New Ashford Vacation Rentals from CA $151: Short-Term Rentals for 2026

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Our top choices for New Ashford vacation rentals

1. Vacation Village in the Berkshires

Williamstown

peter

CA $151 total

includes taxes & fees

Aug 31 - Sep 1

2. Berkshire Mountain Lodge

Pittsfield

Robert

CA $178 total

includes taxes & fees

Aug 31 - Sep 1

3. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

Hancock

Matthew B.

CA $383 total

includes taxes & fees

Aug 18 - Aug 19

4. Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Hancock

Alicia S.

CA $383 total

includes taxes & fees

Aug 18 - Aug 19

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

Hancock

patricia f.

CA $381 total

includes taxes & fees

Aug 16 - Aug 17

6. Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Hancock

John F.

CA $385 total

includes taxes & fees

Aug 19 - Aug 20

7. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

Hancock

Thomas S.

CA $381 total

includes taxes & fees

Aug 16 - Aug 17

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

Hancock

Joe C.

CA $369 total

includes taxes & fees

Aug 18 - Aug 19

9. New Studio In Town, By the Water

Williamstown

Lydia J.

CA $392 total

includes taxes & fees

Aug 18 - Aug 19

10. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Hancock

Jim H.

CA $532 total

includes taxes & fees

Sep 9 - Sep 10

11. Downtown | Waterfront | Walk to Shops

Williamstown

Michael P.

CA $426 total

includes taxes & fees

Aug 23 - Aug 24

12. Penthouse Apartment on Park Street

Adams

Margaret C.

CA $389 total

includes taxes & fees

Aug 25 - Aug 26

13. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Maura L.

CA $757 total

includes taxes & fees

Aug 16 - Aug 17

14. 2-Bdr Apt In Town, By the Water

Williamstown

Dan R.

CA $414 total

includes taxes & fees

Sep 10 - Sep 11

15. Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake

Linda R.

CA $255 total

includes taxes & fees

Aug 17 - Aug 18

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

Hancock

Jen B.

CA $381 total

includes taxes & fees

Aug 16 - Aug 17

17. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

North Adams

Ruthie K.

CA $295 total

includes taxes & fees

Aug 17 - Aug 18

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

Hancock

Todd A.

CA $564 total

includes taxes & fees

Aug 18 - Aug 19

19. Berkshires Apartment at the Stephentown Hotel

Stephentown

Nicole O.

CA $378 total

includes taxes & fees

Aug 17 - Aug 18

20. Cozy Home in Pownal VT

Pownal

Jess M.

CA $269 total

includes taxes & fees

Sep 13 - Sep 14

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Top New Ashford Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"The room was clean and the beds comfortable. The bathroom was small but nice. Lots of construction in the parking areas but luckily we got a parking space. Staff was friendly and helpful. We ate at the hotel, the food was good."

The Yankee Inn

10/10 Excellent

"Seamless stay from check in to check out. All the important things like cleanliness and updated bathroom with working faucets, great shower, lots of towels, etc. and unusual amenities like “two” swimming pools as well as hiking (walking) trail and ponds in the rear of the hotel property. Breakfast offerings had a big variety of foods similar to other hotels that offer full breakfast buffets. Located on a business strip with supermarkets and other useful retail stores however the hotel sits back from the road so is fairly quiet especially at night. Our room had a wide covered balcony with Adirondack chairs. Small fire-pit area out in front of the man entrance. Personally, I would have preferred a softer bed but was not uncomfortable and it did not affect my sleep. Linens and pillows were very nice, fluffy, and very clean. No funky hotel odors in the room or halls. The staff was very friendly, polite and helpful. It shows that this facility makes every effort to run a great hotel and please their customers."

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

8/10 Good

"Shower base was very slippery-dangerous. Air-conditioning controls were poor. Thermostat was difficult to adjust and there was no ability to direct the cold air from the fan away from directly blowing on the bed. Had to move furniture to block it. Everything else was fine."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Loved our two-day stay at the Black Swan Inn. We were in the area because we were taking a few programs at the Kripalu Center for one of the days. The room itself was clean, the hall areas could do with better maintenance (which is why I gave that 4 stars) The staff was helpful with any questions. Continental breakfast was decent (though they could do with better coffee). We wished we could have enjoyed the Indian restaurant "Mint" next door, which I hear is really good, but they were closed on Tuesdays, so it was a matter of timing..., but we hope to have a chance next time we are in the area. One of my favorite parts of the property is that it sits by a clean lovely lake, and there are seating areas to enjoy the view anytime of day just to unwind. They also have kayak rentals for those who enjoy the activity. Another wonderful treat- it is near High Lawn Farm, only a 3-min drive from the Inn. It is beautiful there, and cute Jersey cows roam freely, when they are ready they go on their own time into a building where they lay on heated water beds while being milked (I kid you not!). Their dairy products and ice-cream are excellent, worth taking the short drive there. The town center of Lee has some nice restaurants and boutiques within a 5-8 min drive. It was a memorable stay and hope to be back there again soon."

Berkshires Untold

8/10 Good

"Lovely man at check in for our overnight ( to see Hugh Jackman at 7 pm at Tanglewood lucky us!👍 Checked that food would be available in their bar upon our trying as has driven 2+ hrs assured yes until just before 10 pm closing. Called once on way back at 9:10 for 10 min drive to dbl check as hungry. Woman said no, they stopping serving at 9... luckily she rec one place nearby which was still open for food til midnight! Wow in Lenox! Very packed loud and fun w locals & Jackman fans..got wines, friendly bartenders, ordered yummy plates of tacos , sandwich and ended eve on a great note . Go to OMBRA if hungry after 9! Small complaint this am also.. we ordered a bagel & a berry salad from the hotel's brkfst menu to go as needed to drive back home mid am.. Opened it and about 1/2 cup of mixed berries ..for $11.00... Think the bagel was 8. Oh well -worth the splurge to see Hugh 💕and only 10 min drive to Tanglewood & downtown Lenox! Hotel not walkable to anything but ez parking & very cute interior & bar & seating areas!"

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 $151 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.

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Check prices for these dates

Our top choices for New Ashford vacation rentals

1. Vacation Village in the Berkshires

2. Berkshire Mountain Lodge

3. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

4. Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

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

6. Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

7. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

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

9. New Studio In Town, By the Water

10. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

11. Downtown | Waterfront | Walk to Shops

12. Penthouse Apartment on Park Street

13. Comfortable Berkshires retreat on mtn resort, SISO

14. 2-Bdr Apt In Town, By the Water

15. Taborton Harvest Boulder Pines Cabin in the woods

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

17. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

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

19. Berkshires Apartment at the Stephentown Hotel

20. Cozy Home in Pownal VT

Find vacation rentals that suit your style

Top New Ashford Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Vacation Village in the Berkshires

The Yankee Inn

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Jiminy Peak Mountain Resort

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Berkshires Untold

Hotel Downstreet, an Ascend Collection Hotel

The Williams Inn

Find out more about New Ashford

Frequently asked questions

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