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Berkshires Villas

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360 rentals in Berkshires.
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Unique People & Pet-Welcoming Country Haven

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Gartner House, a charming home in Lenox

Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Berkshire Farmhouse Vacation

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Berkshires: Romantic Cottage with spectacular view

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Close To Skiing! Beautiful +Family Friendly - W Tree House & Tennis Court

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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'Village View'- Elegant, Comfortable, Historic Home in Downtown Lenox

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Recently renovated 4 bedroom lakefront house in The Berkshires.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Room to Roam. Modern home with all amenities + sep. cabin on 10+ wooded acres.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spring Break Special! Stay two nights get one free for March and April!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Antique Farmhouse Totally Restored

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Nestled in the Berkshire Hills, The Manor ensures a joyous experience!

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful Berkshire Lakeside Home In The North Adams/Williamstown Area

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Berkshire Village Carriage House

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming Downtown Williamstown Cottage - 5 Min Walk to Campus

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Private rustic cottage with lake access

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Cozy family friendly home located in the Heart of the Berkshires.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Unique Condo, Quiet Neighborhood, Walk to Town.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Gorgeous Log Cabin in the Berkshires

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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COUPLE(S) PERFECT!! 2 BED/BATHS ; CENTRAL AC; FIREPL; ROMANTIC 'SKI LODGE' FEEL

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Craftsman Home In The Berkshire Forest

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Berkshires Private Large Lakefront Home On Robin Hood Lake

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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STOCKBRIDGE One Of The Finest Homes and Best Locations... Walk To Beach

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Stockbridge Cape Near Tanglewood & Kripalu - Heart Of The Berkshires!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Sfa Lodge Log Cabin 4 Bd - 2 Ba Nestled In The Woods 5 Mins From Berkshire East

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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RANKED #1 for 5 STAR REVIEWS covering 355 properties.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Downtown GB apartment walk to shops and restaurants

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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The perfect getaway: 5 bd, 3 ba, 3 acres. Booking for fall, winter & 2021!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Modern And Spacious Berkshires Retreat 5 bdrm 3 bath

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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A-Frame in Sherwood Forest

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Lovingly restored Victorian in Lee's Historic District **Spring:3rd nt 1/2 off

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Charming historic cottage on scenic road to Mt. Greylock

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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Elegant 19th Century New England 2BR Vacation Rental at Garfield House

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Heart of Lenox!! - renovated downtown apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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PRIVATE LAKEFRONT BEACH PROPERTY ON GOOSE POND near TANGLEWOOD

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
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4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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A Grand Estate in Historic Stockbridge

Holiday Rental House
6 bedrooms
8 bathrooms
Sleeps 12
Match: Sleeps
More info
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Stockbridge! 1/2 mile from Red Lion inn. Great Barrington, Lenox, Lee close by.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Woodland Cottage-NEW! Convenient, private, family friendly- see CLEANING DETAILS

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Tranquil Lake House Getaway on Onota Lake

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Warm your heart this holiday season in this cozy cottage next to downtown Lenox.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Charming Cottage, New Marlborough Village Green in the Berkshires

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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