Downtown Gloucester Holidays

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Our guide on 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.

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Annisquam lighthouse in Massachusetts

Rocky Neck

While visiting Rocky Neck, you might make a stop by sights like Rocky Neck Art Colony and Bryan Gallery.

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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.

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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.

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Our pick of the best Downtown Gloucester Hotel Deals

Beauport Hotel Gloucester

Beauport Hotel Gloucester

55 Commercial Street Gloucester MA
NZ$658
15 Sept - 16 Sept
includes taxes & fees
Beauport Hotel Gloucester
The Highliner Hotel

The Highliner Hotel

108 Main St Gloucester MA
NZ$685
19 Aug - 20 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
NZ$472
30 Aug - 31 Aug
includes taxes & fees
9.6/10 Exceptional! (333 reviews)
"No smoke detector in room, wallpaper and plaster hanging from bathroom ceiling. Closet doors couldn’t close. Bathroom fixtures from the 40’s. Mattress needs replacing. Very strange set of doorways into the room. 1st door had a lock but there was a 2ft opening leading into the stairwell, above the ..."

Reviewed on 12 Aug 2026

Harborview Inn
See all 1,217 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.
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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.
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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?
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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.
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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.
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Gloucester Unitarian Universalist Church

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

Whale Watching Tour

Whale Watching Tour in Gloucester

NZ$83
per adult
98% of travellers recommend
Whale Watching Tour in Gloucester
Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor: Self-Guided Driving Audio Tour

NZ$29
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

NZ$86
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
See all activities in Gloucester
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