A lake surrounded by autumn-colored trees and hills.

Cheshire Vacation Rentals

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Cheshire vacation rentals

Lobby

1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,544 reviews)
"Pool and staff was great"
United States
peter
$128 nightly
The price is $143
Aug 31 - Sep 1
Total with taxes and fees
Vacation Village in the Berkshires
Lobby

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,077 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
$125 nightly
The price is $139
Aug 31 - Sep 1
Total with taxes and fees
Berkshire Mountain Lodge
Living area

3. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (14 reviews)
"Our stay was beautiful! The check in process was super easy and the building was easy to access. The apartment was very clean and it was a lovely stay."
United States
Margaret C.
$252 nightly
The price is $281
Aug 20 - Aug 21
Total with taxes and fees
Penthouse Apartment on Park Street
Outdoor dining

4. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.4 out of 10, Very Good, (10 reviews)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
$482 nightly
The price is $539
Aug 19 - Aug 20
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Property grounds

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

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (39 reviews)
"Gorgeous place.Great stay.Will diff be backG"
United States
Gerard C.
$463 nightly
The price is $517
Aug 24 - Aug 25
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Coffee/tea maker, fridge, microwave, oven

6. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (31 reviews)
"This was a wonderful place to stay. We especially loved the easy access to the toys so the kids could start playing while we unloaded the car. It was perfect and just what we needed."
United States
Megan A.
$293 nightly
The price is $327
Aug 31 - Sep 1
Total with taxes and fees
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Gift shop

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

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (5 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
$216 nightly
The price is $241
Aug 19 - Aug 20
Total with taxes and fees
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Pool

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

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (4 reviews)
"Quiet location"
United States
Alicia S.
$211 nightly
The price is $236
Aug 18 - Aug 19
Total with taxes and fees
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Pool

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

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hancock
9.6 out of 10, Exceptional, (35 reviews)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
$298 nightly
The price is $333
Aug 18 - Aug 19
Total with taxes and fees
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Gift shop

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

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
$227 nightly
The price is $253
Aug 20 - Aug 21
Total with taxes and fees
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A heated pool

11. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very Good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
$535 nightly
The price is $542
Aug 19 - Aug 20
Total with taxes and fees
Comfortable Berkshires retreat on mtn resort, SISO
Pool

12. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
9.8 out of 10, Exceptional, (25 reviews)
"We stayed here twice this season and it was wonderful. The unit was clean, conveniently located and was fully equipped with all the essentials, making our stay comfortable and seamless from start to finish. We will definitely be back!"
United States
Kristina L.
$211 nightly
The price is $236
Aug 18 - Aug 19
Total with taxes and fees
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Dining

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

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
$560 nightly
The price is $602
Sep 16 - Sep 17
Total with taxes and fees
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Outdoor dining

14. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (18 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
$240 nightly
The price is $270
Aug 18 - Aug 19
Total with taxes and fees
New Studio In Town, By the Water
House (3 Bedrooms) | Interior

15. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
$499 nightly
The price is $554
Aug 24 - Aug 25
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Interior

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

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
8.0 out of 10, Very Good, (2 reviews)
"Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again."
United States
Ruthie K.
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
Indoor pool, a heated pool

17. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6 reviews)
"Convenience to slopes and restaurants really great….,had a nice stay"
United States
Thomas S.
$211 nightly
The price is $236
Aug 18 - Aug 19
Total with taxes and fees
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Pool

18. Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock
9.8 out of 10, Exceptional, (76 reviews)
"Helpful host, lovely condo. Great location. Clean, tons of games and movies in unit. Also plenty of coffee pods included!"
United States
Christy F.
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Pool

19. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.8 out of 10, Exceptional, (6 reviews)
"Good stay. Convenient to ski slopes. Thankful for Pet Friendly."
United States
Jim H.
$313 nightly
The price is $349
Aug 18 - Aug 19
Total with taxes and fees
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Outdoor dining

20. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
$1,060 nightly
The price is $1,149
Sep 9 - Sep 10
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cheshire Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Place was clean and well equipped, pool and amenities were great too !"
Nyra 3-night trip
Posted 4 hours ago
Vacation Village in the Berkshires

Find out more about Cheshire

Everything you need to know about Cheshire 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 Cheshire 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 Cheshire vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cheshire vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cheshire. 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 Cheshire 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 $139 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 Cheshire rentals

At Expedia, we put the best Cheshire 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 Cheshire 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 Cheshire 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 Cheshire. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Cheshire?

Yes, we offer vacation rentals close to the most popular sights in Cheshire, or you can go with a more remote option if you're looking for relaxation. Cheshire is known for its ski areas and restaurants. Make sure you have time to check out the lake views and shopping during your trip.

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

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: Visitors like this Cheshire vacation home rental. It 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.

How many vacation rentals are there in Cheshire?

Expedia has 5 vacation rentals for your stay in Cheshire.

What can I see and do in Cheshire?

Mount Greylock State Reservation and Cheshire Reservoir are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find St Mary's of the Assumption Church and Mount Greylock State Reservation Visitor Center.

What are vacation rentals like in Cheshire?

Vacation rentals are private properties you can reserve for a couple days or more in Cheshire. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for families.