Winthrop vacation rentals

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Welcome to the enchanting shores of Winthrop, where stunning beaches meet charming neighborhoods, offering a perfect backdrop for unforgettable group getaways. Immerse yourself in the vibrant local culture, explore scenic walking and cycling paths, or indulge in thrilling water sports against breathtaking river views. With a variety of accommodations—from cozy cabins to spacious condos—your group will enjoy the comforts and amenities of home, ensuring a truly memorable stay by the sea.

Holiday rentals with weekly discounts - Winthrop

Showing deals for:Jan 15 - Jan 22

Image gallery for Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.

View of Spinnaker Island and water from Master Bedroom Suite
8.6 out of 10, Excellent, (48 reviews)
Excellent
(48 reviews)

Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.

Hull

9% off
Price is $244
$1,707 for 7 nights
All fees included
Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.

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Find out more about Winthrop

Why visit Winthrop

  • Beautiful Beaches: Winthrop boasts stunning beaches perfect for family-friendly vacations and relaxation.
  • Charming Downtown: Explore local shops and eateries in the picturesque downtown area.
  • Outdoor Activities: Enjoy a variety of outdoor adventures along the scenic coastline year-round.
  • Vibrant Local Culture: Experience the warm hospitality and friendly locals that define Winthrop.
  • Diverse Accommodations: Choose from a variety of vacation rentals, from cozy apartments to inviting condos.

Popular types of accommodation in Winthrop

Planning a getaway to Winthrop? You're in for a treat. Explore a variety of vacation rentals, from private homes and cozy apartments to inviting condos. Whether you're seeking house rentals, guest houses, or local inns, Winthrop has something for everyone. Discover the perfect accommodation that fits your needs and enjoy a memorable stay in this charming destination.

  • Houses: The top choice for travelers in Winthrop, offering spacious and comfortable living for families and groups.
  • Apartments: A popular option for those seeking convenience and easy access to local attractions, perfect for couples or solo travelers.
  • Condos: Ideal for those wanting a blend of comfort and amenities, providing a modern living experience.
  • Cottages: A charming retreat that offers a cozy atmosphere, perfect for a romantic getaway.
  • House Boats: A unique accommodation option that lets you enjoy life on the water while exploring Winthrop.**

Top attractions near Winthrop

Winthrop, Massachusetts, is an ideal destination for family-friendly beach vacations, offering a mix of outdoor activities and urban charm. Visitors can enjoy beautiful beaches, explore local parks, and attend events at conference venues. With a focus on culture and city experiences, Winthrop caters to travelers seeking a blend of relaxation and exploration. Whether you’re with family or friends, this coastal town has something for everyone to enjoy.

  • TD Garden: A premier event venue located 4 miles from Winthrop, TD Garden hosts a variety of concerts and sports events, providing a vibrant atmosphere perfect for business and entertainment enthusiasts.
  • Boston Common: Located 5 miles from Winthrop, this expansive urban park is ideal for families and outdoor lovers, featuring beautiful landscapes, walking paths, and recreational activities amidst the bustling city vibe.
  • Copley Square: Also 5 miles from Winthrop, this modern square is a cultural hub, surrounded by historic architecture, shops, and cafes, offering a lively urban experience perfect for exploring.

Things to do recommended for couples

Winthrop offers delightful couple experiences. Enjoy a concert at MGM Music Hall, just 6 miles away, or embrace adventure at Courageous Sailing Center, 4 miles away. For a touch of culture, don’t miss the Jose Mateo Ballet Theatre, 7 miles from Winthrop. Perfect for a romantic getaway.

Things to do recommended for families

Your family will have a blast at LEGOLAND® Discovery Center, just 5 miles from Winthrop, where adventure awaits. Visit the Charles Hayden Planetarium for an entertaining experience, also 5 miles away, or catch an exciting game at Agganis Arena, located 7 miles from town.

Things to do recommended for groups

In Winthrop, groups can enjoy the vibrant atmosphere at Faneuil Hall Marketplace, catch a show at the Orpheum Theater, and savor craft beers at Harpoon Brewery. These local spots offer a mix of entertainment, culture, and relaxation, perfect for creating lasting memories together.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your preferences when searching. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Winthrop with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Winthrop with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with amenities suitable for their age, like a private swimming pool. Additionally, think about how close you'll be to attractions that are enjoyable for the whole family.
  • Taking your pets with you to Winthrop: For many families, a trip isn't truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Winthrop: If you’re in search of vacation rentals that offer savings for month-long stays, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Winthrop

Winthrop, Massachusetts, offers a delightful blend of family-friendly fun and beachside relaxation. Explore the charming downtown area, where local shops and eateries await. Enjoy outdoor adventures along the picturesque coastline, perfect for winter getaways or summer vacations. Nearby cities provide a vibrant urban atmosphere, rich history, and friendly locals, making Winthrop an ideal base for your explorations. Experience the warmth and hospitality that make Winthrop a unique destination for travelers.

