New Ashford Holiday Rentals from €90: Search Short-Term Rentals

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Our top choices for New Ashford holiday rentals

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

1. Vacation Village in the Berkshires

Williamstown

Adrianne

includes taxes & fees

1 Nov - 2 Nov

A snow-covered outdoor area with a fire pit, tables, and chairs.

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

Hancock

Maura D.

includes taxes & fees

20 Oct - 21 Oct

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

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

Hancock

Ann

includes taxes & fees

20 Oct - 21 Oct

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

4. Berkshire Mountain Lodge

Pittsfield

Joel

includes taxes & fees

19 Nov - 20 Nov

"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)

5. New Studio In Town, By the Water

Williamstown

Lydia J.

includes taxes & fees

22 Oct - 23 Oct

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

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

Hancock

Tom C.

includes taxes & fees

22 Oct - 23 Oct

Four people seated at a table with food and drinks, wearing winter sports helmets.

7. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Hancock

Wendy D.

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

8. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

Hancock

Thomas S.

includes taxes & fees

22 Oct - 23 Oct

A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

9. Berkshires Apartment at the Stephentown Hotel

Stephentown

Nicole O.

includes taxes & fees

20 Oct - 21 Oct

A wicker sofa with a floral cushion, a wicker table with magazines, and a standing fan in a room with large windows and wooden floors.

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

North Adams

Ruthie K.

includes taxes & fees

20 Oct - 21 Oct

11. Downtown | Waterfront | Walk to Shops

Williamstown

Douglas

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.

12. Penthouse Apartment on Park Street

Adams

Margaret C.

includes taxes & fees

20 Oct - 21 Oct

"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 )

13. 2-Bdr Apt In Town, By the Water

Williamstown

Thomas

includes taxes & fees

15 Nov - 16 Nov

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

Hancock

Shmaya G.

includes taxes & fees

22 Oct - 23 Oct

15. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

includes taxes & fees

16 Nov - 17 Nov

16. Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Hancock

shannon m.

A wooden cabin with a porch, a door, and a window.

17. Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake

Nathan

includes taxes & fees

20 Oct - 21 Oct

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.

includes taxes & fees

20 Oct - 21 Oct

A two-story blue house with a porch, surrounded by a garden with orange flowers.

19. Getaway Near Mass MoCA, Great Hiking, Scenic Views

Stamford

Bill

includes taxes & fees

20 Oct - 21 Oct

20. Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- Home Away From Home

Hancock

Rony N.

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Top New Ashford Hotel Reviews

Jiminy Peak Mountain Resort

10/10 Excellent

"The suite was clean with full kitchen. There are a lot of fun activities within the property. We felt safe during our entire stay."

Berkshire Mountain Lodge

8/10 Good

"I had a one BR suite for 4 nights and it was a perfect amount of space for 3 people. Kitchen was very well-equipped and convenient to have for making simple meals and reheating leftovers. While all the cooking utensils/ basics were provided, remember to bring all your oil/ spices as I did. I can't believe there was even a blender to use! Bedroom was spacious with comfortable bed. I can't say the same for the sofa bed, but that's expected. The entire space may appear slightly dated (doesn't bother me), but everything was clean and completely functional, which was allI wanted and needed. If you are a light sleeper, it may help to be in a corner room as walls might be somewhat thinner for some."

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"We had a fantastic one-night stay at The Cornell Inn! From the moment we checked in—where we were greeted with delicious brownies in the lobby—the staff were super nice and welcoming. They truly went above and beyond to make sure we had everything we needed. We stayed in K11 - The Edith Wharton Room, which featured a comfortable queen bed and was fully equipped with all the essentials, plus a lovely bottle of wine waiting for us. The hotel is spotlessly clean, and the decoration throughout is absolutely beautiful and cozy. The staff did a wonderful job with breakfast. Everything was fresh and delicious—do not skip it! We also loved the outside area. It was so relaxing to sit in a rocker chair, surrounded by beautiful vegetation, watching the fish. We highly recommend this inn and can't wait to return!"

The Yankee Inn

8/10 Good

"Lovely, super clean unit with nice furnishings, however, the dining chair cushions need a good cleaning as the dirt could be seen. There also was candy/gum stuck to one of the cushions and another cushion was completely loose from the chair. There was mention of a "two-burner hotplate" in the description, but the photos showed a two-burner electric stove top. What actually is there is a two-burner infared hotplate. Instructions on how to use it is posted on the wall above the sink, not on the wall above the hotplate. Unfortunately, we were assigned an end unit in Building #13, which is currently being renovated. There was a family occupying the unit above us. The children ran up and down the stair and allowed the outside door to slam each and every time until late in the evening. No noise during quiet hours though. :o)"

Find out more about New Ashford

Everything you need to know about New Ashford holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the New Ashford holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

New Ashford holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of New Ashford holiday rentals we have selected for you start as low as €90 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 holiday 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 holiday.

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.

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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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of New Ashford is located near skiing, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday 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 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.

Holiday Rentals in New Ashford

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Check prices for these dates

Our top choices for New Ashford holiday rentals

1. Vacation Village in the Berkshires

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

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

4. Berkshire Mountain Lodge

5. New Studio In Town, By the Water

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

7. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

8. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

9. Berkshires Apartment at the Stephentown Hotel

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

11. Downtown | Waterfront | Walk to Shops

12. Penthouse Apartment on Park Street

13. 2-Bdr Apt In Town, By the Water

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

15. Comfortable Berkshires retreat on mtn resort, SISO

16. Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

17. Taborton Harvest Boulder Pines Cabin in the woods

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

19. Getaway Near Mass MoCA, Great Hiking, Scenic Views

20. Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- Home Away From Home

Find holiday rentals that suit your style

Top New Ashford Hotel Reviews

Jiminy Peak Mountain Resort

Find out more about New Ashford

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