Photo by Ed Gaffny

Search Cheshire hotels

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Property class

Top hotels and accommodation in Cheshire

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 AU$391
includes taxes & fees
14 Aug - 15 Aug
Harbour House Inn

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Had a wonderful time "
The price is AU$217
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1007)
"Wonderful place to stay"
The price is AU$229
includes taxes & fees
8 Sept - 9 Sept
The Yankee, Trademark Collection by Wyndham

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1944)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is AU$202
includes taxes & fees
27 Aug - 28 Aug
Vacation Village in the Berkshires

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (671)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is AU$275
includes taxes & fees
7 Sept - 8 Sept
Berkshires Untold

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1011)
"Great location!"
The price is AU$246
includes taxes & fees
11 Sept - 12 Sept
Hotel Downstreet, Ascend Hotel Collection

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (516)
"Great place , love it, will return"
The price is AU$260
includes taxes & fees
10 Sept - 11 Sept
The Constance by the Lenox Collection

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1000)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is AU$278
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires

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

3.5 star property
9.0 out of 10, Wonderful, (690)
"This was our third year of two summer weeks at Oak 'n' Spruce. The accommodations are comfortable and convenient, and the staff is wonderful. We hope to be back next summer."
The price is AU$178
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

FairBridge Inn Express

2.5 star property
5.4 out of 10, (766)
"Close to our target event a plus"
The price is AU$122
includes taxes & fees
27 Aug - 28 Aug
FairBridge Inn Express

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (856)
"Consistently a clean room with welcoming staff."
The price is AU$197
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1003)
"Loved our visit"
The price is AU$398
includes taxes & fees
18 Aug - 19 Aug
The Red Lion Inn

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (622)
"It was lovely!"
The price is AU$109
includes taxes & fees
27 Aug - 28 Aug
Econo Lodge Lee - Great Barrington

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (557)
"Amazing place to stay. Can’t wait to go again. "
Berkshire Mountain Lodge

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (864)
"Humble little hotel. Ideal for a visit to nearby Mass MOCA."
The price is AU$188
includes taxes & fees
19 Aug - 20 Aug
Howard Johnson by Wyndham Williamstown

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (432)
"Beautiful scenery. Room was not fancy but comfortable and clean. "
The price is AU$116
includes taxes & fees
18 Aug - 19 Aug
Berkshire Travel Lodge

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1008)
"Very clean rooms and excellent staff."
The price is AU$204
includes taxes & fees
1 Sept - 2 Sept
Best Western Plus Berkshire Hills Inn & Suites

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (284)
"Small comfortable room, accommodating staff, very close to Williams College."
The price is AU$145
includes taxes & fees
2 Sept - 3 Sept
Williamstown Motel

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (726)
"Great quiet stay. "
The price is AU$152
includes taxes & fees
1 Sept - 2 Sept
The Villager Motel

Berkshire Valley Inn

2.5 star property
9.2 out of 10, Wonderful, (554)
"Very clean and very nice staff. Breakfast was great"
The price is AU$285
includes taxes & fees
20 Aug - 21 Aug
Berkshire Valley Inn
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.
Save an average of 15% on thousands of hotels when you're signed in

Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking and lake views.

Photo by Ed Gaffny
Open Photo by Ed Gaffny

Top Cheshire Hotel Reviews

Find out more about Cheshire

Find out more about Cheshire

Top reasons to visit Cheshire

  • Outdoor Adventures: Cheshire is perfect for ski enthusiasts and outdoor adventurers, offering stunning mountain settings and a variety of activities.
  • Charming Countryside: Experience the picturesque Cheshire countryside and quaint village atmosphere, ideal for family outings or romantic getaways.
  • Historic Attractions: Explore nearby historic sites, like the Cheshire Cat and the charming town of Chester.
  • Scenic Weddings: Enjoy unique woodland weddings set in the beautiful surroundings of Cheshire.
  • Diverse Accommodations: Cheshire offers a range of accommodation options, from luxurious resorts to budget-friendly stays.

Find great hotels near Cheshire

Experience the charm of Cheshire, Massachusetts, with a variety of accommodation options tailored for every type of traveller. Whether you're seeking a family-friendly getaway, a romantic escape, or an adventure-filled holiday, Cheshire offers delightful resorts and hotels that cater to your needs. Discover luxurious stays and welcoming hospitality that make your visit unforgettable in this picturesque New England town.

