Downtown Gloucester Holidays from £1,039
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 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 easyPackages with flights are ATOL protected
Price found within the past 48 hours. Click for updated prices.
Sesuit Harbor House
£1,039
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
London (LHR) to Boston (BOS)
9.6/10 Exceptional! (200 reviews)
Super friendly staff right from the check in with Phil , the owner, to our last hour when I met his sweet wife while we were watching the goats eat breakfast. Room had everything we needed personalized with with a a handwritten welcome card.
Reviewed on 23 Aug 2026
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
While visiting Rocky Neck, you might make a stop by sights like Rocky Neck Art Colony and Bryan Gallery.
Annisquam
Though Annisquam may not have many top sights, you can venture to the surrounding area to see attractions like Wingaersheek Beach and Plum Cove Beach.
Magnolia
You'll enjoy the beaches and restaurants in Magnolia. You might want to make time for a stop at Gray Beach or Massachusetts Bay.
Top hotels in Downtown Gloucester
Beauport Hotel Gloucester
55 Commercial Street Gloucester MA
£268
17 Sept - 18 Sept
includes taxes & fees
9.6/10 Exceptional! (1,006 reviews)
"Great rooftop pool and hot tub. Close access to a beach. Great food!"
Reviewed on 22 Aug 2026
The Highliner Hotel
108 Main St Gloucester MA
£244
20 Sept - 21 Sept
includes taxes & fees
Harborview Inn
71 Western Avenue Gloucester MA
£204
30 Aug - 31 Aug
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 15 Aug 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 in Gloucester. Wander through 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 trip to Gloucester. Wander through 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 when you spend time at Fishermen's Memorial Monument. Wander through 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 with a stop at Capt Bill & Sons Whale Watch. Wander the seaside and beautiful beaches in the area.
Schooner Adventure
You can spend time studying the exhibits at Schooner Adventure during your travels in Gloucester. 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.
Sargent House Museum
6.0/10 (1 review)
You can spend time exploring the galleries in Sargent House Museum during your travels in Gloucester. Wander the seaside and beautiful beaches in the area.
Things to do
Cape Ann Harbor: Self-Guided Driving Audio Tour
£13
per traveller
100% of travellers recommend
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
£38
per adult
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
£13
per traveller
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.