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Our top choices for Chester hotels

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.
Indoor pool
A spacious living room with large windows, a fireplace, and a variety of seating options.

1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
United States
Terri
$128 nightly
$143 total
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village in the Berkshires
A bar area with wooden tables and chairs, a central bar counter with taps, and a brick wall with shelves of bottles and glasses.
A modern hotel lobby with leather furniture, a bar area, and a large TV screen.
A hotel room with two beds, a desk, a chair, a lamp, and a large window with curtains.
A casino with multiple blackjack tables, slot machines, and a large chandelier.

2. MGM Springfield

MGM Springfield
Metro Center
United States
Nathan
$169 nightly
$192 total
Nov 1 - Nov 2
Total with taxes and fees
MGM Springfield
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".
A spacious lobby with a fireplace, seating area, and a bar.
A garden with wooden Adirondack chairs and a stone pathway.

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
United States
Barbara
$115 nightly
$128 total
Nov 9 - Nov 10
Total with taxes and fees
Berkshire Mountain Lodge
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".
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
Madhavi R
$136 nightly
$152 total
Nov 1 - Nov 2
Total with taxes and fees
Berkshires Untold
An outdoor patio with white chairs and tables, a central fire feature, and string lights.
A hotel with a sign reading "D. HOTEL & SUITES" on the facade.
A bar area with a wooden counter, bar stools, and a variety of bottles and glasses.
A bedroom with a four-poster bed, a leather sofa, a wooden coffee table, and a view of greenery through the window.

5. D. Hotel Suites & Spa

D. Hotel Suites & Spa
Holyoke
United States
Jim
$142 nightly
$158 total
Oct 26 - Oct 27
Total with taxes and fees
D. Hotel Suites & Spa
A building with a porch and multiple windows, surrounded by purple flowers.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

6. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
United States
Hugh
$135 nightly
$150 total
Oct 13 - Oct 14
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A covered porch with wicker furniture and hanging flower baskets.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

7. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
TAKOSHIA
$195 nightly
$218 total
Nov 4 - Nov 5
Total with taxes and fees
The Red Lion Inn
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

8. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
$106 nightly
$118 total
Nov 1 - Nov 2
Total with taxes and fees
The Yankee Inn
A breakfast area with a counter, seating, and a menu display.
A modern living room with a sofa, armchair, and a small table.
A hotel room with a bed, a desk, a chair, a small table, and a window with a view of a building.
A hotel lobby with reception desks, seating area, and a modern ceiling design.

9. Holiday Inn Express Springfield Downtown by IHG

Holiday Inn Express Springfield Downtown by IHG
Metro Center
United States
Melissa
$111 nightly
$126 total
Nov 9 - Nov 10
Total with taxes and fees
Holiday Inn Express Springfield Downtown by IHG
A multi-story hotel with a prominent "Hotel Northampton" sign, featuring a classic architectural style with a brick facade and multiple windows.
A hotel room with two beds, a TV, a desk, and a chair.
A hotel lobby with a glass vase of white flowers on a table, red chairs, and a wooden reception desk.
An outdoor cafe with tables and chairs, surrounded by hanging flower baskets and a brick building in the background.

10. Hotel Northampton

Hotel Northampton
Northampton
United States
Douglas
$165 nightly
$184 total
Oct 12 - Oct 13
Total with taxes and fees
Hotel Northampton
A Candlewood Suites hotel with a modern design, featuring multiple floors and a well-lit entrance.
A hotel room with a sofa, a bed, a desk, and a framed picture on the wall.
A reception area with a reception desk, a framed welcome sign, a framed abstract artwork, and an exit sign.
A kitchen with a large island, a microwave, cabinets, and a refrigerator.

11. Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG
Windsor Locks
United States
Harold
$88 nightly
$101 total
Nov 2 - Nov 3
Total with taxes and fees
Candlewood Suites Windsor Locks Bradley Arpt by IHG
A modern lounge area with sofas, a pool table, and a unique chandelier.
A hotel room with a large bed, two bedside tables with lamps, a massage chair, and a wall mural of mountains.
A modern coffee bar with espresso machines, a coffee station, and a shelf with coffee products.
A modern hotel with a covered entrance, multiple windows, and a well-maintained lawn.

