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 Wylie Inn and Conference Center at Endicott College
Save 100% on your flight
Price was $567, price is now $394 per person
$394
per person
May 31 - Jun 3
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
A 24-hour gym, free self parking, and wedding services are featured at this hotel. WiFi in public areas is free. A coffee shop, a computer station, and luggage storage are also on offer.
The Inn at Hastings Park, Relais & Chateaux - Boston
Save 100% on your flight
Price was $1,021, price is now $639 per person
$639
per person
Jun 19 - Jun 21
found 12 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) 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.
The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was $1,867, price is now $1,239 per person
$1,239
per person
Jun 1 - Jun 3
found 1 hour ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the 24-hour gym and perks like free WiFi.
Bluegreen Vacations The Soundings, an Ascend Collection Resort
Price was $1,219, price is now $821 per person
$821
per person
May 18 - May 22
found 4 hours ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
This hotel features an indoor pool and a seasonal outdoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, express check-out, and laundry facilities are also on offer.
Life House, Nantucket
Nantucket Town
Save 100% on your flight
Price was $2,077, price is now $1,418 per person
$1,418
per person
Jun 27 - Jul 1
found 5 hours ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
Free WiFi in public areas, a terrace, and a garden are available at this hotel. A snack bar/deli, a communal living room, and a library are also on offer.
Top Chesterfield hotels deals
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
$150 nightly
The price is $168 total per night
$168 total
Apr 20 - Apr 21
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.
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $126 total per night
$126 total
Apr 16 - Apr 17
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.
Comfort Inn & Suites Hadley - Amherst
400 Russell St Hadley MA
Free Cancellation
$127 nightly
The price is $141 total per night
$141 total
Apr 21 - Apr 22
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.
Blue – A Modern Hotel, an Ascend Collection Hotel
1080 Riverdale St West Springfield MA
Free Cancellation
$116 nightly
The price is $133 total per night
$133 total
Apr 26 - Apr 27
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-out. There's a 24-hour gym on site, and laundry facilities and free newspapers are also offered.
Parking included
Free WiFi
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $102 total per night
$102 total
May 3 - May 4
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.
The Ellery
259 Elm Street Northampton MA
Free Cancellation
Reserve now, pay when you stay
$131 nightly
The price is $146 total per night
$146 total
May 5 - May 6
Total with taxes and fees
This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning. A garden, a lobby fireplace, and a picnic area 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.
Chesterfield Gorge Reservation
You can take time to visit Chesterfield Gorge Reservation during your travels to Chesterfield. 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
