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Chester Hotels from S$89

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Check Chester hotel prices

Tonight
30 Sept - 1 Oct
Tomorrow night
1 Oct - 2 Oct
This weekend
4 Oct - 6 Oct
Next weekend
11 Oct - 13 Oct

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Top 10 trending Chester hotels

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, (1004)
"Absolutely awesome with a beautiful view. A little lake in the back a great Indian restaurant."
The price is S$205
includes taxes & fees
16 Oct - 17 Oct
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Red Lion Inn
Outdoor pool, pool loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (992)
"Lovely old hotel with excellent bar and restaurant. Central to all Berkshire sights. Room clean and well-appointed; wonderful shower; lobby and many nooks in which to curl up with drink and a good bookā€¦ Ambassador felines Jane and Jack make Red Lion Inn feel like home."
The price is S$479
includes taxes & fees
1 Oct - 2 Oct
The Red Lion Inn
Holiday Inn Club Vacations Oak nā€™ Spruce Resort in the Berkshires, an IHG Hotel
Property amenity
Holiday Inn Club Vacations Oak nā€™ Spruce Resort in the Berkshires, an IHG Hotel
3.5 star property
9.0 out of 10, Wonderful, (531)
"Liked the whole experience overall. Good rates for the room. The one complaint was a safety issue. Need a bar in the bathtub area. Took a bath and had a lot of trouble getting out of it. Elderly people should be considered."
The price is S$228
includes taxes & fees
1 Oct - 2 Oct
Holiday Inn Club Vacations Oak nā€™ Spruce Resort in the Berkshires, an IHG Hotel
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Free WiFi, bed sheets
The Constance, The Whitlock, & The Dewey By The Lenox Collection
3.5 star property
8.6 out of 10, Excellent, (362)
"Beautiful location."
The price is S$184
includes taxes & fees
6 Oct - 7 Oct
The Constance, The Whitlock, & The Dewey By The Lenox Collection
The Cornell Inn, Lenox
Porch
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, (1006)
"Really nice visit. All of the staff clearly wanted to create a pleasurable experience. Everything is nicely decorated. The full breakfast was quickly served and very nicely done. The atmosphere was really nice - not too big that you felt like a number in a roadside inn/lodge/motel; not so small that you felt obligated to entertain the establishment. "
The price is S$194
includes taxes & fees
1 Oct - 2 Oct
The Cornell Inn, Lenox
Lakehouse Inn
Aerial view
Lakehouse Inn
4.0 star property
9.8 out of 10, Exceptional, (205)
"The Lakehouse Inn was amazing. Very Beautiful and cozy property by the lake with incredible views and the breakfast was delicious. Very friendly staff. We loved it!"
The price is S$212
includes taxes & fees
7 Oct - 8 Oct
Lakehouse Inn
Quality Inn
1 bedroom, premium bedding, pillow-top beds, desk
Quality Inn
2.5 star property
8.2 out of 10, Very good, (1008)
"Very nice, quiet and clean. Friendly staff and comfortable beds."
The price is S$125
includes taxes & fees
27 Oct - 28 Oct
Quality Inn
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, (665)
"Very clean and conveniently located property. The staff were super friendly and helpful."
The price is S$279
includes taxes & fees
3 Oct - 4 Oct
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Quality Inn
Lobby
Quality Inn
2.5 star property
8.2 out of 10, Very good, (1003)
"The floors in the bathroom were sticky and the carpet."
The price is S$148
includes taxes & fees
27 Oct - 28 Oct
Quality Inn
Little Cat Lodge
Seasonal outdoor pool
Little Cat Lodge
2.0 star property
9.0 out of 10, Wonderful, (24)
"I had a lovely stay just in time for the beginning of the fall! The property is surrounded by beautiful mountains, theres a sauna in the property and a zipline walking distance. Theres also a complimentary breakfast in the morning and a coffee machine in your room as well. The customer service was excellent! Mike was amazing and was there to answer any questions at any hour and checked to make sure I was having a nice stay which was greatly appreciated and it really made the stay so much more...
The price is S$274
includes taxes & fees
28 Oct - 29 Oct
Little Cat Lodge
Blackberry River Inn
Library
Blackberry River Inn
3.0 star property
9.4 out of 10, Exceptional, (69)
"Great place to stay for enjoying NW Connecticut activities. Friendly helpful staff, comfortable room, pool, cozy public areas/lobby. The breakfast was delicious in a sunny breakfast room and the servers very gracious about special requests. Am looking forward to future stays here."
The price is S$226
includes taxes & fees
1 Oct - 2 Oct
Blackberry River Inn
The Little Lion
Exterior
The Little Lion
3.0 star property
8.8 out of 10, Excellent, (416)
"Everything about this lodging was nice; the easy access getting in, the large bed and thoughtful decor. "
The price is S$132
includes taxes & fees
27 Oct - 28 Oct
The Little Lion
Locust Tree Bed and Breakfast LLC
Miscellaneous
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (350)
"Classic mom and pop b and b. Comfortable beds and friendly service "
The price is S$155
includes taxes & fees
1 Oct - 2 Oct
Locust Tree Bed and Breakfast LLC
Monument Mountain Motel
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
Monument Mountain Motel
2.5 star property
8.8 out of 10, Excellent, (654)
"Near restaurants "
The price is S$136
includes taxes & fees
1 Oct - 2 Oct
Monument Mountain Motel
Travelodge by Wyndham Great Barrington Berkshires
In-room safe, desk, free cots/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
7.6 out of 10, Good, (504)
"This is a great old-school facility. Clean comfortable. Needs a little TLC. The windows are filthy and some of them are missing screens overall though Iā€™ll come back here again and again great staff nice outdoor sitting area with party lights."
The price is S$99
includes taxes & fees
27 Oct - 28 Oct
Travelodge by Wyndham Great Barrington Berkshires
Econo Lodge Lee - Great Barrington
Desk, iron/ironing board, free cots/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington
2.0 star property
6.4 out of 10, (562)
"I prefer no-frills motels which is what this is. Cheap, clean, great hot water and shower pressure, fridge, microwave, iron, hair dryer and great mountainous view across the street. Pretty quiet except during high traffic times. Outside property looks kind of rundown, my screen door to the balcony wouldn't close and there was a hole in the wall but overall a great place for my basic needs. I will be back."
The price is S$107
includes taxes & fees
1 Oct - 2 Oct
Econo Lodge Lee - Great Barrington
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
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, (546)
"Convenient "
The price is S$165
includes taxes & fees
30 Oct - 31 Oct
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Whistler's Inn Bed & Breakfast
Property grounds
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (459)
"Love this place! Loved the fact that owners kept the 1800s feel throughout. Owners were on-site and joined us for breakfast. Great people. Lenox is good base for road cycling the nearby hills and valleys."
The price is S$255
includes taxes & fees
8 Oct - 9 Oct
Whistler's Inn Bed & Breakfast
Pleasant Valley Motel West Stockbridge
Garden view
Pleasant Valley Motel West Stockbridge
2.0 star property
6.8 out of 10, (947)
"Fine"
The price is S$89
includes taxes & fees
6 Oct - 7 Oct
Pleasant Valley Motel West Stockbridge
Brook Farm Inn
Front of property
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (146)
"Very charming inn. The staff was very friendly and helpful."
The price is S$376
includes taxes & fees
5 Oct - 6 Oct
Brook Farm Inn
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Frequently asked questions

What's the best place to stay in Chester?

La Quinta Inn & Suites by Wyndham Springfield MA, located 22.9 mi (36.8 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 Red Roof Inn PLUS+ West Springfield and D. Hotel Suites & Spa. See all available top hotels, or 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 19Ā°C, while the coldest months are January and February, with an average of -2Ā°C. The snowiest months in Chester are January, February, November and March, with each month seeing an average of 15 cm of snowfall.