12. Blue A Modern Hotel, an Ascend Collection Hotel

Blue A Modern Hotel, an Ascend Collection Hotel
West Springfield
United States
Sumit
$101 nightly
$116 total
Nov 1 - Nov 2
Total with taxes and fees
Blue A Modern Hotel, an Ascend Collection Hotel
A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.
A hotel room with a bed, a sofa, a dining table, and a chair. There are two nightstands with lamps and a framed picture on the wall.
A brick building with a sign reading "The Ellery."
A modern hotel room with a bed, sofa, dining table, and chairs.

13. The Ellery

The Ellery
Northampton
United States
Anjali
$127 nightly
$141 total
Oct 28 - Oct 29
Total with taxes and fees
The Ellery
A building with a flat roof, multiple windows, and a satellite dish.
A hotel room with a large bed, a chair, a nightstand with a lamp, and a window with blinds.
An outdoor patio with a table and chairs, surrounded by wooden deck and greenery.
A dining area with a round table set for four, surrounded by dark chairs. A white door is visible in the background, leading to a kitchen area with white appliances.

14. Becket Motel

Becket Motel
Becket
United States
Alice
$140 nightly
$156 total
Oct 11 - Oct 12
Total with taxes and fees
Becket Motel
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A dining area with large windows, wooden furniture, and a view of a lake.
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
Anthony
$118 nightly
$132 total
Nov 10 - Nov 11
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A multi-story hotel with a prominent 'La Quinta' sign, featuring a symmetrical facade with evenly spaced windows and a central entrance.
An indoor swimming pool with clear blue water, surrounded by chairs and a high ceiling with visible ductwork.
A hotel dining area with multiple tables and chairs, a patterned carpet, and a reception desk in the background.
A spacious lobby with wooden flooring, a reception desk, and two patterned armchairs.

16. La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA
Metro Center
United States
Maria
$111 nightly
$125 total
Nov 1 - Nov 2
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Springfield MA
A hotel room with a large window, a flat-screen TV, red upholstered chairs, a glass coffee table, and a patterned carpet.
A Days Inn van parked at a gas station with a clear view of the sky and distant buildings.
A Days Inn hotel with a two-story building, a covered patio, and a landscaped front yard.
A spacious dining area with high ceilings and large windows, featuring red upholstered chairs and a glass-top table.

17. Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport
Windsor Locks
United States
Loxley
$81 nightly
$93 total
Oct 13 - Oct 14
Total with taxes and fees
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport
A small bathroom with a white sink, a mirror, and a black cabinet.
A multi-level building with a covered walkway and a stone feature in the foreground.
A hotel room with a bed, a window with curtains, a wall-mounted air conditioner, and a nightstand with a lamp.
A reception area with a counter, two chairs, a small table, and a window.

18. Motel 6 Enfield, CT - Hartford

Motel 6 Enfield, CT - Hartford
Enfield
United States
John
$53 nightly
$61 total
Oct 25 - Oct 26
Total with taxes and fees
Motel 6 Enfield, CT - Hartford
A modern hotel lobby with a breakfast bar, a seating area, and a view of the outdoors.
A hotel room with a large bed, a sofa, a chair, and a ceiling fan.
A La Quinta hotel with a modern facade, a large sun logo, and a covered entrance.
A reception area with a cityscape mural, two reception desks, and a tiled floor.

19. La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport
Windsor Locks
United States
Xiaoping
$100 nightly
$115 total
Oct 25 - Oct 26
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A snack bar with shelves of snacks and a refrigerated display.
A modern cafe with a counter, seating area, and large windows.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
United States
James
$99 nightly
$111 total
Nov 8 - Nov 9
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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Where to stay near Chester

Chester offers a perfect blend of outdoor adventure and family-friendly vibes. Explore the scenic beauty in nearby areas, enjoy a romantic getaway in downtown Chester, and embrace the spirit of a Massachusetts vacation. Don’t miss the charm of Cape Cod and the nearby capital for a well-rounded experience.
A large white house with multiple chimneys, surrounded by lush greenery and trees.
A sign for Lenox Library Welles Gallery with operating hours.
A large white colonial-style house with a stone foundation, a white fence, and a green lawn.
A street lamp with a sign reading "VENTFORT HALL" and "LENOX 1767" against a backdrop of autumn-colored trees.
A river surrounded by autumn-colored trees and a forested hill.

