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.
The Boxboro Regency
Price was $708, price is now $554 per person
$554
per person
Jul 17 - Jul 22
found 21 hours ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to Boston (BOS)
Book a stay at this business-friendly hotel in Boxborough. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Harvard Town Beach and Thurston's Beach are located nearby.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $3,091, price is now $1,817 per person
$1,817
per person
Jul 17 - Jul 22
found 21 hours ago
Roundtrip non-stop flight included
West Palm Beach (PBI) 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 New England Aquarium and Boston Harbor are located nearby.
Hotel Ivy Boston Common
Bay Village
Save 100% on your flight
Price was $1,123, price is now $734 per person
$734
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Washington (DCA) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, a 24-hour front desk, and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was $2,232, price is now $1,631 per person
$1,631
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip non-stop 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 New England Aquarium and Boston Harbor are located nearby.
Eurostars The Boxer
West End
Price was $1,282, price is now $990 per person
$990
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip non-stop 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 Boston Common are located nearby.
The Revolution Hotel
South End
Price was $780, price is now $606 per person
$606
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Washington (DCA) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and 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
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
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 ...
Hotel UMass
1 Campus Center Way Amherst MA
25.48 km from city center
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 ...
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
23.29 km from city center
Book a stay at this 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. ...
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 ...
Tru by Hilton Chicopee Springfield
440 Memorial Dr Chicopee MA
32.65 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 ...
Comfort Inn & Suites Hadley - Amherst
400 Russell St Hadley MA
24.38 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 ...
The Ellery
259 Elm Street Northampton MA
17.66 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 breakfast and the helpful ...
Red Roof Inn PLUS+ South Deerfield – Amherst
9 Greenfield Rd South Deerfield MA
20.47 km from city center
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 ...
Blue – A Modern Hotel, an Ascend Collection Hotel
1080 Riverdale St West Springfield MA
33.62 km from city center
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 ...
Riverdale Inn
1500 Riverdale Street 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 MGM Springfield and Naismith Memorial Basketball ...
Candlewood Suites West Springfield by IHG
572 Riverdale St West Springfield MA
34.77 km from city center
Book a stay at this business-friendly hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
Hampton Inn West Springfield
1011 Riverdale St West Springfield MA
33.92 km from city center
Book a stay at this business-friendly hotel in West Springfield. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and ...
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.
Tue, Sep 22 - Wed, Sep 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$232 Roundtrip, found 1 day ago
$232
Roundtrip
found 1 day ago
Wed, Sep 16 - Sat, Sep 26
PDX
Portland Intl.
BOS
Logan Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Wed, Sep 23 - Wed, Sep 30
LAX
Los Angeles Intl.
BOS
Logan Intl.
$237 Roundtrip, found 22 hours ago
$237
Roundtrip
found 22 hours ago
Wed, Sep 23 - Wed, Sep 30
LAX
Los Angeles Intl.
BOS
Logan Intl.
$237 Roundtrip, found 22 hours ago
$237
Roundtrip
found 22 hours ago
Thu, Sep 10 - Tue, Sep 15
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$271 Roundtrip, found 3 hours ago
$271
Roundtrip
found 3 hours ago