Downtown Gloucester Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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
A lighthouse, a white building with a red roof, and a stone walkway leading to the water.

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.

Find hotels in East Gloucester

Top hotels in Downtown Gloucester

Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street Gloucester MA
The price is S$564 per night from 30 Jun to 1 Jul
S$564
30 Jun - 1 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

Beauport Hotel Gloucester
The Highliner Hotel

The Highliner Hotel

2 out of 5
108 Main St Gloucester MA
The price is S$440 per night from 28 Jun to 29 Jun
S$440
28 Jun - 29 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

The Highliner Hotel
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
50 Ferncroft Rd Danvers MA
Fully refundableReserve now, pay when you stay
The price is S$188 per night from 22 Jul to 23 Jul
S$188
22 Jul - 23 Jul
includes taxes & fees
8.2/10 Very good! (2,438 reviews)
"Already stated my assessment when replying to my stay two days earlier."

Reviewed on 21 Jun, 2026

DoubleTree by Hilton Boston North Shore
See all 1,192 properties in Downtown Gloucester
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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.