Top Hotels in Cheshire, MA from SAR 225 - Fully Refundable Options

Q: What are some of the best vacation rentals in Cheshire?

Berkshire Village Carriage House - Super Private!! : This vacation home rental outside of Cheshire is located in the mountains and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind. See all vacation rentals in Cheshire .

Compare 948 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

"Lovely space and welcoming host."

SAR 1,066 total

includes taxes & fees

31 Mar - 1 Apr

"This is a great venue. It is affordably priced, conveniently located, artfully maintained in accordance with it original style (wooden floors and picket rail porch, antique furniture, etc.). I felt unique and pampered in my room. I even heard a train whistle nearby in the early wee hours of the morning, reassuring and comforting rather than disturbing. I hope to return for a longer stay."

SAR 410 total

includes taxes & fees

3 Mar - 4 Mar

Single Room | In-room safe, desk, free WiFi, bed sheets

"I rarely take the time to review anywhere I’ve stayed, but this place has stolen my heart! Its absolutely breathtaking property is second only to the friendliness of the staff. We couldn’t get enough of the sauna and hot tub with a view of the mountains, as well ans the evening firepit surrounded by andirondak chairs. The rooms and building is well maintained seemingly brand new. One of very few places I would stay again over and over! "

SAR 624 total

includes taxes & fees

2 Mar - 3 Mar

"The Trail in Adams offered me exactly what I needed: a quiet and convenient place prepare for a day in the woods the next day. Very convenient walking to nearby restaurants, right in the middle of Adams. There was a snowstorm that night, and the walks were shoveled several times that evening and the next morning. "

SAR 728 total

includes taxes & fees

1 Mar - 2 Mar

Indoor pool, open 6:00 AM to 10 PM, sun loungers

"Newly redecorated in black and white motif. Clean and comfortable"

SAR 495 total

includes taxes & fees

16 Mar - 17 Mar

"Lovely place to stay. Wonderful breakfast."

SAR 834 total

includes taxes & fees

2 Mar - 3 Mar

Individually decorated, individually furnished, desk, laptop workspace

"room was clean heater was noisy bed was too soft pillow mattress no shampoo dont think they checked on our room after 1st night no coffee, cups room 101"

SAR 314 total

includes taxes & fees

3 Mar - 4 Mar

"Nice place. Made fresh waffle mix when I asked. No complaints"

SAR 353 total

includes taxes & fees

16 Mar - 17 Mar

"I think some of the unfavorable reviews I have seen are unfair. Everything is relative and, yes, this is clearly an older property that appears to be privately owned. Notwithstanding its age and some of the dated decor and furnishing, my room was very clean (cleaner than some I have stayed in at upscale hotels). It was one of the coldest nights of the year and the heat worked well and the water was hot. The television and WiFi worked and for my purposes (a one night layover on my way to visit...

SAR 302 total

includes taxes & fees

1 Mar - 2 Mar

Desk, iron/ironing board, free WiFi, bed sheets

"Quiet "

SAR 260 total

includes taxes & fees

13 Mar - 14 Mar

"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."

SAR 796 total

includes taxes & fees

2 Mar - 3 Mar

Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds

"It was close to Butternut on a snowy day. Very good for the value and what it is."

SAR 251 total

includes taxes & fees

2 Mar - 3 Mar

"Beautiful property, great service "

SAR 1,043 total

includes taxes & fees

4 Mar - 5 Mar

"Two adults and a baby to enjoy winter wonderland: it worked very well! Very close to everything! "

SAR 424 total

includes taxes & fees

6 Mar - 7 Mar

"Great stay again. My family has been going here 3 years in a row, and its always a great experience "

SAR 551 total

includes taxes & fees

2 Mar - 3 Mar

"We loved the history of the hotel and how well they preserved many features of the property. Loved the suite and view of the lake. Everyone that works there was very kind and attentive."

SAR 554 total

includes taxes & fees

1 Mar - 2 Mar

"Very clean and comfortable with great restaurant and bar downstairs"

SAR 547 total

includes taxes & fees

2 Mar - 3 Mar

"Great location. Pleasant staff."

SAR 289 total

includes taxes & fees

1 Mar - 2 Mar

"spacious room. "

SAR 331 total

includes taxes & fees

1 Mar - 2 Mar

"Good for a sound sleep and basic breakfast"

SAR 419 total

includes taxes & fees

2 Mar - 3 Mar

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Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking, and natural setting.

See all hotels in Cheshire

The road less traveled sometimes is absolutely beautiful. In a month this will be a great spot for Autumn. I will repost the exact same foliage shot and see if I am correct. Excited to do it actually..

Stay near popular Cheshire attractions

St Mary's of the Assumption Church

5/5(1 review)

Learn about the local history of Cheshire with a stop at St Mary's of the Assumption Church. Discover the area's mountain views, or seek out its ski slopes.

Recent reviews of Cheshire hotels

5/5 Excellent

Dr.’s Orders

"Absolutely outstanding! After a day of skiing at Jiminy my son & I checked into vacation village. Quick and efficient check in at the front desk by the gentleman working. Drove around to our bldg. unloaded our gear, changed into our swim trunks, grabbed a couple of cold ones and walked across the road to the hot tub! Just what the Dr. ordered! Our unit was clean & comfortable, slept great & were up and out early in the morning."

