New Ashford Vacation Rentals from CA $108: Short-Term Rentals for 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for New Ashford vacation rentals

1. Vacation Village in the Berkshires

Williamstown

Carol

CA $142 total

includes taxes & fees

Nov 10 - Nov 11

2. Berkshire Mountain Lodge

Pittsfield

Susan J

CA $153 total

includes taxes & fees

Dec 6 - Dec 7

A cozy living room with a large window, wooden walls, and a television.

3. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Hancock

Maura D.

CA $300 total

includes taxes & fees

Nov 10 - Nov 11

A rustic wooden interior with shelves stocked with various products, a 'Tree-Free' sign, and a section with bottled beverages.

4. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Hancock

Neil J.

CA $300 total

includes taxes & fees

Nov 10 - Nov 11

A spacious living area with a stone fireplace, comfortable seating, and a view of the kitchen.

5. UNIQUE - 1BR Country Condo @ Jiminy Peak

Hancock

Nancy P.

CA $789 total

includes taxes & fees

Nov 10 - Nov 11

6. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

CA $730 total

includes taxes & fees

Nov 10 - Nov 11

A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

7. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Hancock

David

CA $300 total

includes taxes & fees

Nov 10 - Nov 11

A rustic wooden interior with various stalls selling items like books, snacks, and wine.

8. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Hancock

Ann

CA $300 total

includes taxes & fees

Nov 10 - Nov 11

A bedroom with a wooden bed frame, a large window, and a painting of mountains on the wall.

9. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Hancock

patricia f.

CA $300 total

includes taxes & fees

Nov 10 - Nov 11

A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

10. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Hancock

Eileen O.

CA $300 total

includes taxes & fees

Nov 10 - Nov 11

A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.

11. Penthouse Apartment on Park Street

Adams

Lisa M.

CA $377 total

includes taxes & fees

Nov 10 - Nov 11

A row of multi-story buildings with a uniform architectural style, likely a hotel or resort, set against a backdrop of green hills and trees.

12. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Hancock

Dana

CA $300 total

includes taxes & fees

Nov 10 - Nov 11

13. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Hancock

Shmaya G.

CA $418 total

includes taxes & fees

Nov 10 - Nov 11

"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

14. Downtown | Waterfront | Walk to Shops

Williamstown

Douglas

CA $421 total

includes taxes & fees

Nov 15 - Nov 16

"Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping." ...Lina -- "the fire pit and creek are like a private oasis in the backyard." ... Nachama -- ( no firewood fees )

15. 2-Bdr Apt In Town, By the Water

Williamstown

Thomas

CA $412 total

includes taxes & fees

Nov 11 - Nov 12

16. New Studio In Town, By the Water

Williamstown

Lydia J.

CA $394 total

includes taxes & fees

Nov 15 - Nov 16

A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

17. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

CA $1,540 total

includes taxes & fees

Nov 17 - Nov 18

A wooden deck with outdoor furniture, a glass door leading to a view of a grassy area with trees.

18. Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views

Hancock

"I chose this place at the very last minute. It was all that I expected and wanted and more: two bedrooms with three beds, a comfortable living space, two full bathrooms, kitchen with all the basic necessities, TV in each bedroom and in the living room, a dining table and chairs, an outside porch with table, a big open space, and grill, easy parking and access, quiet, .and access to two pools. The place was well tended: clean, with towels and extras blankets ready. Howard, the owner, checked on...

Cecilia S.

CA $401 total

includes taxes & fees

Nov 11 - Nov 12

A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

19. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Williamstown

Michelle B.

CA $772 total

includes taxes & fees

Nov 24 - Nov 25

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

20. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Stephentown

CA $830 total

includes taxes & fees

Nov 10 - Nov 11

View all properties

Find vacation rentals that suit your style

Top New Ashford Hotel Reviews

Vacation Village in the Berkshires

Williamstown

10/10 Excellent

Kiril

A garden with a swing set, a blue chair, and a flower bed.

Maple Terrace Motel

Williamstown

10/10 Excellent

Tanya

A wooden cabin with a porch and steps leading to a door, surrounded by snow.

Jiminy Peak Mountain Resort

Hancock

10/10 Excellent

Rémi

Hotel Downstreet, an Ascend Collection Hotel

North Adams

10/10 Excellent

Tara

A patio area with wooden chairs and tables, surrounded by dense greenery and trees.

Willows Motel Williamstown

Williamstown

10/10 Excellent

Alexander

A building entrance with a large planter with purple flowers and a small tree.

Hotel On North

Pittsfield

10/10 Excellent

alan

A fire feature with a metal frame and a brick wall in the background.

Fairfield Inn & Suites by Marriott Williamstown

Williamstown

10/10 Excellent

Brian

A fire pit with four Adirondack chairs arranged around it, overlooking a snowy landscape with distant mountains.

Blue Vista Motor Lodge

North Adams

10/10 Excellent

patricia

A small, single-story building with a green roof and a white exterior. There are two large trees in front of the building, each with a flower pot on top. The surrounding area has grass, a few pumpkins, and a small garden with red flowers.

Williamstown Motel

Williamstown

10/10 Excellent

Guy

A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

The Trail in Adams - Berkshires’ Art Hotel

Adams

10/10 Excellent

Priscilla

An outdoor seating area with Adirondack chairs and potted plants.

Cozy Corner Motel

Williamstown

10/10 Excellent

alain

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A New Ashford vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of New Ashford vacation rentals we have selected for you start as low as CA $108 per night. Entering your travel dates in the search wizard 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.

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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental outside of New Ashford is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

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.

New Ashford Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for New Ashford vacation rentals

1. Vacation Village in the Berkshires

2. Berkshire Mountain Lodge

3. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

4. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

5. UNIQUE - 1BR Country Condo @ Jiminy Peak

6. Comfortable Berkshires retreat on mtn resort, SISO

7. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

8. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

9. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

10. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

11. Penthouse Apartment on Park Street

12. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

13. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

14. Downtown | Waterfront | Walk to Shops

15. 2-Bdr Apt In Town, By the Water

16. New Studio In Town, By the Water

17. Hancock Village Inn Near Jiminy Peak

18. Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views

19. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

20. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Find vacation rentals that suit your style

Top New Ashford Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

Find out more about New Ashford

New Ashford vacation rentals: An excellent choice for every season

How to find incredible deals on New Ashford rentals

Frequently Asked Questions

Are there vacation rentals in New Ashford?

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

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

What’s a vacation rental in New Ashford like?