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.
John Carver Inn & Spa
Plymouth Cultural District
Save 100% on your flight
per person
Nov 3 - Nov 7
found 12 hours ago
Roundtrip flight included
Nashville (BNA) to Boston (BOS)
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
YOTEL Boston
Seaport District
Save 100% on your flight
per person
Sep 22 - Sep 27
found 1 day ago
Roundtrip 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 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.
Raffles Boston
Back Bay
Save 100% on your flight
per person
Sep 22 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
A full-service spa, 3 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and rooftop terrace.
citizenM Boston North Station
West End
Save 100% on your flight
per person
Sep 22 - Sep 27
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. A coffee shop, a communal living room, and express check-in are also on offer.
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
D. Hotel Suites & Spa
1 Country Club Rd, Holyoke, MA
$119 nightly
The price is $132 total per night
$132 total
Aug 18 - Aug 19
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
Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
Free Cancellation
Reserve now, pay when you stay
$86 nightly
The price is $99 total per night
$99 total
Aug 24 - Aug 25
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
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
Tru by Hilton Chicopee Springfield
440 Memorial Dr, Chicopee, MA
Free Cancellation
Reserve now, pay when you stay
$111 nightly
The price is $126 total per night
$126 total
Aug 24 - Aug 25
Total includes 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
Riverdale Inn
1500 Riverdale Street, On Route 5, West Springfield, MA
Free Cancellation
Reserve now, pay when you stay
$91 nightly
The price is $105 total per night
$105 total
Aug 19 - Aug 20
Total includes taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
Parking included
Free WiFi
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