Gloucester Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Gloucester Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel
South End
Save 100% on your flight
Price was $943, price is now $597 per person
$597
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Stay at this 3.5-star 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.
The Newbury Boston
Back Bay
Save 100% on your flight
Price was $2,463, price is now $1,348 per person
$1,348
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
The Charles Hotel
West Cambridge
Save 100% on your flight
Price was $1,636, price is now $1,017 per person
$1,017
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Stay at this 4-star luxury hotel in Cambridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
The Ritz-Carlton, Boston
Downtown Boston
Save 100% on your flight
Price was $2,106, price is now $1,342 per person
$1,342
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Raffles Boston
Back Bay
Save 100% on your flight
Price was $2,356, price is now $1,505 per person
$1,505
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Stay at this 5-star 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.
The Whitney Hotel
Beacon Hill
Save 100% on your flight
Price was $2,038, price is now $1,347 per person
$1,347
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Stay at this 4-star 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 Boston Common and TD Garden are located nearby.
Gloucester Vacation Packages
Hoping to save both time and money on your upcoming trip to Gloucester? Well, AARP Travel Center Powered by Expedia® is here to help. We're here to book everything you'll need to make your Gloucester trip one to remember. In just a few clicks, you can select the best Gloucester vacation package for you and your family. AARP Travel Center has a fabulous list of flights and hotels, and local things to do to pick from.
Hotels in Gloucester
With 1753 hotels and resorts in Gloucester to choose from, you are bound to find one that meets your needs.
We have competitive rates on everything from luxury hotels that meet all the vacation must-haves to affordable accommodations perfect for those on wanting to save a little money. You can search all the possibilities and choose the hotel that is ideal for you and your family. With AARP Travel Center's Gloucester hotel packages, you not only get a great rate on your flight, but also a great place to stay.
Things to do in Gloucester
Gloucester has around 29,781 people that call this city their home. If you wanted to take a break from the hustle of a big city, then you chose the perfect place. With this area's growing artistic community and a rich past that is a beacon for history buffs you may have a hard time fitting everything into one trip.
Looking for more? Then Check out AARP Travel Center's "Things to Do" Page.
Book Together and Save
With so much happening in Gloucester, you'll be wanting to focus on your itinerary, not devoting time to searching for the cheapest hotel. The AARP Travel Center Powered by Expedia® allows you to quickly book all you wish for, and save money doing it. You can coordinate your whole vacation, including things to do in Gloucester from only one place. So what are you waiting for? Book now and save!
Top Hotel Deals
Castle Manor Inn
141 Essex Avenue, Gloucester, MA
1.98 km from city center
Stay at this hotel in Gloucester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
Ocean House Hotel at Bass Rocks
107 Atlantic Rd, Gloucester, MA
2.54 km from city center
Stay at this 4-star golf hotel in Gloucester. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Sea Lion Motel and Cottages
138 Eastern Avenue, Gloucester, MA
2.4 km from city center
Book a stay at this business-friendly motel in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
The Hotel at Cape Ann Marina
75 Essex Avenue, Gloucester, MA
1.47 km from city center
Stay at this 3.5-star hotel in Gloucester. Enjoy free parking, a marina, and a 24-hour front desk. Our guests praise the breakfast and the restaurant in our ...
The Vista
22 Thatcher Rd., Gloucester, MA
2.28 km from city center
Book a stay at this business-friendly hotel in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Long Beach Suites
28 Rockport Rd, Gloucester, MA
3.74 km from city center
Stay at this aparthotel in Gloucester. Enjoy free WiFi and free parking. Popular attractions Good Harbor Beach and Cape Ann are located nearby.
Beauport Hotel Gloucester
55 Commercial Street, Gloucester, MA
0.27 km from city center
Stay at this 3.5-star beach hotel in Gloucester. Enjoy free WiFi, a beach locale, and a rooftop terrace. Our guests praise the helpful staff and the property ...
Lakeside Inn
595 North Ave, Wakefield, MA
36.13 km from city center
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 ...
Sonesta Select Boston Danvers
275 Independence Way, Danvers, MA
23.29 km from city center
Stay at this 3-star business-friendly hotel in Danvers. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
Comfort Inn & Suites Logan International Airport
85 American Legion Hwy, Revere, MA
35.56 km from city center
Stay at this hotel in Revere. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the restaurant in our reviews. ...
Comfort Inn Danvers - Boston North Shore
102 Newbury St, Danvers, MA
26.01 km from city center
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 helpful staff ...
DoubleTree by Hilton Boston North Shore
50 Ferncroft Rd, Danvers, MA
25.03 km from city center
Stay at this 4-star golf hotel in Danvers. Enjoy free parking, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
Motel 6 Danvers, MA - Boston North
65 Newbury Street/US Route 1 North, Danvers, MA
26.21 km from city center
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 ...
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, Oct 28 - Fri, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$213 Roundtrip, found 1 day ago
$213
Roundtrip
found 1 day ago
Tue, Oct 28 - Fri, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$215 Roundtrip, found 1 day ago
$215
Roundtrip
found 1 day ago
Tue, Oct 28 - Fri, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Tue, Oct 28 - Fri, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Tue, Oct 28 - Fri, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago