Adams, MA
Cozy Family Friendly Home In The Heart Of The Berkshires
2 Bedrooms, 1.5 Baths, Sleeps 6
Adams, MA
Northern Berkshires
Pet Friendly
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Berkshires Gem – Walk To Town And Trails!
4 Bedrooms, 2 Baths, Sleeps 8
Adams, MA
Northern Berkshires
Pet Friendly
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Alford, MA
NEW: Gorgeous, Unique, Craftsman Cottage
2 Bedrooms, 2 Baths, Sleeps 4
Alford, MA
Southern Berkshires
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Beautiful Berkshire Farm House On 160+ Acres
7 Bedrooms, 4.5 Baths, Sleeps 16
Alford, MA
Southern Berkshires
Pet Friendly
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Berkshire Chalet Getaway!
3 Bedrooms, 2 Baths, Sleeps 6
Alford, MA
Southern Berkshires
Pet Friendly
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Becket, MA
A-Frame in Sherwood Forest
1 Bedrooms, 1 Bath, Sleeps 5
Becket, MA
Central Berkshires
Pet Friendly
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Peace And Quiet At Sea
2 Bedrooms, 2 Bath, Sleeps 6
Becket, MA
Central Berkshires
Pet Friendly
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Pristine Home In Becket Woods
3 Bedrooms, 2 Bath, Sleeps 6
Becket, MA
Central Berkshires
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Charlemont, MA
Hidden Gem At Base Of Ski Mountain
2 Bedrooms, 1 Bath, Sleeps 6
Charlemont, MA
Northern Berkshires
Pet Friendly
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StrautmanHaus – All-Season Chalet At Berkshire East
4 Bedrooms, 2 Bath, Sleeps 10
Charlemont, MA
Northern Berkshires
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Charming 2022 Renovated 1867 Farmhouse
4 Bedrooms, 2 Bath, Sleeps 8
Charlemont, MA
NorthernBerkshires
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Cheshire, MA
Ski At 19th C. Renovated Barn In The Berkshires
3 Bedrooms, 2 Bath, Sleeps 10
Cheshire, MA
Northern Berkshires
Pet Friendly
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Luxury Private Lakefront In The Berkshires
4 Bedrooms, 2.5 Bath, Sleeps 8
Cheshire, MA
Northern Berkshires
Pet Friendly
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Egremont, MA
Comfortable, Newly Renovated 2BR
Apartment
2 Bedrooms, 2 Bath, Sleeps 4
Egremont, MA
Southern Berkshires
No Pet
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Charming Cottage w/ Sauna
2 Bedrooms, 1.5 Bath, Sleeps 4
Egremont, MA
Southern Berkshires
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Private Berkshires Retreat
4 Bedrooms, 2.5 Bath, Sleeps 8
Egremont, MA
Southern Berkshires
Pet Friendly
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Great Barrington, MA
Ranch On 5+ Acres & 0.7 Mi To GB Main St.
3 Bedrooms, 2 Bath, Sleeps 10
Great Barrington, MA
Southern Berkshires
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14 Min To Butternut, Great Barrington Guest Cottage
3 Bedrooms, 1.5 Bath, Sleeps 5
Great Barrington, MA
Southern Berkshires
Pet Friendly
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Family Home w/Big Yard On The Hill
4 Bedrooms, 2Bath, Sleeps 10
Great Barrington, MA
Southern Berkshires
Pet Friendly
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New Remodeled 3BR Country Castle
3 Bedrooms, 3 Bath, Sleeps 8
Great Barrington, MA
Southern Berkshires
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Great Barrington Getaway: Lake Access
3 Bedrooms, 2.5 Bath, Sleeps 6Great Barrington, MA
Southern Berkshires
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Lakefront Berkshires Retreat w/Deck, Dock & Boat!
