Chester Rentals

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193 Houses

Barnstable Village Private Pool

Barnstable house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

“Great place to stay” The home was clean and well maintained. The pool was a huge hit with my niece and the rest of the family. We were in a great location, close to a beach, some shops and restaurants.

Match: Bicycles available Private outdoor pool (unheated)

All filters match

Price per night from

$457

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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: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$803

Ocean View West Main Road Residence

Little Compton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), 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: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$230

This is a family and pet friendly, non smoking

Charlottetown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

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: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$168

Waterfront Home on Scenic Cove

Harpswell house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$184

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$127

“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: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$691

Pleasant Street Village Home

Vinalhaven house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$281

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$195

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: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$361

Pool house

Plymouth house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 11

Responds fast! avg. 3 hours 0 minutes

1 of 2 match: Bicycles available, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$516

Short term close to beach and ferry to Boston

Hull house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Bicycles available, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$287

Narragansett Rhode Island Beach Rental

Narragansett house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$394

Executive modern oceanview hilltop home

Martha's Vineyard house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$1,032

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$281

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: Private outdoor pool (unheated), 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: Private outdoor pool (unheated), 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: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$170

Stanhope 1-Bedroom Cottages PEI

Stanhope cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“we had a very relaxing time” we loved the fact that it was a five minute walk to the park and our favourite beach.we have been vacationing in pei for many years now and stanhope cottages is now our favourite.we look foward to returning next year.

Responds fast! avg. 39 minutes

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$92

New Cape House Steps to the Beach in East Falmouth

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$430

Perfect Location & Best Prices! 5th house to beach

Old Orchard Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$190

4 acre private retreat setting

Middleborough house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), 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: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$492

Luxury Harvard/MIT Victorian w/off street parking.

Cambridge apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$454

Charming Harvard Victorian w/pkng.

Cambridge apartment

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$556

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$746

Charming Beach House - Beautifully Updated & Immaculate. Walk to Nantucket Sound

South Chatham house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$430

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: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$310

ROCKPORT MA OLD GARDEN BEACH RENTAL !

Rockport house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$459

Meadow & Mountain View - amazing views & privacy, walk to Bar Harbor

Bar Harbor farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect location” This older farmhouse has a perfect location. Only a mile from town and there is a trail that crosses at end of driveway for easy access hiking. Park loop road is right around the corner. The best part is when you are there it is completely private in the middle of a quiet meadow. The house itself is older but clean and all amenities are there for you. Would definitely recommend it.

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$226

Grace Cottage

Long Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$413

White Cape on the Cove - Year round ocean retreat!

Blandford house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$319

Dont Get Stucked In Boston Traffic

Acushnet apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$958

Walk To Joshua Pond & Main St. 2 Bedroom Cottage, Central Cape Location

Osterville apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$523

Raised Split Ranch Single House in South Dennis

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$402

Luxury Kennebunkport Cottage w/ Private Water Access

Cape Porpoise house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 minutes

1 of 2 match: Private outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$402

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rentals in Chester

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