Book Cheap Hotels in Chesterfield

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Tonight
Check prices in Chesterfield for tonight, Oct 8 - Oct 9
Oct 8 - Oct 9
Tomorrow night
Check prices in Chesterfield for tomorrow night, Oct 9 - Oct 10
Oct 9 - Oct 10
This weekend
Check prices in Chesterfield for this weekend, Oct 9 - Oct 11
Oct 9 - Oct 11
Next weekend
Check prices in Chesterfield for next weekend, Oct 16 - Oct 18
Oct 16 - Oct 18

Most frequently booked Chesterfield hotels

Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
Free cancellation
33.46 km from city centre
The price is CA $125 per night
CA $125
CA $144 total
Nov 1 - Nov 2
includes taxes & fees
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 MGM Springfield and Olympia Ice Center are located nearby.
Pool
Breakfast included
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free cancellation
Reserve now, pay when you stay
34.87 km from city centre
The price is CA $126 per night
CA $126
CA $173 total
Nov 8 - Nov 9
includes taxes & fees
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Free cancellation
Reserve now, pay when you stay
23.29 km from city centre
The price is CA $173 per night
CA $173
CA $203 total
Oct 26 - Oct 27
includes taxes & fees
Book a stay at this spa hotel in Holyoke. Enjoy free breakfast, a full-service spa, and 2 restaurants. Our guests praise the breakfast and the pool in our reviews. Popular attractions Nash's Dinosaur Track Quarry and Historic Summit House are located nearby.
Pool
Hot tub
Hotel UMass

Hotel UMass

2.5 out of 5
1 Campus Center Way Amherst MA
Free cancellation
Reserve now, pay when you stay
25.48 km from city centre
The price is CA $156 per night
CA $156
CA $177 total
Oct 26 - Oct 27
includes taxes & fees
Stay at this hotel in Amherst. Enjoy free breakfast, free WiFi, and 5 coffee shops/cafes. Our guests praise the helpful staff in our reviews. Popular attractions Mullins Center and UMass Fine Arts Center are located nearby.
Breakfast included
Free WiFi
Blue A Modern Hotel, an Ascend Collection Hotel

Blue A Modern Hotel, an Ascend Collection Hotel

2.5 out of 5
1080 Riverdale St West Springfield MA
Free cancellation
33.43 km from city centre
The price is CA $144 per night
CA $144
CA $165 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this business-friendly hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions MGM Springfield and Riverdale Shops are located nearby.
Parking included
Free WiFi
Hampton Inn West Springfield

Hampton Inn West Springfield

2.5 out of 5
1011 Riverdale St West Springfield MA
Free cancellation
Reserve now, pay when you stay
33.92 km from city centre
The price is CA $178 per night
CA $178
CA $204 total
Oct 20 - Oct 21
includes taxes & fees
Book a stay at this business-friendly hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions MGM Springfield and Riverdale Shops are located nearby.
Pool
Breakfast included
Hotel Northampton

Hotel Northampton

3.5 out of 5
36 King Street Northampton MA
Free cancellation
Reserve now, pay when you stay
18.94 km from city centre
The price is CA $176 per night
CA $176
CA $196 total
Oct 12 - Oct 13
includes taxes & fees
Book a stay at this historic hotel in Northampton. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Calvin Theatre and Performing Arts Center and Don Muller Gallery are located nearby.
Parking included
Free WiFi
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
33.17 km from city centre
The price is CA $121 per night
CA $121
CA $139 total
Oct 19 - Oct 20
includes taxes & fees
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 MGM Springfield and Olympia Ice Center are located nearby.
Pet-friendly
Parking included
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Free cancellation
Reserve now, pay when you stay
34.57 km from city centre
The price is CA $143 per night
CA $143
CA $160 total
Nov 2 - Nov 3
includes taxes & fees
Book a stay at this family-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Barrington Stage Company and Lichtenstein Center for the Arts are located nearby.
Pet-friendly
Parking included
Don't see what you're looking for?
See all available properties in Chesterfield
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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.

Top hotels in Chesterfield for Extended Stay

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA
The price is CA $126 per night from Nov 8 to Nov 9
CA $126
CA $173 total
Nov 8 - Nov 9
includes taxes & fees
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.

Chesterfield hotels essential information

Accommodation
505 hotels
Lowest Price
CA $139
Highest Price
CA $204
Popular hotels
Quality Inn West Springfield, Berkshire Mountain Lodge, D. Hotel Suites & Spa, Hotel UMass, Blue A Modern Hotel, an Ascend Collection Hotel, Hampton Inn West Springfield, Hotel Northampton, Red Roof Inn PLUS+ West Springfield, Hotel On North

Frequently asked questions

What are the top kid-friendly hotels in Chesterfield?
Take some of the hassles out of traveling with kids by staying in a family-friendly hotel in Chesterfield. From entertaining amenities to services that bring a smile, these properties offer perks that'll make your getaway smooth sailing: Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck! will help make your vacation the best one yet. It comes with a range of conveniences geared toward families, such as a deck and a fireplace. Elegant Wilderness Cabin 12 Miles From Northampton is another great choice. After a fun day of exploring, come back home to your comfortable room and amenities like a water park and animal viewing activities.
Where can I find cheap hotels in Chesterfield?
At Travelocity you'll find really nice hotels in Chesterfield 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 Chesterfield rather than in Chesterfield. We may find you even better rates, too.
How do I find the best Chesterfield hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Chesterfield 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 Chesterfield?
The cheapest hotel in Chesterfield is CA $139 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 Chesterfield?
There are 505 hotels in Chesterfield on Travelocity.
What are the best hotels in Chesterfield?
Chesterfield 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 Chesterfield for you!
When is the best time to visit Chesterfield?
If you want the joy of a fun-filled trip in peak season, visit Chesterfield 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 Chesterfield?
Based on historic data is usually the cheapest month to visit Chesterfield. 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 Chesterfield?
There are multiple hotels in Chesterfield 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 Chesterfield. We have plenty of kid-friendly hotels in Chesterfield to choose from on Travelocity!
Why book a hotel in Chesterfield through Travelocity?
Because we have the top hotels in Chesterfield! 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 Chesterfield 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 Chesterfield hotel reviews by fellow wanderers

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

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

5 out of 5
Posted 3 hours ago
Travelocity Verified Review
"This hotel was clean and in a good location. The staff was friendly and helpful. I loved their nice pool and jacuzzi and enjoyed it. Breakfast was OK. Rooms are clean and big enough to make your money worth for it. One more important thing for us was its free and big parking lot."
A verified traveller stayed at Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG