Chatham House Rentals

(197 rentals)
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3 BR | 2 BA | Sleeps 6 | Quick View

$471

avg/night

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Key Amenities

  • Kid friendly

About this property

Waterfront(!) on Herring Pond, one of Eastham's finest freshwater ponds. Located on a quiet sandy lane and close to the bike trail, this home is a great spot to vacation!

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Property Type

Eastham House

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2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.0 miles to 1st Encounter

$209

avg/night

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Key Amenities

  • Kid friendly

About this property

Two bedroom cottage offering that characteristic home-spun charm. The vaulted ceiling in the living room gives the illusion of added space and also lets in good natural light. A large wrap-around deck is perfect for sunning and the outdoor shower provides that authentic, Cape Cod experience. Washer/dryer ...

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Eastham House

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2 BR | 1 BA | Sleeps 4 | Quick View

$376

avg/night

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Key Amenities

  • Kid friendly

About this property

This bungalow cottage sits atop a bluff overlooking Cape Cod Bay in Eastham. There are two good-sized bedrooms, a full bathroom (shower), and an open concept kitchen, dining area and living room all with spectacular views of Cape Cod Bay. The house is comfortable and streamlined in its aesthetic, a lot ...

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Property Type

Eastham House

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Key Amenities

  • Kid friendly

About this property

22 Briarfield Rd East Dennis, A real East Dennis Beauty. This fantastic 3 bedroom 2 bath rental sleeps 7 and has all the great features you want for that fabulous Cape Cod Vacation. Located in desirable East Dennis, close to Sesuit Harbor and Cold Storage Beach. This light filled home has a large eat ...

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Dennis House

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4 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 0.2 miles to Herring Pond

$595

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: 0.2 miles to Cole Rd

$484

avg/night

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Key Amenities

  • Kid friendly

About this property

Make this your Cape Cod Summer Rental. Located near Herring Brook Landing, this cottage is near the end of a cul-de-sac. Quiet location with two beach accesses. Views of bay from bedroom on second floor. Walk from your deck down a path to a private beach or use Cole Road Beach. Third house back from the ...

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Property Type

Eastham House

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Key Amenities

  • Kid friendly

About this property

South Dennis: Privacy prevails from this beautifully updated, Waterview three-bedroom, one and a half bath home nestled on a super private lot, surrounded by trees and directly abutting Follins Pond - just steps from the backyard. This home coined “Edi's Place”, is the perfect blend ...

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Property Type

Dennis House

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About this property

Just a short stroll to Follins Pond and under 5 miles to Mayflower Beach. This spacious raised ranch has 3 bedrooms and 2 full baths with sun porch, dining area, living room, and inviting deck-great living space with room to relax. Lower level has large family room for watching TV or gatherings after ...

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Property Type

Dennis 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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Dennis House

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Key Amenities

  • Kid friendly
  • Pet friendly

About this property

Updated 4 Bedroom with great availability. Close to Paradise Pizza and Good Friends cafe, Summer Shanty, Sundancers, playground and more. .8 to West Dennis beach and minutes to scenic Kelly's Pond.This comfortable and clean roomy home will allow you to relax and unwind on your vacation. The beautiful ...

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Property Type

Dennis House

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Key Amenities

  • Kid friendly

About this property

Welcome to CapeCodProperty 119, a sparkling, vacation rental nestled in the charming town of South Dennis, Massachusetts. This spacious 3+ bedroom home offers a perfect blend of comfort and style, making it an ideal retreat for families or groups of friends looking to explore the beauty of Cape Cod.With ...

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Property Type

Dennis House

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Key Amenities

  • Kid friendly

About this property

New Rental with plenty of prime weeks available ! Call Soon !38 Agnes Rd. South Dennis, New rental located in the Mid Cape area close to shopping and beaches. This 3 bedroom, 1 and 1/2 bath ranch home is convenient to shopping, parks and both north and southside beaches. This house even has a brand ...

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Property Type

Dennis House

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About this property

This beautifully maintained home brings on the Olde Cape Cod charm. Nestled in the heart of West Dennis, you can enjoy being less than 1/2 mile to West Dennis Beach, Kelley's Pond, and close to plenty of restaurants, shopping, and activities.This two bedroom cottage has an eat in kitchen, living ...

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Property Type

Dennis House

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3 BR | 1.5 BA | Sleeps 6 | Quick View

Distance to beach: 200 miles to Target View

$452

avg/night

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Key Amenities

  • Kid friendly

About this property

Beautifully situated beach cottage, 200 feet from the beach with peeks of sparkling blue water! Across from the path to one of Easthams best Cape Cod Bay beaches. Walk to Wiley Park on Great Pond and enjoy fresh water swimming and nature trails as well! There are 2 bedrooms with twins and a full bath ...

