Luxury Vacation Rentals in Chatham

(161 rentals)
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3 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 0.8 miles to Skaket Beach

$423

avg/night

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Key Amenities

  • Kid friendly

About this property

Light & bright 3-bedroom + den home with central A/C near Skaket Beach! Lovely 2900 sq. ft. Cape on a quiet lane 8/10 mile from the sandy shores of Cape Cod Bay. Main level features a spacious main bedroom with full bath and laundry area, a large living room, separate den (with queen pullout), an ...

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Property Type

Orleans House

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$422

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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4 BR | 2 BA | Sleeps 8 | Quick View

$414

avg/night

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Key Amenities

  • Kid friendly

About this property

Overlooking Orleans Town Cove and with direct access to the water, this beautifully remodeled home is your perfect Cape Cod vacation retreat! Light and bright, with beautiful hardwood floors and an open floor plan, the main level has a large, fully equipped kitchen with granite counters and breakfast ...

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Property Type

Orleans House

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4 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 1 miles to Boat Meadow / First Encounter

$413

avg/night

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Key Amenities

  • Kid friendly

About this property

Large 4 bedroom home with spectacular views of Cape Cod Bay from every room in the house including a spacious second level screened in porch. Kitchen and all 3 bathrooms were completely redone in 2012 with granite countertops, new Chrystal cabinets and new stainless steel appliances in the kitchen. Ductless ...

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Property Type

Eastham House

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Key Amenities

  • Kid friendly

About this property

Dennis - Recently renovated and new to the vacation rental market for the 2023 season this 5 bedroom 2 bath Cape sleeps 9 and is a short drive to all the popular Cape Cod Bay Beaches! The first floor offers a dine in kitchen in addition to a dining room with sliders leading out to the deck, a living room ...

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Property Type

Dennis House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.1 miles to Thumpertown Beach

$407

avg/night

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Key Amenities

  • Kid friendly

About this property

Great beach house just steps away from private beach near Thumpertown Beach. Located in a quiet, secluded spot, this home offers a glassed in porch, three decks (along with a peek of the bay), three bedrooms and two baths! Between the living area, porch and decks there is plenty of room for the family ...

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Property Type

Eastham House

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Key Amenities

  • Kid friendly

About this property

South Yarmouth - This two bedroom cottage with one bath has been tastefully updated for your enjoyment. Rinse off in the outdoor shower after a day at South Middle Beach which is located just one mile away and a short walk to mini golf, ice cream and restaurants. Primary bedroom with queen bed, second ...

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Property Type

Yarmouth Cottage

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Key Amenities

  • Kid friendly
  • Pet friendly
  • Pool

About this property

Enjoy this classic cape cod oasis directly across the street from Allan Harbor. This space has a private deck with a table for 2, where you can sit, relax and enjoy the fresh air off the comfort of your room. This space has a queen size bed, flat screen tv and a mini split unit for A.C and heat. There ...

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Property Type

Harwich Cottage

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3 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 500 miles to S. Sunken Meadow

$393

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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Key Amenities

  • Beachfront
  • Kid friendly
  • Oceanfront

About this property

Located just 2/10th's of a mile from bay-side Skaket Beach is this sweet 3 bedroom, 1 full bath (tub/shower combination) home offering beautiful tidal marsh views and a spacious deck to enjoy the outdoors. With Central A/C, the property is set back at the end of a sandy lane and is close to the Cape ...

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Property Type

Orleans House

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$382

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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4 BR | 3 BA | Sleeps 10 | Quick View

$382

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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3 BR | 2 BA | Sleeps 6 | Quick View

$379

avg/night

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Key Amenities

  • Kid friendly
  • Oceanfront

About this property

Dennis - Walk to Princess Beach on Scargo Lake from this 3 bedroom 2 bath home is located in the Scargo Hill area of the Village. Rinse off in the outdoor shower after a day at one of the Northside Bay beaches or Scargo Lake. Screen porch and deck are perfect for outdoor entertaining. Central Air ...

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Property Type

Dennis House

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5 BR | 3 BA | Sleeps 10 | Quick View

$371

avg/night

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Key Amenities

  • Kid friendly

About this property

Incredible views from this classic cottage. A unique location makes this an ideal home for the naturalist. Resting above the Boat Meadow River allows easy access to the river and Boat Meadow Beach (via kayak or canoe). Commanding views and incredible privacy and seclusion.

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Property Type

Eastham House

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Key Amenities

  • Rentals by owner

About this property

****PLEASE NOTE: BECAUSE OUR HOME IS ALSO UTILIZED DURING THE SEASON BY SEVERAL FAMILY MEMBERS AND IN ORDER TO ACCOMMODATE THEIR SCHEDULES , WE DO NOT ACCEPT ANY RESERVATIONS EARLIER THAN JANUARY OF EACH RENTAL SEASON. (i.e. JANUARY 2024 FOR SUMMER OF 2024)***Unique rental changeover (Friday to Friday) ...

