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Our top choices for Cheshire hotels

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is CA $320
CA $338 total
includes taxes & fees
Apr 29 - Apr 30
Harbour House Inn

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, (1,000 reviews)
"It was a solid experience at the Best western, staff was super nice, the room was spacious and clean, the breakfast was delicious and the location is superb. Overall it was a great experience and will definitely stay there again "
United States
Kristina
The price is CA $139
CA $155 total
includes taxes & fees
Apr 26 - Apr 27
Best Western Plus Berkshire Hills Inn & Suites

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (900 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
The price is CA $123
CA $138 total
includes taxes & fees
May 7 - May 8
Berkshires Untold

The Revival House

The Revival House
3.0 star property
Adams
9.2 out of 10, Wonderful, (29 reviews)
"Great place to stay one night for the Mt Greylock Road Race. Revival was convenient, close to North Adams and "
United States
melissa
The price is CA $205
CA $230 total
includes taxes & fees
Apr 20 - Apr 21
The Revival House

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (133 reviews)
"The bedroom and entire first floor living area was clean and nicely appointed in period decor. The self-check in process was simple and convenient. Lastly, the staff went above and beyond to find and quickly mail back my forgotten prescription eyeglasses to my home address. Will definitely stay here again if visiting the pioneer valley. "
United States
John
The price is CA $148
CA $232 total
includes taxes & fees
Apr 20 - Apr 21
Blooming Inn

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,000 reviews)
"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
The price is CA $138
CA $155 total
includes taxes & fees
May 4 - May 5
Quality Inn Lee - Lenox South

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is CA $97
CA $107 total
includes taxes & fees
Apr 21 - Apr 22
Pleasant Valley Motel West Stockbridge

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (447 reviews)
"Everything was great— the cleanliness, the plentiful breakfast, the character and coziness, and the proximity to Amici across the street (free dessert with your room key)."
United States
Patrick
The price is CA $155
CA $171 total
includes taxes & fees
May 5 - May 6
Shaker Mill Inn

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, (89 reviews)
"New hotel clean and nice. Heated pool and hot tub a bonus. Timely breakfast for early departures- great on demand coffee. Added bonus they have a car charger."
United States
Charline
The price is CA $162
CA $180 total
includes taxes & fees
Apr 30 - May 1
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (600 reviews)
"Staff is very nice and the rooms are always clean!"
United States
Peter
The price is CA $142
CA $159 total
includes taxes & fees
Apr 21 - Apr 22
Maple Terrace Motel

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (850 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
The price is CA $108
CA $121 total
includes taxes & fees
Apr 19 - Apr 20
Howard Johnson by Wyndham Lenox

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (784 reviews)
"very clean, up to day, no thrills overnighter. perfect stop from NYC to VT skiing"
United States
Martin
The price is CA $108
CA $121 total
includes taxes & fees
Apr 20 - Apr 21
The Villager Motel

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is CA $207
CA $231 total
includes taxes & fees
Apr 29 - Apr 30
Element Lenox Berkshires

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (899 reviews)
"We love Cozy Corner. It's a snug, safe, well-maintained, home away from home. Love the ample breakfast and the genuine welcome we receive every time."
United States
Ann
The price is CA $108
CA $128 total
includes taxes & fees
Apr 28 - Apr 29
Cozy Corner Motel

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (907 reviews)
"Overall pleasant stay; great facilities, staff, and location"
United States
Casey
The price is CA $113
CA $156 total
includes taxes & fees
Apr 21 - Apr 22
Berkshire Mountain Lodge

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (852 reviews)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is CA $106
CA $119 total
includes taxes & fees
May 6 - May 7
Berkshire Inn

UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
10.0 out of 10, Exceptional, (1 review)
"Yes"
United States
Stuart
The price is CA $277
CA $293 total
includes taxes & fees
Apr 19 - Apr 20
UU Rowe Camp and Conference Center

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, (1,000 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is CA $136
CA $152 total
includes taxes & fees
Apr 30 - May 1
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (412 reviews)
"Very comfortable bed and good hot shower. A good value for your money. Nice staff at front desk."
United States
Kathleen
The price is CA $144
CA $161 total
includes taxes & fees
Apr 21 - Apr 22
Sunset Inn

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (60 reviews)
"Comfortable stay "
United States
Paul
The price is CA $144
CA $206 total
includes taxes & fees
Apr 20 - Apr 21
Becket Motel
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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Stay near popular Cheshire attractions

Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking, and local cuisine.

