Deals on vacations and trips to Chesterfield
Save when you book Chesterfield package deals
Chesterfield flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel
South End
Save 100% on your flight
Price was $478, price is now $296 per person
$296
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a terrace are also on offer.
Boston Lodge and Suites
Dorchester
Price was $838, price is now $314 per person
$314
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out are also on offer.
The Inn at Hastings Park, Relais & Chateaux - Boston
Price was $1,829, price is now $909 per person
$909
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
A restaurant and a bar/lounge are featured at this hotel. A terrace, limo/town car service, and a snack bar/deli are also on offer.
citizenM Boston Back Bay
Fenway–Kenmore
Save 100% on your flight
Price was $604, price is now $349 per person
$349
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A coffee shop, a communal living room, and express check-in are also on offer.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $1,238, price is now $745 per person
$745
per person
Jan 29 - Feb 1
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.
Top Chesterfield hotels deals
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
$134 nightly
The price is $149 total per night
$149 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. You'll appreciate the gym, bar/lounge, and laundry facilities.
Pool
Hot Tub
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $104 total per night
$104 total
Dec 23 - Dec 24
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$108 nightly
The price is $120 total per night
$120 total
Jan 19 - Jan 20, 2026
Total with taxes and fees
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $90 total per night
$90 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Pool
Breakfast included
Courtyard by Marriott West Springfield
885 Riverdale Street West Springfield MA
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $135 total per night
$135 total
Dec 24 - Dec 25
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Parking included
Comfort Inn & Suites
400 Russell St Hadley MA
Free Cancellation
Reserve now, pay when you stay
$124 nightly
The price is $138 total per night
$138 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Pool
Breakfast included
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.
Popular places to visit
Chesterfield Gorge
Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forest while you're in the area.
Chesterfield Town Hall
After visiting Chesterfield Town Hall, make a plan to see the other sights and activities in Chesterfield. Amble around the area's parks or visit its shops.
Chesterfield Public Library
Chesterfield Public Library is just one of the places to see in Chesterfield, so why not enjoy the other things to explore during your travels? Amble around the area's parks or visit its shops.
Frequently asked questions
Photos of local treasures
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