Chester hotels from HK$557

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Our top choices for Chester hotels

Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield
3.0 star property
West Springfield
9.2 out of 10, Wonderful, (599 reviews)
  • cleanliness
    Experience comfort and convenience minutes from the Big E and MGM Springfield.
"Nice and very clean hotel ! "
United States
Morgan
The price is HK$923
HK$1,057 total
includes taxes & fees
22 Feb - 23 Feb
Courtyard by Marriott West Springfield

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (292 reviews)
  • cleanliness
    Serene lakeside escape with water activities and complimentary perks.
"A charming inn in the center of the Berkshires."
United States
Danny
The price is HK$1,092
HK$1,281 total
includes taxes & fees
15 Feb - 16 Feb
Lakehouse Inn

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411 reviews)
  • cleanliness
    Relaxing Lee motel near Tanglewood offers seasonal pool and outdoor adventures.
"owners was nice, room was clean"
United States
tom
The price is HK$728
HK$814 total
includes taxes & fees
15 Feb - 16 Feb
Sunset Inn

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Stylish Berkshires B&B with garden setting and free gourmet breakfast in Lenox.
"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
The price is HK$1,043
HK$1,200 total
includes taxes & fees
18 Feb - 19 Feb
The Cornell Inn, Lenox & The Berkshires

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (834 reviews)
  • cleanliness
    Berkshire getaway with 4 swimming pools offers seasonal outdoor retreat.
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is HK$879
HK$1,135 total
includes taxes & fees
10 Mar - 11 Mar
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Modern lakeside retreat with 24-hour fitness and scenic Tanglewood location.
"Clean room, nice staff , decent breakfast. Overall a good stay . "
United States
Anindita
The price is HK$764
HK$853 total
includes taxes & fees
5 Mar - 6 Mar
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Whitlock

The Whitlock
2.0 star property
Lenox
8.6 out of 10, Excellent, (287 reviews)
  • cleanliness
    Chic Lenox escape minutes from Tanglewood with scenic hiking trails nearby.
"Super cute place and walking distance to a bunch of great shops and food! "
United States
Gina
The price is HK$938
HK$1,048 total
includes taxes & fees
18 Feb - 19 Feb
The Whitlock

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (732 reviews)
  • cleanliness
    Unwind in the Berkshires with indoor pool and free hot breakfast each morning.
"Great property, very accommodating. "
United States
Shanice
The price is HK$836
HK$934 total
includes taxes & fees
22 Feb - 23 Feb
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Homewood Suites by Hilton Hadley Amherst

Homewood Suites by Hilton Hadley Amherst
3.0 star property
Hadley
9.4 out of 10, Exceptional, (731 reviews)
  • cleanliness
    Modern hotel near UMass with pool, ideal for comfortable extended stays.
"Room was clean and the size of the room is outstanding."
United States
Gregory
The price is HK$1,115
HK$1,246 total
includes taxes & fees
2 Mar - 3 Mar
Homewood Suites by Hilton Hadley Amherst

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (831 reviews)
  • cleanliness
    Convenient Lenox motel offers outdoor pool and complimentary WiFi and parking.
"Staff was very friendly and helpful."
United States
Pamela
The price is HK$539
HK$602 total
includes taxes & fees
18 Feb - 19 Feb
Howard Johnson by Wyndham Lenox

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (822 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
Monument Mountain Motel

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (553 reviews)
  • cleanliness
    Explore scenic Great Barrington with free perks and helpful staff at this cosy motel.
"Great friendly staff"
United States
Pablo
The price is HK$860
HK$960 total
includes taxes & fees
18 Feb - 19 Feb
The Little Lion

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (601 reviews)
  • cleanliness
    Enjoy the Berkshires with indoor pool and nearby Tanglewood Music Centre.
"Our stay was great! "
United States
Gianna
The price is HK$985
HK$1,100 total
includes taxes & fees
15 Mar - 16 Mar
Courtyard by Marriott Lenox Berkshires

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (823 reviews)
  • cleanliness
    Explore city centre Pittsfield from a stylish hotel with complimentary WiFi and parking.
"Great staff, beautiful hotel. Would definitely recommend "
United States
Shawn
The price is HK$1,165
HK$1,301 total
includes taxes & fees
18 Feb - 19 Feb
Hotel On North

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (375 reviews)
  • cleanliness
    Serene getaway offers hot tub and massage treatments near Tanglewood Music Centre.
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (426 reviews)
  • cleanliness
    Step into Victorian elegance with modern comforts near Springfield attractions.
"Artful and inspiring interior decorating and delicious French toast for breakfast!"
United States
Marielle
The price is HK$789
HK$896 total
includes taxes & fees
15 Mar - 16 Mar
Naomi's Inn Bed & Breakfast

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (855 reviews)
  • cleanliness
    Experience Berkshires charm with on-site American dining and attentive service.
"This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! "
United States
Melissa
The price is HK$943
HK$1,054 total
includes taxes & fees
18 Feb - 19 Feb
Berkshires Untold

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,000 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is HK$1,141
HK$1,624 total
includes taxes & fees
4 Mar - 5 Mar
The Red Lion Inn

Elm Motel

Elm Motel
2.0 star property
Westfield
7.2 out of 10, Good, (123 reviews)
  • cleanliness
    Comfortable motel near Big E with convenient parking and 24/7 service.
"Very clean, lacking bathroom and bathroom storage. Good price."
United States
Daniel
The price is HK$774
HK$864 total
includes taxes & fees
25 Feb - 26 Feb
Elm Motel

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (842 reviews)
  • cleanliness
    Enjoy a tranquil stay near Tanglewood Music Centre with a refreshing pool.
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is HK$612
HK$684 total
includes taxes & fees
23 Feb - 24 Feb
Berkshire Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Chester attractions

Learn more about Chester

Experience the hiking, camping and waterfalls in Chester!

An amazing keystone arch bridge!
Photo by Chris Addams
Open Photo by Chris Addams

Top Chester Hotel Reviews

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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 Berkshire Mountain Lodge and The Yankee, Trademark Collection by Wyndham. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Chester is located near skiing, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. 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 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 Becket Land Trust Historic Quarry and Pyramid Lake 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.

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