Winthrop holiday lettings

We found 174 holiday rentals — enter your dates for availability

Discover a selection of 13 homes and other holiday rentals in Winthrop that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include air conditioning and a pool. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

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Why visit Winthrop

  • Scenic Lakes: Enjoy the tranquil beauty of local lakes, perfect for swimming, kayaking, or picnicking.
  • Winthrop Park: Relax in this urban park, featuring picturesque walking paths and recreational facilities.
  • Winthrop Beach: Experience a charming beach atmosphere, ideal for sunbathing and leisurely strolls.
  • Historic Civic Buildings: Explore the town's rich history through its well-preserved civic architecture.
  • Charming Accommodations: Choose from cosy cottages, rustic cabins, or spacious apartments for a delightful stay.

Popular types of accommodation in Winthrop

Discover an array of charming accommodation options in Winthrop, including houses, cosy cottages, and rustic cabins. Whether you're seeking spacious apartments in Winthrop or inviting holiday rentals, we have something to suit every traveller's needs. Our platform ensures transparency, allowing you to find the perfect Winthrop rentals for your getaway, whether it's a family holiday or a romantic retreat.

  • Houses: The top choice for visitors to Winthrop, offering spacious and comfortable settings ideal for families or groups.
  • Cottages: A delightful option for those seeking a quaint and charming atmosphere, perfect for a relaxing getaway.
  • Cabins: A popular selection for nature enthusiasts, providing a rustic escape surrounded by beautiful scenery.
  • Apartments: Conveniently located, these options are great for couples or solo travellers wanting a homely feel.
  • Condos: A modern choice that combines comfort and amenities, perfect for a leisurely stay.**

Top attractions near Winthrop

Winthrop, Maine, is perfect for outdoor enthusiasts and those seeking a romantic getaway. Explore the scenic beauty of local lakes, historic civic buildings, and urban parks. Notable attractions include Winthrop Park and Winthrop Beach, offering a delightful blend of culture and natural beauty. Whether you're travelling with family, friends, or a partner, Winthrop promises a memorable experience amidst its charming landscapes.

  • Cobbosseecontee Lake: A serene lake perfect for outdoor activities, offering stunning scenery and a romantic atmosphere. Enjoy swimming, picnicking, or simply relaxing on the beach while taking in the breathtaking views.
  • Augusta Civic Center: This versatile event and conference venue hosts a variety of business events and performances, making it a hub of activity and networking opportunities in the region.
  • Maine State House: A beautiful historic building that showcases Maine's rich culture and history. Take a guided tour to explore its stunning architecture and learn about the state's governance.

Things to do recommended for couples

For a romantic getaway in Winthrop, consider skiing at Lost Valley Ski Resort or Spruce Mountain Jay, both offering thrilling slopes just 19 and 9.9km away, respectively. Embrace the snowy landscapes together, creating unforgettable memories while enjoying the invigorating sports vibes of the area.

Things to do recommended for families

Families visiting Winthrop can enjoy a delightful time at the Kennebec Ice Arena, located 5.0km away. This ice skating venue offers a fun-filled atmosphere with sports and adventure, making it a perfect spot for a family day out.

Things to do recommended for groups

Enjoy a round of golf at Augusta Country Club, only 3.1km from Winthrop, or immerse yourselves in culture at the Theatre at Monmouth, also 3.1km away. For adventure, explore the scenic Kennebec River Rail Trail, situated 6.2km from town.

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

Whether you're travelling with a group, as a family, bringing your pets along, or seeking longer stays, it's important to filter your options based on your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Winthrop with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group get-togethers. Thankfully, you can easily refine your search for all of these options, and more, on Vrbo.
  • Traveling to Winthrop with young kids: Travelling with young children can present its challenges. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions is advisable.
  • Taking your pets with you to Winthrop: For many families, a holiday wouldn’t be the same without their furry companion. 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 ease.
  • Planning for a long term stay visiting Winthrop: If you're in search of holiday rentals with discounts 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 features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Winthrop

Winthrop, Maine, offers a delightful blend of outdoor adventures and serene landscapes, perfect for a romantic getaway or a relaxing family holiday. Explore the charming town's friendly atmosphere, where excursions abound, and culture thrives. Venture into nearby regions to uncover stunning houses and vibrant neighbourhoods. Whether you're enjoying tranquil lakes or the lively local scene, Winthrop invites you to immerse yourself in its natural beauty and warm community spirit.

