Chester Rentals

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61 Houses

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".

Match: Cot available Climbing frame

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Price per night from

$270

Slopeside Attitash near StoryLand, White Mountains

Glen condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Cot available Climbing frame

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Price per night from

$229

The Jethro Peckham House

Middletown house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 13

Match: Cot available Climbing frame

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Price per night from

$402

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Sweet Farmhouse with Ocean Views

Rockland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$171

Comfort Home

Boston apartment

  • 4 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$315

Pleasant Forest Shores cottages #3 : So. Chatham

South Chatham cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Cot available, Climbing frame

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Price per night from

$115

Pleasant Forest Shores cottages #2 : So. Chatham

South Chatham cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Cot 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: Cot available, Climbing frame

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Price per night from

$75

"SEAGULLS NEST"

East Dennis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$190

Fabulous 4 BR, Terrific View, Steps to Bay

Brewster house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$687

White Mountain Getaway!

Gorham house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$285

Ocean View Cape on 14 Private Acres

Searsport house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Cot 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: Cot available, Climbing frame

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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: Cot available, Climbing frame

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Price per night from

$916

1 of 2 match: Climbing frame, Cot available

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Price per night from

$615

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: Cot available, Climbing frame

1 of 2 filters match

Price per night from

$631

“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!!!

1 of 2 match: Cot available, Climbing frame

1 of 2 filters match

Price per night from

$396

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

Falmouth apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Cot available, Climbing frame

1 of 2 filters match

Price per night from

$172

4 Season vacation Home Rentals, Van Buren, Maine

Van Buren house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Cot available, Climbing frame

1 of 2 filters match

Price per night from

$206

1 of 2 match: Cot available, Climbing frame

1 of 2 filters match

Price per night from

$396

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

Grand Etang house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Cot available, Climbing frame

1 of 2 filters match

Price per night from

$315

White Mountain Getaway

Lincoln house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Cot available, Climbing frame

1 of 2 filters match

Price per night from

$258

Ultimate Vacation Home

South Yarmouth hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 3 hours 19 minutes

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$114

Taffy Lake Retreat

Nackawic log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$172

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$1,090

Rustic, Romantic, & Spacious Log Chalet BEST PLACE for Family, & Friends

Cape Neddick chalet

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$878

1 of 2 match: Cot available, Climbing frame

1 of 2 filters match

Price per night from

$201

Minutes from Popham Beach - Cozy Maine Coast Cottage

Phippsburg cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$259

2 min walk to the beach - 30 Union Wharf#3

Dennis Port condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$287

"The Bayside Colonial" with guest area

East Dennis house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 15

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$631

Large 3BR, Sleeps 13

Providence apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 13

Responds fast! avg. 3 hours 10 minutes

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$230

Experience Your Jorney with Us

Mexico house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$214

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$746

Very Private 4 bedroom home on 4 Lake Wassookeag

Dexter house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$401

The Harborfront, Beverly/Salem, Boston North Shore

Beverly apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$515

Spacious Rustic Cape-Fenced Yard, Large Group, 7 mins Craigville Beach, Pet

Centerville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$241

Cape Cod 2 BD cottage (June $1200wk) private beach in W. Hyannisport

West Hyannisport house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Our family enjoyed a memorable reunion week in this beach neighb” We spent the week walking to aves, swimming at Squaw Island, golfing, tennis, and dining out at some great restaurants. This beach house has central air, a new gas grill and outdoor shower. All musts for our vacation rental requests. Nice quiet area with great Cape Cod experiences. The house is clean and comfortable. Great master bed. Near boats to the vineyard and Nantucket. We plan on another family reunion vacation at this beach house again this summer.

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$264

Ocean Front House,Breath-taking View

Plymouth house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, Cot available

1 of 2 filters match

Price per night from

$201

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