Romantic Hotels & Resorts in Winthrop

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Best Winthrop Romantic Hotels

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Searching for romantic hotels in Winthrop?
Are you in need of a romantic getaway? Our guests also enjoy Winthrop for its restaurants and beaches. You might consider checking out some of the nearby sights and attractions such as Boston Harbor Islands State Park, Winthrop Beach or Massachusetts Bay. If you’re interested in staying close to a certain attraction, you can sort by neighbourhood or distance to top sights, so you and your partner will get to see everything on your list.
What's the best place to stay for a couple going to Winthrop?
The Winthrop Arms Hotel And Restaurant is a favourite hotel for couples, and features premium bedding and an ocean-view restaurant.
When is the best time of year for a romantic getaway to Winthrop?
If you’re looking forward to lots of outings with your partner, take a look at these details about year-round temperatures in Winthrop: The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 1°C. Average annual precipitation for Winthrop is 1276 mm.
What is there to do in Winthrop?
There’s nothing better than wandering around a new place with your sweetheart, so consider taking time to discover all that Winthrop has to offer. If you and your partner are interested in sampling the area’s cuisine, you’ll enjoy Winthrop for its restaurants. You might think about stopping by Boston Harbor Islands State Park, Winthrop Beach or Massachusetts Bay while you’re seeing the sights.
What's the best way to get to Winthrop and around town during my romantic getaway?
This information about transportation options in Winthrop might help your romantic trip go off without a hitch: If you’re looking to fly to Winthrop, the closest major airport is in Logan International Airport (BOS), located 2.1 mi (3.3 km) from the city centre. If you’d like to venture out around the area, consider renting a car to explore more sights.