Photo by Ed Gaffny

Find hotels in Cheshire, MA from SAR 267

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Check prices for these dates

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20 Jun - 21 Jun
Tomorrow
21 Jun - 22 Jun
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20 Jun - 22 Jun
Next weekend
27 Jun - 29 Jun

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Compare 989 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
9.4 out of 10, Exceptional, (49)
  • cleanliness
    Travelers find mountain serenity at this peaceful haven where guests can relax surrounded by natural beauty or curl up with a favorite book

What verified guests said

"Nice place for a weekend away."

Harbour House Inn highlights

Harbour House Inn welcomes visitors to its mountain retreat where a full breakfast starts each day. Guests can wander through the serene garden, borrow books from the library, access WiFi in their rooms, and take advantage of express check-out when their stay ends.
The price is SAR 886
SAR 936 total
includes taxes & fees
25 Jun - 26 Jun
Harbour House Inn
Blooming Inn
Front of property

Blooming Inn

3.0 star property
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • Kitchen
  • Living/Dining area
9.2 out of 10, Wonderful, (97)
  • cleanliness
    Escape into nature's haven where adventure meets tranquility. Unleash your spirit by exploring local wonders like Bridge of Flowers.

What verified guests said

"Great Place to stay in Small town"

Blooming Inn highlights

Discover the natural beauty of Blooming Inn, nestled close to Glacial Potholes and Bridge of Flowers. Enjoy snowshoeing, snowmobiling, or sledding on site, unwind with coffee/tea in the lobby and connect with free WiFi. With a nature reserve nearby and smoke-free premises for comfort.
The price is SAR 331
SAR 516 total
includes taxes & fees
23 Jun - 24 Jun
Blooming Inn
UU Rowe Camp and Conference Center
Front of property

UU Rowe Camp and Conference Center

2.0 star property
  • Breakfast included
  • Parking included
  • Free WiFi
  • Microwave
The price is SAR 559
SAR 591 total
includes taxes & fees
2 Jul - 3 Jul
UU Rowe Camp and Conference Center
Becket Motel
Front of property

Becket Motel

2.5 star property
  • Parking included
  • Free WiFi
  • Air conditioning
  • Room service
  • Microwave
6.6 out of 10, (55)
  • cleanliness
    Travelers find a peaceful nature retreat near Pyramid Lake where quick check-out makes departure as stress-free as the stay itself

What verified guests said

"Comfortable stay "

Becket Motel highlights

The Becket Motel provides a serene escape in natural surroundings near Pyramid Lake. Guests can relax in the garden while staying connected with complimentary WiFi in their rooms.
The price is SAR 359
SAR 526 total
includes taxes & fees
20 Jul - 21 Jul
Becket Motel
Blue Vista Motor Lodge
Single Room | 1 bedroom, in-room safe, desk, free WiFi

Blue Vista Motor Lodge

2.0 star property
  • Hot Tub
  • Parking included
  • Free WiFi
  • Air conditioning
9.8 out of 10, Exceptional, (172)
  • cleanliness
    Mountain views create a peaceful backdrop for relaxation at the firepit or in two spa tubs, where guests find a perfect balance of nature and comfort

What verified guests said

"Lovely stay!"

Blue Vista Motor Lodge highlights

Blue Vista Motor Lodge, surrounded by mountains, offers a quiet getaway with a firepit, sauna, and dual spa tubs. Guests enjoy WiFi on outdoor furniture or explore the on-site gift shop. Visitors appreciate the attentive staff who ensure a comfortable stay.
The price is SAR 749
SAR 792 total
includes taxes & fees
23 Jun - 24 Jun
Blue Vista Motor Lodge
The Trail in Adams - Berkshires’ Art Hotel
Garden

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
  • Parking included
  • Free WiFi
  • Air conditioning
  • Game room
  • Housekeeping
8.8 out of 10, Excellent, (129)
  • cleanliness
    Immerse in nature's beauty at this art-focused retreat where outdoor adventures and cultural exploration meet in the heart of the Berkshires

