Downtown Gloucester Vacations from $400
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The Latest Downtown Gloucester Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel
South End
Save 100% on your flight
Price was $626, price is now $400 per person
$400
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Boston (BOS)
9/10 Wonderful! (2,241 reviews)
Room was clean and the location was lovely!
Reviewed on Dec 15, 2025
The Charles Hotel
West Cambridge
Save 100% on your flight
Price was $934, price is now $566 per person
$566
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
We love the Charles Hotel. From its helpful and friendly staff, spotless and well appointed rooms, and excellent on-site restaurants. It is the perfect place for a winter getaway.
Reviewed on Dec 14, 2025
The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was $1,136, price is now $761 per person
$761
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Great location and very clean. Friendly staff and overall a wonderful stay in Boston. We would absolutely stay here again.
Reviewed on Dec 15, 2025
The Cove At Yarmouth
Save 100% on your flight
Price was $636, price is now $432 per person
$432
per person
Jan 16 - Jan 19
found 21 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Boston (BOS)
9.2/10 Wonderful! (243 reviews)
The unit on or suite units are on second floor with no elevator. In addition, the bedroom is on another level.
For those with physical issues only.insist on first floor
I found 1st floor bath dirty.
This is a time share rental which suits families with young kids.
Reviewed on Oct 6, 2025
Eurostars The Boxer
West End
Save 100% on your flight
Price was $706, price is now $481 per person
$481
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Boston (BOS)
8.6/10 Excellent! (1,337 reviews)
Hotel was nice, small rooms. But there was a security issue - staff gave the person who stayed in my room before me a key to get in when I was there because this woman’s thought she left her purse there. Apparently there was confusion because the staff member thought she had just left and didn’t know anyone was now in the room. But it was disturbing. Management was apologetic and offered me some comps which was appreciated. I will stay there next week for 1 night. I would hesitate for a longer stay unless I knew this was dealt with.
Reviewed on Dec 11, 2025
Downtown Gloucester Hotel Deals
Beauport Hotel Gloucester
55 Commercial Street Gloucester MA
$203 nightly
The price is $227 total per night from Dec 17 to Dec 18
$227 total
Dec 17 - Dec 18
Total with taxes and fees
9.6/10 Exceptional! (905 reviews)
We loved our stay So comfy, clean and beautiful views!
Reviewed on Dec 6, 2025
Harborview Inn
71 Western Avenue Gloucester MA
$189 nightly
The price is $211 total per night from Dec 18 to Dec 19
$211 total
Dec 18 - Dec 19
Total with taxes and fees
9.4/10 Exceptional! (314 reviews)
The room was clean and comfortable with daily housekeeping. Great location for walking. Nice complimentary breakfast. Wonderful host!
Reviewed on Nov 19, 2025
DoubleTree by Hilton Boston North Shore
50 Ferncroft Rd Danvers MA
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $109 total per night from Dec 21 to Dec 22
$109 total
Dec 21 - Dec 22
Total with taxes and fees
8/10 Very Good! (2,289 reviews)
Breakfast was great
Reviewed on Dec 10, 2025
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.
Discover the most popular places to visit in Downtown Gloucester
Maritime Gloucester
Discover Gloucester’s maritime history at the historic working waterfront with an aquarium, a scenic pier and educational programs on marine sciences.
Cape Ann Museum
5/5(3 reviews)
Step back in time to discover Gloucester’s history at a charming museum featuring fascinating artifacts, maritime artworks and a sculpture park.
Pavilion Beach
Why not spend a lazy afternoon at Pavilion Beach during your trip to Gloucester?
Things to do
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
$17
per traveler
80% of travellers recommend
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
$45
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
$45
per traveler
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.