEAL 6/17 - 6/22: Early summer special, 5 nights, $3000 Relax on deck, stroll to bay beach before the crowds!

Distance to beach: 0.0 miles to Bay

$594

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

"Unique and beautiful home! Luxury & comfort + perfect location!"

We had two glorious weeks here. Beautiful home, loved the gardens and quiet. We went to a different beach just about every day, so many nice bay beaches within walking or biking distance. The owner is ...

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DEAL

4 BR | 2.5 BA | Sleeps 10 | Quick View

Distance to beach: 0.2 miles to Herring Pond

$594

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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3 BR | 1.5 BA | Sleeps 6 | Quick View

Distance to beach: 0.0 miles to Cooks Brook

$587

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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Inquire for rates

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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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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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4 BR | 3 BA | Sleeps 11 | Quick View

Distance to beach: 3 miles to Nauset Beach

$581

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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3 BR | 2.5 BA | Sleeps 10 | Quick View

Distance to beach: 0.2 miles to Mill Pond

$580

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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4 BR | 4 BA | Sleeps 8 | Quick View

Distance to beach: 1000 yards to Crowell Beach

$570

avg/night

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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

  • Pet friendly
  • Rentals by owner

About this property

Visit website capevaca dot com for seasonal rates and availability. From our website you can book direct, save on fees and calculate your stay. Cape Cod - Harwich on Dennis Line - Entire Home; 8 Beds - 4 Bd/2 Ba plus a seasonal outdoor shower - Linens included (a rare find on the Cape), Central ...

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Property Type

Harwich House

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3 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 0.7 miles to Windmill Beach

$552

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Unwind with a bottle of wine in this 2000 square foot home built in 2021, 3 bedrooms, 2 1/2 bath. 2 family rooms and large front porch. Open concept with kitchen island.

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Property Type

Yarmouth 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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About this property

Popular rental! Fingers area in West Dennis. This 4 Bedroom-2 Full Bath beautiful home has been completely renovated and ready for wonderful Cape Cod memories to be made and it is only .3mi to West Dennis Beach. Living room, spacious kitchen, dining room, and bedrooms on both floors. After a day at ...

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Property Type

Dennis House

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4 BR | 2.5 BA | Sleeps 8 | Quick View

last minute deal
LAST MINUTE DEAL 6/6 - 6/21: Week of June 22-29 price reduction due to last minute cancelation. Now $3500 + tax

Distance to beach: 0.1 miles to Atlantic Street Beach

$538

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

FOR 2024: Due to a late hour cancellation, the week of June 22 has just become available, now at a reduced rate ($4,500 now $3,500)…..also available is week of August 24 and from September 21st through October.Highly sought after vacation home in walkable, historic “Campgrounds” ...

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Property Type

Harwich House

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DEAL

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

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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Key Amenities

  • Pet friendly

About this property

Great deal! Owner special! Remaining July weeks $3000 plus taxes and fees if you book before 6/30.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 ...

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Property Type

Yarmouth House

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$526

avg/night

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Key Amenities

  • Kid friendly

About this property

Beautifully renovated 4 bedroom, 3 bath home in Eastham close to Cape Cod National Seashore Beaches--Coast Guard Beach and Nauset Light Beach. Just 1 mile to the Cape Cod Rail Trail. Enter the house to a large great room with cathedral ceilings and open floor plan. Large dining table seats 8. Fully stocked ...

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Property Type

Eastham House

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Key Amenities

  • Kid friendly

About this property

Close to everything Yarmouth has to offer. Under half a mile to Smugglers/Bass River Beach & Windmill Beach. Bass River Sports World, Ice Cream, and shopping nearby. Short distance to public golf, town parks, and access to bike trail.Central AC! This split-level home offers three large bedrooms ...

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Property Type

Yarmouth House

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Chatham Vacation Rentals