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

Top Cheshire Hotel Reviews

Recent Reviews in Cheshire

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Hotels in Cheshire with star rating

Find out more about Cheshire

Top reasons to visit Cheshire

  • Outdoor Adventures: Cheshire is a haven for outdoor enthusiasts, featuring excellent skiing and scenic hiking opportunities.
  • Charming Local Culture: Explore the quaint Cheshire Village and visit the Cheshire Military Museum for a taste of local history.
  • Vibrant Nightlife: Unwind at various pubs and local theatres after a day of adventure.
  • Beautiful Scenery: Enjoy the picturesque landscapes and scenic mountains that surround the area.
  • Diverse Accommodations: Find a range of hotels and resorts catering to families, couples, and adventurers alike.

Find great hotels near Cheshire

Discover the charm of Cheshire, Massachusetts, where a variety of hotels and resorts await to enhance your stay. Whether you’re seeking a family-friendly retreat, a romantic getaway, or an adventure-filled vacation, Cheshire offers accommodations that cater to all your needs. Explore the best Cheshire hotels for a memorable experience, and find the perfect spot to unwind while enjoying the scenic beauty of this delightful town.

  • Holiday Inn & Suites Pittsfield-Berkshires by IHG: Nestled in the heart of Pittsfield, only 14.5km from Cheshire, this 3-star hotel is perfect for families and adventure seekers alike. The property boasts a range of outdoor activities such as snowboarding, hiking, horseback riding, and fishing, making it an excellent choice for those looking to embrace the great outdoors. Families will appreciate the child-friendly amenities, including free cribs and window guards for safety. With its city-themed atmosphere and recreational options nearby, this hotel promises a memorable stay filled with excitement and exploration.
  • Club Wyndham Bentley Brook: Situated just 9.7km from Cheshire, Club Wyndham Bentley Brook is a 3-star resort tailored for ski enthusiasts and adventure lovers. With convenient access to ski shuttles and lifts, guests can hit the slopes in no time. The property features onsite snowboarding and is near hiking and downhill skiing locations, making it an ideal retreat for winter sports enthusiasts. Enjoy the inviting atmosphere and easy access to thrilling outdoor activities that will satisfy your adventurous spirit.
  • Hotel Downstreet, Ascend Hotel Collection: Located 16.1km from Cheshire, Hotel Downstreet is a welcoming 3-star hotel that embraces inclusivity and pet-friendly policies. Ideal for LGBTQIA travellers, the property is affiliated with LGBTQI travel guides and allows pets, ensuring everyone feels at home. With amenities catering to dogs and cats, guests can enjoy their stay without leaving their furry friends behind. This hotel blends comfort and community, making it a great choice for those seeking a warm and welcoming atmosphere.

Where to stay near Cheshire

Cheshire, Massachusetts, offers a delightful blend of adventure and family-friendly experiences, making it an ideal vacation spot. From picturesque locations perfect for weekend getaways to romantic escapes, visitors can explore charming neighborhoods nearby. Enjoy skiing and outdoor activities while soaking in the scenic beauty. With convenient access to lovely locations, Cheshire provides a memorable atmosphere for every type of traveller, whether you're seeking adventure or a peaceful retreat.

  • Williamstown: Nestled 17.7km from Cheshire, Williamstown is a charming city renowned for its vibrant arts scene, historic college university, and stunning natural landscapes. Visitors flock here year-round, with peak seasons in April and June to July, drawn by the allure of skiing and adventure sports. The nearby ski fields and resorts offer excellent winter activities, while the picturesque mountains and tranquil lake provide a perfect backdrop for outdoor exploration. Whether you're hitting the slopes or strolling through the town's cultural landmarks, Williamstown promises a delightful travel experience.
  • Pittsfield: Located just 14.5km from Cheshire, Pittsfield is a dynamic city that comes alive during peak summer months from June to August. Known for its adventurous spirit, this city offers ample opportunities for skiing, as well as access to a stunning lake and mountain scenery. The local waterpark adds an extra element of fun for families, making it a versatile destination for travellers. With its rich history and community events, Pittsfield provides a warm and welcoming atmosphere, perfect for anyone looking to immerse themselves in local culture while enjoying the great outdoors.
  • North Adams: Just 16.1km away from Cheshire, North Adams is a vibrant city that embraces adventure and creativity. Known for its thriving arts community, this city features a renowned art museum and numerous public art installations that invite exploration. With peak visitor numbers in June to July and September, North Adams attracts those seeking outdoor fun and skiing experiences. The surrounding mountains provide fantastic hiking opportunities, while the cultural centre fosters a lively environment for arts and entertainment. North Adams offers a unique blend of nature and culture, ensuring an unforgettable vacation experience.

