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.
Red Roof Inn PLUS+ Boston - Woburn/ Burlington
Save 100% on your flight
Price was $699, price is now $429 per person
$429
per person
Jul 9 - Jul 12
found 19 hours ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.
Eurostars The Boxer
West End
Save 100% on your flight
Price was $3,066, price is now $1,920 per person
$1,920
per person
Jun 24 - Jun 30
found 2 hours ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. A computer station, dry cleaning, and luggage storage are also on offer.
Raffles Boston
Back Bay
Save 100% on your flight
Price was $5,035, price is now $3,247 per person
$3,247
per person
Jun 24 - Jun 30
found 2 hours ago
Roundtrip flight included
Charlotte (CLT) 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.
The Inn at Hastings Park, Relais & Chateaux - Boston
Save 100% on your flight
Price was $1,248, price is now $842 per person
$842
per person
May 30 - Jun 2
found 13 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) 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 Newbury Boston
Back Bay
Save 100% on your flight
Price was $4,207, price is now $2,845 per person
$2,845
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Families will appreciate the onsite laundry facilities and in-room childcare. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.
Top Chesterfield hotels deals
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Free Cancellation
$150 nightly
The price is $168 total per night
$168 total
Apr 14 - Apr 15
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.
Pool
Hot Tub
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
May 12 - May 13
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.
Pool
Hot Tub
Comfort Inn & Suites Hadley - Amherst
400 Russell St Hadley MA
Free Cancellation
$127 nightly
The price is $141 total per night
$141 total
Apr 20 - Apr 21
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.
Pool
Breakfast included
Blue – A Modern Hotel, an Ascend Collection Hotel
1080 Riverdale St West Springfield MA
Free Cancellation
$111 nightly
The price is $127 total per night
$127 total
May 4 - May 5
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.
The Ellery
259 Elm Street Northampton MA
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $155 total per night
$155 total
Apr 28 - Apr 29
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.
Tru by Hilton Chicopee Springfield
440 Memorial Dr Chicopee MA
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $125 total per night
$125 total
Apr 14 - Apr 15
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.
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
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