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 Inn at Hastings Park, Relais & Chateaux - Boston
Save 100% on your flight
Price was $1,213, price is now $765 per person
$765
per person
Aug 28 - Aug 31
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
A restaurant and a bar/lounge are featured at this hotel. A terrace, limo/town car service, and a snack bar/deli are also on offer.
Boston Harbor Hotel
North End
Price was $2,872, price is now $1,418 per person
$1,418
per person
Aug 6 - Aug 11
found 12 hours ago
Roundtrip flight included
Dallas (DAL) 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.
The Charles Hotel
West Cambridge
Save 100% on your flight
Price was $1,957, price is now $1,263 per person
$1,263
per person
Aug 6 - Aug 11
found 12 hours ago
Roundtrip flight included
Dallas (DAL) 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.
Mandarin Oriental, Boston
Back Bay
Save 100% on your flight
Price was $4,077, price is now $2,631 per person
$2,631
per person
Aug 6 - Aug 13
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
A full-service spa, a gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the sauna, bar/lounge, and limo/town car service.
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Save 100% on your flight
Price was $4,829, price is now $3,159 per person
$3,159
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Boston (BOS)
A private beach and a hot tub are featured at this guesthouse. Enjoy a day at the beach kayaking, or relax with sun loungers. WiFi in public areas is free.
Top Chesterfield hotels deals
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $166 total per night
$166 total
Jul 5 - Jul 6
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.
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
Free Cancellation
$93 nightly
The price is $106 total per night
$106 total
Jun 24 - Jun 25
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.
Hotel UMass
1 Campus Center Way Amherst MA
Free Cancellation
$130 nightly
The price is $145 total per night
$145 total
Jun 28 - Jun 29
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.
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Free Cancellation
$142 nightly
The price is $158 total per night
$158 total
Jun 7 - Jun 8
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.
Quality Inn & Suites Northampton - Amherst
117 Conz St Northampton MA
Free Cancellation
$122 nightly
The price is $136 total per night
$136 total
Jun 30 - Jul 1
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
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
Jun 22 - Jun 23
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.
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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