  • Hotel Downstreet, Ascend Hotel Collection: Embrace a warm and welcoming atmosphere at Hotel Downstreet, a 3-star property that champions inclusivity and pet-friendly stays. Located 16.1km from Cheshire, this hotel is particularly appealing to LGBTQIA travellers, with its affiliation with LGBTQI travel guides. Guests can enjoy the comfort of their pets, as the property allows dogs and cats onsite, complete with special amenities such as food and water bowls. The hotel ensures a delightful experience for all, making it a top choice for those seeking a friendly and accommodating environment.
  • Berkshire Inn: A haven for sports enthusiasts, the Berkshire Inn combines comfort with outdoor adventure. Situated 16.1km from Cheshire, this motel offers easy access to nearby skiing and golfing activities, making it perfect for those looking to indulge in local recreation. Guests can unwind in rooms equipped with modern entertainment options like flatscreen and cable TV. With its strategic location near the city centre, guests can explore local attractions while enjoying the quaint charm of the Berkshires.
  • Hotel On North: This 3.5-star lodging presents a blend of business efficiency and pet-friendly hospitality, located just 14.5km from Cheshire. Ideal for business travellers, Hotel On North features a well-equipped business centre and multiple meeting rooms to cater to professional needs. Pets are also welcome, with policies ensuring their comfort and care. Whether you're in town for work or leisure, this hotel stands out for its refined amenities and commitment to providing a productive yet relaxing environment.

Where to stay near Cheshire

Cheshire, Massachusetts, is a gem for those seeking outdoor adventures and tranquil countryside escapes. Experience the charm of the Cheshire countryside and the quaint village atmosphere, perfect for family-friendly outings or romantic getaways. Enjoy memorable stays in scenic spots that cater to all budgets, offering a mix of adventure and relaxation. From picturesque trails to local attractions, Cheshire invites you to immerse yourself in its delightful surroundings.

  • Williamstown: Nestled 17.7km from Cheshire, Williamstown is a picturesque town renowned for its stunning mountain scenery and vibrant cultural scene. It attracts visitors year-round, with peak travel periods in April and from June to July, perfect for those seeking adventure in skiing or outdoor sports. The area boasts a historic college university that adds a unique charm, alongside beautiful lakes and hiking trails that invite exploration. Whether you’re carving down ski slopes or enjoying the local arts, Williamstown promises an engaging experience.
  • Pittsfield: Located 14.5km from Cheshire, Pittsfield is a bustling city that offers an eclectic mix of outdoor adventure and recreational opportunities. With visitor numbers peaking from June to August, the city is ideal for summer activities like hiking and water sports at nearby lakes and waterparks. Ski enthusiasts will also find excellent ski fields and resorts in the area, making it a year-round destination for adventure seekers. Pittsfield's vibrant community and local attractions make it a great spot to soak in the local culture while enjoying the great outdoors.
  • North Adams: Just 16.1km from Cheshire, North Adams is a lively city celebrated for its rich arts scene and outdoor activities. With travel peaks in June to July, visitors flock here for its outdoor adventures and skiing pursuits. The city is home to the renowned art museum and a thriving public art program, providing a cultural feast for art enthusiasts. The stunning natural landscapes surrounding the city offer ample opportunities for exploration, making North Adams a perfect destination for those who appreciate a blend of culture and adventure.

Things to do near Cheshire

Cheshire, Massachusetts, offers a fantastic outdoor adventure for tourists, particularly those keen on skiing. You can enjoy the ski fields and resorts, as well as guided tours and scenic sightseeing in Chester. For a unique experience, consider the picturesque Cheshire woodland weddings, perfect for a romantic getaway. Embrace the natural beauty and outdoor activities that Cheshire has to offer during your vacation!

Shopping

In Cheshire, you can visit the North Adams Center, North Adams Gateway Center, and Colonial Plaza, all offering a mix of city, family, and business vibes. If you're up for a drive, each of these shopping centres is located around 16.1km away and provides great options for gifts and souvenirs.

Recreation

At Skyline Country Club, enjoy a leisurely round of golf amidst scenic views, just 8.0km from Cheshire. For relaxation, Windsor Lake Park, located 14.5km away, offers tranquil walking trails and serene picnic spots. Williams College Taconic Golf Course, 16.1km from Cheshire, combines sport with stunning outdoor landscapes.

Adventure

Experience thrilling skiing at Berkshire East Ski Resort, located 24.1km from Cheshire, offering a fantastic outdoor adventure. Alternatively, visit Jiminy Peak Mountain Resort, 11.3km away, for exciting sports activities. For a scenic hike, head to Williamstown Trailhead, 19.3km from Cheshire, surrounded by stunning natural beauty.

