A lake surrounded by autumn-colored trees and hills.

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Our top choices for Cheshire hotels

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.
A spacious living room with large windows, a fireplace, and a variety of seating options.
An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
United States
Rosario
$122 nightly
$136 total
Sep 24 - Sep 25
Total with taxes and fees
Vacation Village in the Berkshires
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, seating area, and a bar.
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
United States
Jonathan
$109 nightly
$121 total
Oct 1 - Oct 2
Total with taxes and fees
Berkshire Mountain Lodge
A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.
A room with a large sliding glass door leading to a garden. Inside, there is a table with chairs and a small table with a vase.
A gazebo in a garden with a house in the background.
A spacious living room with a large window, a sofa, a chair, and a dining area.

3. Harbour House Inn

Harbour House Inn
Cheshire
United States
Virginia
$233 nightly
$246 total
Sep 24 - Sep 25
Total with taxes and fees
Harbour House Inn
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.
A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.
A cozy library with bookshelves, a fireplace, and comfortable seating.

4. Berkshires Untold

Berkshires Untold
Lenox
United States
Olyvia
$145 nightly
$162 total
Sep 28 - Sep 29
Total with taxes and fees
Berkshires Untold
A resort with multiple buildings, a parking area, and a mountainous backdrop.
A restaurant interior with wooden tables and chairs, hanging light fixtures, and large windows allowing natural light.
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.
A wooden cabin with a porch and steps leading to a door, surrounded by snow.

5. Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
Hancock
United States
Karen
$139 nightly
$155 total
Oct 20 - Oct 21
Total with taxes and fees
Jiminy Peak Mountain Resort
A patio area with outdoor furniture, a fire pit, and potted plants.
A hotel room with a large bed, a desk, a chair, and a view of the outdoors.
A cozy living room with a stone fireplace, comfortable seating, and a television.
A bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".

6. The Springs Motel

The Springs Motel
New Ashford
United States
Chaim
$111 nightly
$122 total
Sep 24 - Sep 25
Total with taxes and fees
The Springs Motel
A building entrance with a large planter with purple flowers and a small tree.
A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.
A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.
A library with bookshelves, a television, and two armchairs.

7. Hotel On North

Hotel On North
Pittsfield
United States
Donna
$152 nightly
$170 total
Sep 24 - Sep 25
Total with taxes and fees
Hotel On North
A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.
A modern interior with a large window, a wooden table, and bar stools.
A reception area with a large landscape painting, a dark reception desk, and a potted plant.
A modern hotel building with the name "Hotel Downtown" on the facade.

8. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
United States
Alexandra
$127 nightly
$142 total
Oct 14 - Oct 15
Total with taxes and fees
Hotel Downstreet, an Ascend Collection Hotel
A round dining table set for a formal event, with white tablecloth, silverware, and purple napkins.
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

9. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Nicole
$109 nightly
$122 total
Oct 22 - Oct 23
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

10. The Yankee Inn

The Yankee Inn
Lenox
United States
William
$117 nightly
$131 total
Sep 28 - Sep 29
Total with taxes and fees
The Yankee Inn
A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.
A garden with a wooden house, a tree, and a person tending to plants.
A room with a hanging bed, a white wall, a window, and a door.
A modern living room with a sofa, armchair, coffee table, and ottoman. There is a large abstract painting on the wall, a dining table with chairs, and a staircase leading to an upper level.

11. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
Adams
United States
Susan
$179 nightly
$200 total
Sep 24 - Sep 25
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.
A spacious living area with a fireplace, wooden beams, and a large window.
An outdoor seating area with stone fire pit, chairs, and a red building in the background.
A bar area with wooden beams, red chairs, and a long wooden table.

12. The Williams Inn

The Williams Inn
Williamstown
United States
Karl
$220 nightly
$246 total
Sep 27 - Sep 28
Total with taxes and fees
The Williams Inn
A building with a porch and multiple windows, surrounded by purple flowers.
A café with a display case, a frozen food section, and a marketplace sign.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A living room with a sofa, armchair, coffee table, and a patterned rug.

13. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
United States
Jared
$135 nightly
$150 total
Sep 27 - Sep 28
Total with taxes and fees
Holiday Inn Club Vacations Oak 'n Spruce Resort
A dining table with plates of food, a coffee cup, and a plant.
A cozy library with wooden bookshelves, a reading area, and a fireplace.
A living room with a grey sectional sofa, a small round coffee table, a brown leather armchair, and a window with curtains.
Two people sitting on white chairs under a covered porch, one reading a book and the other holding a cup. A small dog is sitting on the ground between them.

14. Berkshire Valley Inn

Berkshire Valley Inn
Williamstown
United States
Robert
Berkshire Valley Inn
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lakeside dock with kayaks and a covered boat ramp.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A lodge with a large building and a dock by a lake, surrounded by forest.

15. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
toan
$128 nightly
$143 total
Sep 30 - Oct 1
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.
A hotel room with a TV, microwave, mini-fridge, desk, chair, mirror, and a coat rack.
A dining area with wooden tables and chairs, a television, and a door with a sign.
A hotel room with a fitness center including a weight machine, an elliptical, and a treadmill.

16. FairBridge Inn Express

FairBridge Inn Express
Pittsfield
United States
ERICIA
$69 nightly
$77 total
Sep 24 - Sep 25
Total with taxes and fees
FairBridge Inn Express
A small, single-story building with a green roof and a white exterior. There are two large trees in front of the building, each with a flower pot on top. The surrounding area has grass, a few pumpkins, and a small garden with red flowers.
A blue wooden deck with white picket railings, surrounded by a well-maintained lawn and colorful autumn foliage.
A kitchen with a fireplace, dining area, and a large window with curtains.
A living room with a sofa, chairs, a coffee table, and a rug. There is a kitchen area with a refrigerator and a water dispenser.

17. Williamstown Motel

Williamstown Motel
Williamstown
United States
Baljit
$96 nightly
$107 total
Sep 24 - Sep 25
Total with taxes and fees
Williamstown Motel
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
A fenced outdoor area with a pool, lounge chairs, and umbrellas.
A motel with a parking lot, a swimming pool, and outdoor seating.

18. Berkshire Inn

Berkshire Inn
Pittsfield
United States
Kristina
$86 nightly
$96 total
Sep 24 - Sep 25
Total with taxes and fees
Berkshire Inn
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A backyard with a swimming pool, lounge chairs, and a hot tub.
A bar with wooden floors and shelves filled with bottles.

19. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Gerald
$216 nightly
$242 total
Sep 30 - Oct 1
Total with taxes and fees
The Red Lion Inn
A building with a covered parking area and a grassy front yard.
A dining area with wooden chairs and tables, a kitchen counter with appliances, and framed pictures on the wall.
A motel with multiple rooms, a parking area, and a large tree in the foreground.
A hotel room with a large bed, two bedside tables with lamps, a desk with a chair, and a small window.

20. Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
Williamstown
United States
Suzanne
$100 nightly
$112 total
Sep 24 - Sep 25
Total with taxes and fees
Howard Johnson by Wyndham Williamstown
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Where to stay near Cheshire

Cheshire, MA offers a charming blend of outdoor adventure and family-friendly activities. Explore the scenic Berkshire districts, perfect for a romantic getaway or weekend plans. Enjoy the area's natural beauty and find accommodations with Wi-Fi for a comfortable stay while you create lasting memories in this lovely region.
A sculpture of spirals in a grassy area with autumn trees and a building in the background.
A modern building with outdoor seating, a reflective water feature, and trees with autumn foliage.
A white church with a steeple, surrounded by autumn-colored trees.
A park with autumn trees, a stone building, and a bench.
A park with a large tree, a bench, and a monument.

Williamstown

Discover Williamstown, a charming destination perfectly suited for travelers seeking a blend of culture, nature, and adventure. This vibrant city offers easy access to notable attractions like Williams College, the Massachusetts Museum of Contemporary Art, and The Clark Art Institute, making it ideal for those looking to explore art and history. Located about 17 miles by car from Cheshire, Williamstown serves as a great base for enjoying skiing and outdoor activities, ensuring a memorable stay for all visitors.

