Winthrop holiday lettings

We found 3,061 holiday rentals — enter your dates for availability

Discover a selection of 9 apartments and other holiday rentals in Winthrop that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you expect for your stay, which might include parking and a washer and dryer. What you'll find is a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Winthrop

Showing deals for:29 May - 5 Jun

Image gallery for Ultra-Rare 12BR Compound • Sleeps 40 • Events

Outdoor dining
9.2 out of 10, Wonderful, (7 reviews)
Wonderful
(7 reviews)

Ultra-Rare 12BR Compound • Sleeps 40 • Events

Boston

8% off
Price is £22,914
for 7 nights, 1 home
£3,273 per night
includes taxes & fees
Ultra-Rare 12BR Compound • Sleeps 40 • Events

Find spaces that suit your style

Why visit Winthrop

  • Beautiful Beaches: Winthrop Beach offers stunning seaside views and a relaxing atmosphere for sun-seekers and families alike.
  • Scenic Parks: Winthrop Park provides ample opportunities for outdoor activities and leisurely strolls amidst nature.
  • Charming Streets: Explore delightful streets lined with some of the best houses, reflecting the town's unique character.
  • Local Culture: Experience the warm, friendly vibe of the locals and immerse yourself in the community's culture.
  • Diverse Accommodations: Choose from a range of holiday rentals, from charming homes to modern flats, catering to every traveller's needs.

Popular types of accommodation in Winthrop

At Winthrop, we offer a diverse selection of holiday accommodations to suit every traveller's needs. From charming houses to modern flats and spacious condos, you’ll find the perfect base for your adventures. Whether you're searching for Winthrop rentals or apartments in Winthrop, our platform ensures you have the information you need for a hassle-free getaway. Discover your ideal Winthrop vacation rental today!

  • Houses: The most sought-after option in Winthrop, ideal for families or groups seeking a homely atmosphere during their stay.
  • Apartments: A popular choice for those wanting a self-catering experience with the convenience of a city centre location.
  • Condos: A well-liked accommodation type offering modern amenities and communal facilities, perfect for a comfortable getaway.
  • Cottages: Charming and cosy, these are ideal for a peaceful retreat close to nature.
  • House Boats: A unique option for adventurous travellers wishing to enjoy life on the water.**

Top attractions near Winthrop

Winthrop, Massachusetts, is an ideal destination for families seeking outdoor and beach holidays. With its beautiful Winthrop Beach and scenic Winthrop Park, visitors can enjoy a mix of culture and urban experiences. The area offers a variety of attractions suitable for those looking to unwind by the seaside or explore local urban parks, making it a delightful spot for a memorable getaway.

  • TD Garden: A premier venue for sports and entertainment, TD Garden offers a vibrant atmosphere for events. Experience the excitement of a live game or concert, surrounded by a buzzing crowd just 2.5km from Winthrop.
  • Boston Common: As America’s oldest park, Boston Common is perfect for families and outdoor enthusiasts. Enjoy leisurely strolls, picnics, and various recreational activities in this 5-mile-away urban oasis.
  • Copley Square: This modern square is a bustling hub in the city, featuring stunning architecture and lively events. At just 3.1km from Winthrop, it’s an ideal spot for people-watching and soaking in the local culture.

Things to do recommended for couples

For a romantic getaway in Winthrop, consider catching a concert at the Leader Bank Pavilion, just 1.9km away, or embark on an adventurous sailing experience at Courageous Sailing Center, 2.5km away. Don't miss the enchanting performances at Jose Mateo Ballet Theatre, 4.3km away, for a touch of culture.

Things to do recommended for families

Families visiting Winthrop can enjoy an exciting day at Agganis Arena, just 4.3km away, for sports action. For a cosmic experience, the Charles Hayden Planetarium offers family fun within 3.1km. Meanwhile, Middlesex Fells Reservation, 3.7km distant, provides a serene spot for wellness and relaxation.

Things to do recommended for groups

Explore the vibrant Faneuil Hall Marketplace for shopping and dining, catch a show at the Wilbur Theatre for a cultural experience, and enjoy a tour and tasting at Harpoon Brewery for a delightful afternoon with friends, all within a short distance from Winthrop.

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

If you're travelling with a group, family, or pets, or if you're seeking longer stays, be sure to apply the appropriate filters based on your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Winthrop with a group: Think about how many bedrooms you require, as well as amenities like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Winthrop with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Winthrop: For many, a family holiday isn't truly fulfilled without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winthrop: If you're in search of holiday rentals that offer discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on longer-term rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Winthrop

Winthrop, Massachusetts, offers a delightful blend of family-friendly experiences and serene beach vacations. Stroll through its charming streets to admire some of the best houses in the area, or enjoy the lively atmosphere filled with friendly locals. Just a stone's throw away, explore nearby urban settings rich in history and business vibes. Whether you're after a relaxing seaside escape or a taste of local culture, Winthrop has something for everyone.

