Downtown Gloucester Holidays
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Price found within the past 48 hours. Click for updated prices.
The Wylie Inn and Conference Center at Endicott College
Price was €1,049, price is now €791 per person
€791
per person
5 Sept - 10 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (1,172 reviews)
Friendly, helpful staff and the property and rooms were impeccably clean. I would’ve liked a coffee pot right in the room so I didn’t have to go out in the hall, but it was not a dealbreaker at all.
Reviewed on 16 Jun 2026
Boston Harbor Hotel
North End
Save 100% on your flight
Price was €3,961, price is now €2,395 per person
€2,395
per person
8 Sept - 14 Sept
found 12 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent
Reviewed on 15 Jun 2026
Revere Hotel Boston Common
Bay Village
Price was €1,322, price is now €958 per person
€958
per person
5 Sept - 10 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,024 reviews)
We loved our stay! The hotel was lovely! Convenient walk to Gardens and River.
Reviewed on 18 Jun 2026
Club Quarters Hotel Faneuil Hall, Boston
Downtown Boston
Price was €1,653, price is now €1,241 per person
€1,241
per person
5 Sept - 10 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (3,158 reviews)
Had a great stay at Club Quarters. It's no wonderful to have a pet friendly hotel in the heart of Downtown. The best location, so close to South Station and Faneuil Hall. Special thanks to all the front desk staff, and shoutout to Jumberto (?) for being so kind, and giving my dog, Ferguson, a squeaky plush toy. Would definitely stay here for the location and value and, of course, if I was bringing my dog Ferguson again.
Reviewed on 18 Jun 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
3 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.
Top hotels in Downtown Gloucester
Beauport Hotel Gloucester
55 Commercial Street Gloucester MA
The price is €410 per night from 1 Jul to 2 Jul
€410
1 Jul - 2 Jul
includes taxes & fees
9.6/10 Exceptional! (969 reviews)
"Service was top notch. Everybody - doorman, concierge, bartenders, wait staff and house cleaning went above and beyond. We will definitely be back!"
Reviewed on 19 Jun 2026
The Highliner Hotel
108 Main St Gloucester MA
The price is €285 per night from 25 Jun to 26 Jun
€285
25 Jun - 26 Jun
includes taxes & fees
9.4/10 Exceptional! (6 reviews)
"Good location. Not a fan of off street parking. Walls were a tad thin but sound machine took care of this."
Reviewed on 16 Jun 2026
DoubleTree by Hilton Boston North Shore
50 Ferncroft Rd Danvers MA
Fully refundableReserve now, pay when you stay
The price is €143 per night from 16 Jul to 17 Jul
€143
16 Jul - 17 Jul
includes taxes & fees
8.2/10 Very Good! (2,430 reviews)
"It is a beautiful hotel! The parking lot did have big pot holes but overall it was a great stay!"
Reviewed on 19 Jun 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
Things to do
Cape Ann Harbor: Self-Guided Driving Audio Tour
€13
per traveller
100% of travellers recommend
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
€15
per traveller
80% of travellers recommend
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
€43
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.