Chesterfield flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Beacon Hill Hotel
Beacon Hill
Save 100% on your flight
per person
Jul 25 - Jul 28
found 2 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
This hotel features a restaurant, a rooftop terrace, and a bar/lounge. WiFi in public areas is free. A terrace, luggage storage, and concierge services are also on offer.
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Boston (BOS)
A private beach and a spa tub are featured at this vacation home. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. WiFi in public areas is free.
Raffles Boston
Back Bay
Save 100% on your flight
per person
Aug 19 - Aug 22
found 14 hours ago
Roundtrip flight included
Houston (IAH) 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.
Mandarin Oriental, Boston
Back Bay
Save 100% on your flight
per person
Jul 18 - Jul 21
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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, express check-in, and valet parking. You'll appreciate the sauna, bar/lounge, and limo/town car service.
The Langham, Boston
Downtown Boston
Save 100% on your flight
per person
Aug 30 - Sep 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Top Chesterfield hotels deals
Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
Free Cancellation
Reserve now, pay when you stay
The price is $78 per night
$78
per night
Jul 1 - Jul 2
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
D. Hotel Suites & Spa
1 Country Club Rd, Holyoke, MA
Free Cancellation
The price is $146 per night
$146
per night
Jun 18 - Jun 19
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and free perks like continental breakfast and free self parking.
Pool
Hot Tub
Red Roof Inn PLUS+ West Springfield
1254 Riverdale Street, West Springfield, MA
Free Cancellation
Reserve now, pay when you stay
The price is $78 per night
$78
per night
Jun 27 - Jun 28
This hotel 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.
Pet friendly
Parking included
Red Roof Inn PLUS+ South Deerfield – Amherst
9 Greenfield Rd, South Deerfield, MA
Free Cancellation
Reserve now, pay when you stay
The price is $94 per night
$94
per night
Jun 16 - Jun 17
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.
Pet friendly
Parking included
Howard Johnson by Wyndham Amherst Hadley
401 Russell St, Hadley, MA
Free Cancellation
Reserve now, pay when you stay
The price is $110 per night
$110
per night
Jun 30 - Jul 1
A gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Multilingual staff can provide around-the-clock assistance and free newspapers are on offer.
Breakfast included
Pet friendly
Hotel UMass
1 Campus Center Way, Amherst, MA
The price is $199 per night
$199
per night
Jun 19 - Jun 20
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, a business center, and a coffee shop are also offered.
Breakfast 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.
Photos of local treasures
Browse Chesterfield vacation photos for more inspiration