A church with a green spire and a red brick building with arched windows.
A historic building with a clock, a flag, and a street lamp.
A church with a tall steeple and a green roof.
A lakeside house with a dock and a covered area, a sunset over the water, and mountains in the background.
A cityscape with a rainbow, red buildings, and a church.
Photo by Ed Gaffny

Pittsfield

Experience the charm of Pittsfield, an excellent hub for families and adventure seekers eager to explore attractions such as the National Shrine of the Divine Mercy, Hancock Shaker Village, and the Berkshire Museum. With a variety of outdoor activities, including skiing and water sports, Pittsfield caters to travelers year-round, with peak visits in the summer months. Located about 9 miles by car from Cheshire, Pittsfield serves as a smart choice for your next getaway, offering diverse experiences for everyone.

A white building with a sign reading "Hancock Town Hall 1850" in front of a forested hillside.
Two large wooden silos, a yellow building with a tower, and a fenced area with a stone wall.
A hillside with autumn-colored trees and five wind turbines against a blue sky with clouds.
A rural landscape with sheep grazing, two wooden silos, and a forested hill in the background.
A rural landscape with a fenced field, several sheep grazing, and two wooden barns in the background.

Hancock

Family travelers will love Hancock, known for its stunning natural landscape and outdoor adventures. Nestled near Mount Greylock and the serene Mount Greylock State Reservation, it offers ample opportunities for skiing, hiking, and exploring the local parks. With historic Williams College nearby, visitors can enjoy cultural experiences as well. Located about 6 miles from Cheshire, Hancock makes for a smart choice for those seeking a weekend getaway filled with nature and adventure.

A railway tunnel with a curved ceiling and tracks.
Photo by Chris Addams
A building with 'MASS MoCA' written on it, surrounded by greenery and hills.
Photo by Caminante
A winding road through a forested area with autumn-colored trees and a rocky cliff.
Photo by Heather Beaudry
A street lined with multi-story buildings, including a red brick building and a white building with blue trim. There are storefronts with signs, a fire hydrant, and a street lamp.
A mountainous landscape with a prominent rock formation in the foreground and a valley with scattered buildings in the distance under a sunset sky.
Photo by Chris Addams

North Adams

Optimized for cultural enthusiasts and adventure seekers, North Adams serves as a vibrant gateway to an array of attractions. Here, you can explore the Massachusetts Museum of Contemporary Art, immerse yourself in the history of Williams College, and appreciate the art at The Clark Art Institute. Located about 10 miles by car from Cheshire, North Adams offers easy access for a day trip or a weekend getaway. It’s a smart choice for travelers looking for a blend of culture and outdoor experiences.

A tall tower with a green dome and a pointed top, surrounded by trees and clouds.
A panoramic view of a town nestled in a valley surrounded by dense forests and rolling hills.
A tower with a green glass dome and intricate carvings.
A paved path flanked by trees with autumn foliage, leading to a lakeside area with benches.
Photo by Caitlin Reese

Lanesborough

Travelers visiting the area often choose Lanesborough, especially families and outdoor enthusiasts seeking close proximity to stunning natural attractions. With highlights like Mount Greylock and the Berkshire Museum, Lanesborough offers a perfect blend of adventure and culture, making it an ideal base for exploring the outdoors or enjoying a weekend getaway. Located about 5 miles from Cheshire, Lanesborough provides a great hub for your vacation, ensuring a memorable stay amidst the beauty of the Berkshires.

Stay near popular attractions in and around Cheshire

Cheshire offers a perfect blend of outdoor adventure and cultural experiences. Explore scenic nature reserves, immerse yourself in local culture at the library and cultural center, or enjoy family-friendly activities. This charming destination is ideal for those seeking a memorable getaway in nature.
A tall, conical tower with a spherical top, surrounded by a grassy field and a stone staircase leading up to it.
Photo by Caitlin Reese

Mount Greylock

9.4/10 (180 reviews)
Set the stage for your outdoor adventure at Mount Greylock, a stunning mountain perfect for nature lovers. Experience breathtaking scenery and a variety of outdoor activities. Located about 5 miles from Cheshire, it offers easy access to unforgettable views and experiences, making it an ideal base for your exploration.
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A building with 'MASS MoCA' written on it, surrounded by greenery and hills.
Photo by Caminante

Massachusetts Museum of Contemporary Art

9.4/10 (246 reviews)
Often cited as a favorite among art lovers, the Massachusetts Museum of Contemporary Art in North Adams offers a unique blend of cutting-edge exhibitions and vibrant cultural experiences. Located about 11 miles by car from Cheshire, this museum is a convenient stop for those looking to immerse themselves in contemporary art while exploring the picturesque Berkshires.
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A historic building with ivy-covered brick walls, a large lawn, and a clear blue sky.

