Winthrop vacation rentals

We found 2,671 vacation rentals — enter your dates for availability

Discover a selection of 8 apartments and other vacation rentals in Winthrop that are perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the best amenities for hanging out with the people that matter most, which might include a pool and a washer and dryer. You'll be sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

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Find out more about Winthrop

Why visit Winthrop

  1. Beautiful Beaches: Enjoy the sun and sand at Winthrop Beach and the picturesque Winthrop Shore.
  2. Family-Friendly Activities: Engage in a variety of outdoor experiences perfect for visitors of all ages.
  3. Charming Coastal Town: Experience the friendly atmosphere and historical charm of this quaint community.
  4. Urban and Suburban Vibes: Explore nearby neighborhoods that offer a mix of cultural experiences.
  5. Diverse Accommodations: Choose from private homes, stylish apartments, and cozy condos to fit your needs.

Popular types of accommodation in Winthrop

If you're exploring vacation rentals in Winthrop, you're in for a treat! Our most popular accommodations include houses, stylish apartments, and cozy condos. Whether you're seeking a spacious home rental for the family or an affordable apartment in Winthrop for a romantic getaway, we have a variety of options to suit your needs. Enjoy your stay with transparency and savings in mind!

  • Houses: These are the top choice for visitors seeking a comfortable and spacious place to stay in Winthrop, perfect for families or groups.
  • Apartments: A popular option for travelers wanting a cozy and convenient base, offering amenities for a home-like experience.
  • Condos: Ideal for those who prefer a blend of comfort and luxury, condos in Winthrop provide modern living spaces.
  • Cottages: Quaint and charming, cottages offer a unique retreat for a relaxing getaway by the sea.
  • House Boats: For a distinctive experience, house boats provide a fun and adventurous way to enjoy your stay on the water.**

Top attractions near Winthrop

Winthrop, Massachusetts, is perfect for family and outdoor beach vacations, offering a blend of culture and coastal experiences. Popular attractions include Winthrop Beach and the scenic Winthrop Shore, along with urban parks and event venues. Whether you're looking to relax by the beach or explore local parks, Winthrop has something for everyone to enjoy during their visit.

  1. TD Garden: Located 4 miles from Winthrop, TD Garden is a vibrant event venue that hosts sports, concerts, and entertainment, offering a dynamic atmosphere perfect for fans and visitors alike.
  2. Boston Common: Situated 5 miles away, Boston Common is a sprawling urban park ideal for families and outdoor enthusiasts, featuring walking paths, playgrounds, and lush green spaces amidst the bustling city.
  3. Copley Square: Also 5 miles from Winthrop, Copley Square is a modern square surrounded by historic architecture, shops, and cafes, making it an exciting hub for city life and culture.

Things to do recommended for couples

Experience romance in Winthrop! Enjoy a concert at the Leader Bank Pavilion, sail into adventure at the Courageous Sailing Center, or be captivated by a performance at the Jose Mateo Ballet Theatre. Each venue offers a unique atmosphere perfect for couples looking to create lasting memories together.

Things to do recommended for families

Your family will love visiting Agganis Arena for exciting sports events, exploring the Charles Hayden Planetarium for captivating shows, and enjoying the tranquility of Middlesex Fells Reservation for relaxing outdoor activities. These experiences offer fun and entertainment just a short drive from Winthrop!

What do I need to keep in mind when booking a vacation in Winthrop

When planning your trip—whether you're traveling with a group, family, pets, or seeking extended stays—be sure to use filters that align with your top priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Winthrop with a group: Think about how many bedrooms you'll require, along with amenities like a full kitchen or outdoor space for group gatherings. The good news is that you can easily filter for these options and many more on Vrbo.
  • Traveling to Winthrop with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are enjoyable for the whole family.
  • Taking your pets with you to Winthrop: For many families, a vacation isn't truly fulfilling unless their furry companion is along for the ride. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer amenities like food bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Winthrop: If you're seeking vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Winthrop

Winthrop, Massachusetts, offers a delightful blend of family-friendly activities and beautiful beach experiences. This charming coastal town is perfect for those seeking a vibrant atmosphere filled with friendly locals and historical charm. Nearby cities and neighborhoods provide a variety of urban and suburban vibes, making it an ideal destination for anyone looking to explore the rich culture and scenic beauty of the area. Enjoy your stay in Winthrop, where unforgettable memories await!

