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

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.

Find hotels in East Gloucester
Annisquam lighthouse in Massachusetts

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.

Find hotels in Rocky Neck
A coastal landscape with a lighthouse, rocky shoreline, and a beach.

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.

Find hotels in Annisquam
A garden with purple flowers and a foggy coastline.

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.

Find hotels in Magnolia

Top hotels in Downtown Gloucester

Beauport Hotel Gloucester

Beauport Hotel Gloucester

55 Commercial Street Gloucester MA
S$461
17 Sept - 18 Sept
includes taxes & fees
9.6/10 Exceptional! (1,002 reviews)
"Parking is difficult and the valets are semi useless. Couldn't contact front desk from the room until the 8th try. Overall disappointed."

Reviewed on 19 Aug, 2026

Beauport Hotel Gloucester
The Highliner Hotel

The Highliner Hotel

108 Main St Gloucester MA
S$479
23 Aug - 24 Aug
includes taxes & fees
8.6/10 Excellent! (17 reviews)
"Really well appointed rooms. Accessible and helpful concierge. Convenient to restaurants and shops."

Reviewed on 15 Aug, 2026

The Highliner Hotel
Harborview Inn

Harborview Inn

71 Western Avenue Gloucester MA
S$354
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

Harborview Inn
See all 1,221 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.

Stay near popular Downtown Gloucester attractions

An art gallery with wooden flooring and paintings on the walls.

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.
See properties
A group of people in naval uniforms on a wooden deck, with a ship's rigging and a clear blue sky in the background.

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.
See properties
A beach with people, umbrellas, and beach chairs.

Pavilion Beach

8.0/10 (9 reviews)
Why not spend a lazy afternoon at Pavilion Beach during your trip to Gloucester?
See properties
A statue of a person with a wheel, set against a backdrop of houses and a tree.

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.
See properties

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.
See properties

Gloucester Unitarian Universalist Church

After visiting Gloucester Unitarian Universalist Church, make a plan to see the other sights and activities in Gloucester.
See properties

Cape Ann Historical Museum

6.0/10 (1 review)
You can spend an afternoon browsing the exhibits at Cape Ann Historical Museum during your trip to Gloucester. Wander the seaside and beautiful beaches in the area.
See properties

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.
See properties

Things to do

Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor: Self-Guided Driving Audio Tour

S$22
per traveller
100% of travellers recommend
Cape Ann Harbor: Self-Guided Driving Audio Tour
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

S$65
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

S$22
per traveller
80% of travellers recommend
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
See all activities in Gloucester

* 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.