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Property Type

Eastham House

"Comfortable, Quiet, Convenient and Classy"

Dear John,We really enjoyed staying at your home on the Cape. We loved how quiet the neighborhood was and how close the house is the the rail trail (and Mac's Seafood!). The house was well stocked, ...

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to

$371

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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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 10 | Quick View

Distance to beach: 0.4 miles to Seagull Beach

$370

avg/night

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Key Amenities

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

About this property

Rattlin (Irish adj. meaning splendid) This home truly is a splendid cape cod vacation. This house offers two floors… with three full bedrooms, and a fourth office/spare bedroom attached to the primary. One full bath on each floor of the home, and an outdoor shower. There is ample lounge seating ...

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Property Type

Yarmouth House

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4 BR | 2 BA | Sleeps 6 | Quick View

$367

avg/night

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Key Amenities

  • Kid friendly
  • Pet friendly
  • Rentals by owner

About this property

Beautiful summer rental close to shopping, tennis courts, playground and bike trail. Short drive to bay side beaches and ocean. All the amenities of home. Linens and Towels are provided.

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Property Type

Orleans House

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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 | 1.5 BA | Sleeps 6 | Quick View

Distance to beach: 0.1 miles to Skaket Beach

$357

avg/night

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Key Amenities

  • Kid friendly

About this property

AT SKAKET BEACH! This charming renovated 1927 Cape has ample room for 6, a master bedroom with a vaulted ceiling and a private half-bath, plus a lovely wraparound porch with hammock. The sunny interior features newly-painted floors, comfy furnishings throughout and excellent amenities, including wireless ...

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Property Type

Orleans House

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3 BR | 2.5 BA | Sleeps 6 | Quick View

Distance to beach: 0.5 miles to Silver Spring Beach

$357

avg/night

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Key Amenities

  • Kid friendly

About this property

Cape style home with central air conditioning on the bayside of Eastham with access to Cooks Brook Beach. Fully equipped kitchen and dining room, family room opening onto the four season porch then out to the deck. First floor master bedroom with queen, TV and full bath with soaking tub and separate shower. ...

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Property Type

Eastham House

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About this property

Owner Spring Special! Book before May 25th and weekly rate is $2800 plus fees/taxes! Pretty and spacious year round home in popular Dennis! A little over a mile to Princess Beach, and under 5 minute drive to Corporation Beach. 3.3 Miles to Mayflower beach. This welcoming home offers 4 bedrooms (2 ...

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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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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: 0.2 miles to Skaket

$357

avg/night

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Key Amenities

  • Kid friendly

About this property

Location, Location! Sweet and cozy 2-bedroom Plus bunkhouse just 2/10ths of a mile from gorgeous Skaket Beach on Cape Cod Bay. Corner lot on a quiet sandy road with 3 ductless A/C units, new stove & refrigerator, and outdoor shower. An ideal setting for the smaller gathering just steps to the sand! ...

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Property Type

Orleans House

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3 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 0.0 miles to Pilgrim Lake

$357

avg/night

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Key Amenities

  • Kid friendly

About this property

At the end of a private lane lies your secluded vacation retreat on tranquil Pilgrim Lake. Just 60 feet from the decks and living room window is your private lakefront with swim float for boating, fishing or swimming. The main deck, overlooking the water with comfortable outdoor furniture and gas grill, ...

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Property Type

Orleans House

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About this property

This charming historic Cape is conveniently located on Route 6A in Dennis Village. Just a quick walk to the Cape Playhouse, Cape Theatre, numerous restaurants, shops, and Cape Cod Museum of Art. This beautifully updated and maintained property is a three-bedroom, two bathroom with multiple spots to ...

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Property Type

Dennis House

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4 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 0.8 miles to Crystal Lake

$352

avg/night

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Key Amenities

  • Kid friendly

About this property

Crystal Lake-- Designed to look like an illustration from a children's fairytale, this gracious and comfortable vacation home promises a magical vacation any time of the year. Enter through lush gardens into a surprisingly spacious, fully air conditioned home designed with relaxation, convenience, ...

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Property Type

Orleans House

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4 BR | 2.5 BA | Sleeps 10 | Quick View

Distance to beach: 0.6 miles to Skaket

$350

avg/night

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Key Amenities

  • Kid friendly

About this property

Walk to Skaket Beach! Spacious home with A/C, tucked away at the end of a quiet cul-de-sac. Only .6 miles to the sandy shore of Cape Cod Bay via a neighborhood path. Offering great privacy on 1.3 acres, the highlights of this home are its wonderful family room with cathedral ceiling and wood stove, newly ...

