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Sep 5 - Sep 7
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Sep 12 - Sep 14
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Sep 26 - Sep 28
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Oct 24 - Oct 26

Browse Select Cheshire Chalets

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Recommended hotels in Cheshire

Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (111)
"Lovely Inn and very responsive and approachable staff. "
The price is CA $100
CA $179 total
includes taxes & fees
Sep 9 - Sep 10
Blooming Inn
Huttopia Berkshires
Restaurant

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is CA $135
CA $151 total
includes taxes & fees
Sep 11 - Sep 12
Huttopia Berkshires
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1003)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is CA $174
CA $195 total
includes taxes & fees
Sep 11 - Sep 12
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
The price is CA $325
CA $344 total
includes taxes & fees
Sep 10 - Sep 11
Harbour House Inn
In town, newly remodeled studio with private balcony
Smart TV, Netflix, streaming services

In town, newly remodeled studio with private balcony

10.0 out of 10, Exceptional, (115)
"Great place. Quiet, clean and spacious - thank you so much "
The price is CA $131
CA $215 total
includes taxes & fees
Sep 23 - Sep 24
In town, newly remodeled studio with private balcony
The Revival House
Romantic Room, 1 King Bed (Room 4)

The Revival House

3.0 star property
9.0 out of 10, Wonderful, (12)
"We thoroughly enjoyed our stay at The Revival House! Super comfortable, clean, and the inside has great decor sensibilities. We will be back if we’re ever in the area again!"
The price is CA $248
CA $276 total
includes taxes & fees
Sep 11 - Sep 12
The Revival House
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (732)
"Great quiet stay. "
The price is CA $122
CA $137 total
includes taxes & fees
Sep 11 - Sep 12
The Villager Motel
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (27)
"Do hotel, very clean we had a great day"
The price is CA $195
CA $217 total
includes taxes & fees
Sep 11 - Sep 12
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (599)
"Amazing place to stay. Can’t wait to go again. "
The price is CA $106
CA $149 total
includes taxes & fees
Sep 7 - Sep 8
Berkshire Mountain Lodge
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1004)
"Very clean rooms and excellent staff."
The price is CA $146
CA $163 total
includes taxes & fees
Sep 1 - Sep 2
Best Western Plus Berkshire Hills Inn & Suites
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (787)
"My stay was perfect. I can't wait to stay there again. "
The price is CA $109
CA $121 total
includes taxes & fees
Sep 11 - Sep 12
Howard Johnson by Wyndham Lenox
Willows Motel Williamstown
Exterior

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (942)
"Comfortable, clean, and great continental breakfast options! "
The price is CA $123
CA $137 total
includes taxes & fees
Sep 11 - Sep 12
Willows Motel Williamstown
Hotel Downstreet, an Ascend Collection Hotel
Hypo-allergenic bedding, laptop workspace, blackout drapes

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
8.8 out of 10, Excellent, (1008)
"Great location!"
The price is CA $208
CA $232 total
includes taxes & fees
Sep 28 - Sep 29
Hotel Downstreet, an Ascend Collection Hotel
Element Lenox Berkshires
Lobby lounge

Element Lenox Berkshires

3.0 star property
9.6 out of 10, Exceptional, (4)
"New hotel very nice"
The price is CA $210
CA $234 total
includes taxes & fees
Sep 4 - Sep 5
Element Lenox Berkshires
The Springs Motel
Courtyard

The Springs Motel

2.0 star property
9.2 out of 10, Wonderful, (62)
"I was pleasantly surprised to find this gem in the middle of town. Relatively inexpensive for the area. Clean rooms and property. Nice staff. Beautiful pool. Would definitely recommend "
The price is CA $141
CA $155 total
includes taxes & fees
Sep 1 - Sep 2
The Springs Motel
Becket Motel
Front of property

Becket Motel

2.5 star property
6.6 out of 10, (58)
"Comfortable stay "
The price is CA $111
CA $171 total
includes taxes & fees
Sep 7 - Sep 8
Becket Motel
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (699)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise "
The price is CA $221
CA $247 total
includes taxes & fees
Sep 11 - Sep 12
Berkshires Untold
Cozy Corner Motel
Exterior

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (850)
"We thoroughly enjoyed our 1-night stay at the Cozy Corner! Rooms were very clean, and beds very comfortable! They also had a great breakfast, and I loved the outdoor seating area by the babbling brook!"
The price is CA $117
CA $137 total
includes taxes & fees
Sep 3 - Sep 4
Cozy Corner Motel
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is CA $176
CA $250 total
includes taxes & fees
Sep 11 - Sep 12
The Cornell Inn, Lenox & The Berkshires
The Porches Inn at Mass MoCA
Suite, 2 Bedrooms

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (413)
"Great well managed property with a unique style and nice amenities. Also, a continental breakfast is included with the stay."
The price is CA $245
CA $304 total
includes taxes & fees
Sep 29 - Sep 30
The Porches Inn at Mass MoCA
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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Top Cheshire Hotel Reviews

Find out more about Cheshire

Find out more about Cheshire

Cheshire Chalets information

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Accommodation
5 Chalets
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