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Property Type

Eastham House

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Drop your bags and walk to the beach. All the comforts of home in a clean, all new and refreshed setting.Stunning West Dennis Beach a short, 4/10 of a mile walk down the picturesque Loring Ave. The home comes equipped with beach chairs, umbrella, toys, cooler, and beach wagon to make for a fun and ...

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Property Type

Dennis House

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3 BR | 1 BA | Sleeps 6 | Quick View

Distance to beach: 900 miles to Kingsbury

$303

avg/night

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Key Amenities

  • Kid friendly

About this property

Fresh and Salt Water Beaches! This 3-bedroom home (960 sq/ft) is located at the end of a quiet sand road within a short walk (700ft) to Kingsbury Beach. Features include a wraparound deck, and glassed-in sun porch. Wiley Park (Great Pond) is a mere 1/3 mile walk for fresh water swimming. Amenities include ...

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Property Type

Eastham House

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Key Amenities

  • Kid friendly

About this property

New to our rental program for 2025: Welcome to CapeCodProperty 115, a charming retreat nestled in the heart of South Dennis and in the Mid-Cape area. This adorable 3 bedroom, 1.5 bath home offers a perfect blend of comfort and convenience, making it an ideal getaway for families or groups of friends ...

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Property Type

Dennis House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 800 miles to

$418

avg/night

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Key Amenities

  • Kid friendly

About this property

Well maintained 3 bedroom home only 800 feet to Kingsbury Beach, and also a walk to Great Pond for fresh water swimming. This home features a screened porch, deck, outside shower, high speed internet and is located on a quiet sand road. Perfect location for summer family fun. Bike trail is a short bike ...

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Property Type

Eastham House

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About this property

Pretty and spacious (over 3000 square feet of living space!) year round home in popular Dennis! A little over a mile to Princess Beach, and under 5 minute drive to Corporation and Mayflower beach. 2.7 miles to Corporation, 3.3 miles to MayflowerThis welcoming home offers 4 bedrooms (2 up, 2 down) ...

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Property Type

Dennis House

"Centerville Home"

Great location, very clean, kitchen well equipped. Loved the outdoor shower and deck was perfect to sit out in the morning with a cup of coffee looking out at the pond or in the evening to sit and have ...

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$320

avg/night

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Key Amenities

  • Kid friendly

About this property

Beautifully maintained home on Eastham's Bayside. Just 1/2 mile to Great Pond and approximately 1000 feet to the Cape Cod Rail Trail. New for 2016 is a ductless AC system. Inside the home is beautifully maintained with a bedroom on the first floor, and living/dining/kitchen area plus bath. Sliders ...

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Property Type

Eastham 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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3 BR | 1 BA | Sleeps 6 | Quick View

Distance to beach: 300 miles to Kingsbury Beach

$312

avg/night

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Key Amenities

  • Kid friendly

About this property

Beautiful contemporary cottage just a short walk to Kingsbury beach. Enjoy a quiet summer vacation near one of Eastham's finest bayside beaches. Relax in the screen porch and stroll down Kingsbury Beach Rd and enjoy the sunsets!

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Property Type

Eastham House

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3 BR | 1 BA | Sleeps 6 | Quick View

Distance to beach: 0.5 miles to

$163

avg/night

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Key Amenities

  • Kid friendly

About this property

Looking for a quiet getaway? This nice ranch is tucked in the woods on a sand road. After a long day on the beach a nice shady spot like this could be ideal to relax in. Walk down to Great Pond for a swim in the fresh water. The Cape Cod rail trail is just around the corner. Ride to Wellfleet or down ...

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Property Type

Eastham House

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Key Amenities

  • Kid friendly

About this property

Sesuit Neck Luxury - Enjoy your Cape Cod Vacation at this spectacular home located on desirable Sesuit Neck in East Dennis. Originally built in 1755 and known as the Captain Jonathan Howes House, the home has been completely renovated inside and out sparing no expense. Outside you will enjoy the professionally ...

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Property Type

Dennis House

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3 BR | 2 BA | Sleeps 7 | Quick View

3

Distance to beach: 1 miles to Coast Guard

$760

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

"Fabulous Family Vacation!"

We spent the week with our adult sons and their partners and had a great time. The weather was less than we expected for July- only in the 70s, but the house made being there wonderful anyway. The view ...

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About this property

Beautiful setting directly on Bass River with an option for a dock for deep water access. (floating dock chained around pilings, for boats under 24') Stunning views of the river and out towards the ocean. Near West Dennis Yacht Club and West Dennis beach for long walks and fabulous sunsets.Lovely ...

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Property Type

Dennis House

"Excellent rental"

Great location. Lovely view off the back deck. Very clean house and extremely well supplied. Good living space with the added all-weather porch. Appliances all worked very well. Internet was a bit slow ...

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About this property

Lovely, well maintained, clean, and charming home in South Yarmouth, only .8 miles to beautiful ocean beaches along South Shore Drive.Beautifully updated bright home with eat-in kitchen, dining room, living room with sleep sofa, two bedrooms (queen/ twin), full bath and 3 season porch with futon.Gorgeous ...

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Property Type

Yarmouth House

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About this property

Great deal! Adorable beach cottage with Cape decor. Clean and updated 3 bedroom ranch style home, 1/2 mile to South Middle Beach. Also very near Bass River Beach with snack bar and boat launch.3 bedrooms, 1 bath. Light and bright with cute Cape decor. Window air conditioning in living room. Large ...

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Property Type

Yarmouth House

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2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.4 miles to Kingsbury Beach

$187

avg/night

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Key Amenities

  • Kid friendly

About this property

Perfect for a family getaway. Charming 2 bedroom cottage on the bayside of Eastham. Just 4/10 of a mile to Kingsbury Beach, 3/10 of a mile to Wiley Park and only one mile to biking on the Cape Cod Rail Trail. Spend a day at the beach and relax in the yard with the fire pit and tire swing! A family could ...

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Property Type

Eastham House

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5 BR | 4 BA | Sleeps 13 | Quick View

1
owner special
Owner special: Week of 6/14/25 reduced from $12,000. to $10,000.week of 6/21/25 reduced from $13,000 to $11,500

$1672

avg/night

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Key Amenities

  • Kid friendly
  • Pet friendly
  • Rentals by owner

About this property

UPDATE for 2024 Season! Brand new in ground 20 x 40 Salt Water Heated pool with spa. Brand new ENTIRE Home Furnishing Makeover with Coastal themed furniture. This beautiful, comfortable, and spacious home is nicely furnished and well-equipped. It has 5 large bedrooms, and 4 bathrooms, a spacious new kitchen ...

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Property Type

Dennis House

"love these guys!!"

the best vacation rental on the market, far surpassed all of the other's out there would recommend these guys to absolutely any one! was the trip of a lifetime!

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 1 miles to

$414

avg/night

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Key Amenities

  • Kid friendly

About this property

Beautiful nice home in a wooded location on the bayside. Approximately 6/10ths mile to Cape Cod Bay. Large deck, sun room, enclosed outdoor shower. If you are looking for a new home in impeccable condition, look no further. Ductless AC in the bedrooms! Please note the bedroom on the first floor now has ...

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Property Type

Eastham House

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

SEAS THE DAY is a beautiful open concept, 4 bedroom, 2 full bath home located on a quiet cul-de-sac in historic South Yarmouth. SEAS THE DAY sleeps up to 10 and offers a sun-filled first floor, a kitchen open to the entire living area, and an awesome bunkroom and basement game room for the kids! Spend ...

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Property Type

Yarmouth House

"Perfect getaway rental"

This house was beautifully decorated, designed for both convenience and comfort. The number of beds allowed me to let my kids bring friends and we had so much fun over the course of the week. The owners ...

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 1 miles to

$300

avg/night

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Key Amenities

  • Kid friendly

About this property

Nice ranch on Kingsbury Beach Rd. Bike trail is nearby. Walk to Great Pond and Kingsbury beach is about 3/4 mile away. Nice deck and outside shower. HD TV in living room. Master bedroom with its own bath. Laundry on the first floor.

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Property Type

Eastham House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.5 miles to Dunes Beach Assoc.

$286

avg/night

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Key Amenities

  • Kid friendly

About this property

Nice home (1539 sq/ft) just 1/2 mile to Cape Cod Bay and Wiley Pond Park. Master bedroom with king bed & bath, another bedroom, and sleeping loft upstairs (w/TV) makes this charming cottage just right for 6 people. It also has a screened-in porch overlooking wooded lot, outside/inside showers, high-speed ...

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Property Type

Eastham 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

$1273

avg/night

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Key Amenities

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

About this property

JULY & AUGUST ARE BOOKED, BUT WE STILL HAVE JUNE & SEPTEMBER WEEKS AVAILABLE WITH A HEATED POOL!! ASK ABOUT OUR PROVINCETOWN THEME WEEK AND WELFLEET OYSTERFEST SPECIALS!! Spend the day at the National Seashore then come home for an evening swim in a heated pool. This home is perfect for a ...

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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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2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 1 miles to Kingsbury, Great Pond

$204

avg/night

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Key Amenities

  • Kid friendly

About this property

Very nice two bedroom home on the Bayside. This is one floor living, upstairs is unfinished and not available for rental. Lovely sun room! Bike trail nearby. This home is in great condition. New enclosed sunroom. This is a very comfortable, nicely furnished home, with washer, dryer and dishwasher, lots ...

