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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Browse Select City Meadow Boardwalk Cottages

West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Kitchen features a stainless steel toaster oven, sink, and double oven with a range hood.

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

3.0 star property
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Cozy Litchfield House w/ Fenced-in Yard & Fire Pit
Relax on the outdoor patio with comfortable sofas, a table, and a chair, shaded by a stylish umbrella.

Cozy Litchfield House w/ Fenced-in Yard & Fire Pit

3.0 star property
Cozy Litchfield House w/ Fenced-in Yard & Fire Pit
Peaceful Goshen Cottage w/ Screened Porch & Views!
Enjoy cooking in this well-equipped kitchen with a central island, oven, and microwave, surrounded by cabinetry and a countertop.

Peaceful Goshen Cottage w/ Screened Porch & Views!

3.0 star property
Peaceful Goshen Cottage w/ Screened Porch & Views!
Serene Salisbury Rental Home on 26 Acres w/ Deck!
Kitchen features a sink, stove, and dishwasher, with a window above the sink and a rug on the floor.

Serene Salisbury Rental Home on 26 Acres w/ Deck!

3.0 star property
Serene Salisbury Rental Home on 26 Acres w/ Deck!
Whitney by Avantstay Private Berkshires Estate
Stunning two-story house with a central entrance and beautifully manicured lawns.

Whitney by Avantstay Private Berkshires Estate

3.0 star property
Whitney by Avantstay Private Berkshires Estate
Skiing & Hiking: Water-view Home in the Berkshires
House (3 Bedrooms) | Interior

Skiing & Hiking: Water-view Home in the Berkshires

3.0 star property
Skiing & Hiking: Water-view Home in the Berkshires
Ashley Falls Home w/ Fire Pit: Hike & Ski!
Enjoy cooking in this well-equipped kitchen with a large island, dishwasher, sink, and stove.

Ashley Falls Home w/ Fire Pit: Hike & Ski!

3.0 star property
8.0 out of 10, Very good, (1)
"Nice location. Spacious with ample bedrooms. Would have been nice if there was a second bathroom on the second floor. It might be time to freshen the furniture in the sitting area."
Ashley Falls Home w/ Fire Pit: Hike & Ski!
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Cottage (1 Bedroom) | Interior

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

3.0 star property
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Lakefront Otis Home w/ Stunning Views & Boats!
House (2 Bedrooms) | Interior

Lakefront Otis Home w/ Stunning Views & Boats!

3.0 star property
Lakefront Otis Home w/ Stunning Views & Boats!
Spacious Tolland Home w/ Deck + Screened Porch!
Interior

Spacious Tolland Home w/ Deck + Screened Porch!

3.0 star property
Spacious Tolland Home w/ Deck + Screened Porch!
7 Mi to Catamount & Butternut: Mountain-view Home
House (3 Bedrooms) | Interior

7 Mi to Catamount & Butternut: Mountain-view Home

3.0 star property
7 Mi to Catamount & Butternut: Mountain-view Home
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Interior

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

3.0 star property
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
East Otis Vacation Rental w/ Private Deck & Bbq!
Cottage (0 Bedroom) | Interior

East Otis Vacation Rental w/ Private Deck & Bbq!

3.0 star property
East Otis Vacation Rental w/ Private Deck & Bbq!
Renovated Lakefront House w/ Dock: Pets Welcome!
House (4 Bedrooms) | Interior

Renovated Lakefront House w/ Dock: Pets Welcome!

3.0 star property
Renovated Lakefront House w/ Dock: Pets Welcome!
Modern Sharon Farmhouse: Spacious, Patio, Views
Relax in a spacious room with a high ceiling, large windows, and a cozy seating area.

Modern Sharon Farmhouse: Spacious, Patio, Views

3.0 star property
Modern Sharon Farmhouse: Spacious, Patio, Views
Cozy Great Barrington Home ~ 1 Mi to Ski Resort!
House (4 Bedrooms) | Interior

Cozy Great Barrington Home ~ 1 Mi to Ski Resort!

3.0 star property
Cozy Great Barrington Home ~ 1 Mi to Ski Resort!
Berkshires Cabin 2 Mi to Appalachian Trail!
Enjoy a warm and inviting space with a large window offering a forest view, a round table, and a comfortable seating area.

Berkshires Cabin 2 Mi to Appalachian Trail!

3.0 star property
Berkshires Cabin 2 Mi to Appalachian Trail!
Cozy Monterey Home w/ Porch: Walk to Lake Garfield
Enjoy cooking in this kitchen with a central island, white appliances, and blue cabinetry, featuring a window with a view.

Cozy Monterey Home w/ Porch: Walk to Lake Garfield

3.0 star property
Cozy Monterey Home w/ Porch: Walk to Lake Garfield
Walk to Downtown: Pet-friendly Millerton Home!
Relax in a serene garden setting with a pergola, surrounded by lush greenery and comfortable outdoor seating.

Walk to Downtown: Pet-friendly Millerton Home!

3.0 star property
Walk to Downtown: Pet-friendly Millerton Home!
Monterey Home w/ Hot Tub, Pool & Game Room!
House (6 Bedrooms) | Interior

Monterey Home w/ Hot Tub, Pool & Game Room!

3.0 star property
Monterey Home w/ Hot Tub, Pool & Game Room!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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