Photo by The Curious Zephyr

Vacation rentals near Winthrop Beach

We found 2,357 vacation rentals — enter your dates for availability

Discover a selection of private vacation rentals near Winthrop Beach that are perfect for your trip. Whether you're going on vacation with family or friends, vacation rentals have the amenities you expect for your stay, which might include parking and a garden. No matter what you're looking for, you'll be able to choose a rental for everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Winthrop Beach

Showing deals for:Nov 7 - Nov 14
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value

Find out more about Winthrop Beach

Find out more about Winthrop Beach

Why visit Winthrop Beach

  1. Scenic Beaches: Enjoy the picturesque views and relaxing atmosphere of DCR Winthrop Beach and Winthrop Bay.
  2. Family-Friendly Activities: Experience a welcoming community with numerous picnic spots and recreational areas perfect for families.
  3. Historical Allure: Explore the charming streets of Winthrop Highlands, steeped in history and local culture.
  4. Golf Opportunities: Play a round at the local golf course, suitable for both beginners and seasoned players.
  5. Diverse Accommodation: Choose from cozy vacation rentals, apartments, and hotels to enhance your stay.

Popular types of accommodation around Winthrop Beach

Planning a getaway to Winthrop Beach? You're in for a treat! Explore a variety of vacation rental options, including private homes, apartments, and condos, all tailored to enhance your stay. Whether you're searching for cozy vacation homes or convenient hotels in Winthrop, you'll find the perfect spot to unwind. Experience the beauty of Winthrop with transparency and savings at the forefront of your travel plans.

  • Houses: The most sought-after option for visitors to Winthrop Beach, offering spacious and comfortable accommodations for families, friends, or couples.
  • Apartments: A popular choice for those seeking convenience and access to local amenities while enjoying a home-like atmosphere.
  • Condos: Ideal for guests looking for modern living spaces with added facilities and often stunning views.
  • Cottages: A charming option that provides a cozy, homey feel, perfect for a relaxing getaway.
  • House Boats: A unique and adventurous choice for those wanting to experience life on the water while enjoying the beautiful surroundings.**

Top attractions around Winthrop Beach

Winthrop Beach, Massachusetts, offers a delightful mix of urban parks, scenic beaches, and event venues for tourists seeking culture and relaxation. Enjoy a visit to the picturesque Winthrop Beach, play a round at the local golf course, or explore public beaches and picnic spots. Don’t forget to check out reviews of nearby hotels to enhance your stay. This charming area promises a memorable experience for all visitors!

  1. TD Garden: A premier events venue hosting sports, concerts, and conferences, TD Garden is a hub of excitement and energy, located 8.0km from Winthrop Beach. Experience the vibrant atmosphere that resonates with business and entertainment vibes.
  2. Boston Common: As the oldest public park in the U.S., Boston Common offers a beautiful green space for families to enjoy outdoor activities. Located 8.0km from Winthrop Beach, it's perfect for picnics and leisurely strolls amidst city life.
  3. Copley Square: A modern square that showcases stunning architecture and vibrant city energy, Copley Square is located 9.7km from Winthrop Beach. It's an ideal spot for people-watching and enjoying local events.

Things to do recommended for couples

Planning a romantic getaway at Winthrop Beach? Enjoy a lively concert at the House of Blues Boston, sail together at the Courageous Sailing Center, or immerse yourselves in culture at the Roxbury Center for Arts. Each experience promises unforgettable moments for couples!

Things to do recommended for families

Families visiting Winthrop Beach can have a blast at Agganis Arena for thrilling sports events, explore the wonders of the universe at the Charles Hayden Planetarium, and enjoy exciting adventures at Sky Zone, all within a short drive from the beach!

Things to do recommended for groups

Discover the vibrant Faneuil Hall Marketplace for shopping and dining, enjoy a show at the Orpheum Theater for a cultural experience, and unwind with a tour and tasting at Harpoon Brewery. These activities will create lasting memories for your group near Winthrop Beach!