What verified guests said

"Stayed only one night Very cosy, quiet place "

The Trail in Adams - Berkshires’ Art Hotel highlights

The Trail in Adams - Berkshires' Art Hotel, near the Susan B. Anthony Birthplace Museum, is a perfect exploration base. Guests enjoy nearby hiking/biking paths, relax on the garden terrace, or browse the hotel's library after a day of outdoor activities.
The price is SAR 652
SAR 728 total
includes taxes & fees
22 Jun - 23 Jun
The Trail in Adams - Berkshires’ Art Hotel
The Revival House
Romantic Room, 1 King Bed (Room 4) | 1 bedroom, desk, iron/ironing board, free WiFi

The Revival House

3.0 star property
  • Breakfast included
  • Parking included
  • Free WiFi
  • Microwave
The price is SAR 630
SAR 704 total
includes taxes & fees
25 Jun - 26 Jun
The Revival House
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout drapes

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
  • Pool
  • Hot Tub
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
8.8 out of 10, Excellent, (1000)
  • cleanliness
    Relax by the spa tub or take a dip in our indoor pool then stay productive with our 24 hour business center.

What verified guests said

"Staff super friendly, most comfortable beds imo I’ve slept in. I sleep better there then at my house."

Hotel Downstreet, Ascend Hotel Collection highlights

In the heart of the city, Hotel Downstreet offers a blend of relaxation and productivity. With a spa tub, indoor pool, laundry facilities, 24-hour gym and business center at your disposal you'll feel right at home. Enjoy free self parking and connect to in-room WiFi as well as access an elevator for added convenience. Guests rave about the helpful staff.
The price is SAR 539
SAR 602 total
includes taxes & fees
20 Jul - 21 Jul
Hotel Downstreet, Ascend Hotel Collection
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
  • Pool
  • Hot Tub
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
9.4 out of 10, Exceptional, (390)
  • cleanliness
    Travelers can relax by the poolside oasis or settle in with a good book by the fire at this charming retreat in the heart of the city

What verified guests said

"Phenomenal room, staff and location! We loved The Porches!!"

The Porches Inn at Mass MoCA highlights

The Porches Inn at Mass MoCA offers a continental breakfast, arcade games, and a peaceful garden. Guests can unwind in the sauna or spa tub, enjoy WiFi, or browse books by the lobby fireplace. The staff is consistently praised for their helpfulness.
The price is SAR 740
SAR 910 total
includes taxes & fees
23 Jun - 24 Jun
The Porches Inn at Mass MoCA
Pilgrim Inn
Lobby

Pilgrim Inn

2.5 star property
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
  • Housekeeping
5.8 out of 10, (308)
  • cleanliness
    Golfers find their paradise on the adjacent course with pro shop and caddies, while others enjoy the peaceful garden playground

What verified guests said

"Great location but no staff at check-in or checkout!"

Pilgrim Inn highlights

The Pilgrim Inn, next to a scenic golf course, offers guests a full round of golf or a relaxing outdoor setting. Enjoy access to the golf pro shop, caddies, and a garden playground. Travelers value the practical touches of free in-room WiFi and dry cleaning services.
The price is SAR 308
SAR 344 total
includes taxes & fees
23 Jun - 24 Jun
Pilgrim Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
  • Breakfast included
  • Free WiFi
  • Restaurant
  • Air conditioning
  • Parking available
  • Housekeeping
8.2 out of 10, Very Good, (1000)
  • cleanliness
    Travelers start their day with a free continental breakfast and get expert local attraction tips from the helpful tour assistance desk.

