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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Best Western Springfield West Inn

$256

per person

Nov 7 - Nov 9

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

7.8/10 Good! (1,001 reviews)

My room was comfortable and clean

Reviewed on Aug 21, 2025

D. Hotel Suites & Spa

Save 100% on your flight

$307

per person

Oct 5 - Oct 8

found 1 day ago

Roundtrip flight included

Miami (MIA) to Boston (BOS)

9.4/10 Exceptional! (2,226 reviews)

Very pleasant check in, nice discount on the partner restaurant

Reviewed on Aug 28, 2025

Sesuit Harbor House

Save 100% on your flight

$873

per person

Oct 12 - Oct 18

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

9.6/10 Exceptional! (162 reviews)

We’ve been to the Cape many times over the past 20 years. The Sesuit Harbor House was conveniently located off Route 6a, but it was very quiet; you couldn’t hear the traffic at all. Phil and his staff are very attentive and friendly; the continental breakfast in a basket every morning (with local treats) was perfect! We will come back and hopefully with more family members. It was 10/10!

Reviewed on Aug 25, 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

See all 41 activities

North End Boston Mafia Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 30 activities

Boston to Martha's Vineyard with Optional Island Tour

Free cancellation available

Adventure & outdoor

See all 6 activities

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

Explore the great outdoors at Winthrop Shore Reservation, a lovely green space in 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.