Winthrop Shore Reservation

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 (the end of which you can see in the photo) is a great place to walk in winter, and of course is packed in the summer. Get there early to find a parking space!

Tours & day trips

See all 254 activities
Boston Old Town Trolley Hop-on Hop-Off City Tour

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

Activity duration is 1 day
9.0 out of 10 with 764 reviews
Free cancellation available
Price is S$67 per adult
Boston Old Town Trolley Hop-on Hop-Off City TourOpens in new tab

Private & custom tours

See all 69 activities
Boston: Helicopter Skyline Tour

Boston: Helicopter Skyline Tour

Activity duration is 30 minutes
10.0 out of 10 with 8 reviews
Free cancellation available
Price is S$381 per adult
Boston: Helicopter Skyline TourOpens in new tab

Food, drink & nightlife

See all 36 activities
Behind Boston’s Lobster Scene: Seaport Seafood Experience

Behind Boston’s Lobster Scene: Seaport Seafood Experience

Activity duration is 2 hours and 30 minutes
8.4 out of 10 with 5 reviews
Free cancellation available
The previous price was S$101 and current price is S$86 per adult
Behind Boston’s Lobster Scene: Seaport Seafood ExperienceOpens in new tab

Classes & workshops

See all 12 activities
Italian Dinner with Tiramisu Finale in Boston

Italian Dinner with Tiramisu Finale in Boston

Activity duration is 3 hours
9.4 out of 10 with 56 reviews
Price is S$184 per adult
Italian Dinner with Tiramisu Finale in BostonOpens in new tab

Adventure & outdoor

See all 11 activities
Go City: Boston Explorer Pass - Choose 2 to 5 Attractions

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

Activity duration is 30 days
9.8 out of 10 with 19 reviews
Free cancellation available
Price is S$69 per adult
Go City: Boston Explorer Pass - Choose 2 to 5 AttractionsOpens in new tab

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.

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

Deer Island Park

Explore the great outdoors at Deer Island Park, a lovely green space in Boston. Amble around this vibrant area's waterfront or experience its fascinating museums.

Deer Island Park
Revere Beach

Revere Beach

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

Revere Beach
Across from Kelly's-place for everyone to eat, and go jump in the ocean!

Revere Beach Reservation

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

Revere Beach Reservation
Castle Island showing a garden, a river or creek and a city

Castle Island

The ancient Fort Independence finds its home on this impressive harbor peninsula, a beautiful place to walk and relax along the waterfront.

Castle Island
A sandy path through the dunes and grass leading to the beach on the Cape Cod National Seashore on a blue sky summer day. Waves are visible in the blue ocean and green grasses are growing on a hot day

Pond Beach

Why not spend a lazy afternoon at Pond Beach during your trip to Nahant? Wander the beaches and seaside while you're in the area.

Pond Beach

Top Winthrop Shore Reservation Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Omni Boston Hotel at the Seaport
Hilton Boston Logan Airport

Hilton Boston Logan Airport

4 out of 5
One Hotel Drive Boston MA
Hilton Boston Logan Airport
Château sur Mer Bed & Breakfast

Château sur Mer Bed & Breakfast

3 out of 5
100 Sargent Street Winthrop MA
Château sur Mer Bed & Breakfast
Hampton Inn Boston - Logan Airport

Hampton Inn Boston - Logan Airport

3 out of 5
230 Lee Burbank Hwy Revere MA
Hampton Inn Boston - Logan Airport
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Seaport Hotel Boston
Hilton Garden Inn Boston Logan Airport

Hilton Garden Inn Boston Logan Airport

3 out of 5
100 Boardman St Boston MA
Hilton Garden Inn Boston Logan Airport
Holiday Inn Express Boston Logan Airport - Revere by IHG

Holiday Inn Express Boston Logan Airport - Revere by IHG

2.5 out of 5
245 REVERE BEACH PARKWAY BLDG Revere MA
Holiday Inn Express Boston Logan Airport - Revere by IHG
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
Harborside Inn Of Boston
Staybridge Suites Boston Logan Airport - Revere by IHG

Staybridge Suites Boston Logan Airport - Revere by IHG

3 out of 5
245 REVERE BEACH PARKWAY Revere MA
Staybridge Suites Boston Logan Airport - Revere by IHG
See all 3,706 properties in Winthrop Shore Reservation
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.