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Find hotels in Chester, MA from £59

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Top 10 Chester hotels and places to stay

Lakehouse Inn
Aerial view
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (150)
"Love this Inn, all employees were friendly and knowledgeable about things to do in the area. The breakfast was delicious . I look forward to staying at the Inn again."
The price is £126
per night
5 May - 6 May
Lakehouse Inn
Chambery Inn
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (356)
"Amazing place.."
The price is £192
per night
10 May - 11 May
Chambery Inn
Blackberry River Inn
Library
Blackberry River Inn
3.0 star property
9.6 out of 10, Exceptional, (24)
"Lucas was very accommodating and helpful. Pleasant and great place to stay. Great fresh breakfast!!"
The price is £167
per night
16 May - 17 May
Blackberry River Inn
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Shaker Mill Inn
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (380)
"This is a lovely place to say. Very warm and welcoming. The staff was very helpful and even brought a little doggy basket for my dog. It included a blanket, dog bowls treats and more!! Had a very very nice time. "
The price is £87
per night
5 May - 6 May
Shaker Mill Inn
The Barrington
Junior Suite | Premium bedding, individually decorated, desk, iron/ironing board
The Barrington
4.0 star property
9.6 out of 10, Exceptional, (95)
"Great stay, the room was as advertised, delicious breakfast included and great location. Will stay again. "
The price is £290
per night
4 May - 5 May
The Barrington
Brook Farm Inn
Front of property
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (134)
"This is a charming and very pleasant place to stay."
The price is £139
per night
7 May - 8 May
Brook Farm Inn
Race Brook Lodge
Exterior
Race Brook Lodge
2.0 star property
9.4 out of 10, Exceptional, (8)
"It was quiet setting by the rooms are run down "
The price is £152
per night
8 May - 9 May
Race Brook Lodge
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Reception
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.2 out of 10, Wonderful, (645)
"nice staff "
The price is £143
per night
28 May - 29 May
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior
The Black Swan Lee - Lenox, Ascend Hotel Collection
3.0 star property
9.0 out of 10, Wonderful, (1002)
"Just a nice, cozy and very clean little hotel. We would stay there again if in the area."
The price is £90
per night
9 May - 10 May
The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 star property
9.0 out of 10, Wonderful, (461)
"The room was spacious- 2 bedrooms, large living room, full kitchen, terrace, TV's in every room. It was spotless when we arrived. The stay was exceptional."
The price is £132
per night
5 May - 6 May
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Monument Mountain Motel
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
Monument Mountain Motel
2.5 star property
9.0 out of 10, Wonderful, (587)
"Easy access, very clean, nearby restaurants "
The price is £59
per night
5 May - 6 May
Monument Mountain Motel
Locust Tree Bed and Breakfast LLC
Miscellaneous
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (319)
"The friendly owner and easy nature was a pleasure. Breakfast was perfectly prepared. I really enjoyed staying there. "
The price is £96
per night
4 May - 5 May
Locust Tree Bed and Breakfast LLC
Little Cat Lodge
Seasonal outdoor pool
Little Cat Lodge
2.0 star property
9.0 out of 10, Wonderful, (8)
"Booked a weekend stay at Little Cat Lodge for a girlfriends trip. The lodge was very cute and had just about everything we needed. Complimentary breakfast was also much appreciated. 3 women shared a 2-bed bedroom and it was great for size- we loved our little balcony. Would definitely recommend this spot! "
The price is £171
per night
5 May - 6 May
Little Cat Lodge
The Red Lion Inn
Outdoor pool, pool loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (871)
"What a pleasure to have the opportunity to stay in an historic inn such as the Red Lion. "
The price is £124
per night
6 May - 7 May
The Red Lion Inn
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Standard Room | Premium bedding, pillow-top beds, in-room safe, desk
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (495)
"Really enjoyed the seating outside and pool side was very relaxing. The staff was very helpful and informative. Great experience!!!"
The price is £133
per night
19 May - 20 May
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
The Briarcliff Motel
Exterior
The Briarcliff Motel
3.0 star property
8.8 out of 10, Excellent, (384)
"We loved this place. It's dog friendly, the place is clean and quiet. The proprietor is awesome. It's super friendly. We spent a total of 9 days here, and I'd definitely come back again. Thanks for a great stay"
The price is £98
per night
5 May - 6 May
The Briarcliff Motel
The Cornell Inn, Lenox
Porch
The Cornell Inn, Lenox
3.0 star property
8.6 out of 10, Excellent, (1000)
"Great breakfast. "
The price is £114
per night
5 May - 6 May
The Cornell Inn, Lenox
The Lenox Collection
Front of property
The Lenox Collection
3.5 star property
8.6 out of 10, Excellent, (187)
"We enjoyed staying at the Whitlock. There are not a lot of bells and whistles, just an elegant, traditional inn, within the village of Lenox. It's very walkable, quiet, and charming."
The price is £73
per night
13 May - 14 May
The Lenox Collection
Apple Tree Inn
Seasonal outdoor pool
Apple Tree Inn
3.0 star property
8.0 out of 10, Very good, (211)
"Love it!!!"
The price is £124
per night
9 May - 10 May
Apple Tree Inn
Quality Inn
Standard Room, 2 Queen Beds, Non Smoking | 1 bedroom, premium bedding, pillow-top beds, desk
Quality Inn
2.5 star property
8.0 out of 10, Very good, (1000)
"Generally a good stay, great value"
The price is £71
per night
5 May - 6 May
Quality Inn
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See all available properties in Chester
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.

