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Compare 228 Vacation Homes in New Ashford with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (241)
"This beautiful carriage house is ingeniously designed with no wasted space. Surrounded by nature, it is totally private, yet it is two minutes from shops and restaurants. The window seats are sublime and the heated floors offered relief after afternoons spent hiking in the cold. "
The price is SAR 563
SAR 842 total
includes taxes & fees
17 Apr - 18 Apr
Berkshire Village Carriage House - Super Private!!

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
The price is SAR 2,248
SAR 4,122 total
includes taxes & fees
7 May - 8 May
Hancock Village Inn at Jiminy Peak

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (70)
"Was as nice as the pictures. A plus for a very comfortable king sized bed! Right in town for walking to shops and restaurants. Thank you!"
Heart of Lenox Walk to Town Cozy Cottage!

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (4)
"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Mountain Blossom Retreat by Evergreen Home

10.0 out of 10, Exceptional, (5)
"Had a great long weekend getaway in Lanesboro. The property manager was super communicative, which was helpful. Would highly recommend!"
Mountain Blossom Retreat by Evergreen Home

Near Tanglewood: Historic Summer Retreat

9.4 out of 10, Exceptional, (20)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
Near Tanglewood: Historic Summer Retreat

Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring

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. "
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring

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

10.0 out of 10, Exceptional, (121)
"Would definetely stay again.IF....LOL minor but not so minor.Need t.v. in master bedroom.Would not be a huge iinvestment.Cc"
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.6 out of 10, Exceptional, (42)
"Ben and I enjoyed a good long weekend at the correctly described Beautiful Lenox Home. Mary, your host, has thought of everything to help you feel comfortable and very quickly to adjust to your home away from home. It is very well located so that you can easily visit the many places of interest nearby. The rules for checking in and out were clear and simple. We are delighted give this a 5-star rating. David and Ben will return, for sure!"
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

10.0 out of 10, Exceptional, (4)
"We had a great weekend stay here with our dog. He loved the backyard and felt right at home. Everything was clean and great location."
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

Dancing Horse Lodge

9.4 out of 10, Exceptional, (40)
"Cozy home with a cabin like feel. Plenty of room and warmth. The 3 bedrooms accommodated our group perfectly! Easy check in instructions"
Dancing Horse Lodge

Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond

10.0 out of 10, Exceptional, (34)
"We had a wonderful time at this property! It was perfect for what we wanted- a place to ourselves in nature with beautiful views. Host was great! Would definitely recommend! "
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond

Sophisticated Lenox Retreat by Evergreen Home

9.8 out of 10, Exceptional, (9)
"Terrific location, centrally located in the Berkshires, and easy access to Lenox. The stairs were quite steep, which might make it challenging for anyone with mobility challenges. "
Sophisticated Lenox Retreat by Evergreen Home

Country Living just minutes from Everything!

10.0 out of 10, Exceptional, (28)
"Jandie's was the absolute best rental house we have ever stayed at. The house was clean and well kept, everything felt brand new. The set up was great, open kitchen, dining room and living room and made entertaining very easy. The kids had their own room and enjoyed spending time together in their own space. Julie was a pleasure to work with and accommodated us in anyway she could, from beginning to end. She even made us homemade delicious treats. We would highly recommend Jandie's and we...
Country Living just minutes from Everything!

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (139)
"We have stayed at this property twice before and have been very pleased with the amount of bedrooms and sleeping available. The property is always very clean and is equipped with everything you need for cooking and dining.the property is a half way point for family members in several directions. "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Comfortable Berkshires retreat on mtn resort, SISO

10.0 out of 10, Exceptional, (3)
"Family ski trip was made extremely enjoyable by staying at this property. Everything worked out as advertised"
The price is SAR 604
SAR 1,810 total
includes taxes & fees
29 Apr - 30 Apr
Comfortable Berkshires retreat on mtn resort, SISO

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

9.8 out of 10, Exceptional, (43)
"Did a ski weekend with a bunch of friends, the house was perfect, the character of the place and unique styling of each room was super fun, the hot tub was actually HOT, which was impressive for how cold it was outside. The house used to be an old bed and breakfast and it lends itself beautifully to being a VRBO for a large group. We had a wonderful time and would definitely come back and rent again! "
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

10.0 out of 10, Exceptional, (1)
"My friends and I stayed at this adorable and HUGE home in this lovely condo complex to spend the weekend at Ski Butternut which was only like 10 minutes away. The host even left us 2 bottles of wine! It had FIVE bathrooms which is unheard of, like anywhere, and the beds were the fancy adjustable kinds. TVs and cable in every bedroom. The fireplace was so luxurious. When the living room TV was giving us some connection issues I think it was a total of like 7 minutes to contact the host/co-host...
Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Experience the Beauty of the Berkshires and Hudson Valley in Our Historic Home

9.4 out of 10, Exceptional, (11)
"Of all the properties I have stayed at, this home is my favorite! Excited to be able to stay in a such a historical home in a rich historical area! Amanda was a wonderful host! Provided a comfortable stay. The home had all the necessities! The town has delicious places to eat. Grocery store is great! My hope is to return and spend more time here."
Experience the Beauty of the Berkshires and Hudson Valley in Our Historic Home

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 SAR 402
SAR 1,053 total
includes taxes & fees
17 Apr - 18 Apr
Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
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, (1797)
"The location to jimney peak was great."
The price is SAR 396
SAR 476 total
includes taxes & fees
23 Apr - 24 Apr
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (927)
"Staff was exceptionally helpful and friendly."
The price is SAR 503
SAR 562 total
includes taxes & fees
24 Apr - 25 Apr
Jiminy Peak Mountain Resort

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
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.