Lenox

Discover Lenox, a charming destination perfectly suited for travelers seeking family-friendly activities, nature, and cultural experiences. This vibrant city features the serene National Shrine of the Divine Mercy, the historic Mount, and the renowned Norman Rockwell Museum, offering a rich blend of entertainment and exploration. With visitor numbers peaking from June to August, Lenox provides an inviting atmosphere year-round. Located about 24 miles by car from Chester, it's an ideal choice for a memorable getaway.

A historic street with brick buildings, storefronts, and parked cars.
A street lined with historic buildings, including a Morgan House restaurant.
A red brick building with arched windows and a sign for the Lee 911 Dispatch Police Dept.
A street lined with vintage shops, including Sparrow Singing and a barber shop.
A brick building with white columns and a sign for the Morgan House restaurant.

Lee

Experience the charm of Lee, a delightful hub for family and nature lovers seeking a weekend getaway. Enjoy local attractions like the serene National Shrine of the Divine Mercy, the historic Mount, and the captivating Norman Rockwell Museum, all offering enriching experiences. With Lee located about 20 miles away from Chester, you can easily access exciting activities such as theater, music concerts, and winter sports. Choosing Lee for your stay is a smart decision for an unforgettable escape.

A calm lake surrounded by autumn-colored trees reflecting the sky.
Photo by Ed Gaffny
A calm lake with autumn foliage reflecting on the water, surrounded by trees and a small house.
Photo by Ed Gaffny

Sherwood Forest

Adventure seekers and nature lovers will love Sherwood Forest, a picturesque neighborhood in Becket, Massachusetts, known for its stunning outdoor scenery and family-friendly activities. Enjoy nearby attractions like Pyramid Lake for serene relaxation, the National Shrine of the Divine Mercy for a peaceful retreat, and the Becket Land Trust Historic Quarry for a glimpse into local history. Located about 5 miles by car from Chester, Sherwood Forest is an excellent choice for a memorable getaway.

A rocky cliff with autumn foliage beside a calm lake.
A rocky cliff with autumn foliage and a calm lake.
A forested mountain range with autumn foliage.
A stone bridge over a calm river with autumn foliage.
Photo by Chris Addams
A snowy forest path with two dogs, one in an orange jacket and the other in black.
Photo by Elizabeth Massa Peroulakis

Becket

Ideally situated for weekend getaway enthusiasts and nature lovers, Becket offers a serene escape with access to scenic attractions like Pyramid Lake and the breathtaking landscapes of the national state park. Visitors can explore the historic charm of The Mount or find tranquility at the National Shrine of the Divine Mercy. Located about 10 miles by car from Chester, Becket makes for an easy and delightful retreat, ensuring a memorable stay immersed in natural beauty and rich history.

A snow-covered forest with a stone bridge in the background.
Photo by Elizabeth Massa Peroulakis
A cascading waterfall over rocky terrain surrounded by dense forest.
Photo by Gregg Yutko
A stone bridge over a river with greenery on the sides.
Photo by Elizabeth Massa Peroulakis
A rocky stream with cascading water surrounded by trees.
Photo by Chris Addams
A tall, deteriorating concrete structure with multiple square openings and scattered debris.
Photo by Jason Weagle

Middlefield

Travelers visiting the area often choose Middlefield, especially families and nature enthusiasts seeking close proximity to outdoor adventures. This charming city offers easy access to activities like skiing at nearby resorts and exploring scenic spots such as Glendale Falls and local lakes. With Chester just about a 5-mile drive away, Middlefield serves as an ideal base for a weekend getaway. Choosing Middlefield for your stay ensures a delightful blend of adventure and relaxation.

Stay near popular attractions in and around Chester

Discover the charm of Chester, where outdoor adventures await at Norwich Lake and the state forest. Immerse yourself in local culture by visiting the historic Chester Town Hall and the stunning landscape at Chesterwood. For romance or family fun, Chester is the perfect destination to explore and unwind.

