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.
Comfort Inn & Suites Logan International Airport
Save 100% on your flight
Price was $413, price is now $269 per person
$269
per person
Feb 26 - Mar 1
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
This hotel features an indoor pool, a gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free buffet breakfast and a free airport shuttle. Self parking, a 24-hour business center, and free WiFi in public areas are also offered.
The Charles Hotel
West Cambridge
Save 100% on your flight
Price was $890, price is now $521 per person
$521
per person
Feb 26 - Mar 1
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
A full-service spa, 3 restaurants, and a 24-hour gym are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Self parking, limo/town car service, and a snack bar/deli are also offered.
Four Points by Sheraton Boston Newton
Newton Corner
Price was $716, price is now $443 per person
$443
per person
Feb 6 - Feb 12
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
This smoke-free hotel includes 2 restaurants, 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. A bar/lounge, a 24-hour front desk, and express check-out are also provided.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $901, price is now $571 per person
$571
per person
Jan 16 - Jan 18
found 24 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.
citizenM Boston Back Bay
Fenway–Kenmore
Save 100% on your flight
Price was $513, price is now $326 per person
$326
per person
Feb 26 - Mar 1
found 22 hours ago
Roundtrip non-stop 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.
Top Chesterfield hotels deals
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Free Cancellation
$121 nightly
The price is $135 total per night
$135 total
Dec 15 - Dec 16
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
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
Free Cancellation
Reserve now, pay when you stay
$78 nightly
The price is $89 total per night
$89 total
Jan 4 - Jan 5, 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
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $120 total per night
$120 total
Jan 11 - Jan 12, 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
Comfort Inn & Suites
400 Russell St Hadley MA
Free Cancellation
Reserve now, pay when you stay
$123 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
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Free Cancellation
$93 nightly
The price is $104 total per night
$104 total
Dec 15 - Dec 16
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
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 21 - Dec 22
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
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 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.
Chesterfield Gorge Reservation
You can take time to visit Chesterfield Gorge Reservation during your travels to Chesterfield. Amble around the area's parks or visit its shops.
Frequently asked questions
Photos of local treasures
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