Williams College

9.4/10 (534 reviews)
Ideal for travelers interested in culture, Williams College offers a rich historical experience in Williamstown, Massachusetts. This vibrant campus features stunning architecture and a variety of cultural events. It's about a 17-mile drive from Cheshire, making it a convenient stop for exploring the area’s educational heritage.
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A modern building with outdoor seating, a reflective water feature, and trees with autumn foliage.

The Clark Art Institute

9.8/10 (202 reviews)
Considered a premier spot for art lovers, The Clark Art Institute in Williamstown offers a unique blend of culture and stunning landscapes. Visitors often appreciate its impressive collection and serene surroundings, located about 10 miles from Cheshire, making it a convenient destination for those seeking inspiration and tranquility.
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A waterfall cascading over rocks in a forested area.
Photo by Janine Edmondson

Wahconah Falls State Park

An essential stop for outdoor enthusiasts, Wahconah Falls State Park offers breathtaking scenery and adventurous vibes. Located about 6 miles from Cheshire, this park features stunning waterfalls and lush landscapes, making it a perfect destination for nature lovers. Staying nearby allows easy access to this beautiful natural retreat.
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Brodie Mountain

9.0/10 (30 reviews)
A fascinating mix of adventure and stunning scenery awaits outdoor enthusiasts at Brodie Mountain. Located about 7 miles from Cheshire, this destination offers a perfect backdrop for exploration and relaxation. Its proximity to Cheshire makes it an ideal spot for nature lovers seeking a memorable getaway.
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East Hoosac Quaker Meetinghouse

6.0/10 (1 review)
Perfectly suited for history buffs and those seeking tranquility, the East Hoosac Quaker Meetinghouse offers a glimpse into the rich cultural heritage of the area. Located about 5 miles from Cheshire, this charming church invites visitors to explore its serene atmosphere and unique architectural features, making it a convenient stop during your travels.
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St Mary's of the Assumption Church

10.0/10 (1 review)
A cornerstone of local culture, St Mary's of the Assumption Church in Cheshire, Massachusetts, offers visitors a serene glimpse into the area's rich heritage. This charming church is known for its inviting atmosphere and beautiful architecture. Located within Cheshire, it provides easy access to nearby attractions, making it a convenient stop for travelers exploring the region.
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Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking, and natural setting.

See all hotels in Cheshire
A lake surrounded by autumn-colored trees with a clear sky.

Top Cheshire Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"One of the most important aspects of a good hotel is the smell of it when I first walk in the door. This lodge smelled clean and was clean. The second important thing is the customer service. This place was just okay. Polite but not very friendly. The third important aspect is the plumbing and that was just okay too. Workable enough so we didn’t have to ask for another room but the little soaps were tiny and the toilet was in okay condition. A little hard to flush sometimes. They act like it’s someplace special but it really isn’t. It was a good stay but nothing special. Location was convenient to everything - restaurants and stores."
Karen 2-night trip
Posted less than an hour ago
Berkshire Mountain Lodge
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Perfect will stay there again."
Ann Marie 1-night trip
Posted 1 hour ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Great location; walkable to restaurants. Spacious 7th floor room had a nice town and mountain view. All staff friendly and helpful. Bed was comfortable; room very clean. Breakfast was minimal and uninspiring."
Karl 1-night trip
Posted 3 hours ago
Hotel Downstreet, an Ascend Collection Hotel
The Williams Inn

The Williams Inn

10/10 Excellent
"Great hotel at a great location. Staff were most helpful especially Stephen at the desk. Bartender was top notch as were the restaurant staff. Highly recommend!👍"
William 1-night trip
Posted 17 hours ago
The Williams Inn
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"Every one was very kind and helpful."
Jean 1-night trip
Posted 22 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"I am disappointed that it has been over two weeks and I have yet to receive my room deposit back. They told me 7-10 days"
Graham 2-night trip
Posted 1 day ago
Vacation Village in the Berkshires
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good
"The facilities and property made for a wonderful family visit to the Bershires."
Jared 5-night trip
Posted 1 day ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"Great location for our trip into NE."
Mark 1-night trip
Posted 1 day ago
Quality Inn Lee - Lenox South
Berkshires Untold