Glendale Falls

A fascinating mix of romance and adventure awaits at Glendale Falls, a stunning waterfall located in Huntington, Massachusetts. Just about 9 miles by car from Chester, this natural gem offers a serene escape, perfect for outdoor lovers. Staying nearby makes it easy to explore the area’s beauty.
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Chester Town Hall

Experience the best of Chester, Massachusetts, at Chester Town Hall, a historic civic building that embodies the town's cultural charm. Nestled within Chester, this site offers a glimpse into the community's heritage. Staying nearby provides easy access to local attractions and events, enhancing your visit.
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Becket Land Trust Historic Quarry

8.0/10 (2 reviews)
Often cited as a favorite for families and outdoor enthusiasts, Becket Land Trust Historic Quarry offers a unique glimpse into the area's natural beauty and history. Located about 4 miles by car from Chester, this reserve provides a perfect setting for exploration and adventure, making it an ideal spot to enhance your vacation experience.
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Pyramid Lake

10.0/10 (2 reviews)
This prominent local landmark is ideal for travelers interested in scenic outdoor experiences. Pyramid Lake offers a romantic atmosphere with its beautiful beach vibes, perfect for relaxation and enjoyment. Located about 8 miles by car from Chester, it provides convenient access for a delightful day trip.
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Littleville Lake

The perfect starting point for outdoor lovers, Littleville Lake offers stunning scenery and a romantic atmosphere. Located about 11 miles by car from Chester, this destination is ideal for a day of relaxation or adventure, making it a convenient choice for visitors seeking natural beauty.
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Iroquis Waterfront

An essential stop for beach lovers, Iroquis Waterfront in Becket offers a refreshing escape with its inviting sandy shores and vibrant atmosphere. Located about 8 miles by car from Chester, this beach provides a perfect spot for relaxation and fun in the sun, making it a convenient getaway for travelers.
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Otis Reservoir

9.0/10 (2 reviews)
Perfectly suited for outdoor lovers, Otis Reservoir offers stunning scenery and a romantic atmosphere. This picturesque lake is ideal for swimming, boating, and picnicking along its sandy beaches. Located about 15 miles by car from Chester, it’s a convenient spot to relax and enjoy nature’s beauty.
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National Shrine of the Divine Mercy

9.0/10 (83 reviews)
A must-see for spiritual seekers, the National Shrine of the Divine Mercy in Stockbridge offers a serene space for reflection and devotion. Just 24 miles away from Chester by car, this shrine immerses visitors in a rich atmosphere of faith and culture, making it a convenient addition to your journey.
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Learn more about Chester

Experience the hiking, camping, and theater in Chester!

See all hotels in Chester
A snow-covered forest with a narrow stream running through it.
Photo by Elizabeth Massa Peroulakis

Top Chester Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"The room was incredible. Just need to be a little friendly at the arrival."
Roberto 2-night trip
Posted less than an hour ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
Hotel On North

Hotel On North

10/10 Excellent
"The little things, like a small extra mirror in the bathroom that has a magnifier lens."
Cynthia 1-night trip
Posted 3 hours ago
Hotel On North
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

10/10 Excellent
"We requested a room on the first floor in advance. When we got there there were aware and assigned us accordingly! Staff very accommodating to our questions and food inquiries"
Lisa 1-night trip
Posted 5 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Berkshires Untold

Berkshires Untold

10/10 Excellent
"Great, we'll run hotel"
Geoffrey 1-night trip
Posted 6 hours ago
Berkshires Untold
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"Nice motel located on Laurel Lake. Convenient location. We did not upgrade to a room with a view of lake, but should consider. Lovely breakfast with big windows on the lake. Everything worked fine, would stay again."
Dianna 1-night trip
Posted 8 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

