Over 1,000 stays

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Cottage in Orange
The Lake Cottage: A Sweetwater Stay
2 beds
Mar 22 – 29
$104 per night
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Home in Dalton
The Yellow House
1 queen bed
Feb 24 – Mar 3
$77 per night
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Superhost
Cabin in Warwick
Artsy Pine Cabin in the Woods
1 queen bed
Sep 14 – 21
$73 per night
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Superhost
Home in Amherst
Cozy get-away!
1 king bed
Dec 10 – 17
$80 per night
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Superhost
Treehouse in Lee
Gingerbread House Tower in the Berkshire Hills
2 beds
Nov 13 – 20
$287 per night
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Apartment in Shelburne Falls
In town, newly renovated studio with private deck
1 bed
Oct 23 – 30
$86 per night
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Private room in Amherst
Permaculture homestead retreat travelers room.
1 bed
Aug 18 – 25
$65 per night
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Yurt in Williamsburg
magical yurt in the woods. long term discount
1 bed
Dec 7 – 14
$68 per night
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Superhost
Home in Agawam
Agawam in-Law apt. Airport-6 Flags-Big E
4 beds
Nov 28 – Dec 5
$101 per night
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Place to stay in Buckland
Idyllic, private country retreat
1 bed
Apr 5 – 12
$101 per night
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Private room in Montague
Great location
1 queen bed
Jun 13 – 20
$47 per night
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Cottage in Williamsburg
Cozy Cottage Pet Friendly Pool Hot tub
3 beds
Nov 21 – 28
$136 per night
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Guest suite in Hatfield
Cheerful and Peaceful place to Unwind
1 bed
Nov 6 – 13
$70 per night
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Place to stay in Bernardston
Uniquely Styled Private Studio With Coded Locks
1 queen bed
Mar 10 – 17
$80 per night
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Guesthouse in Northampton
Mill River Cottage (pet friendly!)
2 beds
Nov 28 – Dec 5
$105 per night
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Cottage in Becket
Berkshires Modern Comfy Private Retreat! Hot tub!
2 queen beds
Dec 9 – 16
$113 per night
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Apartment in Great Barrington
Lush Setting, Private Deck, Queen Bed in GB
1 bed
Mar 15 – 22
$87 per night
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Superhost
Tiny home in Monterey
Rustic 1-room A-Frame glamping in the Berkshires
2 beds
Jun 14 – 21
$62 per night
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Superhost
Tiny home in Orange
The Writer's Retreat: A Sweetwater Stay
1 queen bed
Dec 10 – 17
$161 per night
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Private room in Huntington
Ancient Colony
1 double bed
Dec 18 – 25
$37 per night