Top Winter Vacations - Vacation Rentals in Glendale Falls

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From US $174

         

9.6 (231 Reviews)

Cabin

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

• Air Conditioner
• Parking
• Pet Friendly

• Becket
• Sherwood Forest

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From US $533

         

9.3 (3 Reviews)

Ski Chalet

Thrill & Chill Ski & Sauna In Winter Wonderland

• Air Conditioner
• Parking
• Security/Safety

• Massachusetts
• Otis

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From US $137

         

6.8 (60 Reviews)

Hotel

Becket Motel

• Air Conditioner
• Parking
• TV

• Massachusetts
• Becket

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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 $1,105

         

New

House

Tranquil Retreat 6-BRs Total in the Berkshires

• Springfield
• Blandford

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From US $572

         

10.0 (38 Reviews)

House

Berkshires Home on 11 Acres w/Pond & 2 Fire Pits!

• Parking
• TV
• Balcony/Terrace

• Massachusetts
• Becket

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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 $291

         

9.6 (25 Reviews)

House

Becket Contemporary Cottage in the Woods Overlooking a Private Spring Fed Pond

• Parking
• Balcony/Terrace
• Security/Safety

• Massachusetts
• Becket

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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 $315

         

10.0 (64 Reviews)

House

Spacious waterfront Berkshire home family private get-away

• Parking
• TV
• View

• Massachusetts
• Otis

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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 $452

         

10.0 (18 Reviews)

House

Berkshires Lakefront Retreatn

• Air Conditioner
• Parking
• Pet Friendly

• Becket
• Sherwood Forest

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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 $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 $258

         

10.0 (5 Reviews)

House

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

• Air Conditioner
• Parking
• Pet Friendly

• Becket
• Sherwood Forest

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From US $610

         

10.0 (4 Reviews)

House

Lakeside 5-BR Home in Idyllic Berkshires

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Becket

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From US $443

         

10.0 (3 Reviews)

House

Serene 3-BR Berkshires Log Cabin

• Air Conditioner
• Parking
• Pet Friendly

• Springfield
• Blandford

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From US $323

         

10.0 (3 Reviews)

House

Home in the Woods

• Security/Safety
• Sports/Activities
• Bedding/Linens

• Springfield
• Westfield

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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 $438

         

10.0 (2 Reviews)

House

Lakefront Jewel By: Evergreen Home

• Air Conditioner
• Parking
• TV

• Becket
• Sherwood Forest

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★ Pro Tip: Topwintervacations makes it easy to compare the best listings on Topwintervacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Topwintervacations 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 Glendale Falls.