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Berkshires House Rentals

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294 rentals in Berkshires.
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Berkshires: Romantic Cottage with spectacular view
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, Holiday Rental House
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Berkshire Farmhouse Vacation
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps, Holiday Rental House
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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, Holiday Rental House
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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, Holiday Rental House
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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, Holiday Rental House
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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, Holiday Rental House
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'Village View'- Elegant, Comfortable, Historic Home in Downtown Lenox
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps, Holiday Rental House
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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, Holiday Rental House
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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, Holiday Rental House
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Recently renovated 4 bedroom lakefront house in The Berkshires.
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Holiday Rental House
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Save time - get the best Berkshires rentals sent straight to your email!
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, Holiday Rental House
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Private rustic cottage with lake access
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Holiday Rental House
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Antique Farmhouse Totally Restored
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps, Holiday Rental House
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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, Holiday Rental House
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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, Holiday Rental House
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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, Holiday Rental House
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Berkshire Village Carriage House
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Holiday Rental House
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Charming Downtown Williamstown Cottage - 5 Min Walk to Campus
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Holiday Rental House
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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, Holiday Rental House
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Gorgeous Log Cabin in the Berkshires
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Holiday Rental House
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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, Holiday Rental House
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Craftsman Home In The Berkshire Forest
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Holiday Rental House
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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, Holiday Rental House
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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, Holiday Rental House
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Berkshires Private Large Lakefront Home On Robin Hood Lake
Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Holiday Rental House
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Stockbridge Cape Near Tanglewood & Kripalu - Heart Of The Berkshires!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Holiday Rental House
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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, Holiday Rental House
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RANKED #1 for 5 STAR REVIEWS covering 355 properties.
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Holiday Rental House
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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, Holiday Rental House
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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, Holiday Rental House
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Modern And Spacious Berkshires Retreat 5 bdrm 3 bath
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps, Holiday Rental House
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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, Holiday Rental House
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A-Frame in Sherwood Forest
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps, Holiday Rental House
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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, Holiday Rental House
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Charming historic cottage on scenic road to Mt. Greylock
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Holiday Rental House
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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, Holiday Rental House
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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, Holiday Rental House
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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, Holiday Rental House
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PRIVATE LAKEFRONT BEACH PROPERTY ON GOOSE POND near TANGLEWOOD
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps, Holiday Rental House
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Tranquil Lake House Getaway on Onota Lake
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Holiday Rental House
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A Grand Estate in Historic Stockbridge
Holiday Rental House
6 bedrooms
8 bathrooms
Sleeps 12
Match: Sleeps, Holiday Rental House
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Stockbridge! 1/2 mile from Red Lion inn. Great Barrington, Lenox, Lee close by.
Holiday Rental House
0 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, Holiday Rental House
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Charming Cottage, New Marlborough Village Green in the Berkshires
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Holiday Rental House
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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, Holiday Rental House
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Serene, Private Waterfront House --Perfect Summer Retreat!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Holiday Rental House
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Location Location! Comfort and Privacy So Close to Downtown
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Holiday Rental House
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General Williams Estate House Lenox/Stockbridge
Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps, Holiday Rental House
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2 bedroom Riverhouse in the Heart of the Berkshires
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Holiday Rental House
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Vacation in a Berkshire Farmhouse
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps, Holiday Rental House
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Gorgeous, Private, Family-Friendly, Organic Home with a Great Location in Lee
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Holiday Rental House
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