Cheshire Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Cheshire vacation rentals

Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,210 reviews)
"I great place to stay!!"
United Kingdom
Maricel
$126 nightly
The price is $141
Jan 19 - Jan 20
Total with taxes and fees
Vacation Village in the Berkshires
Interior

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$337 nightly
The price is $376
Jan 21 - Jan 22
Total with taxes and fees
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Living area

Spacious Ground Floor 2/3 Bed private suite 5 minutes walk to Bridge of Flowers

Spacious Ground Floor 2/3 Bed private suite 5 minutes walk to Bridge of Flowers
2.0 star property
Shelburne Falls
9.6 out of 10, Exceptional, (4 reviews)
"Great property and location for a visit to Shelburne Falls. "
United States
Kevin K.
$315 nightly
The price is $352
Jan 18 - Jan 19
Total with taxes and fees
Spacious Ground Floor 2/3 Bed private suite 5 minutes walk to Bridge of Flowers
Exterior

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (13 reviews)
"Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "
United States
Joanna R.
$165 nightly
The price is $183
Jan 17 - Jan 18
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
Exterior

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7 reviews)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
$169 nightly
The price is $188
Jan 18 - Jan 19
Total with taxes and fees
Huttopia Berkshires
Exterior

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very Good, (989 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
$219 nightly
The price is $245
Jan 19 - Jan 20
Total with taxes and fees
Jiminy Peak Mountain Resort
WiFi, bed sheets

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse
Lanesborough
9.6 out of 10, Exceptional, (67 reviews)
"What a quaint and comfy place!"
United States
Lori A.
$189 nightly
The price is $208
Jan 19 - Jan 20
Total with taxes and fees
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Outdoor dining

Little Longbow Lakefront Chalet

Little Longbow Lakefront Chalet
Becket
9.8 out of 10, Exceptional, (21 reviews)
"Absolutely perfect quiet get away to relax and recharge will be back! "
United States
Dana V.
Little Longbow Lakefront Chalet
Exterior

2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
$157 nightly
The price is $175
Jan 19 - Jan 20
Total with taxes and fees
2 Twin beds on 1st floor with En-suite bathroom.
TV

Florida Mountain Log Cabin

Florida Mountain Log Cabin
2.0 star property
Florida
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
$317 nightly
The price is $340
Jan 19 - Jan 20
Total with taxes and fees
Florida Mountain Log Cabin
Beach

Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (3 reviews)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
$212 nightly
The price is $226
Jan 19 - Jan 20
Total with taxes and fees
Berkshires Apartment at the Stephentown Hotel
Property grounds

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, (35 reviews)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
$411 nightly
The price is $459
Jan 20 - Jan 21
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Pool

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
2.0 star property
Hancock
10.0 out of 10, Exceptional, (1 review)
"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "
United States
Jeffrey R.
$247 nightly
The price is $276
Jan 19 - Jan 20
Total with taxes and fees
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Exterior

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

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Bennington
8.6 out of 10, Excellent, (34 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
$251 nightly
The price is $266
Feb 4 - Feb 5
Total with taxes and fees
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
House (3 Bedrooms) | Interior

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
Jan 19 - Jan 20
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Interior

Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers
Stephentown
7.0 out of 10, Good, (2 reviews)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
$265 nightly
The price is $294
Jan 31 - Feb 1
Total with taxes and fees
Charming 3-bedroom Cabin for nature lovers
Living area

Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
2.0 star property
Adams
9.6 out of 10, Exceptional, (14 reviews)
"Clean property, easy check in, and the owner was super communicative. "
United States
Amanda W.
$219 nightly
The price is $245
Jan 19 - Jan 20
Total with taxes and fees
Penthouse Apartment on Park Street
Exterior

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.2 out of 10, Wonderful, (25 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
$315 nightly
The price is $352
Jan 20 - Jan 21
Total with taxes and fees
Near Tanglewood: Historic Summer Retreat
Exterior

14mi to Mt. Snow! Arcade, Private Suite, King Bed!

14mi to Mt. Snow! Arcade, Private Suite, King Bed!
Whitingham
10.0 out of 10, Exceptional, (14 reviews)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
$517 nightly
The price is $579
Jan 20 - Jan 21
Total with taxes and fees
14mi to Mt. Snow! Arcade, Private Suite, King Bed!
Exterior

The Allen House historic North Adams Home in the Berkshire Mountains

The Allen House historic North Adams Home in the Berkshire Mountains
2.0 star property
North Adams
10.0 out of 10, Exceptional, (1 review)
"The Allen House was a wonderful stay for my family and we cannot wait to go back! The view was incredible; the host was very approachable for questions; and there were lots of nice touches like ample dishes and silverware.Very spacious, clean and cared for location. "
United States
Annemarie M.
$349 nightly
The price is $390
Jan 20 - Jan 21
Total with taxes and fees
The Allen House historic North Adams Home in the Berkshire Mountains
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
"It is one of my favorite places to go but sometimes it is overcrowded and the people can be rude and rowdy. But the staff is fantastic they do a great job even with the crowds. "
Maria 4-night trip
Posted 9 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 $141 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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: Visitors like this Cheshire vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable 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 selection of games and a hot tub.

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?

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 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.