  • Downtown Boston: Located 4 miles from Winthrop, Downtown Boston is a vibrant hub of city life rich in history and culture. This bustling neighborhood attracts visitors with its iconic educational institutions, extensive shopping options, and historic landmarks. Explore the Freedom Trail, indulge in shopping at renowned malls, or catch a game at a historic sports stadium. Whether you're enjoying fine dining or taking in a conference at a local venue, Downtown Boston provides an exhilarating urban experience that caters to families and culture enthusiasts alike.
  • Harbor View - Orient Heights: Just 1 mile away from Winthrop, Harbor View - Orient Heights is a charming neighborhood that offers a blend of outdoor fun and cultural experiences. Ideal for families, this area features beautiful beaches perfect for a day of relaxation or play. The local shopping center provides various retail therapy options, while educational institutions add to the community's appeal. With its proximity to sports facilities and family-friendly beaches, this neighborhood is perfect for those looking to enjoy a laid-back atmosphere with plenty of engaging activities.
  • Orient Heights: Situated 2 miles from Winthrop, Orient Heights is a culturally rich neighborhood with a strong sense of community. Visitors can explore local theaters and arts centers that highlight the area's vibrant cultural scene. The neighborhood also boasts access to beautiful beaches and sports venues, making it a fantastic destination for families and sports enthusiasts. With its combination of cultural attractions and outdoor activities, Orient Heights offers a welcoming atmosphere that invites exploration and relaxation.

Best time to go to Winthrop

If you're planning a trip to Winthrop, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January30.0°F (-1.1°C)Light RainMostly SunnyAverageSlightly Low
February31.5°F (-0.3°C)Light RainMostly CloudyAverageSlightly Low
March37.9°F (3.3°C)Light RainMostly SunnyAverageSlightly Low
April48.2°F (9.0°C)Light RainMostly SunnySlightly HighAverage
May58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
June66.6°F (19.2°C)Light RainMostly SunnySlightly HighSlightly High
July73.6°F (23.1°C)Light RainMostly SunnySlightly HighSlightly High
August72.7°F (22.6°C)Light RainMostly SunnyAverageSlightly High
September65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
October55.6°F (13.1°C)Light RainMostly SunnySlightly LowAverage
November44.4°F (6.9°C)Light RainMostly SunnySlightly LowAverage
December36.3°F (2.4°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Are you looking to save on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on the full booking amount. Being the planner definitely has its perks! When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash™ on eligible bookings. Sign up today and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers an easy-to-use platform for planning your trips, allowing you to start new adventures, resume your previous plans, or keep your itineraries organized. You can easily access your saved or booked properties, which are sorted into categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

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.

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.

Seasonal weather averages in Winthrop

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 73°F.

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.

Transportation to and around Winthrop

The nearest airport is in Logan International Airport (BOS), located 2.1 mi (3.3 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Boston, MA (BNH-Boston Harbor Seaplane Base), which is 2.7 mi (4.3 km) away.

Frequently asked questions

What is the best area to stay in Winthrop when booking a vacation rental?
When considering a vacation rental in Winthrop, Massachusetts, the best area to stay is the picturesque Winthrop Beach neighborhood. This charming coastal area offers stunning views of the Atlantic Ocean and easy access to the sandy shores, making it a great spot for beach lovers. Here, visitors can enjoy leisurely walks along the waterfront and partake in various water activities, such as kayaking and paddleboarding.

Another appealing option is the downtown area, which boasts a vibrant atmosphere with a selection of local shops, restaurants, and cafes. Staying in this neighborhood allows you to immerse yourself in the local culture while being close to attractions like the Winthrop Marketplace and the historic Winthrop Town Common, where seasonal events often take place.

Both neighborhoods are known for having a mix of vacation rental properties, with Winthrop Beach offering a more relaxed beachfront experience and downtown providing a lively urban vibe.
How much does it cost to rent a vacation home in Winthrop?
Prices for vacation rentals in Winthrop vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winthrop to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winthrop vacation house rentals?
You can find great discounts on house rentals in Winthrop on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Winthrop?
For renting a beach house in Winthrop, Massachusetts, the areas along the coastline provide excellent options. The neighborhood near Winthrop Beach is particularly popular, offering easy access to sandy shores and scenic views of the Boston skyline across the harbor. Here, travelers can find charming beach houses equipped with amenities such as outdoor decks, grills for barbecuing, and spacious living areas ideal for families or groups.

Additionally, the Point Shirley area is another great spot, where beach houses often come with private access to the beach, along with features like fire pits and picnic areas, great for enjoying summer evenings by the water. This neighborhood also boasts close proximity to local eateries and shops, enhancing the convenience for visitors.

For those seeking a bit more adventure, the nearby Deer Island offers scenic walking paths and stunning views of the water. Rentals in this area may include amenities such as access to kayaks or paddleboards, allowing guests to fully enjoy the coastal experience.
What is the most popular type of vacation rental accomodation in Winthrop?
In Winthrop, apartments and vacation houses are both popular types of vacation rentals, with several options available throughout the area. The apartments tend to be situated in convenient locations, offering easy access to local amenities and the picturesque waterfront. Most of these apartments come equipped with modern kitchens, comfortable living spaces, and some may feature balconies with views of the ocean or nearby parks.

