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Featured Cottages in New Ashford

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
3.0 star property
6.0 out of 10, (1)
"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Spacious Historic Home in the Berkshires!
3.0 star property
Spacious Historic Home in the Berkshires!
Charlemont Retreat on Chickley River w/ EV Charger
3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
3.0 star property
10.0 out of 10, Exceptional, (1)
"The host was so kind and helpful. I will definitely cime abck here. "
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Stockbridge Home: Walk to Town Beach!
3.0 star property
Stockbridge Home: Walk to Town Beach!
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
3.0 star property
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
Peaceful Family Home w/ Fire Pit & Large Yard
3.0 star property
Peaceful Family Home w/ Fire Pit & Large Yard
Bennington Gem w/ Smart TV Near Historic District!
3.0 star property
10.0 out of 10, Exceptional, (1)
"We liked staying at the place as it had good amenities (washer, dryer, dishwasher, fridge with a freezer, fan, inflatable bed, wifi, cable, free parking spots. etc) and a lot of space. Where there is no central AC, it had a window unit which worked well - we had a comfortable stay in mid-July."
Bennington Gem w/ Smart TV Near Historic District!
Berkshire Hideaway w/ Fire Pit & Playground!
3.0 star property
Berkshire Hideaway w/ Fire Pit & Playground!
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
3.0 star property
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Lakeside Berkshires Home Near Hiking & Skiing!
3.0 star property
Lakeside Berkshires Home Near Hiking & Skiing!
Lakefront West Sand Lake Home w/ Beach Access!
3.0 star property
Lakefront West Sand Lake Home w/ Beach Access!
Expansive Upstate Home w/ Home Theater!
3.0 star property
Expansive Upstate Home w/ Home Theater!
Breathtaking Mtn Views: Stylish Rustic Retreat!
3.0 star property
Breathtaking Mtn Views: Stylish Rustic Retreat!
Cozy Stockbridge Cabin - Walk to Beach & Lake!
3.0 star property
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Historic New Lebanon Hideaway on 33 Private Acres!
3.0 star property
Historic New Lebanon Hideaway on 33 Private Acres!
Elegant Pittsfield Home Near Downtown & Skiing!
3.0 star property
Elegant Pittsfield Home Near Downtown & Skiing!
Picturesque Cottage With Sunroom on Ashmere Lake!
3.0 star property
Picturesque Cottage With Sunroom on Ashmere Lake!
Luxury Vacation Rental in the Berkshires!
3.0 star property
Luxury Vacation Rental in the Berkshires!
Private Guest House in Dtwn Lenox, Walk to Dining!
3.0 star property
Private Guest House in Dtwn Lenox, Walk to Dining!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in New Ashford

Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1746)
"The pool/clubhouse was a bit chaotic but the overall experience of this location was fantastic. It was lovely."
The price is S$261
includes taxes & fees
16 Nov - 17 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (919)
"Staff was friendly and helpful. The facility is a little run down, but it was clean. A lot was closed (ie. on site bar/restaurants) due to it being between seasons, which was disappointing. We used the hot tub, which was not very hot. We'd stay there again though. "
The price is S$214
includes taxes & fees
20 Nov - 21 Nov
Jiminy Peak Mountain Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

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