Deals on vacations and trips to Chesterfield
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Chesterfield flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Fairfield Inn & Suites by Marriott Plymouth
Save 100% on your flight
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
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 free perks like buffet breakfast and free self parking.
YOTEL Boston
Seaport District
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
The hotel's 24-hour gym, a rooftop terrace, and 2 bars/lounges are among the featured amenities. Enjoy a meal from the restaurant and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
Boston Harbor Hotel
North End
Save 100% on your flight
per person
Sep 19 - Sep 21
found 1 day ago
Roundtrip non-stop 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.
Hotel 1620 Plymouth Harbor
Plymouth Downtown Waterfront District
Save 100% on your flight
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Boston (BOS)
Free water park access and an indoor pool are featured at this smoke-free hotel. Traveling on business? Take advantage of the conference center and conference space on site. Enjoy the 24-hour gym and perks like free self parking.
The Mansion at Ocean Edge
Save 100% on your flight
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
This smoke-free hotel features a private beach, a golf course, and a full-service spa. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities. Enjoy the 3 outdoor pools and get free self parking.
Top Chesterfield hotels deals
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
Sep 7 - Sep 8
Total includes 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
Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $106 total per night
$106 total
Sep 9 - Sep 10
Total includes 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
Free Cancellation
$119 nightly
The price is $132 total per night
$132 total
Aug 17 - Aug 18
Total includes 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
Hotel UMass
1 Campus Center Way, Amherst, MA
Free Cancellation
Reserve now, pay when you stay
$200 nightly
The price is $223 total per night
$223 total
Sep 2 - Sep 3
Total includes taxes and fees
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, a coffee shop, and a snack bar/deli are also offered.
Breakfast included
Free WiFi
FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $79 total per night
$79 total
Aug 24 - Aug 25
Total includes taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. The front desk is staffed around-the-clock and laundry facilities are on offer.
Parking included
Free WiFi
Comfort Inn & Suites
400 Russell St, Hadley, MA
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $160 total per night
$160 total
Sep 3 - Sep 4
Total includes 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
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
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