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.
Anchorage Inn & Suites - Portsmouth
$535
per person
Oct 21 - Oct 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Book a stay at this business-friendly hotel in Portsmouth. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Market Square and Water Country are located nearby.
Boston Harbor Hotel
North End
$1,997
per person
Oct 22 - Oct 26
found 9 hours ago
Roundtrip flight included
Philadelphia (PHL) 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 Faneuil Hall Marketplace are located nearby.
Wow. Just wow. What a stay. Fantastic hotel well looked after. Amazing staff so friendly and welcoming. Great location. A fabulous stay couldn’t recommend more.
Reviewed on Sep 2, 2026
The Boxboro Regency
$555
per person
Oct 21 - Oct 27
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.
Arcadian Hotel
Coolidge Corner
$1,184
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this hotel in Brookline. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Fenway Park and Harvard Square are located nearby.
Ashworth by the Sea
Hampton Beach
$722
per person
Oct 21 - Oct 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Book a stay at this beach hotel in Hampton. Enjoy 3 restaurants, a beach locale, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hampton Beach and Hampton Beach Casino are located nearby.
The hotel was fine. Hampton beach was a disappointment. Paid parking all over town and also there is only one gas station there.
Reviewed on Sep 2, 2026
The Atlas Hotel
Allston
$2,059
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Popular attractions Harvard Square and Fenway Park are located nearby.
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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 ...
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
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. ...
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 ...
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 ...
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 ...
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 ...
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
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 ...
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 ...
Tru by Hilton Chicopee Springfield
440 Memorial Dr Chicopee MA
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 ...
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. ...
Candlewood Suites West Springfield by IHG
572 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. Our guests praise 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 Naismith Memorial Basketball ...
The Ellery
259 Elm Street Northampton MA
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 ...
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, Sep 25 - Fri, Oct 2
LAX
Los Angeles Intl.
BOS
Logan Intl.
$258
Roundtrip
found 4 hours ago
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$277
Roundtrip
found 2 days ago
Tue, Nov 3 - Tue, Nov 10
LAX
Los Angeles Intl.
BOS
Logan Intl.
$302
Roundtrip
found 6 days ago
Mon, Sep 21 - Tue, Sep 29
LAX
Los Angeles Intl.
BOS
Logan Intl.
$307
Roundtrip
found 1 day ago
Fri, Nov 13 - Mon, Nov 16
LAX
Los Angeles Intl.
BOS
Logan Intl.
$327
Roundtrip
found 12 hours ago
Best points of interest in Chesterfield
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