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New Ashford Vacation Rentals

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Jul 20 - Jul 21
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Vacation Rentals in New Ashford

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1889)
"Great stay with all plenty of things to do…"
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, (948)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is ￥23,973
￥26,778 total
includes taxes & fees
Aug 3 - Aug 4
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
Huttopia Berkshires
Deluxe Tent | 2 bedrooms

Huttopia Berkshires

1.0 star property
Huttopia Berkshires
Taborton Harvest Boulder Pines Cabin in the woods
Exterior detail

Taborton Harvest Boulder Pines Cabin in the woods

10.0 out of 10, Exceptional, (11)
"Such a sweet spot in the woods! Can’t wait to come back."
The price is ￥16,071
￥24,446 total
includes taxes & fees
Jul 21 - Jul 22
Taborton Harvest Boulder Pines Cabin in the woods
Taborton Harvest Timber Trails Unique cabin experience
Fridge, microwave, oven, stovetop

Taborton Harvest Timber Trails Unique cabin experience

10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
The price is ￥17,857
￥26,428 total
includes taxes & fees
Jul 21 - Jul 22
Taborton Harvest Timber Trails Unique cabin experience
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Property grounds

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.8 out of 10, Exceptional, (11)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
The Kemble- Built by a US Secretary of State in Lenox
Exterior detail

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox
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, (145)
"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 ￥23,958
￥72,622 total
includes taxes & fees
Jul 21 - Jul 22
Comfortable Berkshires retreat on mtn resort, SISO
2200sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
Property grounds

2200sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

9.8 out of 10, Exceptional, (68)
"Beautiful location, very spacious, comfortable and clean."
2200sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
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, (8)
"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!
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft
Fireplace, books

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

9.6 out of 10, Exceptional, (34)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is ￥88,988
￥163,662 total
includes taxes & fees
Jul 28 - Jul 29
Hancock Village Inn at Jiminy Peak
Charming Apt in 18th c Berkshire Farmhouse
1 bedroom, WiFi, bed sheets

Charming Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (34)
"The property was perfect for us !! Lots of room and the beds are very comfortable. "
The price is ￥20,089
￥30,894 total
includes taxes & fees
Jul 21 - Jul 22
Charming Apt in 18th c Berkshire Farmhouse
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Exterior

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (58)
"We had a wonderful time and loved the house! We will definitely be back!"
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Amore Estate - beautiful room with many places to explore and relax in.
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (25)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Exterior

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

10.0 out of 10, Exceptional, (121)
"Had an amazing weekend in this beautiful cabin! Highly recommend staying here! Great host, amazing views, beautiful property!"
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Exterior

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (128)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Smart TV, fireplace, DVD player, music library

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

9.4 out of 10, Exceptional, (82)
"Nice place, just what we were looking for to stay the weekend. "
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
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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Top New Ashford Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Comfy place very clean "
Peter 2-night trip
Posted 2 days ago
Berkshire Mountain Lodge

Frequently asked questions

Are there vacation rentals in New Ashford?

Yes, there are vacation rentals close to the most popular local attractions in New Ashford, or you can choose a more remote option if you'd like a relaxing place to stay. New Ashford is known for its ski areas and mountain views. Make sure you have time to check out the festivals while you're in the area.

What's the top vacation rental that New Ashford has to offer?

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. : This vacation home rental outside of New Ashford offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What’s there to see and do in New Ashford?

While exploring the area, visit family-friendly sights like Berkshire Museum, or get outside and enjoy nature at Mount Greylock State Reservation. In the larger area, you’ll find Green River Wildlife Management Area and Brodie Mountain.

What’s a vacation rental in New Ashford like?

Vacation rentals are private accommodations you can stay in for a few days or a quick weekend in New Ashford. Vacation rentals provide amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for families.