A verified traveler stayed at Vacation Village in the Berkshires

Posted 12 hours ago

The Constance, The Whitlock, & The Dewey By The Lenox Collection

5/5 Excellent

"Our one night at The Constance recently (February 2025), was fantastic! The inn is warm and welcoming, spotlessly clean, and beautifully decorated with lots of vintage charm and all the comfy, modern conveniences one would expect. We absolutely loved it! Each staff member we had contact with (Logan, Brenda and Stacy) was professional and friendly. Communication was efficient and timely. As we were in Lenox off-season, the inn was exceptionally quiet, with only two other rooms booked during our one-night stay. We got to meet the other guests in the dining area after dinner, and stayed chatting with them long into the evening. The inn offered free snacks (small bags of pretzels, chips, trail mix, etc), fresh fruit (apples), granola bars, super-cute hot chocolate bar, tea and coffee, all self-serve, 24 hours a day! In our room, a beautiful glass decanter was filled with water along with two drinking glasses. An elegant touch! We really appreciated the Eco-friendly liquid soap, lotion, shampoo and conditioner dispensers, and each product had a beautiful scent and felt luxurious. The continental breakfast was fresh and beautifully presented (self-serve) in the dining area from 7:00 am - 9:00 am: hard boiled eggs, bagels, (gluten-free bagels as well), croissants, fresh fruit, yogurt, granola, orange and cranberry juice, tea, coffee. Delicious! Plenty to do in the area, within walking distance of the inn. Can't wait to return! Highly recommend! "

A verified traveler stayed at The Constance, The Whitlock, & The Dewey By The Lenox Collection

Posted 3 days ago

5/5 Excellent

Cozy New England Inn

"This was my first stay at the Williams Inn and I found it the coziest hotel I've stayed at! The furnishings are lovely and the lobby area very inviting (especially in the winter when the fire is always going). There's also - unfortunately, I didn't discover this until the end of my stay - a little nook area off to the side with books, games, and complimentary fruit water. The rooms were lovely and clean. The bathroom and shower were mostly clean except for some black spots near the bottom of one part of the shower wall and floor. The air unit for the most part actually kept the room temperature well controlled (which seems to be rare these days). In all, our little group enjoyed our stay and would definitely like another visit."

A verified traveler stayed at The Williams Inn

Posted 3 days ago

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

5/5 Excellent

"Great stay again. My family has been going here 3 years in a row, and its always a great experience "

A verified traveler stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

Posted 4 days ago

5/5 Excellent

Great option in the Berkshires!!

"There are many small, single room,camp-like former motels in the Berkshires. Many tend towards shabbiness and neglect— not this one! I found my room warm and inviting with lots of little decorative touches that were imaginative and made me smile. The inclusion of a reading chair and writing desk is a huge plus for me. The bed was super comfortable, great pillows, nice linens. HVAC worked beautifully— I could reduce the temperature, a huge thing on a cold night when most folks would want to be toasty— me, not so much. The shower and bathroom were gorgeous with neat tiles and great water pressure. You don’t get the felling of being in a gross cookie cutter corporate gulag, rather pleasantly nestled in a unique and whimsical den."

A verified traveler stayed at Life House Berkshires

Posted 5 days ago

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Frequently asked questions

What's the best place to stay in Cheshire?

Located 9.8 mi (15.8 km) from the heart of Cheshire, Hotel Downstreet, Ascend Hotel Collection is a top choice for your stay based on our traveler data. Other good options for your stay in the area are Vacation Village in the Berkshires and Life House Berkshires. See all available top hotels, or vacation rentals in Cheshire.

What are some of the best vacation rentals in Cheshire?

Berkshire Village Carriage House - Super Private!!: This vacation home rental outside of Cheshire is located in the mountains and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind. See all vacation rentals in Cheshire.

If I need to cancel my hotel reservation in Cheshire, will I receive a refund?

Yes! Most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might be able to still cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Cheshire.

Where can I learn more about changing or cancelling my trip to Cheshire?

To find more details about updating your trip to Cheshire or cancelling it, click here.

What is the favorite LGBTQ-friendly accommodation in Cheshire?

Harbour House Inn is a top LGBTQ-friendly B&B, and features free breakfast and free WiFi.

What is the best hotel near Albany International Airport (ALB)?

Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.

What is staying in Cheshire like?

Visitors can enjoy all that Cheshire has to offer including the ski areas, restaurants, and lake views. Tourists can also enjoy so much more including its shopping. In Cheshire, there are 3 hotels and other accommodations to choose from. Find out more about Cheshire.

What are the top places to visit in Cheshire?

A couple of favorite places to visit are Mount Greylock State Reservation and St Mary's of the Assumption Church. You'll also find Mount Greylock State Reservation Visitor Center and Mount Greylock in the area. Check out what more to see and do in Expedia's Cheshire guide.

What's the seasonal weather like in Cheshire?

The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

Find hotels in Cheshire, MA from SAR 225

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Compare 948 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Harbour House Inn

Harbour House Inn

Blooming Inn

Blooming Inn

Blue Vista Motor Lodge

Blue Vista Motor Lodge

The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

Pilgrim Inn

Pilgrim Inn

Quality Inn

Quality Inn

Sunset Inn

Sunset Inn

FairBridge Inn Express

FairBridge Inn Express

Chambery Inn

Chambery Inn

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

Devonfield Inn B&B

Devonfield Inn B&B

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Lakehouse Inn

Lakehouse Inn

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Wagon Wheel Inn

Wagon Wheel Inn

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown

Learn more about Cheshire

Stay near popular Cheshire attractions

Stay near popular Cheshire attractions

St Mary's of the Assumption Church

Recent reviews of Cheshire hotels

Recent reviews of Cheshire hotels

Vacation Village in the Berkshires

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Stay near popular Cheshire attractions

More Hotel Options in Cheshire

More Accommodation Types in Cheshire

Hotels near Cheshire Airports

Cheshire Hotels by Brand

Other Hotels near Cheshire, Massachusetts

Explore more hotels

Frequently asked questions