Discover a selection of 500 vacation rentals in Winthrop, MA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $115 per night, and houses and condos are popular options for a stay in Winthrop. Either way, you'll find a rental for everyone's needs.
Destination guide

Ocean beauty and rich history in Winthrop

Settled in 1630 by Puritan colonists, Winthrop is a scenic coastal town with pristine, white sandy beaches, abundant sea life, and fascinating forts. Summer days at the beach are marked by soaring seagulls, crashing waves, and cool, refreshing sea breezes, while inland visitors can linger in parks to watch the sunset, listen to live music, or spread a blanket and lay back to watch a movie. Winthrop vacation rentals provide a cozy haven to return to after a day spent cycling paths through town, hitting the courts for rousing games of tennis, or exploring the region's historic sites.

Things to do

Watching dolphins and birds in Winthrop

It's great to sit on the beach and scan the waves for seals and dolphins, but taking a charter cruise out on the water is an excellent chance to see whales and walruses up close. A trip to Deer Island is delightful when staying in Winthrop. With 60 acres of parkland, there's ample room for rollerblading and cycling, fishing, and picnicking. Belle Isle Reservation is Boston's last remaining salt marsh, and is an excellent spot for birdwatching and nature walks. Winthrop vacation rentals are also good places from which to explore historic buildings such as Deane Winthrop House, built in the 1630s.


Park fun and scenic cruises in Winthrop

Winthrop is a fine place for families in summer, with parks offering face painting and pony rides which will get the kids giggling. You could hire a charter boat for an expertly guided tour of the waters, and explore the coastline with a stop for a traditional clam bake. Afterwards, you can freshen up in your Winthrop vacation rental before walking to a park for an inspiring night concert, or taking a romantic twilight cruise on the local ferry and watching the sun set with spectacular colors over the Atlantic Ocean. After a couple days of walking, riding, and swimming, a day at the spa is sheer bliss.


Ocean pleasures in sun or snow

Set with its face to the wild Atlantic Ocean, Winthrop has seasons with temperatures slightly warmer in winter and cooler in summer than nearby Boston. When summer numbers rise into the 80s, it's time to head to the sandy beaches for cool sea breezes and a swim in the sea. When winter blows in with heavy snowfalls and bracing gusts off the ocean, pull on your ice skates for an afternoon of twirls and leaps at a local ice rink. Or, stay warm indoors and explore the historic homes and museums.

Natural features

Sea animals and beaches around Winthrop

Surrounded by water and looking out to the vast expanse of the ocean, Winthrop is a dreamy seaside town only around 20 minutes from downtown Boston. One of the oldest communities in the United States, Winthrop is ringed by sumptuous beaches, hillsides covered with windswept grasses, and a rustic sprawl studded with trees. Animal life abounds in Winthrop, with seagulls soaring overhead looking for scraps to scavenge, and the ocean waters teeming with humpback whales, lobsters, dolphins, gray seals, and walruses. On land, you may spot swooping sparrows and noisy woodpeckers, and squirrels scampering along tree branches and fence tops.

How to get there

Traveling to and around Winthrop

Fly into Boston, MA (BOS-Logan Intl.), the closest airport, located 2.3 mi (3.7 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Beverly, MA (BVY-Beverly Municipal), which is 14.9 mi (24 km) away.

How many vacation rentals are available around Winthrop, MA?

Our 2020 property listings offer a large selection of 699 vacation rentals around Winthrop. From 135 house rentals to 485 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Winthrop?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Winthrop:

  • Beacon Hill: 302 vacation rentals
  • Shawmut: 172 vacation rentals
  • Prudential / St. Botolph: 168 vacation rentals
  • Thompson Square / Bunker Hill: 62 vacation rentals
  • Back Bay: 399 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Winthrop?

Vrbo offers a large selection of vacation rentals near lovely places in Winthrop. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Deer Island HarborWalk: 1,055 vacation rentals
  • Faneuil Hall Marketplace: 1,033 vacation rentals
  • Boston Convention and Exhibition Center: 1,041 vacation rentals
  • Boston Common: 1,030 vacation rentals
  • Wingaersheek Beach: 227 vacation rentals

But there are many other points of interest around Winthrop listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Winthrop?

Yes, of course. Vrbo has 135 Houses in Winthrop. Our other popular types of vacation rentals in Winthrop include:

  • Condos/Apartments: 485 rentals available
  • Studios: 452 rentals available
  • Townhouses: 11 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Cabins and more.

Can I find a vacation rental with pool in Winthrop?

Yes, you can select your preferred vacation rental with pool among our 25 vacation rentals with pool available in Winthrop. Please use our search bar to access the selection of vacation rentals available.

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