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New Ashford Holiday Rentals

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Check prices for these dates

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

Our top choices for New Ashford holiday rentals

Exterior

White Lily Lodge 50 acre estate with private lake

White Lily Lodge 50 acre estate with private lake
Cropseyville
The price is HK$5,645
HK$7,162 total
includes taxes & fees
19 Jul - 20 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.
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 HK$1,633
HK$3,697 total
includes taxes & fees
14 Aug - 15 Aug
Riverbend Berkshire East Basecamp - 3 bedrooms available
Coffee/tea maker, fridge, microwave, stovetop

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 HK$855
HK$1,069 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 HK$2,822
HK$10,474 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 HK$3,136
HK$4,720 total
includes taxes & fees
26 Jul - 27 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 HK$1,990
HK$4,193 total
includes taxes & fees
26 Jul - 27 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 traveller
The price is HK$2,037
HK$3,439 total
includes taxes & fees
17 Aug - 18 Aug
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 HK$1,795
HK$3,774 total
includes taxes & fees
21 Jul - 22 Jul
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 HK$1,242
HK$2,237 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 HK$2,463
HK$4,318 total
includes taxes & fees
26 Jul - 27 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 HK$4,704
HK$6,008 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, (1,010 reviews)
"Great location too"
United States
judith
The price is HK$1,048
HK$1,345 total
includes taxes & fees
17 Aug - 18 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 HK$980
HK$2,169 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 HK$980
HK$2,267 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 HK$1,019
HK$2,266 total
includes taxes & fees
20 Jul - 21 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 HK$874
HK$2,991 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 HK$980
HK$2,472 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 HK$2,744
HK$5,001 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

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"This was a beautiful hotel close to the best part of North Adams. The gallery on the lobby floor gives it an upscale vibe but without too high a price tag. It was very convenient for our college visit to Williams College. It was very quiet even directly across from the elevator. The beds were very comfortable. The coffee was good. But,my one note would be there wasn't anything else offered for breakfast that my picky eater teenager would eat."
Sara 1-night trip
Posted 11 hours ago
Hotel Downstreet, an Ascend Collection Hotel

Find out more about New Ashford

Search for holiday rentals in New Ashford on Expedia! You can easily find your home rentals, villas, holiday apartments in New Ashford using one of the methods below:

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Look no further and take a look at our great range of rental properties in New Ashford!

Frequently asked questions

Are there holiday rentals in New Ashford?

Yes, there are holiday rentals close to the most popular sights in New Ashford, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that New Ashford has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of New Ashford is located near skiing, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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 wider area, you’ll find Green River Wildlife Management Area and Williamstown Theatre Festival.

What’s a holiday rental in New Ashford like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in New Ashford. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a family getaway.