Chester Rentals

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119 Houses

Beautiful Brewster Green Resort Condo with Many Amenities

Brewster villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 14 minutes

Match: Bicycles available Children's pool

All filters match

Price per night from

$294

Wells, Maine Cottage w/Pool, hot tub, Gym & more....

Moody cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Bicycles available Children's pool

All filters match

Price per night from

$241

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Wyndham Long Wharf August 11th - 18th Friday to Friday only

Newport condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Children's pool

1 of 2 filters match

Price per night from

$327

Beach Getaway

Moody cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Bicycles available, Children's pool

1 of 2 filters match

Price per night from

$286

Responds fast! avg. 1 hour 57 minutes

1 of 2 match: Bicycles available, Children's pool

1 of 2 filters match

Price per night from

$132

Responds fast! avg. 1 hour 57 minutes

1 of 2 match: Bicycles available, Children's pool

1 of 2 filters match

Price per night from

$152

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: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$801

Wyndham Longwharf

Newport condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Children's pool

1 of 2 filters match

Price per night from

$523

Ocean View West Main Road Residence

Little Compton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$491

Moosehead Lakefront (Mount Kineo) Cottage Rental

Rockwood cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$229

This is a family and pet friendly, non smoking

Charlottetown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$262

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: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$169

Waterfront Home on Scenic Cove

Harpswell house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$183

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$126

1 of 2 match: Children's pool, 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: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$281

“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: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$690

Seaside cottage

Falmouth cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$491

Narragansett Rhode Island Beach Rental

Narragansett house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Children's pool, 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: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$1,030

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$281

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: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$309

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. 32 minutes

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$131

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. 32 minutes

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$151

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. 32 minutes

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$171

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. 32 minutes

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$101

Perfect Location & Best Prices! 5th house to beach

Old Orchard Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$189

4 acre private retreat setting

Middleborough house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$143

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$744

Luxury Harvard/MIT Victorian w/off street parking.

Cambridge apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 21 minutes

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$453

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

South Chatham house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$429

ROCKPORT MA OLD GARDEN BEACH RENTAL !

Rockport house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$458

Grace Cottage

Long Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$412

Franklin Park zoo near Studio

Brookline studio

  • Studio
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$212

Charming Harvard Victorian w/pkng.

Cambridge apartment

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 21 minutes

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$555

New Cape House Steps to the Beach in East Falmouth

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$429

White Cape on the Cove - Year round ocean retreat!

Blandford house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$320

1 of 2 match: Children's pool, Bicycles available

1 of 2 filters match

Price per night from

$262

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rentals in Chester

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