Dogtown Tours and Activities

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Activities

Gloucester travel guide

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Price found within the past 48 hours. Click for updated prices.

The Langham, Boston

Downtown Boston

CA $1,451

per person

May 2 - May 5

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Boston (BOS)

9.6/10 Exceptional! (1,004 reviews)

Great location within walking distance to many of Boston’s best spots including Faneuil Market, North End “little Italy,” and more! The hotel staff were welcoming and kind during our visit, and our room was well kept. No complaints.

Reviewed on Mar 14, 2026

Boston Harbor Hotel

North End

CA $1,644

per person

Apr 24 - Apr 27

found 10 hours ago

Roundtrip flight included

Hamilton (YHM) to Boston (BOS)

9.8/10 Exceptional! (1,001 reviews)

Excellent hotel- restaurants, room service, all of the staff, spacious room with view, bathroom amenities. Great location. Able to take a leisurely walk along the water, and close to many restaurants and theatre district. Also easy to catch a taxi or uber. Wonderful setting with water and city view. Will definitely return!

Reviewed on Mar 14, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

CA $1,575

per person

Jun 13 - Jun 17

found 8 hours ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

9.6/10 Exceptional! (252 reviews)

Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

Popular places to visit

Cape Ann Museum

You can spend an afternoon exploring the galleries in Cape Ann Museum during your travels in Gloucester. Wander the beautiful beaches and seaside in this family-friendly area.

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.

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.

Fishermen's Memorial Monument

Learn about the local history of Gloucester with a stop at Fishermen's Memorial Monument. Wander the beautiful beaches and seaside in this family-friendly area.

Pavilion Beach

Why not spend a lazy afternoon at Pavilion Beach during your trip to Gloucester?

Good Harbor Beach

Why not spend a carefree afternoon at Good Harbor Beach during your travels in Gloucester? Wander the waterfront or discover the area's sunrises.

Best Lodging Options Near Dogtown

Check availability on hotels close to Dogtown

Rockport Inn And Suites

183 Main Street Rockport MA

Beauport Hotel Gloucester

55 Commercial Street Gloucester MA

River Watch: Waterfront home with river views and a private dock.

Gloucester MA

Evensong: Oceanview Retreat with Dock

Gloucester MA

Mill Pond Cottage: Timeless Gloucester Elegance

Gloucester MA

Terra Nova Cottage Waterfront! Enjoy stunning views & sunsets over the Annisquam

Gloucester MA

Sunset Cove: Waterfront at Goose Cove

Gloucester MA

Clean Waterfront Classic Cottage with Private Beach

Gloucester MA

WATERFRONT 1BDRM SPACIOUS STUDIO APARTMENT

Gloucester MA

See all 520 properties in Dogtown

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.