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Property Type

Orleans House

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3 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 2 miles to Crosby Landin On Cape Cod Bay

$350

avg/night

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About this property

This lovely brand new home in Brewster is in a great location! There are trails adjacent to the property that lead right to Nickerson State Parks for beautiful hiking trails and ponds to swim. Just a short stroll away at apprx. 1/2 a mile is Owl Pond where you can canoe or paddleboard. This home features ...

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Property Type

Brewster House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 1 miles to

$343

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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3 BR | 1.5 BA | Sleeps 6 | Quick View

Distance to beach: 0.0 miles to Cooks Brook

$341

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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Key Amenities

  • Kid friendly

About this property

New Rental for Summer 2023! Spacious and comfortable 4 Bedroom 2.5 Bath home is located in a quiet Eastham neighborhood and surrounded by a peaceful wooded backdrop. It is perfectly situated between the bay and oceanside beaches, minutes to Orleans, and up the street from the Cape Cod Rail Trail. Groceries, ...

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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 Nauset

$336

avg/night

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Key Amenities

  • Kid friendly

About this property

Walk to Nauset Beach! Once part of the historic Mayo Duck Farm and a 2/10 mile from beautiful Nauset Beach and the Atlantic Ocean. This home's furnishings have been refreshed, and include a flat screen television. Steam up the lobster in the country kitchen. Have your morning coffee on the back deck ...

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Property Type

Orleans House

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Key Amenities

  • Kid friendly

About this property

This Cape Cod home is perfect for the beach lover, boater, kayaker or paddle boarder with proximity to Mill Pond and boating to the outer beach! Beautiful home offers 3 spacious bedrooms and two full baths on two levels. Main level features a sunny living room with gas fireplace and flat screen TV ...

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Property Type

Orleans 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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$325

avg/night

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Key Amenities

  • Kid friendly

About this property

Yarmouth Port - This four bedroom three bath colonial is full of charm and character in the beautiful Rolling Hills community just off of Route 6A is a great choice for your summer vacation! New to the rental inventory for 2023 the first floor offers sparkling hardwood flooring, cathedral ceilings with ...

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Property Type

Yarmouth Cottage

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3 BR | 1.5 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Cole Rd

$321

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
  • 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: 3 miles to Ellis Landing, Cape Cod Bay

$314

avg/night

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Key Amenities

  • Kid friendly

About this property

Light-filled, renovated contemporary Cape on a quiet street not far from the sandy shore of Cape Cod Bay and beautiful Nickerson State Park. The circular driveway and welcoming front porch lead to an open floor planr. With A/C units in the living area and all bedrooms. The charming dining area with skylights, ...

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Property Type

Brewster House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Nauset

$314

avg/night

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Key Amenities

  • Kid friendly

About this property

Great privacy in East Orleans! Enjoy this lovely 3-bedroom, 2-bath contemporary home offering a bright and open floor plan and updated furnishings. Front-to-back living room with fireplace and a great screened porch open onto a spacious wraparound deck. This great vacation spot is gracefully tucked up ...

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Property Type

Orleans House

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3 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 0.2 miles to Thumpertown Beach

$314

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

  • Rentals by owner

About this property

Private cul-de-sac 1 mile from beautiful Nauset Light Beach, 1.5 miles from Coast Guard Beach, one of the top 10 beaches in the USA year after year.Google THE BEST BEACH TOWN IN MA according to Stacker.Easy walk or bike ride to the beach.Wellfleet and Truro are nearby; 25 minutes to Provincetown.Near ...

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Property Type

Eastham House

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Key Amenities

  • Kid friendly

About this property

Beautiful custom Cape home on the Bayside. One of the very few homes that are highly appointed yet near the beach. Nicely landscaped outside with patios and outdoor shower. Inside there is a custom dining area, bright, well equipped kitchen, living room is large, going front to back in the main house. ...

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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 Nauset

$307

avg/night

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Key Amenities

  • Kid friendly

About this property

Very spacious one-level apartment only 2/10ths of a mile from gorgeous Nauset Beach on The Atlantic. NOW WITH A/C units! Completely refreshed with new rugs, new furniture and new gas grill. Step down to a second living area to the 'summer room' with a second TV which leads outside to a private ...

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Property Type

Orleans House

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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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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Spacious 2,500 square ft. family home with abundant natural light nestled in a private association of 20 homes in easy walking distance (0.3 miles) to a saltwater pond (Meetinghouse Pod). Our house is on a 0.7 acre lot with a large, wooded backyard offering privacy in a neighborhood surrounded by Pleasant ...

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Property Type

Orleans House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 800 miles to

$298

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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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