New Ashford Holiday Rentals from AU$147: Search Short-Term Rentals

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Our top choices for New Ashford holiday rentals

1. Vacation Village in the Berkshires

Williamstown

Carol

includes taxes & fees

9 Nov - 10 Nov

2. Berkshire Mountain Lodge

Pittsfield

Charline

includes taxes & fees

6 Dec - 7 Dec

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.

includes taxes & fees

9 Nov - 10 Nov

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.

includes taxes & fees

9 Nov - 10 Nov

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.

includes taxes & fees

9 Nov - 10 Nov

6. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

includes taxes & fees

9 Nov - 10 Nov

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

includes taxes & fees

9 Nov - 10 Nov

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

includes taxes & fees

10 Nov - 11 Nov

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.

includes taxes & fees

9 Nov - 10 Nov

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.

includes taxes & fees

9 Nov - 10 Nov

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.

includes taxes & fees

9 Nov - 10 Nov

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

includes taxes & fees

10 Nov - 11 Nov

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

Hancock

Shmaya G.

includes taxes & fees

9 Nov - 10 Nov

14. Downtown | Waterfront | Walk to Shops

Williamstown

Douglas

includes taxes & fees

15 Nov - 16 Nov

"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

includes taxes & fees

9 Nov - 10 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)

16. New Studio In Town, By the Water

Williamstown

Lydia J.

includes taxes & fees

15 Nov - 16 Nov

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.

includes taxes & fees

9 Nov - 10 Nov

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

11 Nov - 12 Nov

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.

includes taxes & fees

23 Nov - 24 Nov

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

includes taxes & fees

9 Nov - 10 Nov

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Top New Ashford Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"We had a very comfortable stay."

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good

"We had a good stay the staff when I arrived was super nice and personable and we really like the amenities. I really like the water that was filtered in the front and the breakfast was very good choices. Our room was very clean and the TV selection was great."

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, 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 favourite 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 depend 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 AU$147 per night. Entering your travel dates in the search wizard might find you 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.

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.

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Check prices for these dates

Our top choices for New Ashford holiday 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 holiday rentals that suit your style

Top New Ashford Hotel Reviews

Berkshire Mountain Lodge

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Williams Inn

Best Western Plus Berkshire Hills Inn & Suites

Find out more about New Ashford

Frequently asked questions

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