What verified guests said

"Friendly staff, easy parking"

Quality Inn highlights

The Quality Inn sits in the city center where guests connect to WiFi from their rooms after enjoying the morning's continental breakfast. The on-site restaurant provides convenient dining options, while complimentary newspapers keep everyone informed about current events.
The price is SAR 406
SAR 453 total
includes taxes & fees
7 Jul - 8 Jul
Quality Inn
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
  • Pool
  • Parking included
  • Free WiFi
  • Air conditioning
  • 24/7 front desk
  • Microwave
7.6 out of 10, Good, (381)
  • cleanliness
    This welcoming motel near Tanglewood Music Center offers a seasonal outdoor pool and convenient express check-out for travelers seeking relaxation

What verified guests said

"The room was clean and perfect for our stay."

Sunset Inn highlights

Sunset Inn combines comfort with practicality for music lovers and travelers alike. Guests can cool off in the seasonal outdoor pool after a day of exploring, connect to WiFi from their rooms, and enjoy a hassle-free departure with express check-out service.
The price is SAR 342
SAR 382 total
includes taxes & fees
7 Jul - 8 Jul
Sunset Inn
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services
  • Laundry
  • Housekeeping
5.4 out of 10, (726)
  • cleanliness
    Travelers stay connected with complimentary WiFi while handling business needs at the center or enjoy the convenience of on-site parking at this suburban hotel

What verified guests said

"Friendly staff and quick checkin "

FairBridge Inn Express highlights

Located in the suburbs, FairBridge Inn Express offers practical amenities for business and leisure travelers. Enjoy laundry facilities, free WiFi, a business center, and meeting rooms. The 24-hour front desk ensures assistance is always available.
The price is SAR 267
SAR 298 total
includes taxes & fees
3 Jul - 4 Jul
FairBridge Inn Express
Chambery Inn
Front of property

Chambery Inn

3.0 star property
  • Hot Tub
  • Spa
  • Parking included
  • Free WiFi
  • Air conditioning
  • Breakfast available
9.6 out of 10, Exceptional, (365)
  • cleanliness
    A peaceful retreat where travelers can relax in the garden, soak in a spa tub, or enjoy aromatherapy treatments after a day of exploring

What verified guests said

"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "

Chambery Inn highlights

The Chambery Inn, near The Mount, offers a tranquil getaway with a spa tub and garden. Guests enjoy terrace views, aromatherapy sessions, and cycling with bike rentals. Free WiFi keeps everyone connected.
Chambery Inn
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
6.2 out of 10, (598)
  • cleanliness
    Travelers can start their Berkshires adventures with a complimentary continental breakfast before enjoying a round on the property's mini golf course

What verified guests said

"We stayed in this hotel for one night because of the Divine Mercy weekend. This hotel is near to the Divine Mercy complex. They also serve breakfast."

Econo Lodge Lee - Great Barrington highlights

Located in Great Barrington, the Econo Lodge Lee - Great Barrington combines comfort with recreation. Guests connect to WiFi throughout their stay, challenge themselves on the mini golf course, and find convenient RV parking on the property.
The price is SAR 253
SAR 283 total
includes taxes & fees
29 Jun - 30 Jun
Econo Lodge Lee - Great Barrington
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
10.0 out of 10, Exceptional, (126)
  • cleanliness
    Golfers find their perfect match at this upscale retreat where poolside relaxation and spa treatments create an ideal balance of activity and downtime

What verified guests said

"Very enjoyable comfortable stay"

Devonfield Inn B&B highlights

Devonfield Inn B&B, next to a golf course, offers a refined experience with full breakfast and evening manager's reception. Guests can lounge by the pool, explore cycling trails, and enjoy amenities like free WiFi, bike rentals, and an on-site hair salon.
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
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
9.0 out of 10, Wonderful, (1002)
  • cleanliness
    Lakeside relaxation meets culinary delights at this Lenox retreat, where guests can enjoy water activities like kayaking or fishing on the tranquil waters

What verified guests said

"Very good service and breakfast!"