More cheap stays in Chester

Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St, West Springfield, MA
The price is £75 per night from May 19 to May 20
£75
per night
19 May - 20 May
7.2/10 Good! (1,005 reviews)

Accommodation near Chester attractions

Image for Chester Town Hall

Chester Town Hall

You can get tickets for a performance at Chester Town Hall on your trip to Chester. Wander the lakeside and forests in this relaxing area.

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Chester Town Hall

Frequently asked questions

What's the best place to stay in Chester?

D. Hotel Suites & Spa, located 19.1 mi (30.7 km) from the heart of Chester, is a top choice for your stay, based on our traveller data. Other good choices for your visit to the area are La Quinta Inn & Suites by Wyndham Springfield MA and Red Roof Inn PLUS+ West Springfield. See all available top hotels, or vacation rentals in Chester.

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

Cozy apartment located in quiet Williamsburg: This holiday home rental outside of Chester is in a rural location, and equipped with air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. See all vacation rentals in Chester.

If I need to cancel my hotel reservation in Chester, will I receive a refund?

Yes, the majority of room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a reservation that's non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

What are some hotels with pools in Chester?

La Quinta Inn & Suites by Wyndham Springfield MA: 3-star hotel located near Springfield Museums. Offers a children's pool, an indoor pool and a snack bar. Tru by Hilton Chicopee Springfield and D. Hotel Suites & Spa are two additional hotels that offer an on-site pool. View all hotels with pools in Chester.

What is staying in Chester like?

Visitors can enjoy all that Chester has to offer, including the waterfalls, shopping and riverfront. Tourists can also enjoy the city's restaurants, theatres and monuments. In Chester, there are 2 hotels and other accommodation options to choose from. Find out more about Chester.

What is there to see in Chester?

A favourite place to visit is Chester Town Hall. You'll also find Jacob's Pillow and Otis Reservoir in the area. Take a look at what more there is to see and do in Expedia's Chester guide.

What's the weather like in Chester?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chester are January, February, November and March, with each month seeing an average of 15 cm of snowfall.

Chester Hotel Reviews
Expedia verified reviews

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

5/5 Excellent
"Just a nice, cozy and very clean little hotel. We would stay there again if in the area."
A verified traveller from Marion stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
Posted 1 day ago
The Black Swan Lee - Lenox, Ascend Hotel Collection