  • Boston: Boston is a vibrant metropolis and the heart of Massachusetts, located directly adjacent to Winthrop. Known for its rich history and cultural attractions, Boston offers a variety of experiences for travelers. Visitors can engage in educational pursuits at renowned institutions, enjoy live music concerts, or shop at bustling mall centers. Key landmarks include the historic Fenway Park, the Boston Convention and Exhibition Center, and various historic sites that pay homage to America's revolutionary past. Whether you're exploring the Freedom Trail or indulging in local cuisine, Boston has something for everyone.
  • Downtown Boston: Just 4 miles from Winthrop, Downtown Boston is a lively neighborhood that combines the charm of historic buildings with modern amenities. It attracts families and culture enthusiasts alike, offering a plethora of shopping options, educational venues, and entertainment choices. Notable attractions in this area include TD Garden, a major sports and concert venue, and various historic sites that showcase Boston's rich heritage. Downtown Boston is perfect for those looking to experience the city's vibrant urban life while being close to Winthrop.
  • Harbor View - Orient Heights: Located 1 mile from Winthrop, Harbor View - Orient Heights is a picturesque neighborhood known for its stunning waterfront views and family-friendly atmosphere. This area is ideal for outdoor enthusiasts, with beautiful beaches and parks to explore. Visitors can enjoy shopping at local centers and partake in various educational activities. Attractions such as the nearby beach and family-friendly recreational areas make it a perfect spot for relaxation and fun. Harbor View - Orient Heights offers a blend of culture and leisure, making it a delightful addition to your itinerary.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you find the best options for your trip.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new adventures, pick up right where you left off, or manage your travel arrangements. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/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, Massachusetts, United States of America when booking a vacation rental?
When considering a vacation rental in Winthrop, Massachusetts, a popular area to stay is near the waterfront. This charming neighborhood offers stunning views of Boston Harbor and easy access to the beach, making it a great spot for those looking to enjoy sun and sea. The proximity to the beach also means you can indulge in activities like swimming, sunbathing, and beachcombing.

Another appealing area is close to the Winthrop Center, where you'll find a delightful array of shops, cafes, and restaurants that reflect the local culture. This area serves as a great base for exploring the town and provides convenient access to attractions such as Deer Island, where visitors can enjoy scenic walks and breathtaking views of the Boston skyline.

Overall, Winthrop boasts a variety of vacation rental properties, allowing visitors to find accommodations that suit their preferences, whether they seek a cozy beachside retreat or a vibrant spot near local amenities.
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, consider the picturesque area along the Winthrop Shore Drive, which offers stunning views of the Atlantic Ocean and easy access to sandy beaches. Properties here often come with amenities such as spacious decks, outdoor dining areas, and fully equipped kitchens, great for families or groups looking to enjoy seaside relaxation. The proximity to local parks, such as the scenic Winthrop Beach and the charming Coughlin Park, adds to the appeal, providing opportunities for beach activities, picnics, and strolls along the shore.

Additionally, the neighborhoods around Point Shirley offer a quaint, residential feel with beach homes that frequently feature private beach access, outdoor showers, and fire pits for evening gatherings. This area is ideal for those looking to unwind while enjoying beautiful sunsets over the water.

Winthrop also boasts several local eateries and shops within walking distance, enhancing the convenience for travelers. For those who enjoy outdoor activities, the nearby Deer Island offers walking and biking paths with breathtaking views of the Boston skyline, making the area not only a great beach destination but also a hub for various recreational pursuits. Find your rental near the beach in Winthrop.
What is the most popular type of vacation rental accomodation in Winthrop?
In Winthrop, apartments and vacation houses are both popular choices among travelers, with several options available throughout the area. The apartments typically offer a cozy atmosphere with amenities such as fully equipped kitchens, comfortable living areas, and easy access to local beaches and parks. Many are located in quaint neighborhoods close to the waterfront, providing beautiful views and a relaxing environment.

