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New Ashford Vacation Rentals

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Vacation Rentals in New Ashford

Lobby
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2097)
"Great place!"
United States
Nicole
$112 nightly
The price is $125
Oct 30 - Oct 31
Total with taxes and fees
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (983)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
$140 nightly
The price is $157
Oct 26 - Oct 27
Total with taxes and fees
Jiminy Peak Mountain Resort
Interior
UNIQUE - 1BR Country Condo @ Jiminy Peak
UNIQUE - 1BR Country Condo @ Jiminy Peak
10.0 out of 10, Exceptional, (14)
"Clean and quiet, nicely decorated! "
United States
Robert
$280 nightly
The price is $313
Oct 24 - Oct 25
Total with taxes and fees
UNIQUE - 1BR Country Condo @ Jiminy Peak
Game room
Park Street Penthouse Apartment
Park Street Penthouse Apartment
9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
$175 nightly
The price is $196
Oct 27 - Oct 28
Total with taxes and fees
Park Street Penthouse Apartment
TV
Florida Mountain Log Cabin!
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.
$383 nightly
The price is $405
Oct 26 - Oct 27
Total with taxes and fees
Florida Mountain Log Cabin!
1 bedroom, iron/ironing board, WiFi, bed sheets
Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi
Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi
10.0 out of 10, Exceptional, (1)
"Great!"
United States
Susan M.
$214 nightly
The price is $239
Oct 27 - Oct 28
Total with taxes and fees
Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi
Exterior
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
10.0 out of 10, Exceptional, (23)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
$214 nightly
The price is $239
Oct 27 - Oct 28
Total with taxes and fees
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Exterior
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
10.0 out of 10, Exceptional, (4)
"It was great experience and we loved the ammenities."
United States
Carrie C.
$214 nightly
The price is $239
Oct 27 - Oct 28
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Outdoor dining
Green Mountain Getaway
Green Mountain Getaway
2.0 star property
9.8 out of 10, Exceptional, (15)
"Great one night stay for a work trip. Common living space and bedrooms are very large. Very clean especially the bathroom. "
United States
Robyn H.
$360 nightly
The price is $382
Oct 27 - Oct 28
Total with taxes and fees
Green Mountain Getaway
3 bedrooms, iron/ironing board, WiFi, bed sheets
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
10.0 out of 10, Exceptional, (2)
"as advertised."
United States
Joshua G.
$561 nightly
The price is $628
Nov 3 - Nov 4
Total with taxes and fees
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Outdoor dining
2-Bdr Apt In Town, By the Water
2-Bdr Apt In Town, By the Water
9.4 out of 10, Exceptional, (9)
"Lovely property, in good shape. Close to many Williamstown attractions."
United States
Scott M.
$240 nightly
The price is $270
Oct 26 - Oct 27
Total with taxes and fees
2-Bdr Apt In Town, By the Water
Outdoor dining
Downtown | Waterfront | Walk to Shops
Downtown | Waterfront | Walk to Shops
10.0 out of 10, Exceptional, (6)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
$246 nightly
The price is $277
Oct 26 - Oct 27
Total with taxes and fees
Downtown | Waterfront | Walk to Shops
Indoor pool
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
10.0 out of 10, Exceptional, (3)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
$214 nightly
The price is $239
Oct 27 - Oct 28
Total with taxes and fees
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Exterior
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
9.4 out of 10, Exceptional, (16)
"We absolutely enjoyed this pleasant apartment. Its within the walking distance from the ski lifts which was perfect for all of us including 5 year old kid. "
United States
Janja
$214 nightly
The price is $239
Oct 27 - Oct 28
Total with taxes and fees
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Outdoor dining
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
9.0 out of 10, Wonderful, (2)
"very nice and roomy! really enjoyed."
United States
Shack M.
$269 nightly
The price is $300
Oct 27 - Oct 28
Total with taxes and fees
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel
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.
$206 nightly
The price is $220
Nov 10 - Nov 11
Total with taxes and fees
Berkshires Apartment at the Stephentown Hotel
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (33)
"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.
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Fridge, microwave, oven, stovetop
New Studio In Town, By the Water
New Studio In Town, By the Water
10.0 out of 10, Exceptional, (8)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
$229 nightly
The price is $257
Oct 26 - Oct 27
Total with taxes and fees
New Studio In Town, By the Water
Pool
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
8.0 out of 10, Very Good, (8)
"Cozy little condo, good for a group of four or five. We stayed there with my two kids 8 &10 and wife. It’s a nice place overall we had a great time. It is a short drive to the slopes, which is fine as long as you have a car but you still need to park at the inn"
United States
Sam R.
$300 nightly
The price is $335
Oct 27 - Oct 28
Total with taxes and fees
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISO
8.8 out of 10, Excellent, (6)
"Kind and responsive host."
United States
Javier
$481 nightly
The price is $488
Oct 26 - Oct 27
Total with taxes and fees
Comfortable Berkshires retreat on mtn resort, SISO
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
"We loved this place. Quiet, very clean,attractive. Loved that it had a kitchen area. Second story, sliding glass doors overlooked the fall foliage in the back of the building. Very peaceful.."
Steven 4-night trip
Posted 1 day ago
Berkshire Mountain Lodge

Find out more about New Ashford

Everything you need to know about New Ashford vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the New Ashford vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect New Ashford vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

New Ashford vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in New Ashford. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit New Ashford in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $125 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on New Ashford rentals

At Expedia, we put the best New Ashford vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top New Ashford rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream New Ashford vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around New Ashford. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox: This vacation home rental outside New Ashford is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.