Plan a trip to see Winthrop Beach

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

Beacon Hill Hotel

Beacon Hill

per person

Sep 7 - Sep 10

found 20 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Boston (BOS)

8.8/10 Excellent! (234 reviews)

We enjoyed having the bistro on site.

Reviewed on Jul. 17, 2025

Encore Boston Harbor

per person

Sep 7 - Sep 10

found 20 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Boston (BOS)

9.6/10 Exceptional! (3,159 reviews)

This was one of our best stays by far on our 30 day road trip in July. Our room was beautiful overlooking the Boston Harbor which was a romantic view at night. We deeply appreciated the convenience of the high-tech set up allowing us to control everything on an iPad. That was a unique experience and one I wish all hotels utilized. The bathtub is a great soaking tub with a TV on the wall and there’s even a place to rest your arms. The shower was nice too. The room was a large size compared to most hotel rooms.

Reviewed on Aug. 2, 2025

Hyatt Regency Boston

Downtown Boston

per person

Sep 25 - Sep 27

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9/10 Wonderful! (1,577 reviews)

Stayed here for 1 night . It’s a clean quiet and walkable to the highlights of Boston downtown .

Reviewed on Aug. 3, 2025

Tours & day trips

See all 245 activities

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

Free cancellation available

Private & custom tours

See all 47 activities

North End Boston Mafia Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 38 activities

Boston to Martha's Vineyard with Optional Island Tour

Free cancellation available

Attractions

See all 8 activities

Boston CityPASS®: Admission to Top 4 Attractions

Free cancellation available

Adventure & outdoor

See all 7 activities

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

Popular places to visit

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.

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.

Revere Beach

If a restful vacation is part of your travel plans, Revere Beach might be the perfect place to seek out during your trip to Revere. Check out the shops and top-notch restaurants in this family-friendly area.

Revere Beach Reservation

Explore the great outdoors at Revere Beach Reservation, a lovely green space in Revere. Check out the shops and top-notch restaurants in this family-friendly area.