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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for New Ashford vacation rentals

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,799 reviews)
"We had an amazing stay."
United States
Luke
The price is ￥12,603
￥15,798 total
includes taxes & fees
Nov 1 - Nov 2
Vacation Village in the Berkshires
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

2. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is ￥15,166
￥35,237 total
includes taxes & fees
Oct 28 - Oct 29
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Exterior

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,233 reviews)
"beautiful location, giant suite room for incredible value"
United States
Michael
The price is ￥13,500
￥18,598 total
includes taxes & fees
Nov 22 - Nov 23
Berkshire Mountain Lodge
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

4. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (18 reviews)
"Nice Place"
United States
Tom C.
The price is ￥15,166
￥35,237 total
includes taxes & fees
Oct 28 - Oct 29
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A Country Inn with a large, welcoming entrance and a parking area.

5. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is ￥15,166
￥35,237 total
includes taxes & fees
Oct 28 - Oct 29
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A lobby with leather sofas, a fireplace, and a stone wall.

6. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
The price is ￥15,166
￥35,237 total
includes taxes & fees
Oct 28 - Oct 29
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

7. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Hancock
9.6 out of 10, Exceptional, (33 reviews)
"The suite was a great. Comfortable, clean and decorated very nicely. Bed was very comfortable with nice linens and pillows. "
United States
Eileen O.
The price is ￥16,851
￥37,470 total
includes taxes & fees
Nov 2 - Nov 3
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Pool

8. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.8 out of 10, Excellent, (12 reviews)
"Host was proactive in communication and answer each and every question."
United States
Amit
The price is ￥25,256
￥84,925 total
includes taxes & fees
Oct 29 - Oct 30
Comfortable Berkshires retreat on mtn resort, SISO
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

9. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6 reviews)
"Convenience to slopes and restaurants really great….,had a nice stay"
United States
Thomas S.
The price is ￥15,166
￥35,237 total
includes taxes & fees
Oct 28 - Oct 29
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.

10. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (19 reviews)
"Our stay was beautiful! The check in process was super easy and the building was easy to access. The apartment was very clean and it was a lovely stay."
United States
Margaret C.
The price is ￥22,746
￥44,156 total
includes taxes & fees
Oct 29 - Oct 30
Penthouse Apartment on Park Street
Private kitchen

11. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (13 reviews)
"Great location, very clean, included washer dryer, picnic area by river, large parking space."
United States
Douglas
The price is ￥19,609
￥44,460 total
includes taxes & fees
Oct 29 - Oct 30
Downtown | Waterfront | Walk to Shops
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

12. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hancock
9.6 out of 10, Exceptional, (35 reviews)
"We really enjoyed our stay it was a very nice place for a family."
United States
Shmaya G.
The price is ￥22,730
￥48,869 total
includes taxes & fees
Oct 29 - Oct 30
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
"The property comes equipped with everything one can need for a relaxing getaway, not to mention a fire pit in the backyard nested on top of a river. It’s truly relaxing and peaceful while still being close to restaurants and a super market." ...Anna

13. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (21 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is ￥18,824
￥41,278 total
includes taxes & fees
Oct 29 - Oct 30
New Studio In Town, By the Water
"We had a lovely week-long stay at this cozy spot by the river. We cook a lot when we visit Airbnbs and we were so thrilled to find a huge variety of cooking pots, pans, utensils, etc. " ...Patrick

14. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (21 reviews)
"Great place with easy access to town and even better access to a nice spot to hangout by the creek. I will definitely stay here again."
United States
Thomas
The price is ￥18,899
￥44,461 total
includes taxes & fees
Nov 3 - Nov 4
2-Bdr Apt In Town, By the Water
A wooden deck with outdoor furniture, a glass door leading to a view of a grassy area with trees.

15. Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views

Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Hancock
8.0 out of 10, Very good, (1 review)
"I chose this place at the very last minute. It was all that I expected and wanted and more: two bedrooms with three beds, a comfortable living space, two full bathrooms, kitchen with all the basic necessities, TV in each bedroom and in the living room, a dining table and chairs, an outside porch with table, a big open space, and grill, easy parking and access, quiet, .and access to two pools. The place was well tended: clean, with towels and extras blankets ready. Howard, the owner, checked on...
United States
Cecilia S.
The price is ￥21,261
￥47,146 total
includes taxes & fees
Oct 28 - Oct 29
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

16. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (34 reviews)
"We were on a girls backpacking trip and this was the perfect location right off the trail to clean up, get some great rest and grab dinner. The people are so friendly in Dalton and this place had everything we needed!"
United States
Allie T.
The price is ￥25,513
￥59,284 total
includes taxes & fees
Oct 28 - Oct 29
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

17. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is ￥39,845
￥92,155 total
includes taxes & fees
Oct 29 - Oct 30
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

18. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is ￥47,649
￥97,069 total
includes taxes & fees
Oct 29 - Oct 30
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

19. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is ￥14,725
￥36,673 total
includes taxes & fees
Oct 28 - Oct 29
Berkshires Apartment at the Stephentown Hotel
A wicker sofa with a floral cushion, a wicker table with magazines, and a standing fan in a room with large windows and wooden floors.

20. 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
8.0 out of 10, Very good, (2 reviews)
"Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again."
United States
Ruthie K.
The price is ￥13,387
￥32,193 total
includes taxes & fees
Oct 28 - Oct 29
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
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 On North

Hotel On North

10/10 Excellent
"Very large room and bathroom. Had parking easily accessible, very nice and helpful staff."
Gaby 2-night trip
Posted 2 hours ago
Hotel On North

Find out more about New Ashford

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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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental outside of New Ashford is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation 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 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.