Gloucester, MA

Travel Guide

Good Harbor Beach featuring a sunset, a sandy beach and general coastal views
Half Moon Beach which includes a beach, general coastal views and a sunset
Maritime Gloucester as well as a small group of people
Maritime Gloucester showing a sunset and a bay or harbor
Good Harbor Beach which includes a sunset and a coastal town

Where to stay in Gloucester

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Annisquam

While Annisquam might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Wingaersheek Beach and Plum Cove Beach.

Annisquam
Beautiful place to walk and enjoy the views. This foggy noon created the atmosphere of an unreal world.

Magnolia

Nestled in Gloucester, this small village boasts its own library, restaurants, and shops. Enjoy Gray Beach at Coolidge Reservation or take in scenic views of Kettle Cove at Surf Park.

Magnolia
Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is ￥23,799 per night from Sep 2 to Sep 3
￥23,799
￥26,584 total
Sep 2 - Sep 3
includes taxes & fees
Stay at this hotel in Gloucester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.2/10 Very Good! (1,011 reviews)
"The stay was amazing! We loved the area and the location was beautiful. John was great and attentive. 1000% recommend!"

Reviewed on Aug 23, 2025

Castle Manor Inn
The Hotel at Cape Ann Marina

The Hotel at Cape Ann Marina

3.5 out of 5
75 Essex Avenue, Gloucester, MA
The price is ￥31,023 per night from Sep 16 to Sep 17
￥31,023
￥34,653 total
Sep 16 - Sep 17
includes taxes & fees
Stay at this 3.5-star hotel in Gloucester. Enjoy free parking, a marina, and a 24-hour front desk. Our guests praise the breakfast and the restaurant in our ...
8.2/10 Very Good! (725 reviews)
Lovely Getaway
"The staff was great, our room was lovely. Had dinner at Mile Marker 1, and it was delicious with a great view."

Reviewed on Aug 15, 2025

The Hotel at Cape Ann Marina
Sea Lion Motel and Cottages

Sea Lion Motel and Cottages

2.5 out of 5
138 Eastern Avenue, Gloucester, MA
The price is ￥24,375 per night from Aug 27 to Aug 28
￥24,375
￥27,228 total
Aug 27 - Aug 28
includes taxes & fees
Book a stay at this business-friendly motel in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (412 reviews)
"Room was very clean, the shower was hot with water pressure and bed was comfortable. Win, win, win!"

Reviewed on Aug 22, 2025

Sea Lion Motel and Cottages
See all 1,764 properties in 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.
Long Beach Suites

Long Beach Suites

2 out of 5
28 Rockport Rd, Gloucester, MA
Stay at this aparthotel in Gloucester. Enjoy free WiFi and free parking. Popular attractions Good Harbor Beach and Cape Ann are located nearby.
9.2/10 Wonderful! (36 reviews)
"Very close to the beach. Apartment is in great condition, new and clean."

Reviewed on Aug 18, 2025

Long Beach Suites
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Gloucester
Stay at this vacation home in Gloucester. Enjoy free WiFi, laundry facilities, and cable/satellite TV service. Popular attractions Wingaersheek Beach and Good ...
9.8/10 Exceptional! (36 reviews)
"Overall we had a very nice time on our vacation to beautiful Coffins Beach. The house was very nice and equipped with everything we needed. The only real concern was the mosquitoes in the yard. They were horrible!! Thank goodness I always leave home with plenty of bug spray. Everyone had their arms ..."

Reviewed on Aug 16, 2025

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.

Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.

Gloucester
Stay at this cottage in Gloucester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Wingaersheek Beach and Good Harbor Beach are located ...
9.8/10 Exceptional! (18 reviews)
"A beautiful cottage with wonderful amenities and host. Couldn’t have asked for a better place to stay!"

Reviewed on Aug 17, 2025

Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
See all properties in 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.

Popular places to visit

Wingaersheek Beach featuring rugged coastline

Wingaersheek Beach

Why not spend a carefree afternoon at Wingaersheek Beach during your travels in Gloucester? While you're in the area, stroll along the seaside.

Wingaersheek Beach
Good Harbor Beach which includes a sunset and a coastal town

Good Harbor Beach

4.5/5(18 reviews)

If a restful vacation is part of your travel plans, Good Harbor Beach might be the perfect place to seek out during your trip to Gloucester. While you're in the area, stroll along the seaside.

Good Harbor Beach
Hammond Castle which includes heritage elements, general coastal views and a sunset

Hammond Castle

4.5/5(8 reviews)

You can browse the exhibits at Hammond Castle, a museum with a story of its own, during your trip to Gloucester. Wander the beautiful beaches and seaside in the area.

Hammond Castle
Half Moon Beach which includes a beach, general coastal views and a sunset

Half Moon Beach

If a restful vacation is part of your travel plans, Half Moon Beach might be the perfect place to seek out during your trip to Gloucester. While you're in the area, stroll along the seaside.

Half Moon Beach
Maritime Gloucester as well as a small group of people

Maritime Gloucester

You can spend an afternoon studying the exhibits at Maritime Gloucester during your travels in Gloucester. Wander the beautiful beaches and seaside in this family-friendly area.

Maritime Gloucester
Eastern Point Lighthouse

Eastern Point Lighthouse

Learn about the local history of Gloucester with a stop at Eastern Point Lighthouse. Wander the beautiful beaches and seaside in this family-friendly area.

Eastern Point Lighthouse

Things to do

Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

￥7,361
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

￥2,511
per traveler
80% of travellers recommend
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

￥7,361
per traveler
Massachusetts: Smartphone-Based Audio Tour Bundle
Top Left: Hammond Castle Top Right: Witch House Bottom Left: Witch Museum Bottom Right: Hammond Castle Arches

Semiprivate Day Trip from Boston to Salem and Hammond Castle

￥33,255
per adult
Semiprivate Day Trip from Boston to Salem and Hammond Castle
Salem: Historic Schooner Sailing Cruise

Salem: Historic Schooner Sailing Cruise

￥5,764
per adult
100% of travellers recommend
Salem: Historic Schooner Sailing Cruise
Salem "Hocus Pocus" Movie Locations Walking Tour

Salem "Hocus Pocus" Movie Locations Tour (31st Anniversary)

￥7,686
per adult
100% of travellers recommend
Salem "Hocus Pocus" Movie Locations Tour (31st Anniversary)
See all activities in Gloucester

Cities near Gloucester

Front Beach showing general coastal views, a sandy beach and swimming

Rockport

Manchester-by-the-Sea showing a sunset and a bay or harbor

Manchester-by-the-Sea