For those seeking more space, vacation houses are also available in Winthrop. These properties often feature multiple bedrooms, private yards, and outdoor seating areas, making them ideal for families or groups. Guests can expect amenities like BBQ grills and outdoor dining spaces, great for enjoying the pleasant coastal weather.
Are there any family house rentals in Winthrop?
In Winthrop, Massachusetts, there are several family-friendly house rentals available. This charming coastal town features properties that provide ample space for families, often including amenities like full kitchens, cozy living rooms, and outdoor areas for kids to play. Many homes are situated near the beach, allowing for easy access to seaside activities, while some may also be close to parks where families can enjoy picnics or outdoor sports.

Visitors can explore local attractions such as the scenic Winthrop Shore Reservation, which offers lovely walking paths and beautiful views of the ocean.
Can I rent a vacation home with a pool or hot tub in Winthrop?
In Winthrop, Massachusetts, there are several vacation homes available for rent that feature pools and hot tubs, making it an appealing option for travelers seeking relaxation and leisure. The town, situated along the picturesque coastline, offers a variety of properties that provide amenities such as private pools, hot tubs, and outdoor spaces superb for enjoying the warm weather. Many rentals also include fully equipped kitchens, spacious living areas, and convenient access to local attractions like beaches and parks. Find your rental in Winthrop with a pool or a hot tub.
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, making it a great option for travelers with furry companions. Many of these homes are conveniently located near the coastline, offering easy access to scenic views and outdoor activities. Expect to find amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, which provide a friendly setting for both guests and their pets. Additionally, the area features nearby parks and beaches where pets can enjoy some exercise and fresh air. See all pet-friendly rentals in Winthrop.
Are there any remote work vacation rentals in Winthrop?
In Winthrop, Massachusetts, there are several remote work vacation rentals available, with around 10 options to choose from. These rentals cater to the needs of travelers looking to work remotely while enjoying a seaside retreat. Many properties are equipped with essential amenities such as high-speed internet and dedicated workspaces, including desks and ergonomic chairs, ensuring a comfortable and productive environment.

Situated near the scenic waterfront, these rentals offer easy access to local attractions, such as beautiful beaches and parks, making it convenient for breaks and leisure activities. 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 kitchens, which allow travelers to prepare their own meals, and onsite parking for convenience. Many rentals also feature coffee and tea makers, making it easy to enjoy a warm beverage at any time. Additionally, a workspace or desk is often available, suiting those who may need to catch up on work while away. Most rentals are situated near the beach, offering easy access for guests looking to enjoy the coastal scenery and activities.
When is the best time to visit Winthrop for a vacation rental?
The best time to book a vacation rental in Winthrop is during the peak season from May to July. This vibrant period attracts travelers looking for a superb blend of sun, sand, and seaside activities. As the weather warms up, with temperatures typically ranging from the mid-60s to low 80s Fahrenheit, visitors can enjoy beautiful beach days, picturesque waterfront strolls, and an array of outdoor adventures.

July stands out as the most popular month, drawing families and beach enthusiasts eager to take advantage of the lively option. The local beaches come alive with activities like swimming, kayaking, and beach volleyball, making it a fantastic time for those who love to engage in outdoor fun. Additionally, the area's proximity to Boston provides easy access to cultural attractions and dining options, enhancing the overall experience.

For travelers seeking a more budget-friendly option, consider planning your visit in November. While this month is quieter, it offers a unique charm as the fall season transitions into winter. Enjoy the scenic coastal views with fewer crowds and the opportunity to explore the local shops and restaurants at a leisurely pace.
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, Massachusetts, United States of America?
In Winthrop, visitors can enjoy a variety of attractions that highlight the town's coastal charm and rich history. The picturesque Winthrop Beach is a major draw, offering scenic views of the ocean and opportunities for sunbathing and swimming. Nearby, the Winthrop Shore Reservation features walking trails and picnic areas, great for outdoor enthusiasts looking to explore the natural beauty of the area.

The historic Winthrop Lighthouse, located on Point Shirley, provides a glimpse into the town's maritime heritage and offers stunning views of the surrounding waters. For those interested in local culture, the Winthrop Arts and Cultural District hosts various events and showcases local artists, making it a vibrant area for art lovers.

Additionally, the quaint downtown area features charming shops, cafes, and restaurants, allowing visitors to experience the local cuisine and hospitality.
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 cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Winthrop vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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