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.
Lakeside Inn
Save 100% on your flight
Price was $652, price is now $448 per person
$448
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this business-friendly hotel in Wakefield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attraction MarketStreet Lynnfield is located nearby.
Hotel Ivy Boston Common
Bay Village
Save 100% on your flight
Price was $2,080, price is now $1,224 per person
$1,224
per person
Jul 12 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $2,860, price is now $1,774 per person
$1,774
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Raffles Boston
Back Bay
Save 100% on your flight
Price was $5,703, price is now $3,946 per person
$3,946
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Club Quarters Hotel Faneuil Hall, Boston
Downtown Boston
Save 100% on your flight
Price was $1,936, price is now $1,357 per person
$1,357
per person
Jul 12 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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.
Cambridge Common House
West Cambridge
Save 100% on your flight
Price was $2,313, price is now $1,630 per person
$1,630
per person
Jul 12 - Jul 19
found 23 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Boston (BOS)
Stay at this guesthouse in Cambridge. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions Harvard 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 Sargent House Museum and Cape Ann Museum 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 Fishermen's ...
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 ...
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 ...
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 MarketStreet Lynnfield ...
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 ...
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 ...
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 ...
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 ...
Hampton Inn Salem Boston
11 DODGE STREET Salem MA
21.68 km from Downtown Gloucester
Book a stay at this business-friendly hotel in Salem. Enjoy free breakfast, a fitness center, and valet parking (surcharge). Our guests praise the breakfast ...
Sonesta Select Boston Danvers
275 Independence Way Danvers MA
23.38 km from Downtown Gloucester
Book a stay at this business-friendly hotel in Danvers. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
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.
Fri, May 29 - Tue, Jun 2
PDX
Portland Intl.
BOS
Logan Intl.
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Wed, Aug 12 - Tue, Sep 1
LAX
Los Angeles Intl.
BOS
Logan Intl.
$227 Roundtrip, found 2 hours ago
$227
Roundtrip
found 2 hours ago
Thu, Jul 9 - Tue, Jul 14
LAX
Los Angeles Intl.
BOS
Logan Intl.
$240 Roundtrip, found 20 hours ago
$240
Roundtrip
found 20 hours ago
Fri, May 29 - Tue, Jun 2
PDX
Portland Intl.
BOS
Logan Intl.
$247 Roundtrip, found 1 hour ago
$247
Roundtrip
found 1 hour ago
Tue, Jul 14 - Thu, Jul 16
LAX
Los Angeles Intl.
BOS
Logan Intl.
$257 Roundtrip, found 2 hours ago
$257
Roundtrip
found 2 hours ago