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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

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

Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (246)
"What a great spot to stay for the few days we were there Can’t wait to come back! "
Berkshire Village Carriage House - Super Private!!
Hancock Village Inn at Jiminy Peak
Miscellaneous

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Very kinda hosts, and wonderful house."
The price is AED 2,016
AED 3,810 total
includes taxes & fees
19 May - 20 May
Hancock Village Inn at Jiminy Peak
Heart of Lenox Walk to Town Cozy Cottage!
Fridge, microwave, oven, stovetop

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (72)
"Going to the Berkshires this is a great place to stay. It is within walking distance to over 8 restaurants in downtown Lenox. Great gas stove and comfortable bed. Owner makes sure your stay is great. Would stay here again. "
Heart of Lenox Walk to Town Cozy Cottage!
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Property grounds

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

10.0 out of 10, Exceptional, (5)
"Our group of 8 were happy in this comfy home. The kitchen was well appointed with everything we needed. The bedding, towels and toiletries provided were very much appreciated. The cozy living room with the pellet stove has a beautiful view for morning coffee. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Mountain Blossom Retreat by Evergreen Home
A heated pool

Mountain Blossom Retreat by Evergreen Home

10.0 out of 10, Exceptional, (5)
"Lovely ski weekend! Best memory: hot tubbing at sunset after skiing with snow falling all around! "
Mountain Blossom Retreat by Evergreen Home
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop

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
Exterior

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

10.0 out of 10, Exceptional, (10)
"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."
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Dining

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

10.0 out of 10, Exceptional, (121)
"The property was great for our group of 8. Slept everyone comfortably, with plenty of places to hangout and lounge all together. We had planned to cook in for a couple meals, so it was a hugely pleasant surprise to see that the kitchen was stocked with every cooking utensil, serving dish, and glassware that you could possibly need. We were maybe even more prepared than in my own kitchen at home. Also very well located. Had an excellent stay and would come back!"
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Interior

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.6 out of 10, Exceptional, (42)
"Absolutely no complaints. Great place to stay, great host! Happy 2025 wishes from our family to everyone reading this post! "
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Dancing Horse Lodge
Fridge, microwave, oven, stovetop

Dancing Horse Lodge

9.4 out of 10, Exceptional, (42)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
Property grounds

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
Exterior

Sophisticated Lenox Retreat by Evergreen Home

9.8 out of 10, Exceptional, (9)
"Very quaint location, clean property, and great place to stay"
Sophisticated Lenox Retreat by Evergreen Home
Country Living just minutes from Everything!
Fridge, microwave, oven, stovetop

Country Living just minutes from Everything!

10.0 out of 10, Exceptional, (28)
"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!
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

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

9.8 out of 10, Exceptional, (142)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Comfortable Berkshires retreat on mtn resort, SISO
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

9.6 out of 10, Exceptional, (4)
"Hosts were very responsiveHouse was clean and well maintainedExcellent locationOverall great stay"
The price is AED 591
AED 1,739 total
includes taxes & fees
19 May - 20 May
Comfortable Berkshires retreat on mtn resort, SISO
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Terrace/patio

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

9.8 out of 10, Exceptional, (43)
"Had a fantastic weekend with a group of 16! The teenagers claimed the upstairs, allowing the adults to relax in the main rooms and kitchen. The beds were cozy, and the bathrooms were spotless, which was a nice bonus since each family had their own. The kitchen is a bit small but has everything we needed. Enjoying the hot tub after a long day of skiing was the highlight! It was the perfect getaway for our group. Thank you Chris!"
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate
Fridge, microwave, oven, stovetop

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
Terrace/patio

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

9.4 out of 10, Exceptional, (11)
"One of the best places we have stayed. Comfortable in every way. Great recommendations from the hosts."
Experience the Beauty of the Berkshires and Hudson Valley in Our Historic Home
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (29)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
The price is AED 411
AED 1,052 total
includes taxes & fees
19 May - 20 May
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
19th c. Barn in the Berkshires
Interior

19th c. Barn in the Berkshires

9.6 out of 10, Exceptional, (87)
"My wedding party and I stayed here for my wedding weekend. It was so magical and an amazing place to stay!"
19th c. Barn in the Berkshires
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
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1806)
"The property was clean and the staff very accommodated."
The price is AED 403
AED 490 total
includes taxes & fees
19 May - 20 May
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (929)
"Out dated not many resort like options "
The price is AED 493
AED 550 total
includes taxes & fees
19 May - 20 May
Jiminy Peak Mountain Resort
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (121)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
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.