4 Bedrooms, 2 Bath, Sleeps 10
Great Barrington, MA
Southern Berkshires
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Modern Victorian, Walk To Town
4 Bedrooms, 3 Bath, Sleeps 8
Great Barrington, MA
Southern Berkshires
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Chic Updated Downtown Great Barrington
3 Bedrooms, 2.5 Bath, Sleeps 14
Great Barrington, MA
Southern Berkshires
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Romantic Berkshires Cottage – Stunning Views, Pool
1 Bedrooms, 1 Bath, Sleeps 3
Great Barrington, MA
Southern Berkshires
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Hancock, MA
Mountain View Suite
1 Bedrooms, 1 Bath, Sleeps 4
Hancock, MA
Northern Berkshires
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1st Floor Mountain View Suite
1 Bedrooms, 1 Bath, Sleeps 4
Hancock, MA
Northern Berkshires
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Quiet & Private, Small Horse Farm
1 Bedrooms, 1 Bath, Sleeps 4
Hancock, MA
Northern Berkshires
Pet Friendly
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Hawley, MA
Country Home w/Babbling Brook And Pond View
3 Bedrooms, 1 Bath, Sleeps 8
Northern, MA
Central Berkshires
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Country Home w/Babbling Brook
3 Bedrooms, 1.5 Bath, Sleeps 8
Hawley, MA
Northern Berkshires
Pet Friendly
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Stunning Mountain Top Lodge
7 Bedrooms, 3.5 Bath, Sleeps 10
Hawley, MA
Northern Berkshires
Pet Friendly
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Hinsdale, MA
Ashmere Lake Log Cabin w/Privacy
2 Bedrooms, 1 Bath, Sleeps 4
Hinsdale, MA
Central Berkshires
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Quiet Lake House w/Beautiful Water Views
2 Bedrooms, 2 Bath, Sleeps 8
Hinsdale, MA
Central Berkshires
Pet Friendly
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Private Lake Front Beach In The Berkshires
3 Bedrooms, 4 Bath, Sleeps 8
Hinsdale, MA
Central Berkshires
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Lanesborough, MA
Berkshire Village Carriage House
1 Bedrooms, 1 Bath, Sleeps 2
Lanesborough, MA
Central Berkshires
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Charming Historic Cottage On Scenic Road To Mt. Greylock
2 Bedrooms, 1 Bath, Sleeps 6
Lanesborough, MA
Central Berkshires
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NEW! Spacious Mtn Home, 5 Miles To Jiminy Peak!
3 Bedrooms, 2 Bath, Sleeps 6
Lanesborough, MA
Central Berkshires
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A Beautiful Log Cabin In The Woods
2 Bedrooms, 1 Bath, Sleeps 5
Lanesborough, MA
Central Berkshires
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Berkshire Pontoosuc Lake Beauty
5 Bedrooms, 3.5 Bath, Sleeps 14
Lanesborough, MA
Central Berkshires
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Wildlife Cottage By The Lake
3 Bedrooms, 1.5 Bath, Sleeps 6
Lanesborough, MA
Central Berkshires
Pet Friendly
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Berkshire Lake House Vacation Rental
4 Bedrooms, 2 Bath, Sleeps 6
Lanesborough, MA
Central Berkshires
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6BR Berkshire Bliss, 38 Acres Of Nature
6 Bedrooms, 4.5 Bath, Sleeps 14
Lanesborough, MA
Central Berkshires
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Lee, MA
Gorgeous, Private, Family-Friendly, Organic Home
3 Bedrooms, 2 Bath, Sleeps 6
Lee, MA
Southern Berkshires
Pet Friendly
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Spacious Berkshire Home – Year Round Retreat
5 Bedrooms, 2.5 Bath, Sleeps 12
Lee, MA
Southern Berkshires
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The Playhouse: 7,000 Sq. Ft. Of Berkshires
6 Bedrooms, 5 Bath, Sleeps 20
Lee, MA
Southern Berkshires
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Lenox, MA
Heart Of Lenox, Walk To Town, Cozy Cottage!
2 Bedrooms, 1 Bath, Sleeps 4
Lenox, MA
Central Berkshires
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Vacation Or Work Away From Home!
2 Bedrooms, 1.5 Bath, Sleeps 5
Lenox, MA
Central Berkshires
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5 Star Casual Elegance For 5 Star Guests
3 Bedrooms, 2.5 Bath, Sleeps 6
Lenox, MA
Central Berkshires
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Large Lenox Home w/Pool; Ideal Berkshire Location!
4 Bedrooms, 2.5 Bath, Sleeps 8
Lenox, MA
Central Berkshires
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Beautiful Lenox Home, 3 Mi To Shakespeare & Co!