The Black Swan Lee - Lenox, Ascend Hotel Collection highlights

The Black Swan Lee - Lenox, Ascend Hotel Collection offers lakefront charm with modern amenities. Enjoy continental breakfast, Indian cuisine at Mint, kayaking or fishing on the lake, a 24-hour gym, and free in-room WiFi, all with attentive staff.
The price is SAR 478
SAR 534 total
includes taxes & fees
30 Jun - 1 Jul
The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior

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

3.5 star property
  • Pool
  • Air conditioning
  • Tennis court
  • Game room
  • Business services
  • Bar
9.0 out of 10, Wonderful, (658)
  • cleanliness
    Families splash in four pools at this Berkshires retreat or compete at mini golf, basketball and volleyball before enjoying American cuisine at two restaurants.

What verified guests said

"Wonderful property we’ve been coming here for years"

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

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires is a perfect family getaway. Enjoy mini golf, basketball, volleyball, billiards, four pools, American dishes at two on-site restaurants, and extra fun in the arcade and game room.
The price is SAR 469
SAR 577 total
includes taxes & fees
22 Jun - 23 Jun
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
  • Pool
  • Kitchen
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
8.6 out of 10, Excellent, (121)
  • cleanliness
    Resort living at The Ponds at Foxhollow combines arcade games, outdoor grilling, and relaxation opportunities for a complete vacation experience

What verified guests said

"A good place for vacation that you can enjoy and rest. Very nice and safe place."

The Ponds at Foxhollow highlights

Located in the entertainment district, The Ponds at Foxhollow by Capital Vacations offers activities for every type of traveler. Guests can enjoy arcade games, unwind in the sauna, or lounge by the pool—creating the perfect balance of fun and relaxation during their stay.
The price is SAR 870
SAR 971 total
includes taxes & fees
13 Jul - 14 Jul
The Ponds at Foxhollow
Holiday Inn Express & Suites Pittsfield - Berkshires
Free daily buffet breakfast

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
  • Pool
  • Hot Tub
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • cleanliness
    Travelers start with a free breakfast before work or exploring, enjoying comfort and convenience throughout their stay.

Holiday Inn Express & Suites Pittsfield - Berkshires highlights

Guests at The Inn At Lenoxview enjoy a free breakfast buffet each morning while staying connected with in-room WiFi. The seasonal outdoor pool offers a perfect spot to unwind on sun loungers, and the business center provides space for catching up on work.
The price is SAR 784
SAR 876 total
includes taxes & fees
20 Jul - 21 Jul
Holiday Inn Express & Suites Pittsfield - Berkshires
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 wildlife.

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..
Photo by Ed Gaffny
Open Photo by Ed Gaffny

More cheap stays in Cheshire

More cheap stays in Cheshire

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield, MA
The price is SAR 380 per night from Jul 1 to Jul 2
SAR 380
SAR 424 total
1 Jul - 2 Jul
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)

Hotels in Cheshire with star-rating

Hotels in Cheshire with star-rating

Stay near popular Cheshire attractions

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.

See properties in St Mary's of the Assumption Church
St Mary's of the Assumption Church

Recent reviews of Cheshire hotels

Recent reviews of Cheshire hotels

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

5/5 Excellent
"Sweet hotel with lovely lake in back"
A verified traveler stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
Posted 1 day ago
The Black Swan Lee - Lenox, Ascend Hotel Collection

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What's the best place to stay in Cheshire?

Located 12.2 mi (19.6 km) from the heart of Cheshire, The Yankee, Trademark Collection by Wyndham is a top choice for your stay based on our traveler data. Other good options for your stay in the area are Best Western Plus Berkshire Hills Inn & Suites and Vacation Village in the Berkshires. See all available top hotels, or vacation rentals in Cheshire.

What are some of the best vacation rentals in Cheshire?

Deluxe Queen Room with 2 Queen Beds: This vacation home rental outside of Cheshire is equipped with an outdoor pool, air-conditioning, and WiFi to help you feel comfortable during your stay. 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.