8/10 Good
"The staff was excellent and very friendly. Always greeted me when I came in the hotel, so the acknowledgement was nice. The room was very clean, but the rug in the hallway had a musty smell to it."
Leslie 2-night trip
Posted 10 hours ago
La Quinta Inn & Suites by Wyndham Springfield MA
D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"I love this hotel. The fall decorations are adorable. When I checked in the room was clean but there had obviously been a work crew in the bathroom caulking and hadn’t fully cleaned up. I alerted the front desk and was immediately moved to a lovely cleaned suite. The onsite restaurant is also great."
Marissa 1-night trip
Posted 20 hours ago
D. Hotel Suites & Spa
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Although it's an older hotel, it's well maintained.Clean and updated also very friendly staff."
Marti 1-night trip
Posted 1 day ago
The Yankee Inn
Blue A Modern Hotel, an Ascend Collection Hotel

Blue A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent
"My 12 yr old step daughter secretly told her mom “can we stay here a few more days”. Clean, comfy and great staff. Loved the openness of the lobby, lots of people hanging out, very friendly."
Robert 1-night trip
Posted 2 days ago
Blue A Modern Hotel, an Ascend Collection Hotel

More cheap stays in Chester

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
$57 nightly
$63 total
Oct 27 - Oct 28
Total with taxes and fees
FairBridge Inn Express
Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St West Springfield MA
$88 nightly
$100 total
Nov 9 - Nov 10
Total with taxes and fees
Quality Inn West Springfield
Blue A Modern Hotel, an Ascend Collection Hotel

Blue A Modern Hotel, an Ascend Collection Hotel

1080 Riverdale St West Springfield MA
$101 nightly
$116 total
Nov 1 - Nov 2
Total with taxes and fees
9.2/10 Wonderful! (358 reviews)
Blue A Modern Hotel, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
$106 nightly
$118 total
Nov 1 - Nov 2
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
The Yankee Inn
Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst

117 Conz St Northampton MA
$122 nightly
$137 total
Nov 8 - Nov 9
Total with taxes and fees
7.2/10 Good! (1,003 reviews)
Quality Inn & Suites Northampton - Amherst
Hampton Inn West Springfield

Hampton Inn West Springfield

1011 Riverdale St West Springfield MA
$127 nightly
$145 total
Nov 1 - Nov 2
Total with taxes and fees
Hampton Inn West Springfield

Hotels in Chester with star-rating

Find out more about Chester

Top reasons to visit Chester

  • Outdoor Adventures: Chester is an ideal destination for hiking, skiing, and enjoying various outdoor activities amidst its scenic landscapes.
  • Charming Accommodations: The town offers a range of cozy stays, from bed and breakfasts to comfortable hotels, catering to all types of travelers.
  • Historic Sites: Explore local history through picturesque historic houses and charming urban parks.
  • Family-Friendly Atmosphere: The town welcomes families with activities that provide fun for all ages.
  • Romantic Getaways: Chester's serene environment makes it perfect for couples seeking a romantic escape.

Find great hotels near Chester

Explore the charming town of Chester, Massachusetts, and discover a variety of hotel accommodations tailored to your needs. From cozy bed and breakfasts to comfortable hotels, you'll find options perfect for family vacations or adventurous getaways. Whether you're looking for pet-friendly options or the best hotels to enjoy a memorable stay, Chester offers a welcoming atmosphere for all travelers.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: This 3.5-star resort, with an impressive guest rating of 9.0, is a fantastic choice for those seeking a family-friendly adventure in the Berkshires. Located 15 miles from Chester, the resort offers easy access to ski lifts and shuttles, making it ideal for winter sports enthusiasts. Families will appreciate the on-site playground, arcade game room, and mini-golf, while adventure seekers can enjoy a variety of activities like skiing, snowboarding, and hiking. With its emphasis on recreation and comfort, this resort ensures a memorable stay for guests of all ages.
  • The Black Swan Lee - Lenox, an Ascend Collection Hotel: Rated 9.2 and conveniently located 15 miles from Chester, this 3-star hotel is perfect for families and pet lovers alike. The Black Swan Lee - Lenox offers a cozy atmosphere with amenities for children, including cribs and safety features. Guests can partake in various activities such as fishing, skiing, and snow tubing. The hotel’s pet-friendly policy allows for a stress-free stay with your furry friends. Whether you're looking for a relaxing getaway or an exciting outdoor adventure, this hotel's unique charm and welcoming environment will make your visit unforgettable.
  • Quality Inn Westfield - Springfield: A budget-friendly option, the Quality Inn Westfield - Springfield is located 16 miles from Chester and offers a comfortable stay for families and business travelers. With a guest rating of 8.0, this hotel provides essential amenities such as free cribs for children and a pet-friendly policy, allowing you to bring your four-legged companions along. The hotel's convenient location offers easy access to local attractions, making it a practical choice for those seeking value and comfort on their trip.

