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New Ashford Vacation Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for New Ashford vacation rentals

Exterior

White Lily Lodge 50 acre estate with private lake

White Lily Lodge 50 acre estate with private lake
Cropseyville
The price is AED 2,645
AED 3,327 total
includes taxes & fees
18 Jul - 19 Jul
White Lily Lodge 50 acre estate with private lake
Smart TV, fireplace, books

5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (4 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is AED 871
AED 2,269 total
includes taxes & fees
20 Jul - 21 Jul
5BR Berkshire Home Mins To The Mountain
Property grounds

Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (4 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is AED 765
AED 1,732 total
includes taxes & fees
14 Aug - 15 Aug
Riverbend Berkshire East Basecamp - 3 bedrooms available
Fridge, microwave, stovetop, dishwasher

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Whitingham
9.8 out of 10, Exceptional, (6 reviews)
"Gorgeous views even in March, ample heating/cooling, wonderful host experience, would just recommend bringing paper plates/utensils as we found ourselves running the dishwasher often. "
United States
avery o.
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Property grounds

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Cummington
10.0 out of 10, Exceptional, (1 review)
"Staff was super friendly, host was also amazing!"
United States
Connor
The price is AED 400
AED 501 total
includes taxes & fees
19 Jul - 20 Jul
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
TV, fireplace, books

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
Charlemont
10.0 out of 10, Exceptional, (2 reviews)
"Our stay at the chalet was exactly what we hoped it would be! The space is in a beautiful location that is perfect for dogs. The host was very helpful and responsive and check in was a breeze. We'll be back for sure!"
United States
Georgia P.
The price is AED 1,322
AED 4,907 total
includes taxes & fees
19 Jul - 20 Jul
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
Exterior

Bear Creek Cabin

Bear Creek Cabin
Charlemont
10.0 out of 10, Exceptional, (47 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
The price is AED 1,469
AED 2,211 total
includes taxes & fees
25 Jul - 26 Jul
Bear Creek Cabin
Property grounds

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (38 reviews)
"Gorgeous place.Great stay.Will diff be backG"
United States
Gerard C.
The price is AED 959
AED 2,002 total
includes taxes & fees
23 Jul - 24 Jul
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful cabin in a beautiful location. Host is amazing, very responsive. "
United States
Anonymous traveler
The price is AED 964
AED 1,622 total
includes taxes & fees
19 Jul - 20 Jul
The Greylock Cabin
Dining

A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (57 reviews)
"Comfortable lovely home with everything we needed to have a great weekend. "
United States
Margaret C.
The price is AED 841
AED 1,764 total
includes taxes & fees
3 Aug - 4 Aug
A roomy remodeled retreat close to MassMoCA
Interior

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
The price is AED 582
AED 1,048 total
includes taxes & fees
19 Jul - 20 Jul
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
Outdoor dining

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.4 out of 10, Very Good, (9 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is AED 1,154
AED 2,015 total
includes taxes & fees
28 Jul - 29 Jul
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Property grounds

Enjoy comfortable elegance in this secluded grand home located in town

Enjoy comfortable elegance in this secluded grand home located in town
Lenox
10.0 out of 10, Exceptional, (82 reviews)
"Amazing property, close to town "
United States
Tricia E.
The price is AED 2,204
AED 2,814 total
includes taxes & fees
19 Jul - 20 Jul
Enjoy comfortable elegance in this secluded grand home located in town
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,008 reviews)
"Great location too"
United States
judith
The price is AED 491
AED 630 total
includes taxes & fees
16 Aug - 17 Aug
Berkshire Mountain Lodge
Outdoor dining

New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (15 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is AED 459
AED 1,016 total
includes taxes & fees
20 Jul - 21 Jul
New Studio In Town, By the Water
Outdoor dining

2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (14 reviews)
"Location was very good-close to campus. Host was responsive. Accommodations were just right"
United States
Dan R.
The price is AED 477
AED 1,087 total
includes taxes & fees
21 Jul - 22 Jul
2-Bdr Apt In Town, By the Water
Outdoor dining

Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (8 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is AED 477
AED 1,062 total
includes taxes & fees
19 Jul - 20 Jul
Downtown | Waterfront | Walk to Shops
Exterior

Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
The price is AED 465
AED 1,462 total
includes taxes & fees
19 Jul - 20 Jul
Two Brooks Lodge
Exterior

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Bennington
8.6 out of 10, Excellent, (35 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is AED 492
AED 1,199 total
includes taxes & fees
19 Jul - 20 Jul
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Beach nearby

Beachwood Cottage

Beachwood Cottage
Stockbridge
9.8 out of 10, Exceptional, (6 reviews)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
United States
Christine P.
The price is AED 1,286
AED 2,343 total
includes taxes & fees
6 Aug - 7 Aug
Beachwood Cottage
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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Top New Ashford Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"The AC went out on my last night. That was the killer. But the pool, game room, and everything else was alright."
Owen 2-night trip
Posted 3 hours ago
Vacation Village in the Berkshires

Frequently asked questions

Are there vacation rentals in New Ashford?

Yes, there are vacation rentals close to the most popular local attractions in New Ashford, or you can choose a more remote option if you'd like a relaxing place to stay. New Ashford is known for its ski areas and mountain views. Make sure you have time to check out the festivals while you're in the area.

What's the top vacation rental that New Ashford has to offer?

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. : This vacation home rental outside of New Ashford offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What’s there to see and do in New Ashford?

While exploring the area, visit family-friendly sights like Berkshire Museum, or get outside and enjoy nature at Mount Greylock State Reservation. In the larger area, you’ll find Green River Wildlife Management Area and Williamstown Theatre Festival.

What’s a vacation rental in New Ashford like?

Vacation rentals are private accommodations you can stay in for a few days or a quick weekend in New Ashford. Vacation rentals provide amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for families.