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Tonight
Check prices in Chester for tonight, Nov. 16 - Nov. 17
Nov. 16 - Nov. 17
Tomorrow night
Check prices in Chester for tomorrow night, Nov. 17 - Nov. 18
Nov. 17 - Nov. 18
Next weekend
Check prices in Chester for next weekend, Nov. 22 - Nov. 24
Nov. 22 - Nov. 24

Most frequently booked Chester hotels

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd, Holyoke, MA
Free cancellation
30.72 km from city centre
The price is CA $190 per night
CA $190
CA $218 total
includes taxes & fees
19 Nov - 20 Nov
Stay at this 3-star spa hotel in Holyoke. Enjoy free breakfast, free parking, and a full-service spa. Our guests praise the breakfast and the pool in our reviews. Popular attractions Mount Tom State Reservation and Nash's Dinosaur Track Quarry are located nearby.
Pool
Hot tub
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St, West Springfield, MA
Free cancellation
Reserve now, pay when you stay
33.03 km from city centre
The price is CA $123 per night
CA $123
CA $140 total
includes taxes & fees
29 Nov - 30 Nov
Book a stay at this golf hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Big E and Eastern States Exposition are located nearby.
Pool
Breakfast included
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

3 out of 5
100 Congress Street, Springfield, MA
Free cancellation
Reserve now, pay when you stay
36.83 km from city centre
The price is CA $156 per night
CA $156
CA $177 total
includes taxes & fees
8 Dec - 9 Dec
Book a stay at this family-friendly hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions MGM Springfield and Eastern States Exposition are located nearby.
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 out of 5
1254 Riverdale Street, West Springfield, MA
Free cancellation
Reserve now, pay when you stay
32.98 km from city centre
The price is CA $125 per night
CA $125
CA $143 total
includes taxes & fees
24 Nov - 25 Nov
Stay at this hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Big E and Eastern States Exposition are located nearby.
Pet-friendly
Parking included
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
26.98 km from city centre
The price is CA $137 per night
CA $137
CA $153 total
includes taxes & fees
17 Nov - 18 Nov
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.
Pet-friendly
Parking included
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Free cancellation
Reserve now, pay when you stay
27.41 km from city centre
The price is CA $195 per night
CA $195
CA $281 total
includes taxes & fees
25 Nov - 26 Nov
Stay at this 3.5-star spa hotel in Stockbridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Tanglewood Music Center and Schantz Galleries are located nearby.
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
27.45 km from city centre
The price is CA $136 per night
CA $136
CA $152 total
includes taxes & fees
25 Nov - 26 Nov
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

2.5 out of 5
440 Memorial Dr, Chicopee, MA
Free cancellation
Reserve now, pay when you stay
35.17 km from city centre
The price is CA $153 per night
CA $153
CA $173 total
includes taxes & fees
1 Dec - 2 Dec
Stay at this hotel in Chicopee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Big E and MGM Springfield are located nearby.
Pool
Breakfast included
The Ellery

The Ellery

3.5 out of 5
259 Elm Street, Northampton, MA
27.81 km from city centre
The price is CA $195 per night
CA $195
CA $218 total
includes taxes & fees
17 Nov - 18 Nov
Stay at this 3.5-star B&B in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Smith College Botanic Garden and Dinosaur Footprints are located nearby.
Breakfast included
Pet-friendly
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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.

Chester hotels essential information

Accommodation
776 hotels
Lowest Price
CA $123
Highest Price
CA $195
Popular hotels
D. Hotel Suites & Spa, Quality Inn West Springfield, La Quinta Inn & Suites by Wyndham Springfield MA, Red Roof Inn PLUS+ West Springfield, Life House Berkshires, The Red Lion Inn, The Yankee, Trademark Collection by Wyndham, Tru by Hilton Chicopee Springfield, The Ellery

Frequently asked questions

What are the top kid-friendly hotels in Chester?
From unique amenities to extra space, kid-friendly hotels are equipped with features that can help turn an everyday family vacation into an amazing one. These Chester options make getting away with your youngsters easier: Unpack your bags at Big farmhouse in the foothills of the Berkshires. It comes with a fireplace, pet-friendly facilities and a passion for making families feel welcome. Also check out the deals at Beautiful retreat to the woods to enjoy the winter season.. It comes with a nearby beach, animal viewing activities and plenty of opportunities to hang out as a family.
Where can I find cheap hotels in Chester?
At Travelocity you’ll find really nice hotels in Chester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Chester rather than in Chester. We may find you even better rates, too.
How do I find the best Chester hotel deals?
Simple! On Travelocity, look through the fantastic offers we’ve already found in Chester then use our filters to find a great deal that’s perfect for you. Enter your travel dates, select the number of rooms you need, and we’ll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Chester?
The cheapest hotel in Chester is CA $123 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel’s location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Chester?
There are 776 hotels in Chester on Travelocity.
What are the best hotels in Chester?
Chester has so many great hotels to choose from at Travelocity — and it’s so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Chester for you!
When is the best time to visit Chester?
If you want the joy of a fun-filled trip in peak season, visit Chester during June, July and August. If you’d prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Chester?
Based on historic data is usually the cheapest month to visit Chester. However, we have incredible deals all year round, so we’re confident you’ll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Chester?
There are multiple hotels in Chester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We’ve got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Chester. We have plenty of kid-friendly hotels in Chester to choose from on Travelocity!
Why book a hotel in Chester through Travelocity?
Because we have the top hotels in Chester! We want to help you travel more and worry less. That’s why we’ve put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you’re getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Chester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Chester hotel reviews by fellow wanderers

The Ellery

The Ellery

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"We were visiting several friends in the area and wanted to bring our dog; not only is the Ellery pet-friendly, it's friendly, convenient and comfortable. We had everything we needed and there are some beautiful trails and dog runs nearby. We will definitely choose the Ellery again."
A verified traveller stayed at The Ellery
The Ellery

Hotels near…

Areas of Chester