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New Ashford Vacation Rentals

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Dec 5 - Dec 6
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Dec 12 - Dec 14

Vacation Rentals in New Ashford

Lobby
Vacation Village in the Berkshires

Condo in Williamstown

3.0 star property
8.8 out of 10, Excellent, (2163)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
The price is ￥13,804
￥17,120 total
includes taxes & fees
Dec 7 - Dec 8
Vacation Village in the Berkshires
Exterior
Huttopia Berkshires

Camping in Williamstown

1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is ￥26,388
￥29,475 total
includes taxes & fees
Dec 16 - Dec 17
Huttopia Berkshires
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

3.0 star property
8.2 out of 10, Very Good, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is ￥28,440
￥31,767 total
includes taxes & fees
Dec 6 - Dec 7
Jiminy Peak Mountain Resort
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

Condo resort in Lenox

3.0 star property
8.6 out of 10, Excellent, (135)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The Ponds at Foxhollow
Exterior detail
Taborton Harvest Boulder Pines Cabin in the woods

Cabin in Sand Lake

10.0 out of 10, Exceptional, (13)
"Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "
United States
Joanna R.
The price is ￥19,385
￥28,403 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Taborton Harvest Boulder Pines Cabin in the woods
Exterior
Bear Creek Cabin

Cabin in Charlemont

10.0 out of 10, Exceptional, (43)
"We enjoyed our stay!!"
United States
Hillary S.
The price is ￥62,052
￥92,879 total
includes taxes & fees
Dec 6 - Dec 7
Bear Creek Cabin
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox

Villa in Lenox

10.0 out of 10, Exceptional, (17)
"Perfect house for our family reunion. Everything was perfect."
United States
Michael C.
The Kemble- Built by a US Secretary of State in Lenox
Property grounds
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Vacation Home in Hinsdale

9.8 out of 10, Exceptional, (19)
"Rich was an amazing host. Beautiful lake and sunsets. I would love to stay there again"
United States
maria f.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Vacation Home in Hancock

9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
The price is ￥49,952
￥113,638 total
includes taxes & fees
Dec 6 - Dec 7
Comfortable Berkshires retreat on mtn resort, SISO
Smart TV, fireplace, DVD player, music library
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

Apartment in Pownal

9.4 out of 10, Exceptional, (85)
"This unique hideaway was great for our family. The open layout might not work for everyone, but suited us just fine! We were only here a couple nights but enjoyed the location and using the hot tub! "
United States
Elizabeth R.
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Outdoor dining
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Vacation Home in Pittsfield

9.8 out of 10, Exceptional, (150)
"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."
United States
Sarah A.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Fridge, microwave, oven, stovetop
Taborton Harvest Timber Trails Unique cabin experience

Cabin in Sand Lake

10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
United States
Georgia M.
The price is ￥19,385
￥28,403 total
includes taxes & fees
Dec 6 - Dec 7
Taborton Harvest Timber Trails Unique cabin experience
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.

Vacation Home in Lenox

9.2 out of 10, Wonderful, (33)
"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."
United States
Jacquie S.
Amore Estate - beautiful room with many places to explore and relax in.
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Vacation Home in Stockbridge

10.0 out of 10, Exceptional, (135)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Exterior
Hancock Village Inn Near Jiminy Peak

Vacation Home in Hancock

10.0 out of 10, Exceptional, (16)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is ￥92,923
￥172,359 total
includes taxes & fees
Dec 9 - Dec 10
Hancock Village Inn Near Jiminy Peak
Terrace/patio
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Vacation Home in Whitingham

9.8 out of 10, Exceptional, (46)
"Home is lovely, fun bedroom themes."
United States
Kate H.
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Fridge, microwave, oven, stovetop
Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq

Vacation Home in Readsboro

10.0 out of 10, Exceptional, (7)
"We loved the tranquility and comfort of the house. The seclusion allowed for a quiet and peaceful getaway. The home had all the comforts needed for a relaxing stay. The view is spectacular and the surrounding landscape is beautiful. Great area for hiking, swimming, and sightseeing."
United States
judy G.
Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq
Interior
Charming 3-bedroom Cabin for nature lovers

Cabin in Stephentown

7.0 out of 10, Good, (2)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
The price is ￥24,045
￥49,592 total
includes taxes & fees
Dec 21 - Dec 22
Charming 3-bedroom Cabin for nature lovers
Terrace/patio
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Vacation Home in Lanesborough

10.0 out of 10, Exceptional, (6)
"Everything was just as advertised and we really enjoyed the view and the hot tub. Perfect spot for a quick getaway! "
United States
Cindy B.
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
Interior
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

Vacation Home in Lanesborough

9.6 out of 10, Exceptional, (74)
"Beautiful house and location that was perfect for a family weekend. Would 100% recommend!"
United States
Shaun L.
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"I enjoyed the holiday inn. I enjoyed the staff made me fell at home. I enjoyed the comfortable atmosphere and the room was nice and clean. I enjoyed the breakfast very much. The staff was very friendly. "
Brendan 1-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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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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?

Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location: This vacation home rental outside New Ashford is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a hot tub.

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 Brodie Mountain.

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.