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

No matter if you're travelling with a group, your family, or pets, or if you're seeking extended stays, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winthrop Beach with a group: Think about how many bedrooms you'll require, as well as any amenities like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Winthrop Beach with young kids: Travelling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can greatly enhance your experience.
  • Taking your pets with you to Winthrop Beach: For many families, a vacation isn’t truly fulfilling without their furry companions. If this resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of your family feels at home.
  • Planning for a long term stay visiting Winthrop Beach: 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 filters, you can effortlessly discover and save on monthly rentals. Don't forget to include your preferences for features such as a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay around Winthrop Beach

Winthrop Beach offers a charming blend of urban vibrancy and coastal beauty, perfect for a relaxing getaway. Explore the picturesque DCR Winthrop Beach and enjoy the serene views of Winthrop Bay. Don't miss the family-friendly atmosphere and historical allure of Winthrop Highlands, as well as the welcoming community at Winthrop Head. This delightful destination promises a memorable experience for every traveller looking to soak in the coastal charm of Massachusetts.

  • Downtown Boston: Located 8.0km from Winthrop Beach, Downtown Boston is a bustling urban hub rich in history and culture. Visitors flock here for an engaging city experience, where they can explore renowned landmarks such as the historic Faneuil Hall and the Boston Common. This vibrant area is perfect for families, with numerous shopping centres and educational venues. Be sure to catch a game at the iconic Fenway Park, a historic sports stadium that offers a glimpse into Boston's passionate sports culture. With its combination of shopping, dining, and cultural attractions, Downtown Boston is an essential stop for any traveller.
  • Harbor View - Orient Heights: Just 3.2km from Winthrop Beach, Harbor View - Orient Heights is a picturesque neighbourhood known for its outdoor activities and family-friendly atmosphere. This area provides easy access to beautiful beaches, perfect for a day of sun and relaxation. Visitors can explore local shopping centres and enjoy educational experiences along the waterfront. The nearby stadium adds to the excitement, offering various events and activities for all ages. With its stunning views and vibrant community, Harbor View - Orient Heights is an ideal destination for those seeking a mix of relaxation and exploration.
  • Orient Heights: Also located 3.2km from Winthrop Beach, Orient Heights is a charming neighbourhood that offers a rich blend of culture, sports, and family experiences. This area is home to an arts centre and theatre, making it a great spot for those interested in the local arts scene. Families will appreciate the close proximity to both beaches and sports venues, ensuring there's something for everyone to enjoy. With its welcoming community and diverse attractions, Orient Heights is a delightful addition to your Winthrop adventure.

Best time to go to Winthrop Beach

If you're planning a trip to Winthrop Beach, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in July to August and October, while off-peak times, like December to February 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 SunnyLowSlightly Low
February31.5°F (-0.3°C)Light RainMostly CloudyLowSlightly Low
March37.9°F (3.3°C)Light RainMostly SunnyAverageSlightly Low
April48.2°F (9.0°C)Light RainMostly SunnyAverageAverage
May58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
June66.6°F (19.2°C)Light RainMostly SunnyAverageSlightly High
July73.6°F (23.1°C)Light RainMostly SunnyHighSlightly High
August72.7°F (22.6°C)Light RainMostly SunnyHighSlightly High
September65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
October55.6°F (13.1°C)Light RainMostly SunnyHighAverage
November44.4°F (6.9°C)Light RainMostly SunnyAverageAverage
December36.3°F (2.4°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Looking to get the most out of your next trip? Consider being flexible with your travel dates, as this can lead to significant savings. Moreover, opting for a longer stay frequently results in even better deals. To discover the ideal Vrbo property that fits your budget, feel free to use our handy filters to search by price, location, and type of vacation rental. We're here to help you make the most of your travel experience!

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a convenient platform where you can create new travel itineraries, manage your existing plans, or review and organize your bookings. Your saved or booked properties are now neatly categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

More Vacation Rentals ideas