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New Ashford Holiday Rentals

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Check prices for these dates

Tonight
6 Jan - 7 Jan
Tomorrow
7 Jan - 8 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

Our top choices for New Ashford holiday rentals

Lobby
Vacation Village in the Berkshires

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2203)
"I great place to stay!!"
United Kingdom
Maricel
The price is HK$809
HK$990 total
includes taxes & fees
8 Jan - 9 Jan
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (988)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is HK$1,705
HK$1,904 total
includes taxes & fees
8 Jan - 9 Jan
Jiminy Peak Mountain Resort
Fridge, microwave, oven, stovetop
Taborton Harvest Timber Trails Unique cabin experience

Cabin in Sand Lake

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."
United States
Georgia M.
The price is HK$973
HK$1,426 total
includes taxes & fees
8 Jan - 9 Jan
Taborton Harvest Timber Trails Unique cabin experience
Exterior
Getaway Near Mass MoCA, Great Hiking, Scenic Views

Apartment in Stamford

Getaway Near Mass MoCA, Great Hiking, Scenic Views
10.0 out of 10, Exceptional, (28)
"Nice property for a quick and simple check-in. Near MassMOCA, the Clark Art Institute and much more."
United States
Mario R.
The price is HK$526
HK$1,112 total
includes taxes & fees
8 Jan - 9 Jan
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Property grounds
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Cabin in Hinsdale

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (35)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
The price is HK$1,261
HK$3,261 total
includes taxes & fees
8 Jan - 9 Jan
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Beach
Berkshires Apartment at the Stephentown Hotel

Apartment in Stephentown

Berkshires Apartment at the Stephentown Hotel
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is HK$958
HK$1,848 total
includes taxes & fees
8 Jan - 9 Jan
Berkshires Apartment at the Stephentown Hotel
Outdoor dining
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Cottage in Nassau

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
10.0 out of 10, Exceptional, (2)
"Cozy home on the lake."
United States
Terry O.
The price is HK$1,226
HK$2,856 total
includes taxes & fees
8 Jan - 9 Jan
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
TV
Florida Mountain Log Cabin

Holiday Home in Florida

Florida Mountain Log Cabin
2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is HK$1,594
HK$2,854 total
includes taxes & fees
8 Jan - 9 Jan
Florida Mountain Log Cabin
Exterior
Near Tanglewood: Historic Summer Retreat

Holiday Home in New Lebanon

Near Tanglewood: Historic Summer Retreat
9.6 out of 10, Exceptional, (24)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is HK$1,098
HK$2,956 total
includes taxes & fees
21 Jan - 22 Jan
Near Tanglewood: Historic Summer Retreat
Interior
Charming 3-bedroom Cabin for nature lovers

Cabin in Stephentown

Charming 3-bedroom Cabin for nature lovers
7.0 out of 10, Good, (2)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
The price is HK$1,207
HK$2,489 total
includes taxes & fees
26 Jan - 27 Jan
Charming 3-bedroom Cabin for nature lovers
Pool
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Apartment in Hancock

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
2.0 star property
10.0 out of 10, Exceptional, (1)
"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "
United States
Jeffrey R.
The price is HK$1,067
HK$2,148 total
includes taxes & fees
8 Jan - 9 Jan
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Exterior
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Holiday Home in Bennington

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
8.6 out of 10, Excellent, (34)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is HK$934
HK$2,194 total
includes taxes & fees
8 Jan - 9 Jan
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Living area
Penthouse Apartment on Park Street

Apartment in Adams

Penthouse Apartment on Park Street
2.0 star property
9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is HK$903
HK$1,896 total
includes taxes & fees
8 Jan - 9 Jan
Penthouse Apartment on Park Street
Property grounds
Riverbend Berkshire East Basecamp - 3 bedrooms available

Holiday Home in Charlemont

Riverbend Berkshire East Basecamp - 3 bedrooms available
10.0 out of 10, Exceptional, (1)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is HK$1,246
HK$3,287 total
includes taxes & fees
12 Jan - 13 Jan
Riverbend Berkshire East Basecamp - 3 bedrooms available
Interior
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Holiday Home in Lebanon Springs

Historic Berkshires Home Near Tanglewood, Trails & Wineries
8.8 out of 10, Excellent, (20)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
The price is HK$1,051
HK$2,895 total
includes taxes & fees
8 Jan - 9 Jan
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Smart TV, books
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Holiday Home in Lee

Sun Filled Lenox Retreat - Minutes to Tanglewood!
9.4 out of 10, Exceptional, (3)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is HK$1,401
HK$3,583 total
includes taxes & fees
8 Jan - 9 Jan
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Interior
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Cottage in Stephentown

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
The price is HK$1,526
HK$4,310 total
includes taxes & fees
14 Jan - 15 Jan
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior
Huttopia Berkshires

Camping in Williamstown

Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is HK$1,489
HK$1,663 total
includes taxes & fees
8 Jan - 9 Jan
Huttopia Berkshires
Fridge, microwave, oven, stovetop
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Holiday Home in Hoosick Falls

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
9.8 out of 10, Exceptional, (100)
"Beautiful, serene location with great penned in area for my lovable, niece pup! Spacious house with all the key amenities. Easy access for my elederly mom. "
United States
Lynn F.
The price is HK$904
HK$2,403 total
includes taxes & fees
18 Jan - 19 Jan
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"The rooms are clean, the pool is nice and the location is perfect for Jiminy Peak! "
Julie 3-night trip
Posted 4 days ago
Vacation Village in the Berkshires

Find out more about New Ashford

Search for holiday rentals in New Ashford on Expedia! You can easily find your home rentals, villas, holiday apartments in New Ashford using one of the methods below:

  • View our selection of featured holiday rentals in New Ashford
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Look no further and take a look at our great range of rental properties in New Ashford!

Frequently asked questions

Are there holiday rentals in New Ashford?

Yes, there are holiday rentals close to the most popular sights in New Ashford, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that New Ashford has to offer?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This holiday home rental outside of New Ashford offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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 wider area, you’ll find Green River Wildlife Management Area and Brodie Mountain.

What’s a holiday rental in New Ashford like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in New Ashford. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a family getaway.