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Berkshires, MA Holiday Rentals, Homes and Villas
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Berkshires, MA Holiday Rentals, Homes and Villas
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360 rentals
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Unique People & Pet-Welcoming Country Haven
180 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Gartner House, a charming home in Lenox
37 reviews
Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 7
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Berkshire Farmhouse Vacation
44 reviews
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 15
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Berkshires: Romantic Cottage with spectacular view
24 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
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4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
114 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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Close To Skiing! Beautiful +Family Friendly - W Tree House & Tennis Court
101 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
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'Village View'- Elegant, Comfortable, Historic Home in Downtown Lenox
91 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
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Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
75 reviews
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
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Recently renovated 4 bedroom lakefront house in The Berkshires.
61 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires
80 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Room to Roam. Modern home with all amenities + sep. cabin on 10+ wooded acres.
60 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Spring Break Special! Stay two nights get one free for March and April!
59 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
65 reviews
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
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Antique Farmhouse Totally Restored
71 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 16
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Nestled in the Berkshire Hills, The Manor ensures a joyous experience!
77 reviews
Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 14
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Beautiful Berkshire Lakeside Home In The North Adams/Williamstown Area
64 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Berkshire Village Carriage House
141 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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Charming Downtown Williamstown Cottage - 5 Min Walk to Campus
66 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
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Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake
65 reviews
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
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Private rustic cottage with lake access
59 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Cozy family friendly home located in the Heart of the Berkshires.
53 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Unique Condo, Quiet Neighborhood, Walk to Town.
91 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Gorgeous Log Cabin in the Berkshires
57 reviews
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
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COUPLE(S) PERFECT!! 2 BED/BATHS ; CENTRAL AC; FIREPL; ROMANTIC 'SKI LODGE' FEEL
71 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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Craftsman Home In The Berkshire Forest
70 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Berkshires Private Large Lakefront Home On Robin Hood Lake
61 reviews
Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
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STOCKBRIDGE One Of The Finest Homes and Best Locations... Walk To Beach
61 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
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Stockbridge Cape Near Tanglewood & Kripalu - Heart Of The Berkshires!
50 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
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Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!
70 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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Sfa Lodge Log Cabin 4 Bd - 2 Ba Nestled In The Woods 5 Mins From Berkshire East
49 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
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Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut!
58 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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RANKED #1 for 5 STAR REVIEWS covering 355 properties.
43 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Downtown GB apartment walk to shops and restaurants
57 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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The perfect getaway: 5 bd, 3 ba, 3 acres. Booking for fall, winter & 2021!
87 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
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Modern And Spacious Berkshires Retreat 5 bdrm 3 bath
41 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
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A-Frame in Sherwood Forest
115 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
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Lovingly restored Victorian in Lee's Historic District **Spring:3rd nt 1/2 off
101 reviews
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
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Charming historic cottage on scenic road to Mt. Greylock
70 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
56 reviews
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
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Elegant 19th Century New England 2BR Vacation Rental at Garfield House
69 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything
64 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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Heart of Lenox!! - renovated downtown apartment
51 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
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PRIVATE LAKEFRONT BEACH PROPERTY ON GOOSE POND near TANGLEWOOD
89 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
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4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town.
54 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
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A Grand Estate in Historic Stockbridge
58 reviews
Holiday Rental House
6 bedrooms
8 bathrooms
Sleeps 12
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Stockbridge! 1/2 mile from Red Lion inn. Great Barrington, Lenox, Lee close by.
53 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
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Woodland Cottage-NEW! Convenient, private, family friendly- see CLEANING DETAILS
40 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Tranquil Lake House Getaway on Onota Lake
43 reviews
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
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Warm your heart this holiday season in this cozy cottage next to downtown Lenox.
39 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
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Charming Cottage, New Marlborough Village Green in the Berkshires
39 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Frequently Asked Questions about Berkshires
Do any holiday rentals in Berkshires have a pool?
Yes, here are some popular holiday rentals in Berkshires that have a pool:\n
\n
Berkshires: Romantic Cottage with spectacular view
\n
Bentley/Wyndham Hancock Mass at Jiminy Peak
\n
LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE
\n
\n
See all holiday rentals with a pool in Berkshires on Tripadvisor
Do any holiday rentals in Berkshires have internet access?
Yes, here are some popular holiday rentals in Berkshires that have internet access:\n
\n
Berkshires Spacious Comfortable Charming Farmhouse
\n
Berkshires: Romantic Cottage with spectacular view
\n
Lakefront Berkshires Ski/Summer House, Great Views
\n
\n
See all holiday rentals in Berkshires on Tripadvisor
What are the best pet friendly rentals in Berkshires?
The best pet friendly rentals in Berkshires are:\n
\n
Lakefront Berkshires Ski/Summer House, Great Views
\n
Unique People & Pet-Welcoming Country Haven
\n
Eco-friendly cozy home in Gt. Barrington
\n
\n
See all pet friendly holiday rentals in Berkshires on Tripadvisor
What are some great rentals in Berkshires that are kid friendly?
Some of the most popular kid friendly rentals in Berkshires are:\n
\n
Berkshires Spacious Comfortable Charming Farmhouse
\n
Lakefront Berkshires Ski/Summer House, Great Views
\n
Gartner House, a charming home in Lenox
\n
\n
See all kid friendly holiday rentals in Berkshires on Tripadvisor