Winthrop Shore Reservation

A lighthouse with a red, white, and blue top, a beach, and a town with houses.

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

€44
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
View Boston Observation Deck General Admission

View Boston Observation Deck General Admission

€30
per adult
View Boston Observation Deck General Admission
City Views

Boston Harbor Narrated Sunset Cruise

€26
per adult
88% of travellers recommend
Boston Harbor Narrated Sunset Cruise
History and Hauntings of Salem Guided Walking Tour

History and Hauntings of Salem Guided Walking Tour

€36
per adult
98% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

€63
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

€75
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
See all activities in Boston
Price found within the past 48 hours. Click for updated prices.
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Price was €870, price is now €538 per person
€538
per person
5 Dec - 8 Dec
found 9 hours ago
Return flight included
Toronto (YYZ) to Boston (BOS)
9/10 Wonderful! (2,041 reviews)

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was €1,475, price is now €863 per person
€863
per person
5 Dec - 8 Dec
found 9 hours ago
Return flight included
Toronto (YYZ) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
Great location

Reviewed on 13 Oct 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was €1,129, price is now €749 per person
€749
per person
5 Dec - 8 Dec
found 9 hours ago
Return flight included
Toronto (YYZ) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Beautiful, clean room. Just lovely all-around.

Reviewed on 13 Oct 2026

Tours & day trips

See all 286 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 799 reviews
Free cancellation available
Price is €49 per adult
Boston Old Town Trolley Hop-on Hop-Off City TourOpens in new tab

Private & custom tours

See all 74 activities
Boston North End Food Tour with Authentic Local Flavours & Dishes

Boston North End Food Tour with Authentic Local Flavours & Dishes

Activity duration is 3 hours
9.6 out of 10 with 600 reviews
Free cancellation available
Price is €77 per adult
Boston North End Food Tour with Authentic Local Flavours & DishesOpens in new tab

Food, drink & nightlife

See all 51 activities
Boston to Martha's Vineyard with Optional Island Tour

Boston to Martha's Vineyard with Optional Island Tour

Activity duration is 13 hours
9.0 out of 10 with 216 reviews
Free cancellation available
Price is €115 per adult
Boston to Martha's Vineyard with Optional Island TourOpens in new tab

Classes & workshops

See all 13 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 60 reviews
Price is €129 per adult
Italian Dinner with Tiramisu Finale in BostonOpens in new tab

Adventure & outdoor

See all 12 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
9.4 out of 10 with 21 reviews
Free cancellation available
Price is €48 per adult
Go City: Boston Explorer Pass - Choose 2 to 5 AttractionsOpens in new tab

Stay near popular Winthrop Shore Reservation attractions

Winthrop Shore Reservation

7.6/10 (5 reviews)
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.
See properties

Top Hotel Deals

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
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches

Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches

Winthrop MA
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
Château sur Mer Bed & Breakfast

Château sur Mer Bed & Breakfast

3 out of 5
100 Sargent Street Winthrop MA
Château sur Mer Bed & Breakfast
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
Modern city & water view 1-bedroom apartment with AC. 5 min from T & beach

Modern city & water view 1-bedroom apartment with AC. 5 min from T & beach

Boston MA
Modern city & water view 1-bedroom apartment with AC. 5 min from T & beach
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
Hilton Boston Logan Airport

Hilton Boston Logan Airport

4 out of 5
One Hotel Drive Boston MA
Hilton Boston Logan Airport
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
See all 3,669 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.