Where to stay near Chester

Chester, Massachusetts, is a charming city perfect for outdoor adventures and romantic getaways. Explore its scenic views and historic sites while enjoying a family-friendly atmosphere. Nearby regions offer a relaxing vibe, ideal for recreation and leisurely strolls. Whether you're hiking through picturesque landscapes or indulging in local culture, Chester and its surroundings promise memories filled with charm and beauty awaiting your discovery.

  • Lenox: Nestled 17 miles from Chester, Lenox is a charming city that attracts visitors year-round, with peak travel in the summer months. Known for its rich cultural scene, Lenox offers a delightful mix of entertainment, romance, and artistic experiences. Enjoy music concerts and theatrical performances at renowned venues, or hit the nearby ski slopes in winter. The scenic beauty of the area is enhanced by picturesque lakes and mountains, making it a perfect spot for outdoor enthusiasts. Don't miss the local event conference venues that often host exciting gatherings and celebrations.
  • The Berkshires: Just 12 miles from Chester, The Berkshires is a diverse region that invites adventure seekers and nature lovers alike. With a steady flow of visitors throughout the year, the area is particularly lively from June to August. Here, you can immerse yourself in outdoor activities, from skiing at top-notch resorts to exploring the stunning scenery of the mountains and lakes. The Berkshires is also home to various events and conferences, adding to its appeal as a vibrant destination for tourists seeking both excitement and relaxation.
  • Lee: Located 14 miles from Chester, Lee is a delightful city that welcomes travelers with its family-friendly atmosphere and romantic charm. With a consistent influx of visitors year-round, peak seasons occur in the summer. Lee boasts a variety of entertainment options, including theaters and live music concerts, ensuring a lively experience. The area's natural beauty is complemented by historical monuments and serene lakes, providing the perfect backdrop for leisurely strolls and family outings. Whether you're seeking a cozy getaway or an action-packed adventure, Lee has something for everyone.

Things to do in Chester

Chester, Massachusetts, is perfect for outdoor adventures and romantic getaways. Visitors can enjoy skiing at local ski fields, catch a performance at the theater, or hit the golf course for a round of golf. With its scenic landscapes and charming attractions, Chester invites exploration through its various amenities and local sights, making it an ideal destination for those seeking both relaxation and adventure.

Shopping

In Chester, you can explore local shops offering unique crafts and souvenirs. If you're up for a drive, head to the nearby shopping malls like the Berkshire Mall in Lanesborough for a wider selection, or check out the Eastfield Mall in Springfield for more mainstream retailers.

Recreation

Chester's Wellness Retreat offers rejuvenating spa treatments, yoga sessions, and guided meditation in a tranquil setting. For outdoor enthusiasts, the surrounding scenic trails provide opportunities for hiking, birdwatching, and peaceful picnics, allowing you to recharge while immersing yourself in nature's beauty.

Adventure

In Chester, explore the scenic hiking trails of the Chester-Blandford State Forest, where you'll encounter breathtaking views and diverse wildlife. For water enthusiasts, the nearby Westfield River offers thrilling kayaking and canoeing experiences amidst beautiful surroundings, perfect for an adventurous day out.

Nightlife

Chester offers a charming nightlife experience with cozy bars and local eateries. Enjoy a drink at the Chester Tavern, where friendly locals gather. For a laid-back evening, try the nearby picnic spots along the river, perfect for stargazing and unwinding after a day of exploration.

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

Booking tips and Expedia advantages for Chester

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chester are March and December to January, 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 Chester is Tuesday. The most expensive day to stay in Chester is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia's search tool to narrow down your preferences, such as your budget, desired location, and type of hotel you’re looking for. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Chester with your flights and activities through an Expedia package deal.

