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Superhost
Condo in New Ashford
Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8
8 guests2 bedrooms4 beds2 baths
Aug 25 – 30
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Aug 25 – 30
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R14,904 ZAR for 5 nights

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Room in New Ashford
Stay with Farah
Bondhu: lush boho foodie Berkshires paradise
Aug 18 – 23
R21,774 ZAR for 5 nights
4.95 out of 5 average rating, 20 reviews
Room in Lanesborough
Stay with Carlton
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
Jul 6 – 11
R11,204 ZAR for 5 nights
4.8 out of 5 average rating, 71 reviews
Home in New Ashford
Berkshire Gorge House/Williamstown
6 beds
Jul 1 – 6
R30,124 ZAR for 5 nights
4.63 out of 5 average rating, 88 reviews
Guest favorite
Room in Cheshire
Stay with LauraOrganic dayspa owner,
Private sweet sunny room ecofriendly tranquil home
Aug 12 – 17
R6,765 ZAR for 5 nights
5.0 out of 5 average rating, 9 reviews
Cabin in New Ashford
Rustic Cabin with Wood Fireplace
Free cancellation
Jul 13 – 18
R25,095 ZAR for 5 nights
5.0 out of 5 average rating, 4 reviews
Cabin in New Ashford
Rustic Cabin with Loft
Free cancellation
Aug 16 – 21
R28,546 ZAR for 5 nights
5.0 out of 5 average rating, 3 reviews
Guest favorite
Home in New Ashford
Rosecroft, Historic Home, Greylock Valley Estate
8 beds
Jul 20 – 25
R45,450 ZAR for 5 nights
4.92 out of 5 average rating, 201 reviews
Top guest favorite
Room in Williamstown
Stay with RobinHosting for 8 years,
Robin's
Aug 10 – 15
R8,921 ZAR for 5 nights
4.87 out of 5 average rating, 597 reviews
Cabin in New Ashford
Charming 2BR Berkshire Cabin
2 queen beds
Jul 5 – 10
R21,592 ZAR for 5 nights
New place to stay
Guest favorite
Guesthouse in Williamstown
Peaceful/modern post and beam studio apartment
Free cancellation
Jul 13 – 18
R18,497 ZAR for 5 nights
4.98 out of 5 average rating, 160 reviews
Guest suite in Hancock
Cozy apartment near Jiminy Peak
3 beds
Jul 7 – 12
R9,788 ZAR for 5 nights
4.81 out of 5 average rating, 181 reviews
Top guest favorite
Apartment in Petersburgh
The Beer Diviner Brewery Apartment
Free cancellation
Jul 13 – 18
R9,619 ZAR for 5 nights
4.88 out of 5 average rating, 186 reviews
Top guest favorite
Cabin in Cummington
Just Be Cabin
Free cancellation
Jul 13 – 18
R7,399 ZAR for 5 nights
4.98 out of 5 average rating, 219 reviews
Guest favorite
Apartment in Williamstown
COLD SPRING
2 queen beds
Aug 12 – 17
R17,460 ZAR for 5 nights
4.94 out of 5 average rating, 305 reviews
Top guest favorite
Apartment in Troy
Stunning studio in the heart of Troy: Raven's Den
1 queen bed
Jul 1 – 6
R7,801 ZAR for 5 nights
4.93 out of 5 average rating, 444 reviews
Guest favorite
Cabin in Cheshire
Private Paradise in the Berkshires
1 bed
Jul 6 – 11
R18,392 ZAR for 5 nights
4.89 out of 5 average rating, 164 reviews
Guest favorite
Vacation home in Hancock
Ski in/Ski Out - Building 1 Condo at Jiminy Peak
2 beds
Jul 6 – 11
R17,134 ZAR for 5 nights
4.96 out of 5 average rating, 24 reviews
Superhost
Cabin in Stephentown
Cabin in the woods w cedar Hot Tub + private pond
2 queen beds
Jul 6 – 11
R18,709 ZAR for 5 nights
4.86 out of 5 average rating, 291 reviews