Old Mansions - Vacation Rentals in Chesterfield Gorge

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From US $258

         

9.6 (133 Reviews)

House

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

• Air Conditioner
• Parking
• Pet Friendly

• Charlemont
• Hawley

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From US $456

         

|

9.5 (2 Reviews)

House

Massachusetts Vacation Rental with Deck and Grill

• Parking
• Pet Friendly
• View

• Massachusetts
• Windsor

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From US $276

         

9.6 (40 Reviews)

House

3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest

• Air Conditioner
• Parking
• Balcony/Terrace

• Massachusetts
• Cummington

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From US $210

         

|

9.0 (30 Reviews)

Cabin

The Retreat At Norwich Lake

• Air Conditioner
• Parking
• Balcony/Terrace

• Springfield
• Norwich Lake

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From US $169

         

10.0 (211 Reviews)

Cottage

The Clearing - Quiet - Close To Nature

• Parking
• Pool
• View

• Massachusetts
• Cummington

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From US $336

         

|

9.0 (2 Reviews)

House

Pet-Friendly Cabin with Fire Pit, BBQ and Great Deck!

• Parking
• Pet Friendly
• View

• Springfield
• Williamsburg

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From US $239

         

10.0 (61 Reviews)

House

Berkshire Lake access

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Hinsdale

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From US $436

         

10.0 (22 Reviews)

House

Gorgeous Lake Ashmere Home with Private Hot Tub & Lake Views, Screened Porch

• Parking
• TV
• Balcony/Terrace

• Massachusetts
• Hinsdale

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From US $457

         

10.0 (19 Reviews)

House

Beautiful Timber Frame Home in the Berkshires /Available for Long Term

• Air Conditioner
• Parking
• TV

• Massachusetts
• Washington

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From US $503

         

10.0 (12 Reviews)

House

Hill Ross Guest Suite on Historic Homestead

• Air Conditioner
• Parking
• TV

• Springfield
• Florence

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From US $723

         

10.0 (11 Reviews)

Cabin

Lakefront Westhampton Cabin w/Beach + Kayaks!

• Parking
• Pet Friendly
• TV

• Massachusetts
• Westhampton

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From US $1,192

         

10.0 (8 Reviews)

Villa

Cozy Valley View Post & Beam Villa!

• Air Conditioner
• Parking
• TV

• South Deerfield
• Whately

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From US $798

         

10.0 (5 Reviews)

House

1840's Whaling Captain's Farm Estate, 6-10 guests

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Middlefield

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From US $336

         

10.0 (5 Reviews)

House

Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.

• Parking
• TV
• View

• Massachusetts
• Hinsdale

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From US $481

         

10.0 (2 Reviews)

House

Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Peru

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From US $262

         

10.0 (2 Reviews)

House

Experience Three Sisters Sanctuary in Goshen, MA

• Security/Safety
• Bedding/Linens
• Fireplace/Heating

• Massachusetts
• Goshen

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From US $157

         

10.0 (2 Reviews)

Apartment

Charming 1-BR Apartment in Conway, WiFi/AC

• Air Conditioner
• Parking
• TV

• Massachusetts
• Conway

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From US $592

         

10.0 (1 Review)

House

Hill Ross Stables Historic Homestead

• Air Conditioner
• Parking
• TV

• Springfield
• Florence

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From US $260

         

10.0 (1 Review)

Cottage

Private Lake Cottage on 3 acres w/350 sq. ft. deckn

• Air Conditioner
• Balcony/Terrace
• Security/Safety

• Massachusetts
• Becket

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From US $236

         

10.0 (1 Review)

House

Cabin Style Rustic Getaway, with mini-splits

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Springfield
• Florence

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From US $177

         

10.0 (1 Review)

Apartment

Cozy Berkshires Vacation Rental Near Hiking!

• Air Conditioner
• Parking
• Pet Friendly

• Springfield
• Chester

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From US $281

         

9.8 (80 Reviews)

House

Bershire Home Rental: Enjoy Berkshire Fall Foliage

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Washington

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From US $242

         

9.8 (59 Reviews)

Cabin

Ashmere Lake Log Cabin with privacy/2 Bedrooms/3 night minimum

• Parking
• TV
• View

• Massachusetts
• Hinsdale

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From US $228

         

9.8 (42 Reviews)

House

Cheerful 1 bedroom

• Air Conditioner
• Parking
• Pet Friendly

• Springfield
• Florence

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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 Chesterfield Gorge.