  • Boston: Boston is a bustling metropolis located 2.5km away from Winthrop, offering a vibrant city-themed experience. This historic city is renowned for its rich culture, making it a favourite among tourists and families alike. Visitors can immerse themselves in educational pursuits, enjoy live music concerts, or indulge in retail therapy at its numerous shopping centres. Key attractions include the iconic Fenway Park, a historic sports stadium, and various event venues that host conferences and concerts, ensuring there's always something happening.
  • Downtown Boston: Situated 2.5km from Winthrop, Downtown Boston is a lively neighbourhood where city life thrives. It's a prime destination for families and culture enthusiasts, with a plethora of activities available. Shopping enthusiasts will delight in the extensive shopping centres, while educational opportunities abound in this historic area. Notable landmarks include the famous Fenway Park and several event venues that cater to various interests, making it a must-visit for those looking to experience Boston's urban charm.
  • Harbor View - Orient Heights: Just 621m away from Winthrop, Harbor View - Orient Heights is a delightful neighbourhood that offers a blend of outdoor adventures and cultural experiences. Families can enjoy the local beaches, including a family-friendly stretch along the coast, perfect for a day of sun and sand. The area also features shopping centres and educational facilities, ensuring a well-rounded visit. With its picturesque views and recreational opportunities, this neighbourhood is an excellent spot for those seeking a more relaxed atmosphere near the city.

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 a breeze

Are you hoping to cut costs on your upcoming journey? We recommend being open to adjusting your travel dates, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's clever Trip Board allows you to plan new adventures, pick up right where you paused, or review and arrange your travel plans. You can easily find the properties you've saved and booked under Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The beachside setting of Winthrop is ready to explore

The beaches and other outdoor surroundings create an inviting atmosphere in Winthrop. Travellers appreciate the restaurants in this welcoming city. Fenway Park and New England Aquarium are just a couple of the must-see attractions in the area. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Winthrop

Do you want to discover top things to see and do while you're in the area? Venture out of your cosy holiday rental and experience everything that Winthrop has to offer. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • New England Aquarium (3.7 mi / 6 km)
  • Encore Boston Harbor (4.7 mi / 7.5 km)
  • Harpoon Brewery (3.5 mi / 5.6 km)
  • LEGO® Discovery Center Boston (5.2 mi / 8.3 km)
  • Boston Marathon Finish Line (5.3 mi / 8.6 km)
  • The Fens (6.6 mi / 10.7 km)

Exploring the natural features in Winthrop

Whether you're an adventurous traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Winthrop. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Boston Common (4.6 mi / 7.4 km)
  • Copley Square (5.2 mi / 8.4 km)
  • Revere Beach (1.9 mi / 3 km)
  • Castle Island (3.2 mi / 5.2 km)
  • Boston Harbor (3.7 mi / 5.9 km)
  • Rose Fitzgerald Kennedy Greenway (3.8 mi / 6.2 km)

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 21°C.

Transport to and around Winthrop

The nearest airport is in Logan International Airport (BOS), located 2.1 mi (3.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to 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 holiday rental?
When considering a holiday rental in Winthrop, Massachusetts, a popular area to stay is near the waterfront, particularly in the neighbourhoods that offer stunning views of Boston Harbour. This location not only provides easy access to beautiful beaches but also the scenic charm of coastal living.

The area boasts various properties, ranging from quaint cottages to more modern rentals, making it suitable for different preferences and budgets. Staying close to the waterfront allows visitors to enjoy top attractions such as Winthrop Beach, where you can relax by the sea or take a leisurely stroll along the shore. Additionally, the historic Winthrop Town Centre is nearby, offering a delightful mix of independent shops, cafes, and eateries that reflect the local character.

Another appealing neighbourhood is the one that surrounds the Winthrop Yacht Club, which is great for those interested in water activities. This area not only provides easy access to boating and sailing but also features picturesque views, making it an inviting place to unwind after a day of exploration.
How much does it cost to rent a holiday home in Winthrop?
Prices for holiday 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 holiday 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 waterfront areas along the eastern coast of Massachusetts. The neighbourhoods near Winthrop Beach offer a selection of charming properties with convenient access to the sandy shores and stunning views of Boston Harbour. Many of these beach houses come equipped with amenities such as outdoor patios or decks, where guests can enjoy al fresco dining, as well as fully stocked kitchens that cater to families or groups looking to make the most of their seaside experience.

In addition, properties around Point Shirley provide a more tranquil environment, often featuring private yards and direct beach access, superb for leisurely strolls along the coast. The local area is also home to parks and walking paths, enhancing the outdoor experience. Many of the rentals here may include features like air conditioning, Wi-Fi, and laundry facilities, ensuring comfort during your stay.

Furthermore, the proximity to local shops and restaurants in the nearby town centre adds convenience for visitors, making it easy to explore the vibrant local culture and cuisine.
What is the most popular type of holiday rental accomodation in Winthrop?
In Winthrop, apartments are the most popular type of holiday rental, with about 36 available throughout the town. These apartments often feature amenities such as fully equipped kitchens, comfortable living areas, and some may include balconies with views of the surrounding area. They are typically located in convenient neighbourhoods, providing easy access to local attractions and the waterfront.

