81 stays

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Cottage in Brimfield
Cheerful 1 bedroom lake cottage with lake access.
1 bed
Aug 30 – Sep 6
$158 per night
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Home in Hillsdale
Berkshire Modern w/ Pool, Mt top views
4 beds
Mar 3 – 10
$578 per night
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Cabin in Becket
Waldtreff - quiet grand cabin
6 beds
Sep 11 – 18
$203 per night
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Superhost
Cabin in Sheffield
Large Cabin in Berkshires near GB & superb hiking
8 beds
Sep 14 – 21
$341 per night
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Superhost
Private room in Worthington
Country Luxury in the Heart of the Berkshires
5 beds
Nov 7 – 14
$91 per night
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Superhost
Apartment in Northampton
Bike Path Hideaway Near Smith, Cooley, Northampton
2 beds
Oct 17 – 24
$133 per night
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Superhost
Home in Sunderland
Historic 5-Bdrm Home Minutes from 5 College Area
10 beds
Jun 4 – 11
$606 per night
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Superhost
Home in Pittsfield
Hidden Oasis in the Berkshire Mountains
6 beds
Dec 3 – 10
$431 per night
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Cottage in Hinsdale
Modern one bed room cottage loft on beautiful Lake
1 king bed
Feb 1 – 8
$200 per night
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Hotel room in Enfield
New, modern hotel in Enfield, CT- RM2 1 King
1 king bed
Aug 7 – 14
$116 per night
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Home in Salisbury
Private, Stylish 3BR Litchfield County Farmhouse
3 queen beds
Oct 1 – 8
$266 per night
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Villa in Richmond
Luxury 5 BR on 47 acre oasis, pond and heated pool
6 beds
Jul 14 – 21
$1,401 per night
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Villa in South Lee
Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna! Great Location!
3 beds
Feb 23 – Mar 2
$175 per night
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Home in Sandisfield
Luxury Lake Home/ Ski House (on lake) All Seasons
8 beds
Oct 7 – 14
$585 per night
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Villa in Great Barrington
1The Freeman- 14K SF Estate 40acrs Tennis Vineyard
19 beds
Feb 28 – Mar 7
$1,455 per night
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Home in West Brookfield
Waterfront New England House on Wickaboag Lake!
5 beds
May 4 – 11
$522 per night
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Home in Hancock
Berkshire Cozy Cabin in Mountain Resort
2 beds
Jun 1 – 8
$135 per night
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Superhost
Home in Great Barrington
Stunning luxury home with pool
4 beds
Oct 28 – Nov 4
$1,041 per night
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Home in Great Barrington
Charming, view, large deck, private/walk downtown
4 beds
Jan 14 – 21
$330 per night
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Villa in South Lee
Villa with Access to 2 Pools, a Hot Tub, an 18-Hole Mini Golf Course, and More
2 beds
Jun 5 – 12
$139 per night