Downtown Gloucester Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Downtown Gloucester Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Wylie Inn and Conference Center at Endicott College
Price was $530, price is now $373 per person
$373
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Boston (BOS)
Book a stay at this beach hotel in Beverly. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Salem Witch Museum and Rice's Beach are located nearby.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $2,228, price is now $1,306 per person
$1,306
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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.
Club Quarters Hotel Faneuil Hall, Boston
Downtown Boston
Save 100% on your flight
Price was $958, price is now $662 per person
$662
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Boston Common and New England Aquarium are located nearby.
The Godfrey Hotel Boston
Downtown Boston
Save 100% on your flight
Price was $917, price is now $664 per person
$664
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Boston Common and New England Aquarium are located nearby.
Arcadian Hotel
Coolidge Corner
Save 100% on your flight
Price was $747, price is now $551 per person
$551
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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.
The Colonnade Hotel Back Bay
Back Bay
Save 100% on your flight
Price was $1,098, price is now $829 per person
$829
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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.
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See all available trips from Columbus to Downtown Gloucester
View all tripsTop Hotel Deals
Beauport Hotel Gloucester
55 Commercial Street Gloucester MA
0.48 km from Downtown Gloucester
Book a stay at this beach hotel in Gloucester. Enjoy free WiFi, a beach locale, and a rooftop terrace. Our guests praise the helpful staff and the property condition ...
The Highliner Hotel
108 Main St Gloucester MA
0.14 km from Downtown Gloucester
Stay at this hotel in Gloucester. Enjoy free WiFi, concierge services, and housekeeping. Popular attractions Good Harbor Beach and Wingaersheek Beach are located ...
Harborview Inn
71 Western Avenue Gloucester MA
0.74 km from Downtown Gloucester
Stay at this B&B in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Good ...
Holiday Inn Hotel & Suites Boston - Peabody by IHG
1 Newbury St Peabody MA
29.35 km from Downtown Gloucester
Book a stay at this business-friendly hotel in Peabody. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Salem Witch Museum and ...
DoubleTree by Hilton Boston North Shore
50 Ferncroft Rd Danvers MA
25.06 km from Downtown Gloucester
Book a stay at this golf hotel in Danvers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
Best Western Plus North Shore Hotel
50 Dayton St Danvers MA
25.98 km from Downtown Gloucester
Book a stay at this business-friendly hotel in Danvers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Hawthorne Hotel
18 Washington Square W Salem MA
21.16 km from Downtown Gloucester
Book a stay at this historic hotel in Salem. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff in our ...
The Northshore Hotel - Boston/Danvers
219 Newbury St. Danvers MA
25.22 km from Downtown Gloucester
Stay at this motel in Danvers. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. ...
Motel 6 Danvers, MA - Boston North
65 Newbury Street/US Route 1 North Danvers MA
26.12 km from Downtown Gloucester
Stay at this motel in Danvers. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Salem Witch Museum and Glen Magna Farms are located ...
The Hotel Salem
209 Essex Street Salem MA
21.51 km from Downtown Gloucester
Stay at this hotel in Salem. Enjoy free WiFi, a rooftop terrace, and a 24-hour front desk. Our guests praise the bar and the helpful staff in our reviews. Popular ...
SpringHill Suites by Marriott Boston Peabody
43 Newbury St./Route 1 North Peabody MA
28.86 km from Downtown Gloucester
Book a stay at this business-friendly hotel in Peabody. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Rockport Inn And Suites
183 Main Street Rockport MA
5.04 km from Downtown Gloucester
Stay at this B&B in Rockport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions ...
The Cove At Salem
40 Bridge St Salem MA
20.5 km from Downtown Gloucester
Stay at this hotel in Salem. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Don't see what you're looking for?
See all available properties in Downtown Gloucester
View all propertiesLowest 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.
$242 Roundtrip, found 2 days ago
$242
Roundtrip
found 2 days ago
Wed, Aug 12 - Tue, Sep 1
LAX
Los Angeles Intl.
BOS
Logan Intl.
$245 Roundtrip, found 16 hours ago
$245
Roundtrip
found 16 hours ago
Sat, Sep 12 - Wed, Sep 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$247 Roundtrip, found 16 hours ago
$247
Roundtrip
found 16 hours ago
Mon, Sep 21 - Tue, Sep 29
LAX
Los Angeles Intl.
BOS
Logan Intl.
$247 Roundtrip, found 18 hours ago
$247
Roundtrip
found 18 hours ago
Sat, Sep 12 - Wed, Sep 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$267 Roundtrip, found 16 hours ago
$267
Roundtrip
found 16 hours ago