Old Mansions - Vacation Rentals in Ashley House

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From US $451

         

10.0 (41 Reviews)

House

Cheerful 3-bedroom cottage with woodstove

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Sheffield

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From US $231

         

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9.0 (1 Review)

House

Ashley Falls Home with Fire Pit Hike and Ski!

• Parking
• Accessibility
• Security/Safety

• Massachusetts
• Ashley Falls

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From US $363

         

10.0 (34 Reviews)

House

Little House in the Woods by Evergreen Home

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Sheffield

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From US $228

         

10.0 (15 Reviews)

Cottage

The Blue Elm - A Historic Berkshire Cottage

• Air Conditioner
• Parking
• TV

• Massachusetts
• Ashley Falls

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From US $194

         

10.0 (6 Reviews)

Apartment

Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts

• Air Conditioner
• Parking
• TV

• Massachusetts
• Sheffield

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From US $340

         

9.8 (21 Reviews)

House

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

• Air Conditioner
• Parking
• TV

• Massachusetts
• Ashley Falls

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New

From US $379

         

New

House

Beautiful Country Home in a great location

• Air Conditioner
• Parking
• TV

• Connecticut
• Taconic

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From US $253

         

9.6 (209 Reviews)

Cottage

Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views

• Air Conditioner
• Parking
• Pet Friendly

• Connecticut
• Taconic

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From US $270

         

9.0 (9 Reviews)

Cottage

Adirondack-Style/Cottage-Beautiful Lake & Mountain Views-Peaceful!

• Parking
• Pet Friendly
• TV

• Torrington
• Weatogue

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From US $700

         

10.0 (52 Reviews)

House

Gorgeous Sheffield Home in Heart of Berkshires

• Air Conditioner
• Parking
• Balcony/Terrace

• Massachusetts
• Sheffield

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From US $560

         

10.0 (15 Reviews)

House

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Sheffield

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From US $600

         

10.0 (5 Reviews)

House

6 BR 'CAMP' House on Twin Lakes - Epic Historic Property

• Air Conditioner
• Parking
• TV

• Torrington
• Weatogue

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From US $904

         

10.0 (4 Reviews)

House

BERKSHIRE MOUNTAIN LAKEFRONT LOG HOUSE FAMILY RETREAT

• TV
• Balcony/Terrace
• Security/Safety

• Connecticut
• Taconic

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From US $729

         

10.0 (3 Reviews)

House

Majestic Mountain Side Sheffield/Great Barrington/SKI

• Air Conditioner
• Parking
• TV

• Massachusetts
• Sheffield

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From US $259

         

10.0 (2 Reviews)

House

COME STAY AT THE SHEFFIELD CHALET!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Sheffield

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From US $475

         

10.0 (1 Review)

House

Modern Dairy Barn with Ample Natural Light and 2 Living Rooms!

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Sheffield

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From US $268

         

10.0 (1 Review)

House

Cabin w/fire pit, close to Ski Catamount, Butternut Ski, Great Barrington

• Air Conditioner
• Parking
• TV

• Massachusetts
• Ashley Falls

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From US $368

         

9.8 (7 Reviews)

House

Berkshires Walk to Brewery or Distillery with Peloton!

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Sheffield

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From US $716

         

9.6 (9 Reviews)

House

Luxurious Mountain Retreat - Private 40-Acre Family Haven

• Air Conditioner
• Parking
• TV

• Massachusetts
• Ashley Falls

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From US $362

         

9.6 (8 Reviews)

House

Cozy Log Cabin Retreat with Pool on 4 Acres

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Ashley Falls

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From US $465

         

8.0 (1 Review)

House

Bellhaven- Charming 4-bedroom house in Canaan, CT

• Parking
• Balcony/Terrace
• Security/Safety

• Torrington
• Canaan

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From US $678

         

New

House

BEAUTIFUL 4-SEASON RENTAL DIRECTLY ON TWIN LAKES

• Air Conditioner
• Pet Friendly
• Security/Safety

• Torrington
• Weatogue

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From US $542

         

New

Cottage

BEAUTIFUL TWIN LAKES RENTAL - Weekly or Seasonal Term Available

• Air Conditioner
• Parking
• TV

• Torrington
• Salisbury

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New

From US $235

         

New

House

Modern 3-bedroom home in the Berkshires!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Ashley Falls

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★ Pro Tip: Old Mansions makes it easy to compare the best listings on Old Mansions homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Old Mansions homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Ashley House.