Berkshires Untold

8/10 Good
"Liked he cleanliness. Room was very cold and no heat was available."
Anne E 2-night trip
Posted 2 days ago
Berkshires Untold

More cheap stays in Cheshire

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
$69 nightly
$77 total
Sep 24 - Sep 25
Total with taxes and fees
FairBridge Inn Express
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA
$106 nightly
$118 total
Oct 18 - Oct 19
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA
$110 nightly
$122 total
Oct 19 - Oct 20
Total with taxes and fees
Quality Inn Lee - Lenox South
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

1055 South Street Pittsfield MA
$114 nightly
$127 total
Oct 22 - Oct 23
Total with taxes and fees
9.4/10 Exceptional! (217 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
$117 nightly
$131 total
Sep 28 - Sep 29
Total with taxes and fees
9.2/10 Wonderful! (1,005 reviews)
The Yankee Inn
The Whitlock

The Whitlock

16 Church St Lenox MA
$139 nightly
$155 total
Sep 24 - Sep 25
Total with taxes and fees
The Whitlock

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, offering skiing at local resorts and scenic hiking trails in the Berkshires.
  • Relaxation and Wellness: Enjoy wellness retreats and spa services for a rejuvenating experience in a serene setting.
  • Family-Friendly Attractions: Engage in cultural experiences and activities suitable for all ages, including visits to the local library.
  • Romantic Getaways: Couples can find romance amidst nature, perfect for a peaceful retreat.
  • Charming Accommodations: A variety of hotels cater to different preferences, ensuring a comfortable stay.

Find great hotels near Cheshire

Discover the charm of Cheshire, Massachusetts, where a variety of hotel accommodations await to enhance your travel experience. Whether you're seeking a family-friendly resort, a romantic getaway, or an adventurous stay, Cheshire offers top-notch options to suit every preference. Explore the best hotels in the area and enjoy easy access to nearby attractions, ensuring a memorable vacation filled with comfort and excitement.

  • Holiday Inn & Suites Pittsfield-Berkshires by IHG: Nestled about 9 miles from Cheshire, the Holiday Inn & Suites Pittsfield-Berkshires is a family-friendly 3-star hotel that boasts a guest rating of 8.0. This property is perfect for adventure seekers and those traveling with pets. Enjoy a variety of onsite and nearby adventure sports, including skiing, snowboarding, horseback riding, and fishing. The hotel caters to families with amenities like free cribs and breakfast options for children. Pets are welcome, with a flexible policy to accommodate your furry friends.
  • Hotel Downstreet, an Ascend Collection Hotel: Located approximately 10 miles from Cheshire, Hotel Downstreet is a charming 3-star property with a guest rating of 8.8. This hotel is ideal for business travelers and pet owners alike. With a welcoming atmosphere, it provides essential amenities and comfortable accommodations for a productive stay. The hotel’s pet policy allows dogs and cats, ensuring that you can bring your beloved pets along for the journey, with service animals welcomed at no extra charge.
  • Club Wyndham Bentley Brook: Just 6 miles from Cheshire, Club Wyndham Bentley Brook is a top-rated 3-star hotel with an impressive guest rating of 9.2. This property is a haven for ski and adventure enthusiasts, with easy access to ski lifts and shuttles. Guests can enjoy onsite snowboarding and nearby hiking and biking trails, making it a perfect choice for outdoor adventures. With spacious accommodations and excellent amenities, this hotel ensures a memorable stay amidst the beautiful Berkshires.

Where to stay near Cheshire

Cheshire, Massachusetts offers a perfect blend of outdoor adventure and family-friendly fun. Explore the scenic beauty of the Berkshires by hiking local trails or enjoy thrilling winter sports at nearby ski resorts. This charming town is an ideal getaway for couples seeking romance amidst nature, while also catering to families looking for budget-friendly activities. Discover the rich New England atmosphere and create unforgettable memories in and around Cheshire.

