If your idea of a fantastic vacation means being by the water, visit Little Brewster. Whatever you choose to do here, you're unlikely to get bored of those pretty views.

Lots of travelers to Boston have this water-surrounded land mass on their to-do list. But Little Brewster is just one of many spots worth visiting in this area. If you've got time on your side, Winthrop Beach will keep you entertained.

Plan a trip to see Little Brewster

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The Revolution Hotel

South End

Save 100% on your flight

$178

per person

Dec 6 - Dec 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9/10 Wonderful! (2,149 reviews)

Fast check in very convenient exactly what you need it for. Well decorated

Reviewed on Oct 12, 2025

Boston Lodge and Suites

Dorchester

$286

per person

Dec 6 - Dec 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

8.4/10 Very Good! (186 reviews)

Raffles Boston

Back Bay

$793

per person

Dec 19 - Dec 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9.8/10 Exceptional! (160 reviews)

I wish the water was hotter, had to ask to have room cleaned after 1st day as housekeeping did not come. Very responsive though when inquiries made.

Reviewed on Oct 7, 2025

Browse tours and tickets to explore Little Brewster

Tours & day trips

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Boston Old Town Trolley Hop-on Hop-Off City Tour

Free cancellation available

Private & custom tours

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Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Free cancellation available

Food, drink & nightlife

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Boston to Martha's Vineyard with Optional Island Tour

Free cancellation available

Adventure & outdoor

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Go City: Boston Explorer Pass - Choose 2 to 5 Attractions

Free cancellation available

Attractions

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Boston CityPASS®: Admission to Top 4 Attractions

Free cancellation available

Popular places to visit

Boston Harbor Islands State Park

Discover the hiking trails, historic forts and majestic lighthouses that are sprinkled across this group of 34 islands located just off the coast of Boston.

The location of Boston 's sewage treatment plant, but also home to some stunning sunsets.

Deer Island HarborWalk

You can take time to visit Deer Island HarborWalk during your travels to Boston. Stroll along the waterfront or attend a sporting event in this vibrant area.

Nantasket Beach

Why not spend a carefree afternoon at Nantasket Beach during your travels in Boston? Discover the area's sunrises and shops.

As seen from Deer Island, this is the town of Winthrop, just north of Boston, MA. It's a cute, condensed town with houses stacked right on top of each other on the hills. The long beach

Winthrop Shore Reservation

You can take time to visit Winthrop Shore Reservation during your travels to Winthrop. Stroll along this family-friendly area's beaches, or simply enjoy its restaurants.

Winthrop Beach

Why not spend a lazy afternoon at Winthrop Beach during your trip to Winthrop? Wander the beaches and seaside in this family-friendly area.

Hull Lifesaving Museum

You can browse the exhibits at Hull Lifesaving Museum, a museum with a storied past, during your travels to Hull. Stroll along the waterfront or attend a sporting event in this vibrant area.