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!
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!

Plan a trip to see Winthrop Shore Reservation

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

Eurostars The Boxer

4 out of 5
West End
Price was ￥468,938, price is now ￥345,496 per person
￥345,496
per person
May 13 - May 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
8.6/10 Excellent! (1,337 reviews)
Everything was perfect! No complain.

Reviewed on Mar 1, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was ￥811,240, price is now ￥547,834 per person
￥547,834
per person
May 13 - May 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was ￥928,686, price is now ￥657,442 per person
￥657,442
per person
May 13 - May 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
The most perfect hotel and service I’ve ever experienced in my lifetime!

Reviewed on Feb 24, 2026

Browse tours and tickets to explore Winthrop Shore Reservation

Tours & day trips

See all 227 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 763 reviews
Free cancellation available
Price is ￥8,185 per adult
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Private & custom tours

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Boston: Helicopter Skyline Tour

Boston: Helicopter Skyline Tour

Activity duration is 30 minutes
10.0 out of 10 with 7 reviews
Free cancellation available
Price is ￥46,659 per adult
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Food, drink & nightlife

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

Behind Boston’s Lobster Scene: Small Group 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 ￥12,328 and current price is ￥10,479 per adult
Behind Boston’s Lobster Scene: Small Group Seaport Seafood ExperienceOpens in new tab

Attractions

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Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

Activity duration is 9 days
9.2 out of 10 with 145 reviews
Free cancellation available
Price is ￥12,328 per adult
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Adventure & outdoor

See all 7 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 ￥7,646 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 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
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. Check out 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

Best Lodging Options Near Winthrop Shore Reservation

The Winthrop Arms Hotel And Restaurant

The Winthrop Arms Hotel And Restaurant

3 out of 5
130 Grovers Ave. Winthrop MA
The Winthrop Arms Hotel And Restaurant
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Winthrop MA
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available
Hilton Boston Logan Airport

Hilton Boston Logan Airport

4 out of 5
One Hotel Drive Boston MA
Hilton Boston Logan Airport
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Seaport Hotel Boston
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
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
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
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
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 3,756 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.