  • Williamstown: Nestled 11 miles from Cheshire, Williamstown is a charming town known for its vibrant arts scene and outdoor adventures. Visitors flock here year-round, with peak times in April and the summer months. The area is a haven for ski enthusiasts, offering access to ski fields and resorts for the ultimate winter sports experience. Beyond skiing, you can explore the picturesque mountains and serene lakes, making it perfect for hiking and relaxation. Don’t miss the historic college university that adds a cultural flair to the town.
  • Pittsfield: Located 9 miles from Cheshire, Pittsfield is a dynamic city that attracts adventurers and sports lovers alike. The peak visitor season runs from June to August, offering plenty of summer activities. This city is known for its ski resorts and fields, providing ample opportunities for winter sports enthusiasts. In addition to skiing, you can enjoy the beautiful lakes and scenic mountains nearby. For family fun, the local waterpark is a must-visit, ensuring a day of excitement and thrills.
  • Hancock: Just 6 miles away from Cheshire, Hancock is a small city that captures the essence of New England charm. With peak travel times in March through April and during the summer, it's a popular destination for adventure seekers. Hancock offers fantastic skiing opportunities at its nearby resorts, making it a favorite among winter sports fans. The stunning mountains and tranquil lakes are perfect for outdoor activities year-round, while the urban park provides a peaceful retreat for leisurely strolls and picnics.

Things to do in Cheshire

Cheshire, Massachusetts, is perfect for outdoor and adventure enthusiasts, particularly those interested in skiing. Visitors can enjoy activities like skiing at local resorts and exploring the picturesque landscape. In addition to skiing, Cheshire offers wellness retreats and spa services, making it an ideal destination for relaxation and rejuvenation. Local attractions further enhance the experience, providing a well-rounded vacation for both adventure seekers and those looking to unwind.

Shopping

In Cheshire, visit local shops for unique gifts and souvenirs. If you're up for a drive, head to the Berkshire Mall in Lanesborough, about 12 miles away, which features a mix of national retailers and dining options, perfect for a day of shopping.

Recreation

Cheshire Wellness Retreat offers a tranquil environment with yoga classes, meditation sessions, and holistic treatments. Enjoy peaceful nature walks and rejuvenating spa services. Nearby, the scenic Cheshire Lake provides opportunities for kayaking, fishing, and picnicking, perfect for unwinding amidst beautiful landscapes.

Adventure

In Cheshire, explore the scenic trails at the Berkshire Scenic Railway Museum for a unique rail adventure. Experience the thrill of hiking at Mount Greylock State Reservation, where breathtaking views await at the summit. Enjoy fishing or kayaking at Cheshire Lake, perfect for a refreshing day on the water.

Nightlife

Experience the cozy atmosphere at the Cheshire Wine Bar, where you can enjoy a selection of fine wines and small plates. For a relaxed evening, visit the local tavern for craft beers and trivia nights, perfect for mingling with friendly locals and enjoying a laid-back vibe.

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

Booking tips and Expedia advantages for Cheshire

  • 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: Utilize Expedia's search tool to customize your options based on your budget, desired location, and preferred type of accommodation. To find the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money 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 a fantastic destination for outdoor enthusiasts and adventure seekers, offering a variety of activities such as skiing and exploring local mountains and nature reserves. Visitors can enjoy cultural experiences and family-friendly activities at attractions like the local library. Whether you're looking to immerse yourself in nature or engage in outdoor adventures, Cheshire has something for everyone to enjoy.

  • Massachusetts Museum of Contemporary Art: Located 10 miles from Cheshire, this vibrant cultural center showcases innovative contemporary artworks. With its dynamic exhibitions and installations, visitors can immerse themselves in the ever-evolving world of modern art, making it a must-visit for art enthusiasts.
  • Mount Greylock: Just 5 miles away, Mount Greylock offers breathtaking scenery and thrilling outdoor adventures. As the highest peak in Massachusetts, it features hiking trails and stunning panoramic views that are perfect for nature lovers and adventure seekers alike.
  • The Clark Art Institute: Also situated 10 miles from Cheshire, The Clark Art Institute combines a stunning art collection with beautiful landscapes. Visitors can explore its impressive galleries and enjoy serene outdoor spaces, making it a delightful blend of culture and nature.

