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Check prices for these dates

Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul
In one month
8 Aug - 10 Aug
In two months
5 Sept - 7 Sept

Featured Cottages in New Ashford

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay
Interior

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

3.0 star property
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay
Bennington Gem w/ Smart TV Near Historic District!
Front of property

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!
Charlemont Retreat on Chickley River w/ EV Charger
Interior

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
Spacious Historic Home in the Berkshires!
TV, fireplace, books

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Cozy Stockbridge Cabin - Walk to Beach & Lake!
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Cozy Stockbridge Cabin - Walk to Beach & Lake!

3.0 star property
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
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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
Luxury Vacation Rental in the Berkshires!
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Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!
Expansive Upstate Home w/ Home Theater!
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Expansive Upstate Home w/ Home Theater!

3.0 star property
Expansive Upstate Home w/ Home Theater!
Berkshire Hideaway w/ Fire Pit & Playground!
Interior

Berkshire Hideaway w/ Fire Pit & Playground!

3.0 star property
Berkshire Hideaway w/ Fire Pit & Playground!
Stockbridge Home: Walk to Town Beach!
Private kitchen

Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge Home: Walk to Town Beach!
Picturesque Cottage With Sunroom on Ashmere Lake!
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Picturesque Cottage With Sunroom on Ashmere Lake!

3.0 star property
Picturesque Cottage With Sunroom on Ashmere Lake!
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
TV, fireplace

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!

3.0 star property
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
12-acre Vacation Rental in the Berkshires!
Property grounds

12-acre Vacation Rental in the Berkshires!

3.0 star property
12-acre Vacation Rental in the Berkshires!
Elegant Pittsfield Home Near Downtown & Skiing!
Interior

Elegant Pittsfield Home Near Downtown & Skiing!

3.0 star property
Elegant Pittsfield Home Near Downtown & Skiing!
Lakefront West Sand Lake Home w/ Beach Access!
Interior

Lakefront West Sand Lake Home w/ Beach Access!

3.0 star property
Lakefront West Sand Lake Home w/ Beach Access!
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
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Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

3.0 star property
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
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4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!

3.0 star property
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!
Outdoor dining

Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!

3.0 star property
Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!
Family-friendly Richmond Cottage w/ Private Yard
Microwave, oven, stovetop, coffee/tea maker

Family-friendly Richmond Cottage w/ Private Yard

3.0 star property
Family-friendly Richmond Cottage w/ Private Yard
Massachusetts Vacation Rental w/ Deck & Grill
4 bedrooms, desk, laptop workspace, bed sheets

Massachusetts Vacation Rental w/ Deck & Grill

3.0 star property
Massachusetts Vacation Rental w/ Deck & Grill
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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