Chester Rentals

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106 Houses

The ultimate Downeast vacation compound with oceanfront pool!

Prospect Harbor house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 14

Responds fast! avg. 1 hour 27 minutes

Match: Private outdoor pool (unheated) Pets allowed

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Price per night from

$913

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Rustico Tides Cottages - Unit 1

North Rustico cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

“Great central location in North Rustico” My family and I stayed at Rustico Tides for 4 nights in August. The cottage was very clean, tastefully decorated (loved the photographs of local scenes) and great for our needs (family of 4). Cottage is well situated (easy access to north shore attractions/Cavendish, Charlottetown etc.) Floor plan was very convenient (loved having 2 bedrooms upstairs and master on main floor). Full laundry in unit was great as was having Keurig (its the little things!!). Amenities at cottage were appreciated, (eg kids play set and outdoor pool), and Park Pass was put to good use. Would definitely stay again.

Responds fast! avg. 15 minutes

1 of 2 match: Pets allowed, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$209

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Birch Harbor boathouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$1,031

Quaint Cottage

Wytopitlock cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$14

Schlafmans Hollow Solar Camping Rental Cabin #1

Lincoln cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$91

Schlafmans Hollow Solar Camping Rental Cabin #2

Lincoln cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$91

West Lee Cottage

Swans Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 46 minutes

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$184

Magic Pond Maine Woods Suite

Blaine apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 1

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$155

Magic Pond Maine Sky Suite

Blaine apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$155

Howe Bay Beach House - PEI Oceanfront Vacation Rental

Souris house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

“Very enjoyable stay and Howe Bay Beach House” This is a beautifull property at a wonderful location. We stayed with 5 adults and 5 childres and loved it. There is plenty of space with fantastic views. Our only regret is that we were only able to stay for 3 days. We would have loved to stay longer. The service was excellent.

Responds fast! avg. 20 minutes

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$330

Memories of Meadowbank.

Clyde River cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$205

Maine lake house

Lincoln house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$458

Quintessential Rustic Maine Oceanfront Cottage with Sunset Views

Tremont cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$344

Knotty Pine Cabin

Otis house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$327

Lucky Stone Retreat - private beach & Acadia view

Sullivan house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$122

The Homestead, in Lower Bedeque

Lower Bedeque house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 14

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$251

Waterfront GUEST HOUSE 2/2 WI-FI, VIEWS, QUIET

Jonesport house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$456

Cast Away Lodge...cast your worries away!

Miramichi lodge

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$250

Bungalow On The Bay

Saint John house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$147

Beachside Cottage by the Sea w/beach access - Aboiteau Beach

Cap-Pelé chalet

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$209

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), Pets allowed

1 of 2 filters match

Price per night from

$360

Epic Water View. Pet Friendly Fenced-In Yard. Add'l Private Suite.

Sullivan house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$576

Waterfront Cottage on Mount Desert Isle - 8 Mi from Acadia

Mount Desert cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$729

Seal Cove Beach Smokeshed Cottages

Grand Manan house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$114

Cozy Clean NorthShore PEI - A Darnley Retreat

Kensington cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$251

Sandbar Haven Cottage

Morell house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 11

Responds fast! avg. 35 minutes

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$179

The Pickering House - an 1854 Harbor View Home

Deer Isle farmhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$458

4 Bdrm Country Home, 12 km West of Summerside

Summerside house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 34 minutes

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$197

Special Guest Farmhouse

Tignish house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$167

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), Pets allowed

1 of 2 filters match

Price per night from

$167

Prud'homme Cottage: architect-designed, bright, private cottage on Cove

Bernard cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$413

Cliffside at Sandcliff by the Sea

Bar Harbor house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“We had a great vacation experience at Cliffside..” We had a marvelous time during our stay at Cliffside and thoroughly enjoyed our trip and the use of this beautiful home with our friends. It was a great location-close to the park and town, but nestled amongst the trees for relaxing privacy. We saw deer behind the house several mornings and took some great pictures of a hawk perched in the tree just beyond our deck. The trails behind the house and Sand Point Road were convenient for morning hiking and jogging. Several mornings we enjoyed our coffee on the decks with their peaceful views of the bay. This lovely home provided a great base for visiting Bar Harbor and acadia- whale watching, visits to Cadillac Mountain, Sand Beach, Thunder Hole, and the Thuya Gardens. We hiked around Jordan Pond and enjoyed the tea and popovers, visited Schoodic Peninsula, and took a carriage tour of the bridges. We really appreciated Bonnie's suggestions for dining and activities to enjoy, and everything went very smoothly from beginning to end. The weather was great and we had a wonderful time.

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$401

Percy Hill Vacation Home

Montague house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“Pampered tranquility” Simply the best accommodations we've experienced in years. The ambiance created by Sebastian and Jennifer's fine touch transported us to another, gentler time. The most modern amenities are provided, in excellent order and function, yet the atmosphere is nurturing and from a kinder time.The kitchen has every device necessary for an accomplished chef, the bedrooms replete for guests of all ages, the views spectacular, and the generous living space tastefully whimsical. We found the nearby dining and shopping in Montague and Georgetown excellent. Trout fishing was good and we were alone on the stream. Can think of no deficiencies. No doubt we'll return.

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$184

Responds fast! avg. 33 minutes

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$171

Responds fast! avg. 33 minutes

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$171

Red Point Tourist Home

Red Point house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 58 minutes

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$109

Beach NS Beachfront Cottage on Beautiful St Margaret's Bay

Boutiliers Point cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$347

Mc Innis Northside Cottage

Elmira cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$146

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