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Compare 174 Vacation Homes in New Ashford with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is AED 536
AED 821 total
includes taxes & fees
2 Dec - 3 Dec
Berkshire Village Carriage House - Super Private!!
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Comfortable New Decor in Living Room Equipped w Smart TV and Deck

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
1 Dec - 2 Dec
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Breakfast Nook - wake up to the best sunshine ever!

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
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.
Christmas at Lakeview Retreat

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

10.0 out of 10, Exceptional, (20)
"clean, wonderful views of the lake. "
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
the house

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

10.0 out of 10, Exceptional, (33)
"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
Hearts Desire is a furnished whole house in a small, colorful garden center.
Exterior

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

10.0 out of 10, Exceptional, (82)
"My mom and I did a mother/daughter trip to the Berkshires in October. Everything about this property is perfect! Location was 5/10 min from groceries/restaurants but felt like we were in the middle of nowhere. The house itself was very clean and so comfortable (the bed felt like a dream)! We spent our days exploring the surrounding towns and our evenings relaxing at he house. We saw deer in the mornings and 2 bald eagles! Thank you for the incredible stay!! "
Hearts Desire is a furnished whole house in a small, colorful garden center.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Marina

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.
Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!
Lush woodland setting is private, yet five minutes to Spring Street.

Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!

9.8 out of 10, Exceptional, (19)
"Such a gorgeous house! We loved walking the nearby trails and how close it was to Williams. Venetia was the best!"
Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!
Plainfield House in a 10,000 acre state forest and private pond
Front lawn for sledding

Plainfield House in a 10,000 acre state forest and private pond

9.6 out of 10, Exceptional, (82)
"Perry was awesome and easy to connect with. Beds were all very comfortable and there are 2 large bathrooms easy to share with a big family. Everything is labeled in the house and it makes it so easy to do everything. We will look forward to staying here in the future! "
Plainfield House in a 10,000 acre state forest and private pond
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Exterior

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

The price is AED 1,348
AED 2,415 total
includes taxes & fees
1 Dec - 2 Dec
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Room

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
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
The house was originally built in 1864 and completely updated in 2009

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

9.6 out of 10, Exceptional, (40)
"This property is stunning. It fit our group of 14 perfectly. There are so many unique details and beautiful furniture. The kitchen was well-stocked for pots/pans/utensils/cleaning supplies which I always appreciate - makes group meals so much easier to manage. Quiet area, would be great all year round depending on what activities you like. Hot tub was a major highlight!"
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Perfect for Leaf Peeping w/Bar Room, Hot Tub
Bar Room

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
Near Tanglewood: Historic Summer Retreat
Living area

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (15)
"Amanda is a very responsive and accommodating host. The house was comfortable and perfect for our girls weekend with plenty of space for us to relax and feel at home. "
The price is AED 422
AED 1,161 total
includes taxes & fees
4 Dec - 5 Dec
Near Tanglewood: Historic Summer Retreat
Enjoy comfortable elegance in this secluded grand home located in town
Property grounds

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (65)
"Beautiful home perfect for our multi-generational family. We loved the separate spaces and easy walk to the town center. We can’t wait to come back!"
Enjoy comfortable elegance in this secluded grand home located in town
Private Access To Laurel Lake, Enjoy Lake Life

Private Access To Laurel Lake, Enjoy Lake Life

10.0 out of 10, Exceptional, (14)
"The property was better than advertised. Everything anyone could need was provided and we could not have hoped for a better experience. Very large home and could easily accomodate 8 people or more. The Berkshires are magical and this home was great for out time there."
Private Access To Laurel Lake, Enjoy Lake Life
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
Nighttime view

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
Dancing Horse Lodge
Dancing Horse Lodge - Entrance View

Dancing Horse Lodge

9.6 out of 10, Exceptional, (36)
"nice"
Dancing Horse Lodge
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!
Welcome! Plenty of space to yourselves to relax and soak in great outdoors!

Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

10.0 out of 10, Exceptional, (76)
"Very cute and quiet location! Cabin has everything ine would need! Plenty of parking, and there are trails throughout the property. Its in the perfect spot, only 18 minutes from town. "
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!
Spacious Historic Home in the Berkshires!
Pittsfield Vacation Rental | 5BR | 2BA | Stairs Required | 3,300 Sq Ft

Spacious Historic Home in the Berkshires!

9.6 out of 10, Exceptional, (5)
"This lovely home was ideal for my family of 8: my children and their spouses, two grandchildren, myself and two pups. The beds were plentiful and comfortable. The house, while old, was newly remodeled, adding modern appliances to the charm of the original building. Very bright and spacious in a quiet neighborhood, convenient to Lenox, Tanglewood, and other special towns. I highly recommend this home to anyone looking for a pleasant retreat. We loved every minute!"
Spacious Historic Home 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
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1746)
"Staff was very professional and polite "
The price is AED 620
AED 717 total
includes taxes & fees
1 Dec - 2 Dec
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, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is AED 657
AED 721 total
includes taxes & fees
29 Nov - 30 Nov
Jiminy Peak Mountain Resort
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is AED 536
AED 821 total
includes taxes & fees
2 Dec - 3 Dec
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.