In addition to apartments, there are several holiday houses available for those seeking more space, ideal for families or groups. These homes usually come with multiple bedrooms, private outdoor areas, and amenities such as BBQ facilities, making them great for larger gatherings.
Are there any family house rentals in Winthrop?
In Winthrop, Massachusetts, there are several family-friendly house rentals available, making it a great spot for families looking to enjoy coastal living. Many of these homes are situated close to the beach, providing easy access for sandcastle building and seaside picnics. Properties often feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces like decks or patios where children can play safely.

The town's proximity to local parks and playgrounds adds to its appeal, giving families plenty of options for outdoor activities. Additionally, visitors can explore the charming neighbourhoods, with their quaint shops and restaurants, creating a friendly setting for everyone.
Can I rent a holiday home with a pool or hot tub in Winthrop?
In Winthrop, there are several holiday homes available for rent that come with pools or hot tubs, providing a great option for travellers looking to relax and unwind during their stay. This charming coastal town, located just a short drive from Boston, offers a mix of beachside living and local amenities. Many of the holiday rentals feature private pools, inviting hot tubs, and outdoor spaces great for family gatherings or leisurely afternoons. Additionally, fully equipped kitchens and comfortable living areas are common, allowing guests to enjoy a cozy feel.
Can I find long-stay holiday rentals in Winthrop?
A long-stay holiday rental in Winthrop is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Winthrop?
In Winthrop, there are several pet-friendly holiday house rentals available, making it a welcoming destination for travellers with pets. The area features charming homes that often come equipped with amenities such as fully stocked kitchens, private outdoor spaces, and comfortable living rooms, great for relaxing after a day of exploring.

Winthrop's proximity to scenic waterfront parks, such as Winthrop Beach and Deer Island, provides ample opportunities for pet owners to enjoy leisurely walks and outdoor activities with their furry companions. Additionally, the local community is known for its pet-friendly atmosphere, with various cafes and shops that welcome pets, enhancing the overall experience for travellers.
Are there any remote work holiday rentals in Winthrop?
In Winthrop, there are around 40 holiday rentals that cater to remote work needs. This coastal town, located just a short distance from Boston, offers a variety of properties that provide essential amenities for those looking to work while enjoying a getaway. Many of these rentals come equipped with reliable Wi-Fi, dedicated workspaces with desks and chairs, and comfortable living spaces conducive to productivity.

The area itself is charming, with scenic views of the waterfront and easy access to local parks. After a day of work, you can explore Winthrop's lovely beaches or enjoy the nearby restaurants and cafes. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winthrop holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Winthrop with parking available—perfect for families or travellers 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 rental amenities include a kitchen, which allows guests to prepare their own meals, and a coffee and tea maker for a comforting morning brew. Many properties also offer onsite parking, making it convenient for those travelling by car. A desk is available in several rentals, providing a workspace for guests who may need to catch up on business or studies. Additionally, the proximity to the beach enhances the appeal of these rentals, allowing visitors to enjoy seaside activities and relaxation.
When is the best time to visit Winthrop for a holiday rental?
July marks the peak time to visit Winthrop, where sun-seekers flock to enjoy the charming coastal atmosphere. This period, from May to July, offers the best weather for beach activities, with pleasant temperatures averaging around 20 to 30 degrees Celsius. Visitors can indulge in swimming, sunbathing, and exploring the beautiful waterfront, all while soaking up the vibrant summer vibe.

July is particularly bustling, making it an exciting choice for those who thrive in lively environments filled with fellow holidaymakers. The local restaurants and cafes buzz with energy, and various summer events add to the festive spirit.

For those looking for a more budget-friendly option, consider planning your trip around November. During this time, this month provides a unique opportunity to experience Winthrop's coastal charm without the crowds. You can enjoy peaceful walks along the beach and capture stunning photographs of the tranquil landscape.

Ultimately, your choice of when to visit Winthrop will depend on whether you prefer the vibrant energy of peak season or the serene beauty of the off-peak months.
How early should I book a Winthrop holiday rental?
Book your Winthrop holiday 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 holiday 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 showcase the town's coastal charm and community spirit. The picturesque Winthrop Beach offers a lovely seaside experience, great for leisurely walks and enjoying the ocean views. Close to the beach, the Winthrop Lighthouse stands as a historic landmark, providing a lovely backdrop for photographs and a glimpse into the area's maritime history.

The quaint town centre features a selection of local shops, cafes, and restaurants, where travellers can savour fresh seafood and other regional delicacies. For outdoor enthusiasts, the Belle Isle Marsh Reservation provides walking trails and opportunities for birdwatching, allowing visitors to connect with nature.

Additionally, the nearby Deer Island offers scenic views of the Boston skyline and is accessible for walking and biking, making it a great spot for a day out.
Can I change or cancel my Winthrop home rental booking on Vrbo?
To find Winthrop holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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