Luxury Vacation Rentals in Chatham

(94 rentals)
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Key Amenities

  • Kid friendly
  • Pet friendly
  • Rentals by owner

About this property

Perfect spot to relax for your fall cape wedding, or just a quiet stay during the capes most beautiful time-the shoulder season!Our family and pet friendly sunny 2100 sq foot 3 bedroom, 2.5 bathroom immaculate home boasts of a quiet lot, newer large fully stocked kitchen, laundry room, relaxing farmers ...

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Property Type

Harwich House

"Spacious, pet-friendly, and close to everything!"

Communication from the host before you even check-in is amazing. If you have never been to Harwich you already feel like you have been coming here for years with her guide that she sends. This was also ...

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3 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 0.7 miles to Windmill Beach

$300

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

$300

avg/night

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Key Amenities

  • Kid friendly

About this property

Enjoy the best Cape Cod has to offer. At Marsh View house, you will enjoy a short walk (1/4 mile) to South Sunken Meadow Beach along a quiet road lined with views of the marsh. Views of the bay and marsh from an expansive upper deck. Unique reverse floor plan maximizes views from bright, open living area ...

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Property Type

Eastham House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.4 miles to Cooks Brook

$286

avg/night

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Key Amenities

  • Kid friendly

About this property

Secluded contemporary Cape on quiet cul-de-sac 4/10 mile to deeded association beach on Cape Cod Bay. Airy living space with cathedral ceiling opening to large deck and wooded private yard. Newly added ductless AC units to the living area and bedroom upstairs keep you cool on those hot summer days. Master ...

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Property Type

Eastham House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 1 miles to

$286

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 Thumpertown Beach

$286

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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Key Amenities

  • Kid friendly

About this property

Spectacular views from this contemporary cottage located directly on Cape Cod Bay. Beautiful sunsets and a great beach to walk right off the back deck!

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Property Type

Eastham House

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4 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 2 miles to Nauset Light Beach

$286

avg/night

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Key Amenities

  • Kid friendly

About this property

Make this well equipped home your Cape summer destination! In addition to being ideally located near both the popular Bike Trail and Nauset Light Beach, this home features conveniences like WIFI, 5 window A/C units for comfort, Washer/Dryer, Dishwasher, Expanded Cable, deck, Outside Shower, standard and ...

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Property Type

Eastham House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 800 miles to

$286

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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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.5 miles to Dunes Beach Assoc.

$271

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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Key Amenities

  • Oceanfront

About this property

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 sailing to the islands. There is plenty of room for the whole group to relax and enjoy the stunning views! Comfortable ...

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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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3 BR | 3 BA | Sleeps 6 | Quick View

1

Distance to beach: 1 miles to

$264

avg/night

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Key Amenities

  • Kid friendly

About this property

Bayside~This well maintained three bedroom, 3 bath Cape style home sits on a quiet side road about a mile to Cooks Brook Beach. A large screened-in porch with adjoining bathroom, roomy deck, and outside shower were all added in 2022. The kitchen with stainless steel appliances and quartz counter tops ...

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Property Type

Eastham House

"Great House"

The house exceeded all of our expectations. We certainly felt at home. Very private and quiet location. Will definitely return and recommend.

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2 BR | 2 BA | Sleeps 6 | Quick View

$257

avg/night

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Key Amenities

  • Kid friendly

About this property

Sunny 1960's style contemporary ranch in a gorgeous, private setting offers your perfect Cape Cod vacation! This one level home has 2 bedrooms and 2 updated full bathrooms with walk-in showers, a fully equipped kitchen, cozy living room and large dining room overlooking private yard. Primary Bedroom ...

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Property Type

Orleans House

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Key Amenities

  • Kid friendly

About this property

Owner offering nice off season specials, both weekly and nightly (2 night minimum $268.75 a night plus taxes and fees) Enjoy your Cape Cod vacation in this bright and clean 3 bedroom 1 full bath cottage. Central Air! Updated eat-in kitchen with beautiful hardwood floors.A spacious 3 season porch to spend ...

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Property Type

Yarmouth 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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Key Amenities

  • Kid friendly
  • Pet friendly
  • Rentals by owner

About this property

Recently Renovated 3/1 with new kitchen & bath & close to beach w Central ACThis cozy, recently renovated cottage has a brand-new kitchen, new bathroom, and new flooring and is an excellent location, close to the Bay and just 0.9 miles to Saints Landing Beach. Situated on a 1.4 acre wooded ...

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Property Type

Brewster House

"A Restful Piece of Paradise !"

There aren't enough accolades in a dictionary to describe Shannon OR this Cape Cod cottage! Open the front door and you can't help but say "WOW!" Then walk through the three bedrooms and you'll note that ...

