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5 Dec - 6 Dec
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Top hotels and accommodation in Cheshire

Exterior
Harbour House Inn

Harbour House Inn

3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"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!! "
United States
Lorie
The price is AU$394
includes taxes & fees
9 Dec - 10 Dec
Harbour House Inn
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"The room was very clean and updated."
United States
Daniel
Travelling for leisure
The price is AU$151
includes taxes & fees
11 Dec - 12 Dec
The Yankee, Trademark Collection by Wyndham
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1002)
"Hotel was clean, nice view on the lake."
United States
LIsa
The price is AU$171
includes taxes & fees
15 Dec - 16 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2163)
"Room was clean and well-stocked"
United States
Bonnie
Travelling with family
The price is AU$167
includes taxes & fees
7 Dec - 8 Dec
Vacation Village in the Berkshires
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (806)
"A motel style well thought out hotel, tastefully designed,very comfortable room with fabulous beds."
United States
Peter
Travelling with partner
The price is AU$185
includes taxes & fees
7 Dec - 8 Dec
Berkshires Untold
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very good, (980)
"The room was very clean"
United States
Tracy
Travelling for leisure
The price is AU$155
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Property amenity
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

3.5 star property
South Lee
9.0 out of 10, Wonderful, (795)
"The location is beautiful and close to great hiking spots and nice towns ."
United States
Angelica
Travelling for leisure
The price is AU$210
includes taxes & fees
9 Dec - 10 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (64)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
United States
Marti
The price is AU$164
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I did love the bed."
United States
Robert
Travelling with partner
The price is AU$271
includes taxes & fees
5 Jan - 6 Jan 2026
The Red Lion Inn
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1000)
"Lovely property with clean rooms."
United States
Lynne
The price is AU$291
includes taxes & fees
10 Dec - 11 Dec
The Cornell Inn, Lenox & The Berkshires
Hypo-allergenic bedding, desk, laptop workspace, blackout curtains
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
North Adams
8.8 out of 10, Excellent, (1003)
"Hotel is clean and up to date"
United States
Jason
The price is AU$181
includes taxes & fees
20 Dec - 21 Dec
Hotel Downstreet, an Ascend Collection Hotel
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (778)
"Large rooms with good amenities and great location."
United States
Nitsat Hadas
Travelling with partner
Berkshire Mountain Lodge
Suite, 2 Bedrooms
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 star property
North Adams
9.4 out of 10, Exceptional, (445)
"Fantastic breakfast, perfect location, fun vibe, beautiful pool area, an environment that encourages conversation with other guests."
United States
Leigh
Travelling for leisure
The price is AU$277
includes taxes & fees
4 Jan - 5 Jan 2026
The Porches Inn at Mass MoCA
Front of property – evening/night
Hotel On North

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (805)
"Room was clean and incredibly comfortable."
United States
Jessica
Travelling with partner
The price is AU$226
includes taxes & fees
22 Dec - 23 Dec
Hotel On North
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1000)
"Very clean rooms and excellent staff."
United States
Kenneth R.
Travelling for leisure
The price is AU$158
includes taxes & fees
8 Dec - 9 Dec
Best Western Plus Berkshire Hills Inn & Suites
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
"The jetted tubs were divine with plenty of hot water the towel warmer was a nice bonus."
United States
Samuel
Travelling with partner
Chambery Inn
Front of property – evening/night
The Williams Inn

The Williams Inn

4.0 star property
Williamstown
9.6 out of 10, Exceptional, (546)
"Loved the coffee bar and the fitness room!"
United States
Laura
Travelling with family
The price is AU$320
includes taxes & fees
8 Dec - 9 Dec
The Williams Inn
Exterior
The Villager Motel

The Villager Motel

2.0 star property
Williamstown
8.8 out of 10, Excellent, (764)
"The hotel was exceptionally clean"
United States
Mary
Travelling for leisure
The price is AU$117
includes taxes & fees
7 Dec - 8 Dec
The Villager Motel
Exterior
Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
Williamstown
8.8 out of 10, Excellent, (394)
"conveniently located close to Williams and to 2 grocery stores. easy parking"
United States
Ilaria
The price is AU$265
includes taxes & fees
10 Dec - 11 Dec
Fairfield Inn & Suites by Marriott Williamstown
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
9.2 out of 10, Wonderful, (588)
"The hotel is very clean, well-managed, and quiet, and it [hotel] is conveniently located near Tanglewood and other attractions."
United States
EUNJUNG
Travelling for leisure
The price is AU$228
includes taxes & fees
14 Dec - 15 Dec
Courtyard by Marriott Lenox 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 local cuisine.

See all hotels in Cheshire
An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.

Top Cheshire Hotel Reviews

Recent Reviews in Cheshire

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"so quiet"
robert 7-night trip
Posted 4 days ago
Vacation Village in the Berkshires

More cheap accommodation in Cheshire

Quality Inn

Quality Inn

170 Housatonic Street Lee MA
The price is AU$153 per night from 28 Dec to 29 Dec
AU$153
28 Dec - 29 Dec
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)

Frequently asked questions

What's the best place to stay in Cheshire?
Harbour House Inn is one of the top choices for your stay based on our traveller data. This B&B offers free breakfast and free parking. Two other choices for your trip to the area are Vacation Village in the Berkshires and Hotel Downstreet, an Ascend Collection Hotel. See all available top hotels, or vacation rentals in Cheshire.
What are some of the best holiday rentals that Cheshire has to offer?
Peace and quiet on the lake: This holiday home rental outside of Cheshire is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games 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 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 are some hotels with pools in Cheshire?
Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool and free self parking. Hotel Downstreet, an Ascend Collection Hotel and Berkshire Mountain Lodge are two additional hotels that feature an on-site pool. View all hotels with pools 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 5 hotels and other accommodation options to choose from. Find out more about Cheshire.
What is there to see in Cheshire?
A favourite place to visit is Mount Greylock State Reservation. 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.

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