On the other hand, vacation houses provide a more spacious alternative, ideal for families or groups seeking additional room. These homes typically offer multiple bedrooms, private outdoor spaces for relaxation, and often include amenities like BBQ grills and laundry facilities.
Are there any family house rentals in Winthrop?
In Winthrop, Massachusetts, there are several family-friendly house rentals available, making it a suitable destination for families. The town features charming neighborhoods with easy access to local beaches, parks, and picturesque waterfront areas. Many properties in this locale provide spacious living areas, full kitchens for preparing family meals, and outdoor spaces for children to play.

Visitors can enjoy amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay. Nearby points of interest include the scenic Winthrop Shore Reservation, which offers beautiful walking paths along the coastline, and local eateries serving delicious seafood.
Can I rent a vacation home with a pool or hot tub in Winthrop?
In Winthrop, there are several vacation homes available for rent that feature pools and hot tubs, making it a great choice for travelers seeking relaxation and leisure. This coastal town offers a charming atmosphere with proximity to Boston, allowing visitors to enjoy both beachside activities and city excursions. Many of the rental properties come equipped with private pools, hot tubs, and outdoor dining areas, ideal for enjoying warm summer evenings. Additionally, expect amenities such as fully equipped kitchens, air conditioning, and spacious living areas, providing a comfortable and enjoyable stay.
Can I find long-stay vacation rentals in Winthrop?
A long-stay vacation rental in Winthrop is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Winthrop?
In Winthrop, there are several pet-friendly house rentals available, offering a comfortable stay for travelers accompanied by their furry friends. These vacation homes typically feature amenities such as fully equipped kitchens, spacious living areas, and private outdoor spaces, allowing guests to relax and enjoy their time together.

The town itself is charming and situated along the coastline, providing easy access to beautiful beaches and parks where pets can enjoy the outdoors. The nearby Winthrop Beach is a popular spot for dog owners, offering ample space for walking and playing. Additionally, the area is known for its scenic waterfront views and local eateries that often welcome pets, enhancing the overall experience for visitors traveling with pets.
Are there any remote work vacation rentals in Winthrop?
In Winthrop, Massachusetts, there are several vacation rentals that cater to remote workers. These properties typically feature amenities such as Wi-Fi, dedicated workspaces with desks and chairs, and comfortable living areas conducive to productivity. Many rentals also offer additional conveniences like kitchen facilities for easy meal preparation and laundry services, ensuring a comfortable extended stay.

The town is close to the scenic coastline, providing opportunities for breaks by the beach or enjoying local parks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winthrop vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winthrop with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Winthrop?
In Winthrop, popular vacation rental amenities include WiFi, kitchens, coffee and tea makers, as well as patios or decks, allowing guests to enjoy the outdoor space. Many rentals provide a comfortable setting for visitors, with well-equipped kitchens for cooking and cozy living areas for relaxation. The availability of outdoor spaces enhances the experience, making it easy to unwind after a day of exploring the nearby beaches or local attractions.
When is the best time to visit Winthrop for a vacation rental?
The peak season for visiting Winthrop typically spans from May to July, making it the most vibrant time for travelers seeking a lively atmosphere filled with outdoor activities and local events. During these months, the weather is pleasantly warm, with temperatures ranging from the mid-60s to the low 80s Fahrenheit, great for beach outings, picnics, and exploring the scenic coastline.

July stands out as the most popular month, where families and adventure enthusiasts flock to enjoy the beautiful beaches and partake in water sports. The community comes alive with summer festivals, making it an ideal time for visitors looking to immerse themselves in the local culture and engage with fellow travelers.

If you're considering a more budget-friendly option, October is a fantastic choice. While temperatures begin to cool, typically hovering in the upper 50s to low 70s Fahrenheit, this month offers a serene atmosphere great for those who prefer a quieter getaway.
How early should I book a Winthrop vacation rental?
Book your Winthrop vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winthrop?
In Winthrop, visitors can enjoy a variety of attractions that highlight the town's coastal charm. The scenic Winthrop Beach offers beautiful views of the Atlantic Ocean and is a popular spot for sunbathing and walking along the shore. Nearby, the historic Winthrop Lighthouse provides a picturesque backdrop and is a great area for photography.

The town also features the quaint waterfront area of Point Shirley, which is known for its stunning sunsets and tranquil atmosphere. For those interested in local history, the Winthrop Historical Society offers insights into the town's past and showcases various artifacts.
Can I change or cancel my Winthrop home rental booking on Vrbo?
To find Winthrop vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.

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