Plan a trip to see Winthrop Shore Reservation

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

Sunbird ANNEX Resort

per person

Sep 2 - Sep 8

found 4 hours ago

Roundtrip flight included

Cincinnati (CVG) to Boston (BOS)

7.8/10 Good! (707 reviews)

The staff were kind. My son and I enjoyed our stay. I would recommend more attention payed to the cleanliness of the pools. I do understand staff is busy doing other things. The first day we arrived we discovered something we would rather not have in the outdoor pool.. not their fault. I have had a bacterial skin infection since I got home. I am not blaming them as I’m not sure where I got it…The pool is beautiful at night and lit up by LED lights the rooms are nice and bright and everyone was nice. The kids all had plenty of space to swim and play. It was a welcoming environment.

Reviewed on 2025/6/24

Sea Mist Resort

Save 100% on your flight

per person

Sep 2 - Sep 8

found 4 hours ago

Roundtrip flight included

Cincinnati (CVG) to Boston (BOS)

8.8/10 Excellent! (124 reviews)

Great place just had another family staying above our room that was very noisy the last night we were there

Reviewed on 2025/6/2

Holly Tree Resort

Save 100% on your flight

per person

Sep 2 - Sep 8

found 4 hours ago

Roundtrip flight included

Cincinnati (CVG) to Boston (BOS)

9/10 Wonderful! (343 reviews)

The staff is incredibly kind. One of our a/c wasn’t working and they replaced it with a new one with minutes of reporting it The property is clean but there is no housekeeping so you have to take towels etc to the front desk and receive new ones. I felt very safe there. Something I didn’t know was that they have condominiums for rent but you have to call the hotel directly for dates. They have racquetball center which is nice. Light does come through the doorways at night like others have said. Overall I would come here again and it was a good value for the price (except June/July/Aug when prices are close to double! You won’t be disappointed.

Reviewed on 2025/6/23

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 45 activities

North End Boston Mafia Exploration Game and Tour

Free cancellation available

Holiday & seasonal tours

See all 11 activities

Boston: Haunted Pub Crawl of Historic Pubs and Taverns

Free cancellation available

Attractions

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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

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

4.5/5(7 reviews)

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.