Gloucester Vacations

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Gloucester Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Iris Hotel Boston

Iris Hotel Boston

Coolidge Corner
Save 100% on your flight
$979
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Boston (BOS)
Book a stay at this business-friendly hotel in Brookline. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Fenway Park and Harvard Square are located nearby.
The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

$1,162
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Houston (IAH) 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 Common and Salem Witch Museum are located nearby.
Stayed on the 3rd floor. The walls were thin. Keurig coffee on that floor not good. But the coffee in the Lobby was a lot better. Free WiFi but very slow, especially in the evenings. But the room was very clean and water pressure was decent

Reviewed on Aug 26, 2026

Eurostars The Boxer

Eurostars The Boxer

West End
$1,399
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Houston (IAH) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Faneuil Hall Marketplace are located nearby.
Encore Boston Harbor

Encore Boston Harbor

Save 100% on your flight
$1,174
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Boston (BOS)
Book a stay at this luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
Hotel AKA Boston Common

Hotel AKA Boston Common

Downtown Boston
$1,467
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Houston (IAH) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.
Good hotel, no issues, great location, comfortable and clean rooms

Reviewed on Aug 27, 2026

The Westin Boston Seaport District

The Westin Boston Seaport District

Seaport District
$1,084
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Houston (IAH) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy 2 bars/lounges, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
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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 1886 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

Castle Manor Inn

141 Essex Avenue Gloucester MA
1.99 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. ...
Sea Lion Motel and Cottages

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 ...
Beauport Hotel Gloucester

Beauport Hotel Gloucester

55 Commercial Street Gloucester MA
0.27 km from city center
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 Vista

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. ...
Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

107 Atlantic Rd Gloucester MA
2.54 km from city center
Book a stay at this golf hotel in Gloucester. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Long Beach Suites

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.
The Highliner Hotel

The Highliner Hotel

108 Main St Gloucester MA
0.09 km from city center
Stay at this hotel in Gloucester. Enjoy free WiFi, concierge services, and housekeeping. Popular attractions Good Harbor Beach and Wingaersheek Beach are located ...
Atlantis Oceanfront Inn

Atlantis Oceanfront Inn

125 Atlantic Road Gloucester MA
2.56 km from city center
Stay at this motel in Gloucester. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
Ashworth by the Sea

Ashworth by the Sea

295 Ocean Blvd Hampton NH
35.57 km from city center
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 ...
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

50 Ferncroft Rd Danvers MA
25.04 km from city center
Book a stay at this golf hotel in Danvers. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms ...
Holiday Inn Hotel & Suites Boston - Peabody by IHG

Holiday Inn Hotel & Suites Boston - Peabody by IHG

1 Newbury St Peabody MA
29.27 km from city center
Book a stay at this business-friendly hotel in Peabody. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Salem Witch Museum and ...
Lakeside Inn

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

Sonesta Select Boston Danvers

275 Independence Way Danvers MA
23.31 km from city center
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 ...
The Northshore Hotel - Boston/Danvers

The Northshore Hotel - Boston/Danvers

219 Newbury St. Danvers MA
25.18 km from city center
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. ...
Holiday Inn Express Boston - Saugus by IHG

Holiday Inn Express Boston - Saugus by IHG

999 Broadway Saugus MA
33.55 km from city center
Book a stay at this business-friendly hotel in Saugus. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
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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.

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American Airlines
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United