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

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

Boston Lodge and Suites

Dorchester

$439

per person

Jan 28 - Feb 2

found 18 hours ago

Roundtrip flight included

Orlando (MCO) to Boston (BOS)

8.4/10 Very Good! (188 reviews)

Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available.

Reviewed on Nov 10, 2025

The Whitney Hotel

Beacon Hill

Save 100% on your flight

$1,003

per person

Jan 29 - Feb 3

found 1 day ago

Roundtrip non-stop flight included

Dallas (DAL) to Boston (BOS)

9.6/10 Exceptional! (482 reviews)

Phenomenon phenomenon will definitely will be back

Reviewed on Nov 26, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

Save 100% on your flight

$583

per person

Feb 20 - Feb 22

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Boston (BOS)

9.6/10 Exceptional! (247 reviews)

Beautiful property! Room was excellent. Great amenities and free continental breakfast brought to our room.

Reviewed on Oct 21, 2025

Browse tours and tickets to explore Little Brewster

Tours & day trips

See all 168 activities

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

Free cancellation available

Private & custom tours

See all 52 activities

Boston: Helicopter Skyline Tour

Free cancellation available

Food, drink & nightlife

See all 28 activities

City Cruises Boston: Signature Dinner Cruise

Attractions

See all 8 activities

Boston CityPASS®: Admission to Top 4 Attractions

Free cancellation available

Classes & workshops

See all 5 activities

Italian Dinner with Tiramisu Finale in Boston

Popular places to visit

Boston Harbor Islands State Park

5/5(1 review)

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

4.5/5(6 reviews)

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.