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New Ashford Holiday Rentals

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Holiday Rentals in New Ashford

Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1746)
"The pool/clubhouse was a bit chaotic but the overall experience of this location was fantastic. It was lovely."
The price is AU$297
includes taxes & fees
16 Nov - 17 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (918)
"Staff was friendly and helpful. The facility is a little run down, but it was clean. A lot was closed (ie. on site bar/restaurants) due to it being between seasons, which was disappointing. We used the hot tub, which was not very hot. We'd stay there again though. "
The price is AU$248
includes taxes & fees
16 Nov - 17 Nov
Jiminy Peak Mountain Resort
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (223)
"One of the best properties i've ever stayed at "
The price is AU$314
includes taxes & fees
18 Nov - 19 Nov
Berkshire Village Carriage House - Super Private!!
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, (39)
"We enjoyed our stay at the tiny home!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (125)
"We stayed two days but were mostly for sleep and sightseeing/visits. Certainly fit the bill for our needs. Would recommend to friends "
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
9.6 out of 10, Exceptional, (40)
"We stayed at Chris' mansion for my wedding this past weekend and it was everything I expected and more. Although it isn't a full service venue, the owner Chris was sooooo helpful in getting everything we needed for our wedding. He owns a restaurant as well and was able to provide all of our appetizers, servers and bartenders! We even had our rehearsal dinner at his bar down the street called Jax on Tap. The bartenders were absolutely amazing and made us feel so welcome. They even made a sign...
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Berkshire Lake access
10.0 out of 10, Exceptional, (47)
"The house was very clean and the yard is large. It's a great place for family vacations."
Berkshire Lake access
Bear Creek Cabin
9.8 out of 10, Exceptional, (20)
"The land was nice. "
The price is AU$929
includes taxes & fees
14 Nov - 15 Nov
Bear Creek Cabin
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Amore Estate - beautiful room with many places to explore and relax in.
9.8 out of 10, Exceptional, (17)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (16)
"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....
The Kemble- Built by a US Secretary of State in Lenox
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
10.0 out of 10, Exceptional, (23)
"My partner and I really enjoyed our relaxing stay at this quaint cottage. It was clean, comfortable, and tucked away in a very quiet area. It was easy to get to restaurants and theaters in Pittsfield / Lenox / Stockbridge. The hot tub was also a great way to spend a cozy fall afternoon!"
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Chic Pittsfield Home With A View!
9.6 out of 10, Exceptional, (7)
"Great view from the property, lovely house and yard. Coiuldn't have been a better stay. "
Chic Pittsfield Home With A View!
The Winthrop Estate - 12K SF 32 Acres
10.0 out of 10, Exceptional, (4)
"Everyone enjoyed the stay"
The Winthrop Estate - 12K SF 32 Acres
Wellspring by AvantStay | Indoor Pool + Views
10.0 out of 10, Exceptional, (8)
"The location is absolutely beautiful, the pool was great, and there was plenty of room for everyone. This was our second time staying at this house and we will be back."
Wellspring by AvantStay | Indoor Pool + Views
Perfect for Leaf Peeping w/Bar Room, Hot Tub
9.8 out of 10, Exceptional, (10)
"We had 15 members of my family in this old house. Another 5 at another VRBO , and 4 others that joined us all day Saturday. Good weather and the annual recognition of the Battle of Bennington was a wonderful surprise The house needs many repairs. The kitchen was a big disappointment "
Perfect for Leaf Peeping w/Bar Room, Hot Tub
Near Tanglewood: Historic Summer Retreat
9.6 out of 10, Exceptional, (15)
"This was a beautiful, spacious, and peaceful place for us in our friends to get together. It was centrally located to everything we wanted to do. Amanda was wonderful in her communications and everything was clean and ready for us."
Near Tanglewood: Historic Summer Retreat
Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!
10.0 out of 10, Exceptional, (26)
"The house was perfect for a group of five of us. The kitchen and grill were great for our culinary needs. Thanks for letting us stay!"
Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!
Mountainside Condo Ski In Ski Out
8.8 out of 10, Excellent, (20)
"Stay at Jiminey for the 13 nights. Condo was clean and had anything you could ever need! "
The price is AU$288
includes taxes & fees
18 Nov - 19 Nov
Mountainside Condo Ski In Ski Out
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (104)
"Great cottage, pretty much at the foot of Mount Greylock - very spacious and comfortable - in the country but close to many of the towns of the Berkshires - the hosts Cheryl and Rich were very kind and informative about the area -thank you Cheryl and Rich - I hope to return sometime -"
Charming historic cottage on scenic road to Mt. Greylock
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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Other types of properties in New Ashford you may be interested in

Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, (437)
"Beautiful hotel close enough drive to multiple towns and hiking areas. Very comfortable beds. Beautiful restroom! TV has Apple compatibility if you are looking for that. The restaurant was absolutely amazing and they use all local business. Absolutely amazing!"
The price is AU$165
includes taxes & fees
18 Nov - 19 Nov
Life House Berkshires
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1000)
"Hot tub was great, good breakfast selection. Staff was courteous and very helpful. We would have liked the pool a bit warmer."
The price is AU$165
includes taxes & fees
19 Nov - 20 Nov
The Yankee, Trademark Collection by Wyndham
The Black Swan Lee - Lenox, Ascend Hotel Collection
3.0 star property
9.0 out of 10, Wonderful, (1002)
"We booked this place for a one-night stay to check out the Berkshires. This was pretty much centrally located from everything we wanted to visit. We chose this place for the country feel rather than the big city type hotels. The place was a little outdated but had the more of a home feel. There is some updating due there, but it wasn't a disappointment. We will book again when we visit the area to go hiking. Plus, the lake view was ok, and the water looked very clean. I will say this is an...
The price is AU$171
includes taxes & fees
27 Nov - 28 Nov
The Black Swan Lee - Lenox, Ascend Hotel Collection
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.

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?

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of New Ashford is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

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 Brodie Mountain 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.