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Cheap Hotels in Cheshire, United States of America

Cheshire hotels
Cheshire

Choose from 89 Cheshire Hotel Deals

Jiminy Peak Mountain Resort - Hancock Hotels
Rating: 3.0 Stars

Jiminy Peak Mountain Resort

37 Corey Rd, Hancock - Map
 
 
"beautiful location"
nice spot large room w/2 tvs pub food in lounge convenient to Williamstown
A Traveller
Located in the mountains, this Hancock condominium resort offering ski-in/ski-out access is 6.1 mi (9.8 km) from Mount …More
The Williams Inn - Williamstown Hotels
Rating: 3.0 Stars

The Williams Inn

1090 Main Street, Williamstown - Map
 
 
"good hotel conveniently located"
Very good advice about restaurants and helpful for directions on leaving
Traveller from Syracuse NY
Situated in Williamstown, this hotel is within a 5-minute walk of Williamstown Historical Museum and 62 Center for Theater …More
The Orchards Hotel - Williamstown Hotels
Rating: 3.5 Stars

The Orchards Hotel

222 Adams Rd, Williamstown - Map
 
 
"facilities charge"
for some reason management decided to add an additional 'facilities' charge onto the bill. never had this before. the pool , by the way was closed early.
A Traveller
Situated in a rural location, this hotel is within 1 mi (2 km) of Hopkins Observatory, Williams College Museum of Art, and …More
Yankee Inn - Lenox Hotels
Rating: 2.5 Stars
$166

Yankee Inn

461 Pittsfield Rd, Lenox - Map
 
 
"Nice for the price"
This was a good place to stay for a few days, as the price was reasonable and it was clean. The bed was uncomfortable, the shower was slow to drain and there was a crack in the sink There could have been more hangers and towels in the room. No it is not a luxury hotel, but I knew that when I booked it. The free breakfast was great, and there were 2 pools, which I did not use, but others seemed to enjoy. I did not use the exercise room, but will try it on another visit, a nice perk. There was a coffeemaker, microwave, fridge, iron and board and hairdryer in the room. The location is great, as it is nearby to many amenities. I would stay there again on my next visit to the Berkshires..
Traveller from Quincy, Mass.
Located in the heart of Lenox, this hotel is 0.5 mi (0.9 km) from Kennedy Park and within 3 mi (5 km) of Pleasant Valley …More
Vacation Village in the Berkshires - Hancock Hotels
Rating: 3.0 Stars

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Hancock - Map
 
 
"Roomy"
Units are big, clean, and close to summer and winter activities. Great for families.
A Traveller
Situated in Hancock, this condo is 5.8 mi (9.3 km) from Mount Greylock State Reservation Visitor Center and within 12 mi (20 …More
Berkshire Valley Inn - Williamstown Hotels
Rating: 2.5 Stars

Berkshire Valley Inn

2541 Hancock Rd, Williamstown - Map
 
 
"clean and close to Clark & MassMOCA"
Clean, confortable, friendly staff and hirsts. Excellent breakfast with great coffee and fresh fruit. Pool. We extended our stsy!
Traveller from Yonkers NY
Situated in Williamstown, this hotel is 5.3 mi (8.5 km) from Waubeeka Golf Links and within 12 mi (20 km) of Mount Greylock …More
Williamstown Motel - Williamstown Hotels
Rating: 2.0 Stars

Williamstown Motel

295 Main Street, Williamstown - Map
 
 
"Clean, simple, good value"
I stayed here recently just one night for a fishing trip. The physical structure is a bit tired and I need of upgrade, but it was clean, simple, and a very good price. The young couple managing the motel are lovely, very customer oriented, and do a nice job (on top of dealing with 3 small children). The complimentary breakfast was all prepackaged baked goods, yogurt, cereal, and was fine.
A Traveller
Situated in Williamstown, this hotel is within 1 mi (2 km) of Hopkins Observatory, Williams College Museum of Art, and Chapin …More
Kemble Inn - Lenox Hotels
Rating: 3.5 Stars

Kemble Inn

2 Kemble Street, Lenox - Map
 
 
4.0 out of 5 (5 reviews)
Located in the heart of Lenox, this romantic inn is within a 5-minute walk of Shakespeare and Company and Ventfort Hall …More
Best Western Plus Berkshire Hills Inn & Suites - Pittsfield Hotels
Rating: 2.5 Stars

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield - Map
 
 
"Nice hotel; noisy neighbors"
The difficulty with late night noise coming from an undetermined room greatly compromised our quality of sleep. Our dissatisfaction was understood and compensated for, as a result of our conversation the next morning with Sunjay Desaj, Operations & Sales Manager. Other than this, we found it to be a very nice place and were pleased with the breakfast offerings. Were we ever to pass thru there again, we wouldn't hesitate to stay at this facility.
Traveller from Keene, NH
Located in the heart of Pittsfield, this hotel is 1.7 mi (2.8 km) from Hancock Shaker Village and 2.9 mi (4.7 km) from …More
Sunset Inn - Lee Hotels
Rating: 1.5 Stars

Sunset Inn

150 Housatonic Street, Lee - Map
 
 
"Simple and average"
Simple place to sleep. Great location near downtown Lee, and near mass pike. Pool was clean and pleasant to swim in. No frills. Nothing fancy. Price average.
Traveller from boston
Located in the heart of Lee, this motel is within a 15-minute walk of Lee Library, Lee Prime Outlets, and Animagic Museum of …More

Search from 89 Cheshire Hotels


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    Get away for the weekend

    Hotels in bigger cities usually charge higher rates during the week, when people are traveling for business. Weekends can be a bargain! It’s the other way around for vacation spots, so if you’re looking for a beach escape, consider a mid-week trip.

    Give yourself some wiggle room

    If your plans are flexible, play around with some different travel dates – a shift of a few days either way can help you save big. Prices usually jump the weekends before and after popular holidays, so we recommend steering clear of them. Or consider visiting during the off-season, when prices are generally lower.

    Plan around big events

    Are prices surprisingly high? There might be a huge conference or festival in town. Consider shifting your dates if you can. Of course, if that’s why you’re going, you’ll have to bite the bullet. We’ll still work to get you the best rates out there.

    Noodle over new adventures

    Set aside time to plan what you want to see, taste and discover. Nothing completes a trip, big or small, like a few new experiences! Check city apps or area websites to find out what’s new and what events are happening during your stay. Even during a family reunion, you can detour to that locals-only fish taco stand or under-the-radar music club. Your cousins will be impressed.

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