Find the best attractions near Chester

Chester, Massachusetts, is an ideal destination for outdoor enthusiasts, adventure seekers, and couples looking for a romantic getaway. Visitors can explore a variety of attractions, including urban parks, nature reserves, and historic houses. Whether you're seeking family-friendly activities or thrilling outdoor experiences, Chester offers a delightful mix of points of interest that cater to diverse tastes and interests.

  • National Shrine of the Divine Mercy: Located 17 miles from Chester, this serene shrine offers a peaceful retreat with stunning architecture and beautiful gardens, perfect for reflection and spiritual growth.
  • Becket Land Trust Historic Quarry: Just 3 miles away, this preserve combines adventure and family-friendly activities, featuring hiking trails and scenic views, making it a trendy spot for both luxury and budget travelers.
  • Littleville Lake: Located 5 miles from Chester, this picturesque lake is ideal for outdoor enthusiasts, offering opportunities for swimming, picnicking, and enjoying romantic sunset views along its scenic shoreline.

Best time to go to Chester

The best time to visit Chester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly 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
January23.5°F (-4.7°C)Light RainMostly CloudyAverageSlightly Low
February25.3°F (-3.7°C)Light RainMostly CloudySlightly LowAverage
March33.1°F (0.6°C)Light RainMostly CloudyAverageSlightly Low
April44.8°F (7.1°C)Light RainMostly CloudyAverageAverage
May56.5°F (13.6°C)Light RainMostly SunnyAverageAverage
June64.4°F (18.0°C)Light RainMostly SunnySlightly HighAverage
July70.5°F (21.4°C)Light RainMostly SunnySlightly HighSlightly High
August68.7°F (20.4°C)Light RainMostly SunnyAverageSlightly High
September61.9°F (16.6°C)Light RainMostly SunnySlightly HighAverage
October50.7°F (10.4°C)Light RainMostly SunnyAverageSlightly High
November38.8°F (3.8°C)Light RainMostly SunnySlightly LowAverage
December30.2°F (-1.0°C)Light RainMostly CloudySlightly LowSlightly Low

The nearest major airports for your trip to Chester

When traveling to Chester, Massachusetts, you have several airport options. Hartford, CT (BDL-Bradley Intl.) is located 28 miles away, with nearby hotels like DoubleTree by Hilton Hartford - Bradley Airport and Marriott Hartford Downtown, both offering convenient access to the airport. Providence, RI (PVD-T.F. Green) is 88 miles from Chester, with excellent hotel choices such as Omni Providence Hotel and Hotel Providence situated 7 miles from the airport. ALBany, NY (ALB-Albany Intl.) is 53 miles away, featuring hotels like The Landing Hotel at Rivers Casino & Resort and DoubleTree by Hilton Schenectady Downtown, both 8 miles from the airport. Each location provides accessible transportation options for travelers.

Frequently asked questions

What is the best area to stay in Chester?
The best area to stay in Chester is the village center, particularly for those seeking convenience and a connection to local life.This compact area is where you'll find the town's general store, post office, and a few local eateries. It's centered around Main Street and Middlefield Road, offering easy access to the scenic Westfield River and the start of many local hiking trails. The Chester Railway Station Museum is also a prominent feature here, providing a glimpse into the town's history.For couples looking for a relaxed retreat with convenient access to outdoor activities, the village center is an excellent choice. It provides a comfortable base from which to explore the surrounding Berkshire Hills and enjoy activities like fishing, kayaking, or simply taking a scenic drive.Solo travelers will also find the village center appealing due to its central location and the ease of accessing local amenities.
When is the best time to go to Chester?
The best time to go to Chester, Massachusetts, is during the summer months, from June to August, and the early fall, in September and October.Summer offers warm, pleasant weather, ideal for exploring the outdoor attractions around Chester. You can enjoy hiking or biking on the trails of the Chester-Blandford State Forest or kayaking on the Westfield River. This period is great for active travelers and families looking to spend time outdoors without the chill of cooler seasons.For those who appreciate scenic beauty and comfortable temperatures, early fall is an excellent choice. The foliage in the Berkshire Mountains surrounding Chester transforms into vibrant colors, creating stunning landscapes.
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 Chester.
How much is the nightly rate at a Chester hotel?
Prices for hotels in Chester often vary, but you can find a great deal from $63 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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