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4 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 0.0 miles to S. Sunken Meadow / Cooks Brook

$257

avg/night

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Key Amenities

  • Kid friendly

About this property

This generously sized 4 BR home is conveniently located about 1 mile to So Sunken Meadow or Cooks Brook Beach. It has 2 BR's upstairs and 2 BR's down with a full-sized bath on both levels. Mini split units provide AC for the house! A slider in the bright living room yields to an oversized, deck ...

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Property Type

Eastham House

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Key Amenities

  • Kid friendly

About this property

This lovely bow-roofed Cape features a large screened ‘summer room’ with sitting and dining areas, cable TV, and floor-to-ceiling windows looking out on the spacious, secluded yard.  The house is in a private, tree-lined setting on a quiet cul-de-sac. The interior is open, bright, and ...

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Property Type

Eastham House

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2 BR | 1 BA | Sleeps 4 | Quick View

3

Distance to beach: 0.4 miles to Colonial Acress

$257

avg/night

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Key Amenities

  • Kid friendly
  • Pet friendly
  • Rentals by owner

About this property

We are not taking Reservations for 2025. If you are a past guest wishing to return please feel free to contact us. New guests check back after January.Please Email for other sites where you may read additional reviews..Park your car in the sparkling white clam shell driveway at The Hibiscus ...

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Property Type

Yarmouth Cottage

"South Yarmouth"

Dear Jim and Regina, Thank you so much for the very lovely stay at your Cottage B home ! We love being in this neighborhood and PRBeach ️Was a wonderful trip with Mom and the 2 girls !! Lots of great ...

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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
  • Rentals by owner

About this property

0.3 mile walk to Brook Rd beach and 0.5 mile to Earle St beach. within 2 miles to 12 harwich Port beaches! Conveniently located in mid Cape which is the center of everything you want to go in Cape Cod! Accommodate extended familyWe provide everything you need for your vacation stay from linens ...

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Property Type

Harwich House

"Great Home and Great Location"

Regardless of the weather, we had a great week. House was very comfortable and close to everything. Can walk to a few beaches close by, but they had a lot of seaweed. If want to go to other beaches, ...

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Key Amenities

  • Beachfront
  • Kid friendly
  • Pet friendly

About this property

Coastal living! Spacious 3 bedroom home with lots of space to relax and enjoy your Cape vacation. Just .2 miles to Englewood beach on Lewis Bay with playground and boat launch. Short drive to Colonial Acres and Seagull beach as well. View the fireworks from the neighborhood too!This comfortable year ...

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Property Type

Yarmouth House

"Spacious, comfortable, nice neighborhood, close to the beach"

We truly enjoyed our stay at this beautiful family home. 4 adults, 2 children and 1 dog stayed comfortably in this spacious, comfortable home. We loved walking just down the street to the beach, a short ...

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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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2 BR | 1 BA | Sleeps 4 | Quick View

$250

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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4 BR | 2 BA | Sleeps 8 | Quick View

$245

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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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to

$243

avg/night

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Key Amenities

  • Kid friendly

About this property

This comfortable home has been recently renovated! New paint, flooring and furniture. Quiet location on the Oceanside, approximately 3/10ths of a mile from the bike trail, 2.5 miles from the Atlantic Ocean and about 3 miles to Cape Cod Bay. A convenient location to enjoy the many beaches and activities ...

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Property Type

Eastham House

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3 BR | 1 BA | Sleeps 6 | Quick View

Distance to beach: 300 miles to Kingsbury Beach

$243

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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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, 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 sun ...

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Property Type

Dennis House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 500 miles to First Encounter Beach

$229

avg/night

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Key Amenities

  • Kid friendly

About this property

Short walk to swimming and viewing the gorgeous sunsets at First Encounter Beach from this cozy home (1464 sq/ft). Features include AC units in the bedrooms and living room, screen porch in the back yard and a quiet setting. Now offering wireless internet! Perfect for a family summer vacation. Don't ...

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Property Type

Eastham House

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Indulge in luxury during your vacation at this impeccably renovated house. Pristine and tastefully decorated, it boasts central air conditioning with mini splits in each room, stunning hardwood flooring throughout, and a gourmet kitchen equipped with soapstone countertops, high-end appliances, including ...

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Property Type

Eastham House

"Wonderful child-friendly home in a great location."

The location is fantastic - close to many restaurants and beaches in Orleans, Eastham, and Wellfleet. It's also a 30 second walk from the front door to the Cape Cod Rail Trail. The house has a nice, modern ...

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4 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 1 miles to Herring Pond

$225

avg/night

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Key Amenities

  • Kid friendly

About this property

Beautifully renovated home on Eastham's bayside. Located on a quiet side road, easy bike ride or short drive to Great Pond, a large Pond with swimming and beach area, great for boating, kayaking and fishing. Bayside beeches, Encounter Beach, Bee's River which is same area as Encounter, Boat ...

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Property Type

Eastham House

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4 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 1 miles to South Sunken Meadow

$221

avg/night

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Key Amenities

  • Kid friendly

About this property

This spacious four-bedroom home has sweeping views of Cape Cod Bay from nearly every room. Located between Cooks Brook and Sunken Meadow Public Beaches, you will be only five minutes from our private association Salt Works Beach. Our home is fully air conditioned with 5 mini split AC units. WiFi is available ...

