Chesterfield Vacations
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Chesterfield Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer
West End
$735
per person
Dec 26 - Dec 30
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Faneuil Hall Marketplace are located nearby.
My only issue was breakfast. Breakfast was something I had planned for this trip but it's not a self service, it's a sit down restaurant that you get "tickets" for. This was not usable for our busy weekend, which I was hoping to grab something to go quickly on the way out the door in the morning. This hotel is otherwise in an ideal location for all parts of north end and west end travel, easy access to train, still far enough away you don't get terrible traffic noise for sleep!
Reviewed on Oct 18, 2026
Boston Harbor Hotel
North End
$1,228
per person
Dec 26 - Dec 30
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this 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 Faneuil Hall Marketplace and Boston Harbor are located nearby.
Amazing staff and property
Reviewed on Oct 18, 2026
Battery Wharf Hotel, Boston Waterfront
North End
$891
per person
Dec 26 - Dec 30
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Harbor and Faneuil Hall Marketplace are located nearby.
Loved it!
Reviewed on Oct 19, 2026
The Langham, Boston
Downtown Boston
$1,190
per person
Dec 26 - Dec 30
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Faneuil Hall Marketplace and Boston Harbor are located nearby.
The Colonnade Hotel Back Bay
Back Bay
$896
per person
Dec 26 - Dec 30
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
Breakfast at Lucie understaffed
Reviewed on Oct 19, 2026
Fairmont Copley Plaza, Boston
Back Bay
$820
per person
Dec 26 - Dec 30
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The hotel is in the perfect location. Everything is walking distance. The staff was amazing. However, plan for small old school rooms.
Reviewed on Oct 18, 2026
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Quality Inn West Springfield
1150 Riverdale St West Springfield MA
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 ...
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Book a stay at this spa hotel in Holyoke. Enjoy free breakfast, a full-service spa, and 2 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
Hotel UMass
1 Campus Center Way Amherst MA
Stay at this hotel in Amherst. Enjoy free breakfast, free WiFi, and 5 coffee shops/cafes. Our guests praise the helpful staff in our reviews. Popular attractions ...
Blue A Modern Hotel, an Ascend Collection Hotel
1080 Riverdale St West Springfield MA
Book a stay at this business-friendly hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions MGM Springfield ...
Red Roof Inn PLUS+ West Springfield
1254 Riverdale Street West Springfield MA
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 ...
Hotel Northampton
36 King Street Northampton MA
Book a stay at this historic hotel in Northampton. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
Hampton Inn West Springfield
1011 Riverdale St West Springfield MA
Book a stay at this business-friendly hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Hotel On North
297 North Street Pittsfield MA
Book a stay at this family-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms ...
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and ...
Comfort Inn & Suites Hadley - Amherst
400 Russell St Hadley MA
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 ...
Riverdale Inn
1500 Riverdale Street West Springfield MA
Stay at this motel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions MGM Springfield and Olympia Ice Center are ...
Inn on Boltwood
30 Boltwood Ave. Amherst MA
Book a stay at this business-friendly hotel in Amherst. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. ...
Quality Inn & Suites Northampton - Amherst
117 Conz St Northampton MA
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 ...
Red Roof Inn PLUS+ South Deerfield – Amherst
9 Greenfield Rd South Deerfield MA
Stay at this hotel in South Deerfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
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, Dec 4 - Tue, Dec 15
LAX
Los Angeles Intl.
BOS
Logan Intl.
$327
Roundtrip
found 1 day ago
Fri, Dec 4 - Tue, Dec 15
LAX
Los Angeles Intl.
BOS
Logan Intl.
$328
Roundtrip
found 1 day ago
Fri, Dec 4 - Tue, Dec 15
LAX
Los Angeles Intl.
BOS
Logan Intl.
$337
Roundtrip
found 1 day ago
Fri, Dec 4 - Tue, Dec 15
LAX
Los Angeles Intl.
BOS
Logan Intl.
$337
Roundtrip
found 1 day ago
Fri, Dec 4 - Tue, Dec 15
LAX
Los Angeles Intl.
BOS
Logan Intl.
$337
Roundtrip
found 1 day ago
Best points of interest in Chesterfield
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