Best time to go to Cheshire

The best time to visit Cheshire is dependent 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 planning your trip to Cheshire, Massachusetts, you have several airport options. Bradley International Airport (BDL) in Hartford, CT, is 50 miles away, with nearby hotels like the DoubleTree by Hilton Hartford - Bradley Airport, just 1 mile from the airport, and the Marriott Hartford Downtown, located 12 miles away. ALBany International Airport (ALB) is closer at 35 miles, featuring hotels such as The Landing Hotel at Rivers Casino & Resort and the DoubleTree by Hilton Schenectady Downtown, both about 8 miles from the airport. Lastly, Manchester-Boston Regional Airport (MHT) is 91 miles away, with options like The Grand at Bedford Village Inn and DoubleTree by Hilton Manchester Downtown, both 4 miles from MHT.

Frequently asked questions

What is the best area to stay in Cheshire?
The best area to stay in Cheshire is the center of the town, particularly around Main Street and North Street.This area serves as the town's core, offering convenient access to local amenities and a pleasant, small-town atmosphere. You'll find the historic Cheshire Town Hall, the Cheshire Public Library, and several local shops and eateries concentrated here. The layout is straightforward, making it easy to navigate on foot.This central area is ideal for travelers looking for a relaxing and convenient base to explore the region. Its central location allows for easy drives to nearby natural attractions and other Berkshire towns. You'll appreciate being able to walk to local establishments.For those seeking a quieter experience with direct access to nature, the areas bordering the Ashuwillticook Rail Trail are an excellent choice. These accommodations often provide direct access to the paved trail, superb for walking or biking.
What are the best family hotels in Cheshire?
For family-friendly hotels in Cheshire, the Harbour House Inn is an excellent choice.This 3.5-star hotel, with an outstanding 9.6 rating, offers amenities that cater to families, including connecting rooms for convenience and complimentary breakfast. Guests appreciate the free WiFi and free self-parking. The inn also boasts a mountain view and is located near the mountains, providing a scenic backdrop for a family getaway. It is also conveniently located approximately 4.7 miles from Mount Greylock State Reservation, offering easy access to outdoor activities.
What hotels in Cheshire offer free breakfast?
For a hotel in Cheshire offering complimentary breakfast, the Harbour House Inn is an excellent option.The 3.5-star Harbour House Inn, boasting an impressive 9.6 rating, provides guests with a free full breakfast to start their day. This hotel also offers free WiFi and free self-parking, and many guests appreciate the mountain views and its convenient location near Mount Greylock State Reservation. Find more hotels with free breakfast in Cheshire
What are the most romantic hotels in Cheshire for couples?
For a romantic escape in Cheshire, the Harbour House Inn is an excellent choice for couples.This 3.5-star inn, with an exceptional 9.6 rating, is highly regarded for its beautiful mountain views, providing a serene backdrop for a couples' getaway. Guests appreciate the complimentary full breakfast and free WiFi, adding to the convenience and comfort of their stay. The inn's location is also convenient for exploring the natural beauty of the area, as it is just 4.7 miles from Mount Greylock State Reservation.
What are the best hotels in Cheshire near Mount Greylock State Reservation?
For hotels in Cheshire near Mount Greylock State Reservation, consider the Harbour House Inn.The 3.5-star Harbour House Inn, with an outstanding 9.6 rating, is an excellent choice for its proximity to Mount Greylock State Reservation, located just 4.7 miles away. This hotel offers complimentary breakfast, including a full breakfast option, and free WiFi, making it convenient for families. Guests can also enjoy amenities such as connecting rooms and mountain views. Free self-parking and complimentary toiletries add to the comfort and convenience for travelers.
When is the best time to go to Cheshire?
The best time to visit Cheshire, Massachusetts, is during the fall, from September to October, for its stunning foliage, or in the summer, from June to August, for warm weather and outdoor activities.Fall brings vibrant displays of red, orange, and gold leaves across the Berkshire Mountains, making it ideal for scenic drives and hiking. The cooler temperatures are comfortable for exploring the outdoors, and local farms often host harvest festivals. This season is particularly appealing to couples looking for a picturesque and romantic getaway.Summer offers pleasant temperatures, great for enjoying the area's natural beauty. Visitors can explore the Ashuwillticook Rail Trail for walking or biking, or enjoy water activities on Cheshire Lake.
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 much is the nightly rate at a Cheshire hotel?
Prices for hotels in Cheshire often vary, but you can find a great deal from $77 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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