Plan a trip to see Winthrop Shore Reservation

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

The Charles Hotel

West Cambridge

￥309,323

per person

Dec 27 - Jan 3

found 19 hours ago

Roundtrip non-stop flight included

Tokyo (HND) to Boston (BOS)

9.4/10 Exceptional! (1,005 reviews)

Clean and stylish room

Reviewed on Oct 13, 2025

Raffles Boston

Back Bay

￥3,495,172

per person

Dec 27 - Jan 3

found 19 hours ago

Roundtrip non-stop flight included

Tokyo (HND) 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

The Newbury Boston

Back Bay

￥343,538

per person

Dec 27 - Jan 3

found 15 hours ago

Roundtrip non-stop flight included

Tokyo (HND) to Boston (BOS)

9.4/10 Exceptional! (510 reviews)

Great location but they have no concierge , and for the price you will think they would. Rooms are small

Reviewed on Oct 8, 2025

Browse tours and tickets to explore Winthrop Shore Reservation

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

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Free cancellation available

Food, drink & nightlife

See all 37 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

Free cancellation available

Popular places to visit

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 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.

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.

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

You can take time to visit Revere Beach Reservation during your travels to Revere. Check out the shops and top-notch restaurants in this family-friendly area.