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Smoking Allowed Holiday Rentals in Berkshires

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246 rentals in Berkshires.
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'Too Good' With 11 Private Acres. Contact us for Monthly Specials!
4 bedrooms
4 bathrooms
Sleeps 12
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Fox Hollow Laurel Lake Ranch
4 bedrooms
5 bathrooms
Sleeps 11
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3 other travellers have booked this property
'The Mill River Cabin’ w/ Fireplace & River View!
2 bedrooms
1 bathroom
Sleeps 5
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Tranquil 3BR Stockbridge House w/Private Deck
3 bedrooms
2 bathrooms
Sleeps 6
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3 other travellers have booked this property
Unique People & Pet-Welcoming Country Haven
1 bedroom
1 bathroom
Sleeps 4
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24 other travellers have booked this property
Berkshire Farmhouse Vacation
5 bedrooms
2 bathrooms
Sleeps 15
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18 other travellers have booked this property
Berkshires: Romantic Cottage with spectacular view
1 bedroom
1 bathroom
Sleeps 3
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17 other travellers have booked this property
Gartner House, a charming home in Lenox
4 bedrooms
1 bathroom
Sleeps 7
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40 other travellers have booked this property
Whitman Woods - A Berkshire Vacation
4 bedrooms
2 bathrooms
Sleeps 8
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2 other travellers have booked this property
Close To Skiing! Beautiful +Family Friendly - W Tree House & Tennis Court
4 bedrooms
3 bathrooms
Sleeps 9
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Elterwater--Your beautiful, stress-free lakefront getaway in the Berkshires.
3 bedrooms
2 bathrooms
Sleeps 4
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Antique Farmhouse Totally Restored
4 bedrooms
3 bathrooms
Sleeps 16
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Berkshire Village Carriage House
1 bedroom
1 bathroom
Sleeps 2
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New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires
2 bedrooms
2 bathrooms
Sleeps 6
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Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
5 bedrooms
4 bathrooms
Sleeps 14
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Beautiful 1920's Colonial 20 Minutes from Tanglewood
4 bedrooms
2 bathrooms
Sleeps 8
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Charming Downtown Williamstown Cottage - 5 Min Walk to Campus
3 bedrooms
2 bathrooms
Sleeps 7
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Spring Break Special! Stay two nights get one free for March and April!
3 bedrooms
3 bathrooms
Sleeps 8
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COUPLE(S) PERFECT!! 2 BED/BATHS ; CENTRAL AC; FIREPL; ROMANTIC 'SKI LODGE' FEEL
2 bedrooms
2 bathrooms
Sleeps 6
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Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
5 bedrooms
6 bathrooms
Sleeps 15
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Room to Roam. Modern home with all amenities + sep. cabin on 10+ wooded acres.
4 bedrooms
3 bathrooms
Sleeps 8
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Recently renovated 4 bedroom lakefront house in The Berkshires.
4 bedrooms
3 bathrooms
Sleeps 8
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Great Barrington Retreat ! Booking for the Fall & Winter Now!
3 bedrooms
3 bathrooms
Sleeps 7
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Serene Lakefront Cottage
2 bedrooms
2 bathrooms
Sleeps 6
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1 other traveller has booked this property
Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake
5 bedrooms
4 bathrooms
Sleeps 14
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A-Frame in Sherwood Forest
1 bedroom
1 bathroom
Sleeps 5
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Private rustic cottage with lake access
2 bedrooms
1 bathroom
Sleeps 6
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Lovingly restored Victorian in Lee's Historic District **Spring:3rd nt 1/2 off
5 bedrooms
5 bathrooms
Sleeps 10
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PRIVATE LAKEFRONT BEACH PROPERTY ON GOOSE POND near TANGLEWOOD
1 bedroom
1 bathroom
Sleeps 5
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A Grand Estate in Historic Stockbridge
6 bedrooms
8 bathrooms
Sleeps 12
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RANKED #1 for 5 STAR REVIEWS covering 355 properties.
3 bedrooms
3 bathrooms
Sleeps 6
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Elegant 19th Century New England 2BR Vacation Rental at Garfield House
2 bedrooms
2 bathrooms
Sleeps 6
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The perfect getaway: 5 bd, 3 ba, 3 acres. Booking for fall, winter & 2021!
5 bedrooms
3 bathrooms
Sleeps 12
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Vacation in a Berkshire Farmhouse
5 bedrooms
2 bathrooms
Sleeps 15
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A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything
2 bedrooms
1 bathroom
Sleeps 5
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Gorgeous Log Cabin in the Berkshires
3 bedrooms
4 bathrooms
Sleeps 9
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General Williams Estate House Lenox/Stockbridge
6 bedrooms
6 bathrooms
Sleeps 16
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Retreat in the Woods
2 bedrooms
1 bathroom
Sleeps 4
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25 other travellers have booked this property
Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.
5 bedrooms
3 bathrooms
Sleeps 12
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4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town.
4 bedrooms
2 bathrooms
Sleeps 10
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Beautiful Waterfront home with deep water dock on Onota Lake
3 bedrooms
2 bathrooms
Sleeps 10
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Tranquil Lake House Getaway on Onota Lake
5 bedrooms
2 bathrooms
Sleeps 11
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Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special
1 bedroom
1 bathroom
Sleeps 4
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2 bedroom Riverhouse in the Heart of the Berkshires
2 bedrooms
1 bathroom
Sleeps 4
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A Small Oasis in the Heart of Lenox
1 bedroom
1 bathroom
Sleeps 3
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Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
8 bedrooms
3 bathrooms
Sleeps 21
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Warm your heart this holiday season in this cozy cottage next to downtown Lenox.
3 bedrooms
2 bathrooms
Sleeps 5
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Modern Secluded Home In Wooded Setting
3 bedrooms
3 bathrooms
Sleeps 8
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COZY LOG HOME* fireplace, skiing,fall foliage Hiking, Berkshires*
2 bedrooms
1 bathroom
Sleeps 8
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Peace And Quiet On The Lake
2 bedrooms
2 bathrooms
Sleeps 6
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