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 Atlas Hotel
Allston
Save 100% on your flight
Price was $1,801, price is now $982 per person
$982
per person
Aug 19 - Aug 26
found 1 day 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 laundry service and WiFi in public areas. A communal living room, luggage storage, and concierge services are also on offer.
Boston Harbor Hotel
North End
Price was $4,053, price is now $1,855 per person
$1,855
per person
Aug 19 - Aug 26
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 $2,146, price is now $1,278 per person
$1,278
per person
Aug 19 - Aug 26
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
The Charles Hotel
West Cambridge
Save 100% on your flight
Price was $2,447, price is now $1,473 per person
$1,473
per person
Aug 19 - Aug 26
found 1 day 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.
Eurostars The Boxer
West End
Save 100% on your flight
Price was $1,891, price is now $1,205 per person
$1,205
per person
Aug 19 - Aug 26
found 1 day 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.
Top Chesterfield hotels deals
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$149 nightly
The price is $166 total per night
$166 total
Jul 8 - Jul 9
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
Hotel UMass
1 Campus Center Way Amherst MA
Free Cancellation
$127 nightly
The price is $142 total per night
$142 total
Jul 2 - Jul 3
Total with taxes and fees
This hotel features 5 coffee shops/cafes and a bar/lounge. Enjoy a meal from the restaurant and perks like free continental breakfast and free WiFi. Self parking, a snack bar/deli, and a lobby fireplace are also offered.
Breakfast included
Free WiFi
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
Free Cancellation
$89 nightly
The price is $102 total per night
$102 total
Jul 1 - Jul 2
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
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
$142 nightly
The price is $158 total per night
$158 total
Jun 10 - Jun 11
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
Tru by Hilton Chicopee Springfield
440 Memorial Dr Chicopee MA
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $129 total per night
$129 total
Jul 6 - Jul 7
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.
Pool
Breakfast included
The Ellery
259 Elm Street Northampton MA
$107 nightly
The price is $120 total per night
$120 total
Jun 30 - Jul 1
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. A fireplace in the lobby and a picnic area are also provided.
Breakfast included
Pet friendly
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.
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.
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
Browse Chesterfield vacation photos for more inspiration