Things to do near Cheshire

Cheshire, Massachusetts, is perfect for outdoor enthusiasts and adventure seekers, offering fantastic skiing opportunities at its local ski resorts and fields. Visitors can enjoy scenic walks, vibrant nightlife, and a variety of pubs to unwind after a day on the slopes. For those looking to relax, the area also features charming local theatres and championship golf courses, making it an ideal destination for a well-rounded vacation experience.

Shopping

Cheshire offers a quaint shopping experience with local charm. For a broader selection, head to the North Adams Center, North Adams Gateway Center, or Colonial Plaza, all located 16.1km away, featuring a mix of business and family vibes. If you're up for a drive, you'll find more unique shops along the way.

Recreation

Skyline Country Club offers a scenic golf experience with stunning views and outdoor sports activities, perfect for golf enthusiasts. For a more tranquil atmosphere, visit Windsor Lake Park, where you can unwind amidst nature and enjoy wellness-focused relaxation. Waubeeka Golf Links also provides an excellent golfing experience surrounded by beautiful landscapes.

Adventure

At Jiminy Peak Mountain Resort, experience thrilling skiing and winter sports vibes only 11.3km from Cheshire. At Berkshire East Ski Resort, 24.1km away, enjoy outdoor adventures amidst breathtaking scenery. For hiking enthusiasts, the Skyline Trail, also 24.1km from Cheshire, offers stunning views and a true adventure experience.

Nightlife

Experience the vibrant nightlife in Cheshire by attending a show at the Williamstown Theatre Festival or the Adams Theater, both offering a mix of culture and entertainment. For something more adventurous, take a thrilling ride at the Alpine Super Slide, adding excitement to your evening.

*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 during your visit to Cheshire, plan your trip for the cheaper months of March to April or November, and aim for a Tuesday stay, as Saturdays tend to be pricier. Use Expedia’s search tool to find budget-friendly accommodations by sorting results from lowest to highest prices and applying filters for eco-friendly options. Consider booking a package that combines your hotel, flights, and activities for additional savings. Lastly, take advantage of free local attractions and consider using public transport to keep your costs down while exploring the area.

  • 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: Expedia’s search tool enables you to set your budget, choose your desired location, and much more. You can easily arrange your search results from the lowest to highest prices, ensuring you find the most affordable hotels first. Additionally, you have the option to narrow down your choices by hotel type. For instance, selecting the Eco-certified filter will display sustainable and environmentally-friendly hotels available for booking.
  • Consider bundling your trip: You can save money by combining your hotel stay in Cheshire with your flights and activities through an Expedia package.

Find the best attractions near Cheshire

Cheshire, Massachusetts, is an excellent destination for outdoor enthusiasts, offering skiing, adventure, and various cultural experiences. Key points of interest include the local library, scenic mountains, and arts centre. Visitors can explore the Cheshire Military Museum, the charming Cheshire Village, and nearby attractions like Chester, the Cheshire Ring, and Cheshire Oaks, making it a delightful spot for families and culture seekers alike.

  • Mount Greylock: Experience the beauty of Massachusetts' highest peak, just 8.0km from Cheshire. This mountain offers stunning vistas and thrilling outdoor adventures, perfect for hiking and nature photography.
  • Mount Greylock State Reservation Visitor Center: Located 4.8km away, this visitor centre is an ideal spot for families. It provides information on the area's natural wonders and access to various outdoor activities, ensuring a fun-filled day for all ages.
  • Williams College: A historic institution situated 16.1km from Cheshire, Williams College boasts a rich cultural atmosphere. Explore its beautiful campus, art galleries, and vibrant community events that reflect the college's esteemed heritage.

