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.
Eurostars The Boxer
West End
Price was $1,213, price is now $891 per person
$891
per person
Apr 17 - Apr 19
found 22 hours ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. A computer station, dry cleaning, and luggage storage are also on offer.
The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was $2,840, price is now $1,960 per person
$1,960
per person
Apr 18 - Apr 21
found 20 hours ago
Roundtrip flight included
Charlotte (CLT) 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 $1,612, price is now $1,124 per person
$1,124
per person
Apr 18 - Apr 21
found 20 hours ago
Roundtrip flight included
Charlotte (CLT) 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.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $1,720, price is now $1,268 per person
$1,268
per person
May 16 - May 18
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
Fairmont Copley Plaza, Boston
Back Bay
Save 100% on your flight
Price was $1,291, price is now $966 per person
$966
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a rooftop terrace on site, and laundry facilities and concierge services 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 15 - Mar 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.
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$115 nightly
The price is $128 total per night
$128 total
Apr 12 - Apr 13
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 Hadley - Amherst
400 Russell St Hadley MA
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $123 total per night
$123 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.
Courtyard by Marriott West Springfield
885 Riverdale Street West Springfield MA
Free Cancellation
Reserve now, pay when you stay
$131 nightly
The price is $150 total per night
$150 total
Mar 19 - Mar 20
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.
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Free Cancellation
$122 nightly
The price is $137 total per night
$137 total
Mar 14 - Mar 15
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.
Red Roof Inn PLUS+ South Deerfield – Amherst
9 Greenfield Rd South Deerfield MA
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $95 total per night
$95 total
Apr 1 - Apr 2
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are 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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