3 Bedrooms, 2 Bath, Sleeps 6
Lenox, MA
Central Berkshires
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Private Guest House In Dtwn Lenox, Walk To Dining!
3 Bedrooms, 2.5 Bath, Sleeps 6
Lenox, MA
Central Berkshires
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Private Access To Laurel Lake – Winter Sports Fun!
4 Bedrooms, 2 Bath, Sleeps 10
Lenox, MA
Central Berkshires
Pet Friendly
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Lovely Home In Heart Of Lenox 
2 Bedrooms, 2 Bath, Sleeps 4
Lenox, MA
Central Berkshires
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Middlefield, MA
Sunny, Stylish Berkshire Mountain Retreat
4 Bedrooms, 2 Bath, Sleeps 8
Middlefield, MA
Central Berkshires
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Monterey, MA
Cozy Monterey Family Chalet
2 Bedrooms, 1 Bath, Sleeps 6
Monterey, MA
Southern Berkshires
Pet Friendly
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Country Cottage For 2 On Private Setting
1 Bedrooms, 1 Bath, Sleeps 2
Southern, MA
Central Berkshires
Pet Friendly
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Stunning Lakefront Berkshire Rental, Lake Garfield
5 Bedrooms, 2 Bath, Sleeps 8
Southern, MA
Central Berkshires
Pet Friendly
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New Marlborough, MA
Private Rustic Cottage w/Lake Access
2 Bedrooms, 1 Bath, Sleeps 6
New Marlborough, MA
Southern Berkshires
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The Mill River Cabin w/ Fireplace & River View!
2 Bedrooms, 1 Bath, Sleeps 5
New Marlborough, MA
Southern Berkshires
Pet Friendly
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Perfect Vacation Get Away
1 Bedrooms, 1 Bath, Sleeps 4
New Marlborough, MA
Southern Berkshires
Pet Friendly
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North Adams, MA
Lovley, Romantic, Fun, En Suite
1 Bedrooms, 1 Bath, Sleeps 4
North Adams, MA
Northern Berkshires
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Beautiful Berkshire Lakeside Home
3 Bedrooms, 1.5 Bath, Sleeps 8
North Adams, MA
Northern Berkshires
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Art House! Spacious Getaway By Mass Moca
6 Bedrooms, 2 Bath, Sleeps 10
North Adams, MA
Northern Berkshires
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Otis, MA
The Meadows House
1 Bedrooms, 1 Bath, Sleeps 7
Otis, MA
Southern Berkshires
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4BR/3BA Lakefront/Ski House In Berkshires
4 Bedrooms, 3 Bath, Sleeps 10
Otis, MA
Southern Berkshires
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NEW! Berkshires Cabin 2 Mi To Appalachian Trail!
3 Bedrooms, 2 Bath, Sleeps 7
Otis, MA
Southern Berkshires
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Pittsfield, MA
Lovely Family Retreat In The ♥️ Of The Berkshires!
4 Bedrooms, 2 Bath, Sleeps 7
Pittsfield, MA
Central Berkshires
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Charming Historic Home
5 Bedrooms, 3.5 Bath, Sleeps 10
Pittsfield, MA
Central Berkshires
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Dancing Horse Lodge
3 Bedrooms, 1 Bath, Sleeps 6
Pittsfield, MA
Central Berkshires
Pet Friendly
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Chic Pittsfield Home With A View!
