
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.

Even Hotels Manchester Airport by IHG
South End
Save 100% on your flight
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
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. Free self parking, a snack bar/deli, and a lobby fireplace are also offered.

Motel 6 Danvers, MA - Boston North
Save 100% on your flight
per person
Oct 20 - Oct 27
just found
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a snack bar/deli, and laundry facilities are also on offer.

Ashworth by the Sea
Hampton Beach
Save 100% on your flight
per person
Oct 20 - Oct 27
just found
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This smoke-free hotel features 3 restaurants, a bar/lounge, and an indoor pool. There's a rooftop terrace on site, and a 24-hour front desk and a snack bar/deli are also provided.

Sonesta Simply Suites Boston Burlington
Save 100% on your flight
per person
Oct 20 - Oct 27
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A picnic area, a computer station, and barbecue grills are also on offer.

DoubleTree by Hilton Boston North Shore
Save 100% on your flight
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
This hotel features 2 restaurants, an indoor pool, and a gym. Families will appreciate the arcade/game room and convenience store. Enjoy the sauna and perks like 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

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 $98 total per night
$98 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
$110 nightly
The price is $124 total per night
$124 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