Chesterfield Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Chesterfield Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hilton Boston/Woburn
Save 100% on your flight
Price was $732, price is now $490 per person
$490
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3.5-star business-friendly hotel in Woburn. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attraction Burlington Mall is located nearby.
The Newbury Boston
Back Bay
Price was $2,723, price is now $1,418 per person
$1,418
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
DoubleTree Suites by Hilton Hotel Boston - Cambridge
Allston
Save 100% on your flight
Price was $1,196, price is now $691 per person
$691
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $3,573, price is now $2,270 per person
$2,270
per person
Oct 28 - Nov 2
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
The Ritz-Carlton, Boston
Downtown Boston
Save 100% on your flight
Price was $2,204, price is now $1,415 per person
$1,415
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy breakfast (surcharge), 24-hour room service, and a health club. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.
Raffles Boston
Back Bay
Save 100% on your flight
Price was $3,121, price is now $2,054 per person
$2,054
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
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Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
34.87 km from city center
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
Red Roof Inn PLUS+ West Springfield
1254 Riverdale Street, West Springfield, MA
33.2 km from city center
Stay at this hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
33.46 km from city center
Book a stay at this golf hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
D. Hotel Suites & Spa
1 Country Club Rd, Holyoke, MA
23.29 km from city center
Stay at this 3-star spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. ...
Riverdale Inn
1500 Riverdale Street, On Route 5, West Springfield, MA
32.52 km from city center
Stay at this motel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Big E and Eastern States Exposition are ...
Tru by Hilton Chicopee Springfield
440 Memorial Dr, Chicopee, MA
32.74 km from city center
Stay at this hotel in Chicopee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Motel 6 Chicopee, MA - Springfield
36 Burnett Rd, Chicopee, MA
34.77 km from city center
Stay at this motel in Chicopee. Enjoy free WiFi, a 24-hour front desk, and laundry facilities. Our guests praise the helpful staff and the clean rooms in our ...
Quality Inn & Suites Northampton - Amherst
117 Conz St, Northampton, MA
19.76 km from city center
Book a stay at this business-friendly hotel in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Comfort Inn & Suites
400 Russell St, Hadley, MA
24.36 km from city center
Book a stay at this business-friendly hotel in Hadley. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Courtyard by Marriott West Springfield
885 Riverdale Street, West Springfield, MA
34.25 km from city center
Stay at this 3-star business-friendly hotel in West Springfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff ...
The Ellery
259 Elm Street, Northampton, MA
17.67 km from city center
Stay at this 3.5-star hotel in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Quality Inn Chicopee - Springfield
463 Memorial Dr, Chicopee, MA
32.87 km from city center
Book a stay at this business-friendly hotel in Chicopee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Big E and MGM Springfield are ...
Quality Inn Westfield - Springfield
2 Southampton Rd, Westfield, MA
29.18 km from city center
Book a stay at this business-friendly hotel in Westfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Fri, Oct 31 - Wed, Nov 12
LAX
Los Angeles Intl.
BOS
Logan Intl.
$217 Roundtrip, found 3 days ago
$217
Roundtrip
found 3 days ago
Tue, Oct 28 - Thu, Oct 30
LAX
Los Angeles Intl.
BOS
Logan Intl.
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Thu, Oct 30 - Sun, Nov 2
LAX
Los Angeles Intl.
BOS
Logan Intl.
$222 Roundtrip, found 2 days ago
$222
Roundtrip
found 2 days ago
Fri, Oct 31 - Wed, Nov 12
LAX
Los Angeles Intl.
BOS
Logan Intl.
$222 Roundtrip, found 3 days ago
$222
Roundtrip
found 3 days ago
Sat, Sep 27 - Sat, Oct 4
LAX
Los Angeles Intl.
BOS
Logan Intl.
$233 Roundtrip, found 6 days ago
$233
Roundtrip
found 6 days ago