3 Bedrooms, 1.5 Bath, Sleeps 6
Pittsfield, MA
Central Berkshires
Pet Friendly
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Honeysuckle Rose Cottage
2 Bedrooms, 1 Bath, Sleeps 4
Pittsfield, MA
Central Berkshires
Pet Friendly
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Peru, MA
Swiss Chalet Style Timber Frame Home
3 Bedrooms, 2 Bath, Sleeps 6
Peru, MA
Central Berkshires
Pet Friendly
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Remote & Relaxing Cabin In The Berkshires
3 Bedrooms, 2 Bath, Sleeps 8
Peru, MA
Central Berkshires
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The Perfect Escape
3 Bedrooms, 2 Bath, Sleeps 8
Peru, MA
Central Berkshires
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Richmond, MA
Spacious Berkshire Summer Rental
3 Bedrooms, 3 Bath, Sleeps 7
Richmond, MA
Central Berkshires
Pet Friendly
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Private Apartment In Beautiful Country Barn
1 Bedrooms, 1 Bath, Sleeps 4
Richmond, MA
Central Berkshires
Pet Friendly
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Relaxing Getaway In The Beautiful Berkshires
4 Bedrooms, 2.5 Bath, Sleeps 12
Richmond, MA
Central Berkshires
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Sandisfield, MA
Sweet Dreams Retreat
1 Bedrooms, 1 Bath, Sleeps 3
Sandisfield, MA
Southern Berkshires
Pet Friendly
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Cabin With 3 Acres
4 Bedrooms, 3 Bath, Sleeps 10
Sandisfield, MA
Southern Berkshires
Pet Friendly
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Iconic Cabin In The Berkshires
6 Bedrooms, 3.5 Bath, Sleeps 12
Sandisfield, MA
Southern Berkshires
Pet Friendly
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Savoy, MA
Retreat In The Woods
2 Bedrooms, 1 Bath, Sleeps 4
Savoy, MA
Northern Berkshires
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Sheffield, MA
Elterwater–Your lakefront Oasis
2 Bedrooms, 2 Bath, Sleeps 4
Sheffield, MA
Southern Berkshires
Pet Friendly
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Cheerful 3BR Cottage With Woodstove
3 Bedrooms, 2.5 Bath, Sleeps 8
Sheffield, MA
Southern Berkshires
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NEW! Waterfront Sheffield Escape
3 Bedrooms, 2 Bath, Sleeps 6
Sheffield, MA
Southern Berkshires
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South Lee, MA
Upscale Architecturally Designed Berkshire Home
4 Bedrooms, 3 Bath, Sleeps 8
South Lee, MA
Southern Berkshires
Pet Friendly
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Architect Designed Home
4 Bedrooms, 3 Bath, Sleeps 8
South Lee, MA
Southern Berkshires
Pet Friendly
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Stockbridge, MA
Location!!! Location!!! Berkshire Glamour
4 Bedrooms, 3 Bath, Sleeps 8
Stockbridge, MA
Southern Berkshires
Pet Friendly
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Stockbridge Cape Near Tanglewood
4 Bedrooms, 2 Bath, Sleeps 7
Stockbridge, MA
Southern Berkshires
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Spectacular Housatonic River View
2 Bedrooms, 2 Bath, Sleeps 4
Stockbridge, MA
Southern Berkshires
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Washington, MA
Berkshires Log Cabin, Peace & Tranquility Awaits
3 Bedrooms, 1 Bath, Sleeps 8
Washington, MA
Southern Berkshires
Pet Friendly
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Beautiful Timber Frame Home
2 Bedrooms, 1 Bath, Sleeps 6
Washington, MA
Southern Berkshires
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Shingle Style, Timber Frame, Berkshire Cottage
3 Bedrooms, 2 Bath, Sleeps 8
Washington, MA
Southern Berkshires
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West Stockbridge, MA
Charming Unique Cottage Relax & Enjoy
2 Bedrooms, 1 Bath, Sleeps 5
West Stockbridge, MA
Southern Berkshires
Pet Friendly
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Gorgeous Home, Nature Lover’s Delight
4 Bedrooms, 4 Bath, Sleeps 8
West Stockbridge, MA
Southern Berkshires
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Sweet Escape w/Indoor Pool 
4 Bedrooms, 4 Bath, Sleeps 7
West Stockbridge, MA
Southern Berkshires
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Williamstown, MA
Charming Downtown Williamstown Cottage
3 Bedrooms, 2 Bath, Sleeps 7
Williamstown, MA
Northern Berkshires
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North Getaway Cottage
4 Bedrooms, 2 Bath, Sleeps 7
Williamstown, MA
Northern Berkshires
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Cozy & Quaint Country Cottage
2 Bedrooms, 1 Bath, Sleeps 4
Williamstown, MA
Northern Berkshires
Pet Friendly
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Huge Luxe Williamstown Updated Victorian
5 Bedrooms, 5.5 Bath, Sleeps 10
Williamstown, MA
Northern Berkshires
Pet Friendly
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