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 Cove At Yarmouth
Save 100% on your flight
Price was $515, price is now $345 per person
$345
per person
Apr 23 - Apr 26
found 17 hours ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free aparthotel. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
Eurostars The Boxer
West End
Save 100% on your flight
Price was $769, price is now $468 per person
$468
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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.
Battery Wharf Hotel, Boston Waterfront
North End
Save 100% on your flight
Price was $692, price is now $442 per person
$442
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. There's a sauna on site, and laundry facilities and concierge services are also offered.
Hyatt Regency Boston/Cambridge
MIT
Save 100% on your flight
Price was $579, price is now $384 per person
$384
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. Self parking, a coffee shop, and a terrace are also offered.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $2,639, price is now $1,770 per person
$1,770
per person
Apr 2 - Apr 7
found 1 day ago
Roundtrip 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.
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.
Pool
Hot Tub
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.
Pool
Hot Tub
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 3 - Mar 4
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
$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.
Pool
Parking included
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.
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 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
Browse Chesterfield vacation photos for more inspiration
