New Ashford Vacation Rentals from $121: Search Short-Term Rentals

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Our top choices for New Ashford vacation rentals

Vacation Village in the Berkshires

Williamstown

Melissa

$145 nightly

Jun 7 - Jun 8

Total with taxes and fees

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Sand Lake

$166 nightly

Jun 6 - Jun 7

Total with taxes and fees

The Greylock Cabin

Florida

Ron L.

$407 nightly

Jun 7 - Jun 8

Total with taxes and fees

Bear Creek Cabin

Charlemont

Andrew P.

$539 nightly

Jun 10 - Jun 11

Total with taxes and fees

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

Stephentown

$499 nightly

Jun 7 - Jun 8

Total with taxes and fees

A stunning, modern Lodge with rustic charm at June Farms!

West Sand Lake

LisaL

$712 nightly

Jun 21 - Jun 22

Total with taxes and fees

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Hinsdale

Gerard C.

$400 nightly

Jun 9 - Jun 10

Total with taxes and fees

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Whitingham

Joshua G.

$718 nightly

Jun 14 - Jun 15

Total with taxes and fees

Brookside cottage near the mountains and outdoor recreation

Readsboro

Seva L.

$212 nightly

Jun 8 - Jun 9

Total with taxes and fees

Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake

Lea

$165 nightly

Jun 6 - Jun 7

Total with taxes and fees

Treat yourself at the stunning June Farms Wellness Huts!

West Sand Lake

Lauren C.

$509 nightly

Jun 15 - Jun 16

Total with taxes and fees

Green Mountain Getaway

Bennington

Meredith Y.

$383 nightly

Jun 7 - Jun 8

Total with taxes and fees

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Bennington

"We had a great family getaway here! The hot tub was amazing and the views from the hot tub were perfect. What a beautiful location - quiet, peaceful and a fun space for kids to explore. We had an amazing time trekking out in the woods in the snow.Kitchen was well stocked and the treats, coffee and tea were a nice bonus. My kids enjoyed the extra games as well! Extremely quick responses from the host as well! Thanks for a good time, we are already thinking about coming back in the summer."

Amanda H.

$281 nightly

Jun 8 - Jun 9

Total with taxes and fees

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Stamford

Bill

$128 nightly

Jun 7 - Jun 8

Total with taxes and fees

Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont

Marianne B.

$466 nightly

Jun 12 - Jun 13

Total with taxes and fees

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Hancock

Jason P.

$307 nightly

Jun 9 - Jun 10

Total with taxes and fees

Near Tanglewood: Historic Summer Retreat

New Lebanon

Karen H.

$343 nightly

Jun 7 - Jun 8

Total with taxes and fees

Luxury, modern AIRSTREAM at June Farms!

West Sand Lake

StephenS

$498 nightly

Jun 15 - Jun 16

Total with taxes and fees

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

Hancock

Maura D.

$218 nightly

Jun 9 - Jun 10

Total with taxes and fees

Cozy Home in Pownal VT

Pownal

Jess M.

$182 nightly

Jun 9 - Jun 10

Total with taxes and fees

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Top New Ashford Hotel Reviews

Hotel Vervana, Trademark Collection by Wyndham

10/10 Excellent

"Great staff and the stay was what we needed in a quiet peaceful town. Thank you"

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good

"Hi, for the most part, my stay was fantastic. The staff were excellent. Breakfast was awesome! The Restaurant and Bar were great! My one negative comment is about the lack of hot water in the morning for me to take a shower. Very disappointing. I am coming back there the next 2 weeks and I hope that the Hot Water situation will be rectified."

The Whitlock

8/10 Good

"We had a late arrival, which worked out with self checkout. Left the next morning after 9am, didn't see a single staff member during our whole stay, Was a bit of a challenge getting luggage up to the top floor without an elevator but we probably should have realized that when we booked. Nice property, nice big room with separate area for visiting. TV channel choices, which included streaming services, was excellent. Overall a good experience, just didn't see anyone there."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Wonderful hidden gem of a little hotel. Right on lake laurel we had a beautiful lake view. Rooms were very clean. Decent breakfast. Well Located and close to Lee downtown main st, the Lennox Main Street and Stockbridge as well. Looking forward to returning"

Berkshires Untold

8/10 Good

"Here’s what we liked: If we were just reviewing BERKSHIRES UNTOLD based on the staff, we’d be giving it a 5. The staff were extremely friendly, helpful and gracious. When we asked for extra towels and requested a room change, they accommodated those requests immediately. After we switched rooms they checked to see if we were happier. This is exactly the kind of service you want in a hotel or inn. Other good things - The bed was comfortable and there was enough counter space in the bathroom and at the desk area. We also liked that there was a breakfast seating area, bar and small indoor seating area plus outdoor seating with gas fire pits. So, why are we giving the place a 3 overall? It really needed more attention to detail. The carpet in our original room was not in good shape and the fitted bed sheet had a small rip on my side. Some of the room furniture was dinged up and a sofa in the common seating area had some shredded fabric. One thing we didn’t like (that they couldn’t exactly help) was that we were there on a late spring wedding weekend, so there were buses idling in front of our room with loud talkers and smokers nearby. It felt like they were in our room along with the smoke and fumes. The trend of turning motels into better motels is interesting. They’re less expensive and are sometimes more original. But you’re still in a motel. If you value soundproofing and consistently better quality, a mid range chain may be a better choice."

Berkshire Mountain Lodge

10/10 Excellent

"We love the Bershire Mountain Lodge. We've stayed here five other times but this time we do have a few very minor negatives. 1) The cabinet door under the kitchenette sink had a loose hinge. We messaged the staff and requested that they wait until after we checked out to repair the hinge. We hope the hinge was repaired before the next guest checked in. 2) The toilet flush handle was slightly cracked but still functional. We forgot to notify the staff; it was barely noticeable. 3) The guest or owner in the room above our room walked very loudly. We were used to hearing noises from people walking in the hall but this was our first time hearing footsteps through the ceiling. Other than those three items, our stay was excellent. The front desk staff were courteous and helpful. The housekeeping crew were unobtrusive. The long driveway to the ample parking lot gives enough distance from the busy"

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 $121 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.

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?

120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views: This vacation home rental outside of New Ashford offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 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 balcony, a garden, and a selection of games 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 Williamstown Theatre Festival.

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

Vacation Village in the Berkshires

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

The Greylock Cabin

Bear Creek Cabin

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

A stunning, modern Lodge with rustic charm at June Farms!

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Brookside cottage near the mountains and outdoor recreation

Taborton Harvest Boulder Pines Cabin in the woods

Treat yourself at the stunning June Farms Wellness Huts!

Green Mountain Getaway

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Riverbend Berkshire East Basecamp - 3 bedrooms available

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Near Tanglewood: Historic Summer Retreat

Luxury, modern AIRSTREAM at June Farms!

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

Cozy Home in Pownal VT

Find vacation rentals that suit your style

Top New Ashford Hotel Reviews

Hotel Vervana, Trademark Collection by Wyndham

Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Whitlock

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Berkshires Untold

Berkshire Mountain Lodge

Vacation Village in the Berkshires

Hampton Inn & Suites Berkshires-Lenox

Courtyard by Marriott Lenox Berkshires

Find out more about New Ashford

Frequently asked questions

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