Downtown Gloucester Vacations from ￥357,898
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Downtown Gloucester Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Arcadian Hotel
Coolidge Corner
￥365,926
per person
Sep 27 - Oct 3
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.2/10 Very Good! (4,382 reviews)
loved this hotel. great neighborhood! Green line right out front and easy to use. Easy 1 mile walk to Fenway . Will definitely stay here again when in Boston.
Reviewed on Aug 22, 2026
Hyatus Luxury Residences Somerville
Assembly Square
￥389,089
per person
Sep 24 - Sep 28
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
10/10 Exceptional! (1 review)
I have lived a long time, but I have never experienced a stay as warm and beautiful as this luxury furnished apartment. Every corner felt lovingly prepared, and I often caught myself smiling at how comfortable and peaceful the home was. The modern touches wowed me and the place wrapped me in the familiar coziness of being in a real home. I will remember this stay fondly and with great gratitude to the team at building and leasing team.
Reviewed on Dec 6, 2025
Where to stay in Downtown Gloucester
Find the best Downtown Gloucester areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Gloucester
East Gloucester
2 out of top 10 points of interest in this area
If you're spending some time in East Gloucester, Good Harbor Beach and Niles Beach are top sights worth seeing.
Rocky Neck
1 out of top 10 points of interest in this area
If you're spending some time in Rocky Neck, Rocky Neck Art Colony and Bryan Gallery are top sights worth seeing.
Annisquam
While Annisquam might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Wingaersheek Beach and Plum Cove Beach.
Magnolia
Nestled in Gloucester, this small village boasts its own library, restaurants, and shops. Enjoy Gray Beach at Coolidge Reservation or take in scenic views of Kettle Cove at Surf Park.
Downtown Gloucester Hotel Deals
Beauport Hotel Gloucester
55 Commercial Street Gloucester MA
￥49,732
￥55,551 total
Sep 21 - Sep 22
includes taxes & fees
9.6/10 Exceptional! (1,004 reviews)
"I am very happy I found this hotel on Expedia. Beautiful hotel. Food was very good if you plan on staying onsite to relax it’s perfect. The location is amazing. Staff is very accommodating and kind. Definitely will return. Definitely would recommend. If available I would suggest getting an ocean ..."
Reviewed on Aug 21, 2026
The Highliner Hotel
108 Main St Gloucester MA
￥30,309
￥58,712 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (17 reviews)
"Really well appointed rooms. Accessible and helpful concierge. Convenient to restaurants and shops."
Reviewed on Aug 15, 2026
Harborview Inn
71 Western Avenue Gloucester MA
￥39,579
￥44,209 total
Aug 30 - Aug 31
includes taxes & fees
9.6/10 Exceptional! (334 reviews)
"Love love love this place!!! John is so friendly and helpful, breakfast bar was perfect , the atmosphere of the room and breakfast area was so very relaxing. Can’t wait to go back again next year!!!"
Reviewed on Aug 15, 2026
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.
Stay near popular Downtown Gloucester attractions
Cape Ann Museum
9.0/10 (23 reviews)
You can spend an afternoon exploring the galleries in Cape Ann Museum during your travels in Gloucester. Wander the beautiful beaches and seaside in this family-friendly area.
Maritime Gloucester
9.4/10 (63 reviews)
You can spend an afternoon studying the exhibits at Maritime Gloucester during your travels in Gloucester. Wander the beautiful beaches and seaside in this family-friendly area.
Pavilion Beach
8.0/10 (9 reviews)
Why not spend a lazy afternoon at Pavilion Beach during your trip to Gloucester?
Fishermen's Memorial Monument
9.6/10 (18 reviews)
Learn about the local history of Gloucester with a stop at Fishermen's Memorial Monument. Wander the beautiful beaches and seaside in this family-friendly area.
Capt Bill & Sons Whale Watch
8.2/10 (12 reviews)
You can learn about the history of Gloucester when you stop by Capt Bill & Sons Whale Watch. Wander the seaside and beautiful beaches in the area.
Gloucester Unitarian Universalist Church
After visiting Gloucester Unitarian Universalist Church, make a plan to see the other sights and activities in Gloucester.
Cape Ann Historical Museum
6.0/10 (1 review)
You can spend an afternoon exploring the galleries in Cape Ann Historical Museum during your trip to Gloucester. Wander the seaside and beautiful beaches in the area.
Sargent House Museum
6.0/10 (1 review)
You can spend time studying the exhibits at Sargent House Museum in Gloucester. Wander the seaside and beautiful beaches in the area.
Things to do
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
￥7,979
per adult
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
￥2,712
per traveler
80% of travellers recommend
Massachusetts: Smartphone-Based Audio Tour Bundle
￥7,979
per traveler
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.