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Property Type

Eastham House

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3 BR | 2 BA | Sleeps 7 | Quick View

3

$215

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Welcome to Harwich Getaway! Immaculately clean open concept and bright cape house with 2 zone central AC is perfect for your year round getaway! We are the #1 rated Harwich home on Airbnb with 4.97 star rating from 65+ reviews, save hundreds by booking with us direct!Minutes to cc rail trail and ...

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Property Type

Harwich House

"Harwich Getaway is fantastic!"

We LOVED staying in Harwich for the first time and LOVED Harwich Getaway house. We have rented MANY times on the Cape and this home rates at the top of our experiences. We were comfortable, it had everything ...

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3 BR | 1.5 BA | Sleeps 6 | Quick View

1

Distance to beach: 1 miles to Red River Beach

$215

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

BEAUTIFUL Cape style home in quiet neighborhood. Open floor plan with deck off the kitchen. On 1/2 acre flat lot, 3/4 of a mile to the beech. Bike path at end of street. 8 Rooms, 3 Bedrooms 1 Bath and 1 Half Bath.1st floor: Large open living room. Dining room that seats 6, kitchen with dishwasher, ...

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Property Type

Harwich House

"Cute cottage"

The cottage was as described. It was cute, comfortable, well equipped and clean. Great for a family.

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3 BR | 1.5 BA | Sleeps 6 | Quick View

Distance to beach: 0.0 miles to Cooks Brook

$214

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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$214

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Come enjoy this Cape Cod cozy home that's just a 10 minute walk from the beach. This Cape house offers tons of amenities including 2 bedrooms. One full bed other queen. Living room has a pull out queen sofa and 2 cots for extra sleeping. Outside is the best to enjoy a fire, Read in the swing ...

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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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Key Amenities

  • Rentals by owner

About this property

Nestled on quiet street, in a peaceful bayside neighborhood, beautifully renovated and appointed 3 Bedroom 1.5 Bath, with an enclosed outdoor shower. This pristine one-level cottage is now booking year round vacations! All new furnishings, beds and appliances!Featuring central AC, sliders to back ...

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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

$200

avg/night

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Key Amenities

  • Kid friendly

About this property

Pleasant cottage on side street. Deck and outdoor shower for outdoor enjoyment. Fully remodeled kitchen and bath and bedrooms. Centrally located on the bayside. Charming and cozy interior. Very fairly priced.

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Property Type

Eastham House

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2 BR | 1 BA | Sleeps 6 | Quick View

5

Distance to beach: 0.9 miles to Sea Gull Beach

$200

avg/night

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Key Amenities

  • Rentals by owner

About this property

Welcome aboard The Wheelhouse! Cozy 2 bedroom/1 bathroom cottage is Old Cape Cod charm at its best.Less than 3/4 mile to Sea Gull Beach, minutes from local shops, restaurants, and attractions, The Wheelhouse offers a peaceful seaside escape. You will enjoy sprawling marsh views while enjoying your ...

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Property Type

Yarmouth Cottage

"Wheelhouse Cottage"

Everything was perfect! I plan to return again. Tha view of the marshes and pond were gorgeous. The cottage is very well appointed and maintained. Power Bobby very kind and accommodating. You won’t go ...

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

This expanded and newly updated cottage is filled with sunlight. It's a one-level home with a wonderful mix of classic-cottage and contemporary style. Situated in a family-friendly, quiet area of town, this is a cottage filled with love and CENTRAL AC, and a new EV charger!The cottage is just ...

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Property Type

Yarmouth Cottage

"Filipp Family"

Lovely location and stay. The kitchen well stocked with great dishes, glass ware, pots and pans not scuffed up or scratched. Liked having a washer and dryer! The place had a nice backyard for relaxing and ...

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3 BR | 1 BA | Sleeps 6 | Quick View

Distance to beach: 900 miles to Kingsbury

$200

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 sand road within a short walk (900ft) to Kingsbury Beach for a salt water beach. Features include a wraparound deck, and glassed-in sun porch. This is an ideal location that features privacy and the ability to also ...

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Property Type

Eastham House

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3 BR | 1.5 BA | Sleeps 8 | Quick View

$200

avg/night

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Key Amenities

  • Kid friendly

About this property

Dennis - Modern three bedroom 1.5 bath rental. Fully equipped kitchen. Finished basement with full bunk-bed and single. Outdoor shower, gas grill and new outside furniture. Large beautiful backyard for entertaining. Less than a 10 minute drive to bay side beaches. A/C, Wi-Fi, beach accessories. Multiple ...

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Property Type

Dennis Cottage

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2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.0 miles to 1st Encounter

$200

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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Property Type

Eastham House

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Chatham Vacation Rentals