Cheshire Holiday Rentals from €94: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Cheshire has to offer?

Peace and quiet on the lake : This holiday home rental outside of Cheshire is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

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In two weeks

In two months

In three months

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Our top choices for Cheshire holiday rentals

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

Sand Lake

includes taxes & fees

12 Jun - 13 Jun

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

includes taxes & fees

10 Jun - 11 Jun

Private bed with En-suite bathroom Marigold Room

Shelburne Falls

includes taxes & fees

8 Jun - 9 Jun

Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake

Lea

includes taxes & fees

6 Jul - 7 Jul

Brookside cottage near the mountains and outdoor recreation

Readsboro

Seva L.

includes taxes & fees

9 Jun - 10 Jun

Rose room Victorian home queen bed private bath

Shelburne Falls

includes taxes & fees

8 Jun - 9 Jun

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Stamford

Bill

includes taxes & fees

7 Jun - 8 Jun

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

North Adams

includes taxes & fees

7 Jun - 8 Jun

The Greylock Cabin

Florida

Ron L.

includes taxes & fees

7 Jun - 8 Jun

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.

includes taxes & fees

8 Jun - 9 Jun

stylish Berkshires Retreat

Lee

includes taxes & fees

8 Jun - 9 Jun

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

Hinsdale

Gerard C.

includes taxes & fees

9 Jun - 10 Jun

Cozy Home in Pownal VT

Pownal

Jess M.

includes taxes & fees

7 Jun - 8 Jun

Huttopia Berkshires

Williamstown

GEORGINA

includes taxes & fees

7 Jun - 8 Jun

Downtown | Waterfront | Walk to Shops

Williamstown

Michael P.

includes taxes & fees

10 Jun - 11 Jun

Vacation Village in the Berkshires

Williamstown

Melissa

includes taxes & fees

9 Jun - 10 Jun

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

Stephentown

includes taxes & fees

5 Jul - 6 Jul

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

Hancock

Maura D.

includes taxes & fees

8 Jun - 9 Jun

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Whitingham

Jacklyn D.

includes taxes & fees

17 Jun - 18 Jun

Bear Creek Cabin

Charlemont

Andrew P.

includes taxes & fees

10 Jun - 11 Jun

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Top Cheshire Hotel Reviews

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 Cheshire

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

Cheshire holiday 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 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 Cheshire 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 Cheshire holiday rentals we have selected for you start as low as €94 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cheshire rentals

At Expedia, we put the best Cheshire 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 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 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 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.

Frequently asked questions

Can I find a holiday rental in Cheshire?

Yes, there are holiday rentals close to the most popular sights in Cheshire, or you can select a more secluded option if you're looking for a relaxing stay. 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 are some of the best holiday rentals that Cheshire has to offer?

Peace and quiet on the lake: This holiday home rental outside of Cheshire is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Cheshire?

Expedia has 5 holiday 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 wider area, you’ll find St Mary's of the Assumption Church and Mount Greylock State Reservation Visitor Center.

What are holiday rentals like in Cheshire?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cheshire. Holiday rentals feature extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family gatherings.

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Check prices for these dates

Our top choices for Cheshire holiday rentals

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

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Private bed with En-suite bathroom Marigold Room

Taborton Harvest Boulder Pines Cabin in the woods

Brookside cottage near the mountains and outdoor recreation

Rose room Victorian home queen bed private bath

Getaway Near Mass MoCA, Great Hiking, Scenic Views