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Compare 169 Vacation Homes in New Ashford with updated reviews, rates, and availability.

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
10.0 out of 10, Exceptional, (63)
"It was an amazing stay. The host was very proactive and helpful. "
The price is AED 962
AED 1,969 total
includes taxes & fees
18 Nov - 19 Nov
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
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.
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 AED 481
AED 751 total
includes taxes & fees
18 Nov - 19 Nov
Berkshire Village Carriage House - Super Private!!
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
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
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, (105)
"We really enjoyed our stay at Julie’s home. We will definitely to look to stay here again the next time we visit the area. Highly recommended! "
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
9.4 out of 10, Exceptional, (35)
"The home is very nice and cozy. It really felt like a comfy home."
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
8.8 out of 10, Excellent, (27)
"In town for a long weekend and loved the location. The owner was prompt and very helpful as we made a mistake in booking. FYI, The pictures are great but it’s a bit more rustic than they make it seem. Still, it was great to sit outside and hear the brooks flowing. Very quiet street! Housecleaning was a bit lacking though as there were some huge cobwebs in the corners. That was fine for us as we spend our time in a barn anyway. "
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
Expansive Upstate Home w/ Home Theater!
10.0 out of 10, Exceptional, (12)
"Owner was very responsive. House was spacious with everything we could have needed. Back yard and theater was amazing. 10 out of 10 recommend"
Expansive Upstate Home w/ Home Theater!
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
10.0 out of 10, Exceptional, (32)
"Relaxing, quiet, beautiful property. We really enjoyed the views, exploring the grounds and it is a short trip to Stockbridge. We had a wonderful stay. "
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
SPACIOUS Mountain Retreat with HOT TUB, Fire Pit & Hiking Trails
10.0 out of 10, Exceptional, (5)
"We did have a team member slip and fall on the bottom step. He was just bruised up but a safety tread might not be a bad idea"
SPACIOUS Mountain Retreat with HOT TUB, Fire Pit & Hiking Trails
Victorian Home in Bennington, Vermont
10.0 out of 10, Exceptional, (86)
"The home is spacious, clean, bright, nicely decorated and well-equipped. An easy walk to shops and restaurants. It was great for our annual family gathering in southwestern Vermont."
Victorian Home in Bennington, Vermont
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
10.0 out of 10, Exceptional, (2)
"Delightful property, worked well for our needs"
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
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
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
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
Hancock Village Inn at Jiminy Peak
9.8 out of 10, Exceptional, (7)
"Very kinda hosts, and wonderful house."
The price is AED 2,196
AED 3,853 total
includes taxes & fees
19 Nov - 20 Nov
Hancock Village Inn at Jiminy Peak
Family-Friendly Hancock Home: Walk to Slopes!
9.6 out of 10, Exceptional, (14)
"Great size for our family of 8."
Family-Friendly Hancock Home: Walk to Slopes!
Private Access To Laurel Lake, Enjoy Lake Life
10.0 out of 10, Exceptional, (14)
"We had a wonderful time in the Berkshires. The fall foliage was in full glory! Loved the location of the house right near the lake and the house had everything we needed, even kayaks! Nice lay out, clean, very comfortable and the house was well situated in Lenox and close to all the wonderful nearby towns, sites, hikes and things to do!"
Private Access To Laurel Lake, Enjoy Lake Life
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 property types in New Ashford

Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1746)
"Love staying here "
The price is AED 620
AED 717 total
includes taxes & fees
15 Nov - 16 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (919)
"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 AED 547
AED 600 total
includes taxes & fees
15 Nov - 16 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 AED 481
AED 751 total
includes taxes & fees
18 Nov - 19 Nov
Berkshire Village Carriage House - Super Private!!
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.