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

When visiting Cheshire, Massachusetts, you can fly into several major airports. Bradley International Airport (BDL) in Hartford, CT, is 80.5km away, with nearby accommodations like the DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport. Albany International Airport (ALB) is closer at 56.3km and offers options such as the Park Manor Hotel, located 12.9km away. The nearest airport is Pittsfield Municipal Airport (PSF), only 19.3km from Cheshire, where you can stay at The Central Downtown Inn & Suites, just 3.2km from the airport. Each airport provides convenient access to nearby hotels for your stay.

Frequently asked questions

What is the best area to stay in Cheshire?
The best area to stay in Cheshire is the village centre, particularly around Main Street, for convenient access to local amenities and a pleasant, quiet setting.

This central area offers a classic New England village experience. Main Street is where you'll find the local post office, a few small shops, and the town hall, all within a short walk of each other. The layout is quite simple, with residential streets branching off the main thoroughfare, and it's generally easy to navigate.

Couples looking for a relaxing escape will find the village centre appealing. It's a great base for enjoying the natural beauty of the Berkshires, with easy access to scenic drives and walks. The proximity to local eateries means a convenient evening out without needing to travel far.

For those planning to explore the wider Berkshire region by car, staying near the main roads that pass through Cheshire, such as Route 8, offers excellent convenience.
What are the best family hotels in Cheshire?
For a wonderful family stay in Cheshire, the Harbour House Inn is an excellent choice.

This 3.5-star inn boasts an impressive 9.6 rating and is highly recommended for families. It offers convenient connecting rooms, which are ideal for larger families, and many rooms provide stunning mountain views. Guests particularly appreciate the complimentary full breakfast and free WiFi. The inn is also well-located for exploring the outdoors, being just 7.6 km from Mount Greylock State Reservation.
What hotels in Cheshire offer free breakfast?
For a hotel in Cheshire offering complimentary breakfast, the Harbour House Inn is an excellent choice.

The 3.5-star Harbour House Inn, with an outstanding 9.6 rating, provides guests with both free breakfast and a full breakfast option. This hotel is praised for its tranquil mountain views and its convenient amenities, including free toiletries, free self-parking, and free WiFi. It is also well-located for exploring the area, with Mount Greylock State Reservation just 7.6 kilometres away. Find more hotels with free breakfast in Cheshire
What are the most romantic hotels in Cheshire for couples?
For a romantic stay in Cheshire, the Harbour House Inn is a wonderful option for couples.

This 3.5-star inn, with an impressive 9.6 rating, is celebrated for its beautiful mountain views, making it ideal for a romantic escape. Guests can enjoy a complimentary full breakfast, and the inn also provides free toiletries, free self-parking, and free WiFi. Its proximity to Mount Greylock State Reservation, just 7.6 km away, offers opportunities for scenic walks and enjoying nature together. See all romantic hotels in Cheshire
What are the best hotels in Cheshire near Mount Greylock State Reservation?
For hotels in Cheshire near Mount Greylock State Reservation, the Harbour House Inn is an excellent choice.

The 3.5-star Harbour House Inn, with an outstanding 9.6 rating, is located approximately 7.6 kilometres from Mount Greylock State Reservation, making it a convenient base for exploring the area. Guests frequently appreciate the complimentary full breakfast and free Wi-Fi. The hotel also offers connecting rooms, which is a great feature for families travelling together, and many rooms boast lovely mountain views.
When is the best time to go to Cheshire?
The best time to visit Cheshire is during the late spring, summer, and early autumn months, roughly from May to October, when the weather is most pleasant for outdoor activities.

During these months, the Berkshire Mountains offer ideal conditions for hiking, cycling, and exploring the natural beauty of the area. The foliage in autumn, particularly in late September and early October, is especially stunning, drawing many visitors to witness the vibrant colours. This period also sees the most local events and farmers' markets, adding to the experience.

For those interested in winter sports, the months of December through March offer opportunities for skiing and snowboarding at nearby resorts, though Cheshire itself is primarily a quiet, residential town without its own ski slopes.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Cheshire.
How can I save on a Cheshire hotel booking with Expedia?
Members always get our best prices. Find our best Cheshire hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Cheshire hotel?
Prices for hotels in Cheshire often vary, but you can find a great deal from CA $97 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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