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Compare 177 Vacation Homes in New Ashford with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is AED 551
AED 833 total
includes taxes & fees
21 Feb - 22 Feb
Berkshire Village Carriage House - Super Private!!

Charlemont Retreat on Chickley River w/ EV Charger

9.6 out of 10, Exceptional, (26)
"Very close to Berkshire East. Beautifully rustic house that was extremely well maintained."
Charlemont Retreat on Chickley River w/ EV Charger

Amore Estate - beautiful room with many places to explore and relax in.

9.4 out of 10, Exceptional, (21)
"Fantastic, large house with tons of places to explore in the house and on the property. We came for a long weekend with 3 families and both the adults and kids felt quickly at home and really enjoyed our stay. We cannot wait to some back!"
Amore Estate - beautiful room with many places to explore and relax in.

Comfortable Berkshires retreat on mtn resort, SISO

The price is AED 1,183
AED 2,472 total
includes taxes & fees
23 Feb - 24 Feb
Comfortable Berkshires retreat on mtn resort, SISO

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

10.0 out of 10, Exceptional, (65)
"Great stay! Kids and adults both loved it and very easy to access the slopes. "
The price is AED 1,153
AED 2,197 total
includes taxes & fees
23 Feb - 24 Feb
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Country Living just minutes from Everything!

10.0 out of 10, Exceptional, (27)
"Very nice, very clean property. Everything you need. Communication with owner is excellent. My family and I were extremely comfortable here!"
Country Living just minutes from Everything!

Hearts Desire is a furnished whole house in a small, colorful garden center.

10.0 out of 10, Exceptional, (88)
"We thoroughly enjoyed our stay at “Hearts Desire”! Everything was set up for our relaxation and enjoyment! The weather outside was terrible but the atmosphere in the house was warms and so comfortable. We were able to enjoy watching the tv which sometimes doesn’t give many choices in some other stays. We are definitely getting the game “Fake News or Not”! Lots of fun. If we plan on visiting the area again, we will definitely return! Thank you!"
Hearts Desire is a furnished whole house in a small, colorful garden center.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (10)
"As advertised "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

8.8 out of 10, Excellent, (28)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
The price is AED 503
AED 1,150 total
includes taxes & fees
24 Feb - 25 Feb
Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (9)
"Annual mother/son ski and food fest!Lots of fun with family and friends. Plenty of space for everyone.. Kitchen wascwell"
The price is AED 2,196
AED 3,898 total
includes taxes & fees
25 Feb - 26 Feb
Hancock Village Inn at Jiminy Peak

Chic Pittsfield Home With A View!

8.6 out of 10, Excellent, (10)
"This property was just as shown in the listing and met our needs very well. It was well appointed and had many inviting areas to gather and relax in. The kitchen was well equipped and easy to use. Some very nice touches with closets and bathroom storage areas that made staying there user friendly. "
Chic Pittsfield Home With A View!

Perfect for Leaf Peeping w/Bar Room, Hot Tub

10.0 out of 10, Exceptional, (11)
"Wonderful experience, extremely communicative and helpful management, and just a beautiful building to stay in. We wanted for nothing. Thank you!"
Perfect for Leaf Peeping w/Bar Room, Hot Tub

Wellspring by AvantStay | Indoor Pool + Views

10.0 out of 10, Exceptional, (10)
"We all enjoyed our stay. The house and indoor pool were wonderful. There are plenty of comfortable places to sit and enjoy the gorgeous views. We loved the location which is both close to Lenox restaurants, as well as, the southern Berkshires for food markets and activities for kids. The property manager was attentive, and the owner was very responsive. We loved our week at this family friendly property and highly recommend it. "
Wellspring by AvantStay | Indoor Pool + Views

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (118)
"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (19)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is AED 441
AED 1,192 total
includes taxes & fees
24 Feb - 25 Feb
Near Tanglewood: Historic Summer Retreat

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (40)
"We have stayed here twice and it is a great spot, located a few minute drive north of downtown Lenox. The house is cozy yet spacious and is great for our family to stay in while visiting family in the area. We used the kitchen to cook a meal during one of the stays and we had everything we needed. There is an air hockey table in the basement which the kids enjoyed. The house is on a main road, but it was still easy enough to pull in and out of and the noise of the road did not bother us at all....
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.

10.0 out of 10, Exceptional, (22)
"This was our third year in a row staying at this house for our annual ski trip with 4 adults and 6 kids. It is always immaculate and has great common rooms for all of us. Kari and Glenn think of everything and Glenn even came to shovel the walkway and driveway for us during a snow storm (without even having to enter the house). We look forward to our time at this beautiful property every year! "
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.

Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

9.4 out of 10, Exceptional, (6)
"Location is minutes away from town. Location was easy to find. House was very clean and had all that we needed. Perfect size for our group of 5 adults, each having our own bedroom. We found plenty to do in the area. Jane was very helpful giving us information of things to do, especially being a girl's weekend, she informed us of spas, shopping and great spots to see foliage, and nice restaurant nearby that had music. Would definitely stay here again."
Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

Massachusetts Vacation Rental w/ Deck & Grill

9.2 out of 10, Wonderful, (12)
"This place was spectacular. Definitely suggest staying here if you're looking in the area. Everything was spotless. "
Massachusetts Vacation Rental w/ Deck & Grill

SPACIOUS Mountain Retreat with HOT TUB, Fire Pit & Hiking Trails

10.0 out of 10, Exceptional, (9)
"The property was beautiful. The owners were responsive and helpful. There were 6 of us plus an infant. Plenty of normal amenities and supplies. We had an amazing time and will consider staying again in the future."
SPACIOUS Mountain Retreat with HOT TUB, Fire Pit & Hiking Trails
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, (1764)
"Super clean and spacious. Rooms have everything you need for a long stay."
The price is AED 400
AED 476 total
includes taxes & fees
3 Mar - 4 Mar
Vacation Village in the Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is AED 694
AED 762 total
includes taxes & fees
23 Feb - 24 Feb
Jiminy Peak Mountain Resort
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.