Downtown Gloucester Holidays
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Price found within the past 48 hours. Click for updated prices.
The Newbury Boston
Back Bay
Price was €1,767, price is now €1,310 per person
€1,310
per person
25 Jan - 30 Jan
found 1 hour ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (536 reviews)
Very friendly staff. Amazing location. The room was perfect. Didn’t go to Contessa, but we ran into the Chef in the elevator and he was super fun and courteous. The bar is cool, we ate there a couple nights. We had a very pleasant Thanksgiving week there. Festive and lively hotel. There’s Tatte around the corner and every store you can think of within walking distance. Looking forward to our next stay!
Reviewed on 4 Dec 2025
The Charles Hotel
West Cambridge
Price was €1,083, price is now €926 per person
€926
per person
20 Jan - 23 Jan
found 6 hours ago
Return direct flight included
Dublin (DUB) 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 14 Dec 2025
Top hotels in Downtown Gloucester
Beauport Hotel Gloucester
55 Commercial Street Gloucester MA
9.6/10 Exceptional! (905 reviews)
We loved our stay So comfy, clean and beautiful views!
Reviewed on 6 Dec 2025
Harborview Inn
71 Western Avenue Gloucester MA
The price is €180 per night from 18 Dec to 19 Dec
€180
18 Dec - 19 Dec
includes taxes & 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 19 Nov 2025
DoubleTree by Hilton Boston North Shore
50 Ferncroft Rd Danvers MA
Fully refundableReserve now, pay when you stay
The price is €93 per night from 1 Jan to 2 Jan
€93
1 Jan - 2 Jan 2026
includes taxes & fees
8/10 Very Good! (2,283 reviews)
Everything fine.
Reviewed on 9 Dec 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.
Popular places to visit
Maritime Gloucester
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.
Wingaersheek Beach
Why not spend a care-free afternoon at Wingaersheek Beach during your travels in Gloucester? While you're in the area, stroll along the seaside.
Good Harbor Beach
Why not spend a care-free afternoon at Good Harbor Beach during your travels in Gloucester? Wander the waterfront or discover the area's sunrises.
Things to do
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
€15
per traveller
80% of travellers recommend
Cape Ann Harbor: Self-Guided Driving Audio Tour
€15
per traveller
100% of travellers recommend
Salem: Pirate Museum with Authentic Treasures Entry Ticket
€18
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.