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 Godfrey Hotel Boston
Downtown Boston
Price was $390, price is now $287 per person
$287
per person
Apr 11 - Apr 13
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. Valet parking, a business center, and a coffee shop are also offered.
The Colonnade Hotel Back Bay
Back Bay
Save 100% on your flight
Price was $685, price is now $456 per person
$456
per person
May 26 - May 28
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. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the seasonal outdoor pool, poolside bar, and laundry facilities.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $1,560, price is now $1,063 per person
$1,063
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was $1,144, price is now $795 per person
$795
per person
Apr 9 - Apr 12
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the 24-hour gym and perks like free WiFi.
The Charles Hotel
West Cambridge
Save 100% on your flight
Price was $1,625, price is now $1,162 per person
$1,162
per person
May 13 - May 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Top Chesterfield hotels deals
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Free Cancellation
Reserve now, pay when you stay
$121 nightly
The price is $135 total per night
$135 total
Mar 1 - Mar 2
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.
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$121 nightly
The price is $136 total per night
$136 total
Mar 29 - Mar 30
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.
Comfort Inn & Suites
400 Russell St Hadley MA
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $122 total per night
$122 total
Mar 22 - Mar 23
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
$103 nightly
The price is $115 total per night
$115 total
Mar 2 - Mar 3
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.
Courtyard by Marriott West Springfield
885 Riverdale Street West Springfield MA
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $145 total per night
$145 total
Mar 5 - Mar 6
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.
Tru by Hilton Chicopee Springfield
440 Memorial Dr Chicopee MA
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $120 total per night
$120 total
Mar 8 - Mar 9
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Relax with a drink at the bar/lounge and enjoy free perks like on-the-go breakfast and free self parking. A 24-hour business center, free WiFi in public areas, and a terrace are also on offer.
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.
Krug Sugarbush
You can take time to visit Krug Sugarbush 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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