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Compare 172 Vacation Homes in New Ashford with updated reviews, rates, and availability.

Private Lake House in the Berkshires
9.8 out of 10, Exceptional, (15)
"This was our first VRBO experience, and we are hooked. We had a wedding in Pittsfield with events over three days, so we decided to try this lakeside retreat, and it was a treat! The Berkshires in the fall are absolutely beautiful and Hinsdale is a pretty little town. Ozzie's is definitely worth the trip for breakfast. The lake is lovely and we were looking forward to kayaking and fishing. Unfortunately the weather was not on our side, but we still got one fish! Mary is a wonderful host who is...
Private Lake House in the Berkshires
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (118)
"Comfortable, quiet and convenient country location. This is our third time staying at the property for fishing and exploring the Deerfield and Westfield rivers and we will definitely return."
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, (68)
"What an amazing find to stay at while attending a yoga festival at Jiminy Peak. The house was immaculate and didn't miss a thing! Not only was there a bottle of wine waiting, but an adorable history of the home. The house was HUGE and the beds very comfortable. I wouldn't call it a 3 bedroom house though, it's a 2 bedroom with a pull out sofa in the living room. The hot tub is amazing and watching the starts and fireflies in the backyard at night was magical. Highly recommend and would stay...
Hearts Desire is a furnished whole house in a small, colorful garden center.
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Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo
9.8 out of 10, Exceptional, (59)
"Worked well for our small team. Close enough to the base area to walk."
The price is SAR 1,309
SAR 2,415 total
includes taxes & fees
30 Jun - 1 Jul
30 Jum. II - 1 Raj.
Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, (28)
"This is a great spot for a getaway! The space was spotless. There was a lot of privacy. The location was close to everything we needed. The space is cozy and super fun with the hot tub and fore pit! We we are able to enjoy the included breakfast, which was great before skiing!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, (4)
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, (93)
"Everything is basic but solid and comfortable. Beds were nice and firm, my preference. Host was lovely. Wish we could have stayed longer to explore the area more."
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Private Access To Laurel Lake, Enjoy Lake Life
10.0 out of 10, Exceptional, (6)
"My brother and I came to honor our late father, our family used to own property on Laurel lake so it was especially meaningful to us to have access to it for kayaking. The house has central ac which is harder to find, it's got plenty of bedrooms, two of which are on the first floor."
Private Access To Laurel Lake, Enjoy Lake Life
Hudson Valley Chalet
9.2 out of 10, Wonderful, (5)
"We had such a nice weekend at this beautiful home! The location was great, there were awesome views, and Marc was a very kind, courteous host! He was very easy to get ahold of if we had any questions. The hot tub was very relaxing and spacious. Also, it had all of the necessities. If you are looking for a family-friendly winter rental this is a great place to book."
Hudson Valley Chalet
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
9.4 out of 10, Exceptional, (3)
"My BF and I really enjoyed the Hawley Home. The location was stunning and quiet. The owner was very kind and responsive when I reached out with questions before we started out on our drive to the location. There was a welcome book with all of the information on the home and it included information about the local attractions. The property is clean, the bed is comfortable and the views are breathtaking. There is no cell service ( not that is a bad thing with as much as we work) but the home has...
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Tiny house & hot tub nestled on 150+ acres of the Green Mtns of Vermont.
10.0 out of 10, Exceptional, (2)
"The tiny house was absolutely relaxing. It was perfectly located close enough to the main are but yet far enough away for peace. The hosts were so quick to respond and the house was clean and welcoming, hot tub was amazing! Can’t wait to go back!!"
Tiny house & hot tub nestled on 150+ acres of the Green Mtns of Vermont.
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (206)
"Had an absolutely amazing time! great location, quiet, close to everything! Plenty of things to do nearby, and host left plenty of brochures to find food or activities. Only minor downer was that the oven seemed touchy"
Berkshire Village Carriage House - Super Private!!
Amore Estate - sleeps 12 in beds
9.6 out of 10, Exceptional, (8)
"Great space for a group of friends! House has a lot of character. Beautiful property and great location! Easy access to downtown Lenox and surrounding area. We really enjoyed our stay!"
Amore Estate - sleeps 12 in beds
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
9.8 out of 10, Exceptional, (8)
"House was perfect for our family to gather and celebrate my son’s graduation from Bennington. Sean was very quick to respond to questions."
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!
10.0 out of 10, Exceptional, (25)
"Great home, truly beautiful surroundings and easy drive to lots of stuff. We tackled Mass MoCA, kayaking in Brattleboro and mountain adventures at Bromley. Plus all the small towns and pit stops along the way. Very family friendly house with basement for older kids and well child-proofed for any youngsters."
Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
9.0 out of 10, Wonderful, (24)
"The cabin was clean and quiet and suited our needs for the weekend. The hot tub was enjoyable, although I would recommend that the owners purchase stairs to make exit and entry a bit easier."
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
Gorgeous Lake Ashmere Home with Private Hot Tub & Lake Views, Screened Porch
10.0 out of 10, Exceptional, (11)
"This was the perfect venue for our family getaway with our adult children and their spouses."
Gorgeous Lake Ashmere Home with Private Hot Tub & Lake Views, Screened Porch
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!
10.0 out of 10, Exceptional, (70)
"A beautiful cabin in the woods. Very clean and a perfect stay."
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!
Lovely Secluded Vermont Home: Stocked Pond, Trails, A/C. 5 Mins to Williamstown!
9.6 out of 10, Exceptional, (9)
"We will be back! Our stay was top notch. Everything we hoped and more. The owner was very responsive and kind, the property is breathtaking and peaceful and the location is very convenient."
Lovely Secluded Vermont Home: Stocked Pond, Trails, A/C. 5 Mins to Williamstown!
North Getaway Cottage
9.6 out of 10, Exceptional, (18)
"This home was perfect for five of us to reconnect after many years! Williamstown was beautiful and suited our needs. We enjoyed both the nearby Clark Museum and Mass MOCA, as well as Mt. Greylock. Since all of us were coming from different directions, we had five cars and thankfully, this house has plenty of parking. I’d recommend this VRBO highly, especially for family of students at Williams College."
The price is SAR 844
SAR 1,790 total
includes taxes & fees
27 Jun - 28 Jun
27 Jum. II - 28 Jum. II
North Getaway Cottage
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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.

Other property types in New Ashford

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (860)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is SAR 597
SAR 654 total
includes taxes & fees
20 Jun - 21 Jun
20 Jum. II - 21 Jum. II
Jiminy Peak Mountain Resort
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (118)
"Comfortable, quiet and convenient country location. This is our third time staying at the property for fishing and exploring the Deerfield and Westfield rivers and we will definitely return."
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, (28)
"This is a great spot for a getaway! The space was spotless. There was a lot of privacy. The location was close to everything we needed. The space is cozy and super fun with the hot tub and fore pit! We we are able to enjoy the included breakfast, which was great before skiing!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
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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