
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.

Ramada by Wyndham Boston
Dorchester
per person
Sep 11 - Sep 15
found 16 hours ago
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

Boston Harbor Hotel
North End
Save 100% on your flight
per person
Sep 25 - Sep 29
found 16 hours ago
Roundtrip flight included
Philadelphia (PHL) 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
per person
Sep 11 - Sep 15
found 16 hours ago
Roundtrip flight included
Philadelphia (PHL) 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.

The Beverly
Save 100% on your flight
per person
Sep 11 - Sep 15
found 16 hours ago
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
Stay at this 3-star business-friendly hotel in Beverly. Enjoy free WiFi, free parking, and an in-room coffeemaker. Our guests praise the clean rooms in our reviews. Popular attractions Salem Witch Museum and North Shore Music Theatre are located nearby.

YOTEL Boston
Seaport District
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Boston (BOS)
Stay at this 4-star hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and a rooftop terrace. Our guests praise the restaurant and the bar in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.

Mandarin Oriental, Boston
Back Bay
Save 100% on your flight
per person
Sep 11 - Sep 15
found 16 hours ago
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
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See all available trips from Columbus to Chesterfield
View all tripsTop Hotel Deals

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 ...

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 fitness center. Our guests praise the helpful staff and the clean rooms in ...

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. ...

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 room service. Our guests praise the helpful staff in our reviews. Popular attractions Mullins ...

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 ...

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 ...

FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
31 km from city center
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 ...

Hotel Northampton
36 King Street, Northampton, MA
18.94 km from city center
Stay at this 3.5-star historic hotel in Northampton. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...

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 B&B in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...

Inn on Boltwood
30 Boltwood Ave., Amherst, MA
26.46 km from city center
Stay at this 3-star business-friendly hotel in Amherst. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. ...

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
34.67 km from city center
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...

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 ...
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 16 - Mon, Sep 29
LAX
Los Angeles Intl.
BOS
Logan Intl.
$196 Roundtrip, found 6 days ago
$196
Roundtrip
found 6 days ago

Fri, Sep 12 - Tue, Sep 16
PDX
Portland Intl.
BOS
Logan Intl.
$217 Roundtrip, found 4 days ago
$217
Roundtrip
found 4 days ago

Wed, Sep 24 - Wed, Oct 1
LAX
Los Angeles Intl.
BOS
Logan Intl.
$221 Roundtrip, found 22 hours ago
$221
Roundtrip
found 22 hours ago

Tue, Sep 16 - Mon, Sep 29
LAX
Los Angeles Intl.
BOS
Logan Intl.
$225 Roundtrip, found 6 days ago
$225
Roundtrip
found 6 days ago

Tue, Sep 9 - Sat, Sep 13
PDX
Portland Intl.
BOS
Logan Intl.
$227 Roundtrip, found 4 days ago
$227
Roundtrip
found 4 days ago
Best points of interest in Chesterfield
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