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Property Type

Eastham 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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3 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 0.7 miles to Windmill Beach

$584

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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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.1 miles to Thumpertown Beach

$421

avg/night

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Key Amenities

  • Kid friendly

About this property

This welcoming 3-bedroom, 2-bath home is just steps away (approx 500 feet) from an association bayside beach, perfect soaking up the sun and enjoying peaceful walks along the shore. Nestled in a quiet wooded location, this property offers tranquility and escape from the bustle of the modern world. Step ...

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Property Type

Eastham House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.5 miles to Thumpertown Beach

$370

avg/night

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Key Amenities

  • Kid friendly

About this property

Step into the comfort of a fully renovated home. This home, on a quiet sandy lane, has been completely renovated from the ground up for your enjoyment and convenience. Enjoy the large living area with flat screen smart TV. Open concept living with the kitchen, dining and living areas open to each other ...

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Property Type

Eastham House

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3 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 0.2 miles to Thumpertown Beach

$324

avg/night

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Key Amenities

  • Kid friendly

About this property

Charming three bedroom cottage just a short stroll to Thumpertown Beach. Enjoy the screen porch in the evenings or the patio during the day. Inside there are three bedrooms with ceiling fans, and a nicely sized living, kitchen, dining area with smart TV. Laundry room with washer/dryer is also on the main ...

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Property Type

Eastham House

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Key Amenities

  • Kid friendly

About this property

Welcome to CapeCodProperty 178, a stunning 6-bedroom retreat located just steps away from the serene Follins Pond in Dennis, MA. Only 1/2 mile to the boat ramp and the beach at Follins Pond for swimming, kayaking, fishing, and boating. Just a short drive to all the popular Cape Cod Bay Beaches! This spacious ...

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Property Type

Dennis House

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

"Our Wee Cottage" is a newly renovated Cape style home with a partial view of Long Pond and central air. Linens/towels Included! Located in a peaceful neighborhood in the heart of mid cape. Our cape is only a 1 minute walk to Wings Grove Beach, a fresh water pond beach in the neighborhood with ...

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Property Type

Yarmouth House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to

$386

avg/night

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Key Amenities

  • Kid friendly

About this property

Nice large 3 bedroom home on Eastham's Oceanside. Drive or bike to either Coast Guard Beach or Nauset Light beach. Large deck/patio for outdoor living. Central AC keeps you cool in the summer. Separate family room/TV room plus living room. Nice outdoor space and located on a quiet side road.

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Property Type

Eastham House

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4 BR | 2 BA | Sleeps 8 | Quick View

$372

avg/night

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Key Amenities

  • Beachfront
  • Kid friendly
  • Oceanfront

About this property

A true Cape Cod Gem located on the edge of the National Seashore and just 2 miles to Coast Guard Beach or Nauset Light Beach! You will love coming home after a day on the beach to this private house on a wooded lot on a quiet cul-de-sac road. All the bells and whistles you want in a vacation including ...

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Property Type

Eastham House

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2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 3 miles to Private Beach

$240

avg/night

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Key Amenities

  • Kid friendly

About this property

Welcome to your cozy rental less than 1/2 mile to pristine Cape Cod Bay. This charming property features 2-bedrooms, 1-bath and is set along a quiet sand road. Stay cool and connected with A/C units in the bedrooms and the convenience of WiFi throughout. Rinse off from a day at the beach in the refreshing ...

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Property Type

Eastham House

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4 BR | 2 BA | Sleeps 10 | Quick View

last minute deal
LAST MINUTE DEAL 5/27 - 6/6: 15% off any of the dates up to June 6th. Minimum of 3 night or more.

Distance to beach: 1 miles to Smugglers Beach

$751

avg/night

View Details

Key Amenities

  • Beachfront
  • Kid friendly
  • Rentals by owner

About this property

Located on Long Pond in Yarmouth. Enjoy what this recently renovated 4-bedroom house has to offer. Private (clean and Swimmable) Beach with dock. Canoe, Kayaks, Paddle Boards and plenty of beach supplies. Long Pond also has 2 public sandy beaches and 1 association beach. Our house offers sleeping up ...

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Property Type

Yarmouth House

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DEAL

Key Amenities

  • Pet friendly
  • Rentals by owner

About this property

Unique and special Cape Cod Family Compound boasts 2 houses, Sleeps 28! Your own private dock and beach on Bass River, and right around the corner from Nantucket Sound ocean beach. Self contained property-you won't need to leave. Can rent separately- call for pricing. Dock on Bass River, fishing ...

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Property Type

Yarmouth House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to

$236

avg/night

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Key Amenities

  • Kid friendly

About this property

This congenial 3-bedroom, 2-bath home is welcoming retreat to both you and your furry friends (with owner's permission). Recently renovated kitchen and baths offer a modern touch, while the added convenience of WiFi ensures you stay connected during your stay. Enjoy the fresh air with an outside ...

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Property Type

Eastham House

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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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Chatham Vacation Rentals