Chester Rentals

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124 Houses

“Great time!!” This wonderful home was great for our Cape vacation! The home is beautiful and the owner's pride and love for their home shows throughout the property. The owners were excellent to work with, very professional and very responsive to inquiries. The house is beautifully decorated and extremely well stocked with everything we needed to make our vacation perfect. We appreciated all the amenities - inside and out, the huge rear deck was one of our favorite places to relax and enjoy the quiet area and the beautiful landscaping, we could even hear the waves at night. The location was very convenient to restaurants, shops and beaches and is centrally located to exploring anywhere on the Cape. We are looking forward to calling this our "home away from home" again!!!

Match: Bicycles available Climbing frame

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Price per night from

$395

Match: Bicycles available Climbing frame

All filters match

Price per night from

$395

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Pleasant Forest Shores cottages #2 : So. Chatham

South Chatham cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Bicycles available, Climbing frame

1 of 2 filters match

Price per night from

$102

Pleasant Forest Shores cottages #Apt : So. Chatham

South Chatham cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Bicycles available, Climbing frame

1 of 2 filters match

Price per night from

$75

Pleasant Forest Shores cottages #3 : So. Chatham

South Chatham cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Bicycles available, Climbing frame

1 of 2 filters match

Price per night from

$115

Oar Island

Bremen cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

“perfect” We love Oar Island. It is the perfect vacation place for families with children of different ages, or just a couple. There is hiking, sunning, relaxation, but mostly what we love about Oar Island is the isolation. It is an adventure as well, since the only way to get there is by the little motorboat. It is a getaway for certain kinds of people; but if you prefer the Marriott type of stay, this is not that kind, it is much more "out-doorsy".

1 of 2 match: Bicycles available, Climbing frame

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Price per night from

$269

Ocean View Cape on 14 Private Acres

Searsport house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Bicycles available, Climbing frame

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Price per night from

$373

Modern Luxe Loft

Needham apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Bicycles available, Climbing frame

1 of 2 filters match

Price per night from

$172

Beautiful new house + classic cottage Seal Harbor

Seal Harbor house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Bicycles available, Climbing frame

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Price per night from

$916

Renovated Cottage near center and beaches

Edgartown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 3 hours 15 minutes

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$802

4 Season vacation Home Rentals, Van Buren, Maine

Van Buren house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Bicycles available, Climbing frame

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Price per night from

$205

Waterfront home - Spectacular Sunsets

Bourne house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

“Peace & Tranquility” I have stayed here 4+ times, and I come home relaxed and rejuvenated. It's centrally located in the middle of the western cape, the sunsets are perfect, we usually have meals out on the expansive deck, we bring our kayaks, watch the shipping entering the canal, walk/run/bike the canal path(both sides), cook or grill fresh seafood from local stores, enjoy the wine tastings at the Belfry, jump over to the vineyard for the day, and did I mention the sunsets? The home is roomy, light and airy, plenty of parking, just perfect for us.

1 of 2 match: Bicycles available, Climbing frame

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Price per night from

$630

The Jethro Peckham House

Middletown house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 13

1 of 2 match: Bicycles available, Climbing frame

1 of 2 filters match

Price per night from

$401

Waterfront Resort in Falmouth - 5/31/24 - 6/7/24

Falmouth apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Bicycles available, Climbing frame

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Price per night from

$172

White Mountain Getaway

Lincoln house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Climbing frame

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Price per night from

$258

Ocean front, 4 bedrooms, on Cabot trail, N.S.

Grand Etang house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Bicycles available, Climbing frame

1 of 2 filters match

Price per night from

$315

This is a family and pet friendly, non smoking

Charlottetown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Bicycles available

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Price per night from

$260

Breath taking Ocean Harbour Front 3 Bedroom 2 Bath

Chester condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 42 minutes

1 of 2 match: Climbing frame, Bicycles available

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Price per night from

$168

Ocean View West Main Road Residence

Little Compton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$492

Moosehead Lakefront (Mount Kineo) Cottage Rental

Rockwood cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$229

Waterfront Home on Scenic Cove

Harpswell house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$184

1 of 2 match: Climbing frame, Bicycles available

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Price per night from

$126

“Absolute best house -” Wonderful home right on point in Bar Harbor - spend evenings watching the sunset on the rocks - only wish it had more bedrooms -

1 of 2 match: Climbing frame, Bicycles available

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Price per night from

$690

Camp Pond's End -- Beautiful view and private dock on Long Pond

Mount Desert log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$360

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$195

Pleasant Street Village Home

Vinalhaven house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$281

Slopeside Attitash near StoryLand, White Mountains

Glen condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Bicycles available, Climbing frame

1 of 2 filters match

Price per night from

$229

1 of 2 match: Bicycles available, Climbing frame

1 of 2 filters match

Price per night from

$201

Raised Split Ranch Single House in South Dennis

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$401

Narragansett Rhode Island Beach Rental

Narragansett house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$393

Executive modern oceanview hilltop home

Martha's Vineyard house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$1,031

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$281

4 acre private retreat setting

Middleborough house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$144

Seaside cottage

Falmouth cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$492

Spectacular Private Waterfront and Beachfront Home

Wellfleet cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Unforgettable” Heaven on earth at Drew and Heather's ! Very pleasant house, with all facilities, and a hudge sundeck. High tide, and it's like a private pool at 30 ft. Low tide, and a wonderful sandbeach appears 6 hours for fantastic walks. Can you imagine nicer bike rides very early in the morning to PB's restaurant and baker at highway 6 (about 20 mn ), for a wonderful croissant breakfast ! So much to say about the stay at Wellfleet, Just come and see by yourself. It's sure, I'll be back (from France)

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$310

Stanhope 2-Bedroom Cottages PEI

Stanhope cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“The owners were so hospitable our vacation was enhanced by them.” I had stayed in these same cottages last summer, and was pleased with their cleanliness and accessibility to the beach, so felt comfortable booking another stay there this year, as although they are under different management, thought I knew what to expect. We received so much more. We were a group of 5 adults, and one of our party is in poor health and rather frail. The owners went well out of their way to be helpful, gracious, and kind. It was a generosity of spirit that was so nurturing to our group, and we were very grateful for this unexpected kindness.

Responds fast! avg. 39 minutes

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$117

Stanhope 3-Bedroom Cottages PEI

Stanhope cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

“Pei Beach access family cottages feel like your PEI home” Over the past 12 years our family has returned many times to Stanhope cottages. They are located within easy walking distance of excellent PEI beaches in the National Park as well as golf, Covehead wharf fishing,and bike rentals for the trails. The cottages are well equipped, scrupulously clean and arranged for both privacy and easy supervision of younger children in a large grassed park area. Families should expect to enjoy pleasant days in the National Park, easy day trips to Charlottetown, Bbqs with plenty of seafood and peaceful sleeps to the sound of the surf.

Responds fast! avg. 39 minutes

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$150

Stanhope 4-Bedroom Cottages PEI

Stanhope cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“A great place for a family vacation.” Our large extended family had a wonderful time at Stanhope Cottages. Our cottage was very clean and equipped with everything we needed and more. Susie was very accomodating and gave us great advice for local dining. The setting was quiet and an easy walk to the beach. Altogether, we were very happy with our stay.

Responds fast! avg. 39 minutes

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$170

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