Photo by Ed Gaffny

Cheshire Hotels from S$90

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Check prices for these dates

Tonight
25 Feb - 26 Feb
Tomorrow
26 Feb - 27 Feb
This weekend
28 Feb - 2 Mar
Next weekend
7 Mar - 9 Mar

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Top 10 trending Cheshire hotels

Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Lovely space and welcoming host."
The price is S$381
includes taxes & fees
17 Mar - 18 Mar
Harbour House Inn
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (78)
"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."
The price is S$173
includes taxes & fees
8 Mar - 9 Mar
Blooming Inn
Blue Vista Motor Lodge
In-room safe, desk, free WiFi, bed sheets

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (165)
"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! "
The price is S$222
includes taxes & fees
2 Mar - 3 Mar
Blue Vista Motor Lodge
The Trail in Adams - Berkshires’ Art Hotel
Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (128)
"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. "
The price is S$259
includes taxes & fees
27 Feb - 28 Feb
The Trail in Adams - Berkshires’ Art Hotel
Hotel Downstreet, Ascend Hotel Collection
Indoor pool, open 6:00 AM to 10 PM, pool loungers

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.6 out of 10, Excellent, (1002)
"Only stayed for one nigh during road trip through area. Didn't really use any amenities. Can't speak for area. Room was clean, updated sometime in past few years. Nothing stood out in terms of the room. The parking lot in long and narrow, and I had to park the equivalent of about 1 block away. A lot of the parking was taken up by utility vehicles. Not the end of the world, but it was rough walking through it during a snow storm. "
The price is S$177
includes taxes & fees
16 Mar - 17 Mar
Hotel Downstreet, Ascend Hotel Collection
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (376)
"Lovely place to stay. Wonderful breakfast."
The price is S$297
includes taxes & fees
2 Mar - 3 Mar
The Porches Inn at Mass MoCA
Pilgrim Inn
Individually decorated, individually furnished, desk, laptop workspace

Pilgrim Inn

2.5 star property
5.8 out of 10, (303)
"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"
The price is S$103
includes taxes & fees
27 Feb - 28 Feb
Pilgrim Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1001)
"Nice place. Made fresh waffle mix when I asked. No complaints"
The price is S$126
includes taxes & fees
16 Mar - 17 Mar
Quality Inn
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (379)
"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...
The price is S$120
includes taxes & fees
1 Mar - 2 Mar
Sunset Inn
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

2.5 star property
5.4 out of 10, (705)
"Quiet "
The price is S$93
includes taxes & fees
12 Mar - 13 Mar
FairBridge Inn Express
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (363)
"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."
The price is S$283
includes taxes & fees
2 Mar - 3 Mar
Chambery Inn
Econo Lodge Lee - Great Barrington
Desk, iron/ironing board, free cots/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (585)
"It was close to Butternut on a snowy day. Very good for the value and what it is."
The price is S$90
includes taxes & fees
3 Mar - 4 Mar
Econo Lodge Lee - Great Barrington
Devonfield Inn B&B
Front of property – evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (122)
"Beautiful property, great service "
The price is S$373
includes taxes & fees
4 Mar - 5 Mar
Devonfield Inn B&B
The Black Swan Lee - Lenox, Ascend Hotel Collection
Lobby

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (999)
"Two adults and a baby to enjoy winter wonderland: it worked very well! Very close to everything! "
The price is S$151
includes taxes & fees
4 Mar - 5 Mar
The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

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

3.5 star property
9.0 out of 10, Wonderful, (600)
"Great family vacation"
The price is S$196
includes taxes & fees
2 Mar - 3 Mar
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (247)
"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."
The price is S$197
includes taxes & fees
7 Mar - 8 Mar
Lakehouse Inn
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is S$214
includes taxes & fees
27 Feb - 28 Feb
The Ponds at Foxhollow
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (628)
"Very clean and comfortable with great restaurant and bar downstairs"
The price is S$195
includes taxes & fees
2 Mar - 3 Mar
Hilton Garden Inn Lenox Pittsfield
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.2 out of 10, Good, (600)
"Great location. Pleasant staff."
The price is S$103
includes taxes & fees
6 Mar - 7 Mar
Wagon Wheel Inn
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (713)
"spacious room. "
The price is S$118
includes taxes & fees
2 Mar - 3 Mar
Howard Johnson by Wyndham Lenox
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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Learn more about Cheshire

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

See all hotels in Cheshire
Photo by Ed Gaffny
Open Photo by Ed Gaffny

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 traveller data. Two other choices for your trip to the area are Vacation Village in the Berkshires and Life House Berkshires. See all available top hotels, or vacation rentals in Cheshire.

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

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

What's the best LGBTQ-friendly place to stay in Cheshire?

Harbour House Inn is a top LGBTQ-friendly B&B, and features free breakfast and free WiFi. See all available hotels listed as LGBTQ-friendly in Cheshire.

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 accommodation options to choose from. Find out more about Cheshire.

What is there to see in Cheshire?

A couple of favourite 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. Take a look at what more there is to see and do in Expedia's Cheshire guide.

What's the seasonal weather in Cheshire?

The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cheshire are January, March, February and November, with each month seeing an average of 17 cm of snowfall.