Nightlife

Experience the vibrant nightlife in Cheshire with a visit to the Williamstown Theatre Festival, just 12.9km away, offering captivating performances. For some thrill, try the Alpine Super Slide, located 11.3km away, or catch a show at the charming Adams Theater, only 8.0km from Cheshire.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Cheshire

To save money on your trip to Cheshire, Massachusetts, consider visiting during the cheaper months of March to April or November, and aim for a stay on a Tuesday, the least expensive day. Use Expedia to compare prices, sort by lowest to highest, and look for package deals that combine flights, accommodation, and activities for added savings. Explore free activities in the area, and be sure to earn rewards through your bookings for additional value. Avoid visiting during the peak season in July and August to keep costs down.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Cheshire are March to April and November, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Cheshire is Tuesday. The most expensive day to stay in Cheshire is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your preferences, such as your budget, desired location, and preferred type of accommodation. To find the most affordable options and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save some dollars by combining your hotel stay in Cheshire with your flights and activities through an Expedia package deal.

Find the best attractions near Cheshire

Cheshire, Massachusetts, is perfect for ski enthusiasts and outdoor adventurers, offering a range of activities in stunning mountain settings. Explore historic sites, local universities, and libraries that cater to culture and family experiences. Don't miss attractions like the Cheshire Cat and nearby historic Chester, which add to the charm of the Cheshire area. With its blend of nature and history, Cheshire promises an unforgettable holiday for all visitors.

  • Mount Greylock: Experience the stunning vistas and invigorating hiking trails of Mount Greylock, the highest peak in Massachusetts. It's perfect for outdoor enthusiasts seeking adventure amidst breathtaking scenery, making it a fantastic spot for nature lovers.
  • Mount Greylock State Reservation Visitor Center: This visitor centre is your gateway to the Mount Greylock State Reservation, offering engaging exhibits and information on local wildlife. Ideal for families, it serves as the perfect starting point for outdoor activities and exploration.
  • Williams College: Immerse yourself in the rich culture and history of Williams College, one of the oldest liberal arts colleges in the United States. Its picturesque campus and art galleries provide a unique blend of education and beauty, making it a cultural highlight.

Best time to go to Cheshire

The best time to visit Cheshire is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January19.9°F (-6.7°C)Light RainMostly CloudyAverageAverage
February22.1°F (-5.5°C)Light RainMostly CloudyModerately LowAverage
March29.7°F (-1.3°C)Light RainMostly CloudyAverageSlightly Low
April41.4°F (5.2°C)Light RainMostly CloudyAverageSlightly Low
May53.8°F (12.1°C)Light RainMostly SunnyAverageAverage
June61.5°F (16.4°C)Light RainMostly SunnyModerately HighAverage
July67.6°F (19.8°C)Light RainMostly SunnyModerately HighSlightly High
August65.7°F (18.7°C)Light RainMostly SunnyModerately HighSlightly High
September58.6°F (14.8°C)Light RainMostly SunnyAverageAverage
October47.7°F (8.7°C)Light RainMostly CloudyAverageSlightly High
November35.4°F (1.9°C)Light RainMostly SunnyModerately LowSlightly Low
December27.0°F (-2.8°C)Light RainMostly CloudyModerately LowAverage

The nearest major airports for your trip to Cheshire

Cheshire, Massachusetts is conveniently accessible via several airports. Hartford, CT (BDL-Bradley Intl.) is located 80.5km away, with notable hotels such as the 4-star Simsbury 1820 House, 11.3km from the airport, and the Sheraton Hartford Hotel at Bradley Airport, right next to the terminal. Albany, NY (ALB-Albany Intl.) is 56.3km distant, featuring excellent accommodations like the 4-star Landing Hotel at Rivers Casino & Resort, just 12.9km away. Closer still, Pittsfield, MA (PSF-Pittsfield Municipal) is only 19.3km from Cheshire, with options like the 4-star Hampton Terrace Inn, just 8.0km from the airport. Each hotel provides easy access to their respective airports.

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 Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Cheshire.

What are some of the best holiday rentals that Cheshire has to offer?

Contemporary Berkshire Home with Views of Taconic Golf Course: This holiday home rental outside of Cheshire offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. 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?

Modern Berkshires home + private pool: Provides TVs, an outdoor pool and air conditioning. Vacation Village in the Berkshires and Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel are two additional hotels that feature an on-site pool.

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.