  • North Monmouth: North Monmouth is a charming town located a mere 1.9km from Winthrop. Renowned for its scenic beauty, this destination is perfect for those seeking outdoor adventures and romantic getaways. Visitors can enjoy a variety of recreational activities amid its picturesque landscapes, featuring serene lakes and inviting beaches. The area is ideal for leisurely strolls, picnics, and water-based fun, making it a splendid choice for families and couples alike. With its tranquil atmosphere, North Monmouth provides a refreshing escape into nature.
  • Manchester: Situated 3.7km from Winthrop, Manchester invites travellers to indulge in its delightful outdoor offerings. This lovely city is popular among golf enthusiasts, boasting several golf courses and country clubs that cater to players of all skill levels. Beyond golf, visitors can relish the stunning scenery and enjoy the family-friendly beaches and lakes. The town's welcoming vibe and picturesque surroundings make it a favourite spot for those looking to unwind and connect with nature while enjoying some recreational activities.
  • Wayne: Located 3.1km from Winthrop, Wayne is a picturesque town that captivates visitors with its outdoor allure. Known for its skiing facilities and recreational areas, Wayne is perfect for adventure seekers, especially in winter when the ski resorts come alive. The proximity to beautiful lakes and family-friendly beaches further enhances the charm of this destination. Whether you're hitting the slopes or enjoying a relaxing day by the water, Wayne offers a delightful blend of scenic beauty and outdoor activities for all ages.

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 from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January20.8°F (-6.2°C)Light RainMostly SunnyLowSlightly Low
February22.5°F (-5.3°C)Light RainMostly CloudyAverageAverage
March30.4°F (-0.9°C)Light RainMostly CloudyAverageSlightly Low
April42.4°F (5.8°C)Light RainMostly CloudyAverageSlightly Low
May54.1°F (12.3°C)Light RainMostly SunnyAverageAverage
June62.1°F (16.7°C)Light RainMostly SunnyHighSlightly High
July69.1°F (20.6°C)Light RainMostly SunnyHighSlightly High
August68.0°F (20.0°C)Light RainMostly SunnyHighSlightly High
September61.0°F (16.1°C)Light RainMostly SunnyAverageAverage
October49.6°F (9.8°C)Light RainMostly SunnyAverageAverage
November37.6°F (3.1°C)Light RainMostly SunnyLowAverage
December28.2°F (-2.1°C)Light RainMostly CloudyLowAverage

Booking with Vrbo is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo accommodation that fits your budget, make use of our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's innovative Trip Board offers you a dedicated area to plan new trips, pick up from where you left off, or review and organise your travel arrangements. You can easily find the properties you’ve previously saved and booked under Potential, Upcoming, or Current Trips. To explore Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Find the perfect holiday rental for your Winthrop getaway

Learn about the unique charm of Winthrop with a stay in a holiday home rental. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Winthrop

Do you want to find top things to see and do while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Winthrop a fun spot to go on holiday. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Augusta Country Club (5 mi / 8.1 km)
  • Belgrade Lakes Golf (15.5 mi / 24.9 km)
  • Cobbossee Colony Golf Course (6.2 mi / 10 km)
  • Samantha Smith (9.9 mi / 16 km)
  • Spruce Mountain Jay (16.4 mi / 26.4 km)
  • Natanis Golf Course (16.9 mi / 27.3 km)

Exploring the natural landscape of Winthrop

Whether you're looking for adventure or just want to take in the scenery, Winthrop is a great place to get out in nature. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Maranacook Lake (2.7 mi / 4.4 km)
  • Cobbosseecontee Lake (4 mi / 6.4 km)
  • Echo Lake (9.5 mi / 15.3 km)
  • Capitol Park (9.8 mi / 15.8 km)
  • Kennebec River Rail Trail (10 mi / 16.1 km)
  • Belgrade Lakes Chain (16.1 mi / 25.8 km)

Transport to and around Winthrop

The nearest airport is in Augusta, ME (AUG-Augusta State), located 9.1 mi (14.7 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Waterville, ME (WVL-Robert Lafleur), which is 21.5 mi (34.6 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, Maine, the area around Lake Maranacook is an excellent choice. This picturesque neighbourhood offers a tranquil setting with stunning views of the lake, making it great for those looking to enjoy nature and outdoor activities. The lake is a hub for fishing, kayaking, and swimming, allowing visitors to fully embrace the Maine summer experience.

Another appealing area is the vicinity of Main Street, where you can find charming local shops and cafes. This part of Winthrop offers easy access to nearby attractions, including the Winthrop Historical Society and the scenic walking trails that weave through the surrounding landscapes.

With a variety of properties available in these areas, ranging from cosy cabins to family-sized homes, you're sure to find a rental that suits your needs.
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 scenic area along the shores of Maranacook Lake, where properties provide stunning waterfront views and easy access to swimming and kayaking. Many of the rental homes in this vicinity are equipped with amenities such as spacious decks, outdoor grills, and fire pits, making them superb for families or groups looking to enjoy lakeside activities and evening gatherings under the stars.

Additionally, the nearby Winthrop Town Beach offers a more community-oriented experience, with sandy shores and picnic areas. Here, you can find charming cottages that often come with modern conveniences like fully equipped kitchens, comfortable living areas, and sometimes even kayaks or paddleboards for guests to use. The local area is also home to walking trails and parks, allowing for enjoyable strolls or hikes in the surrounding natural beauty.

For those looking for a bit of local culture, the town centre of Winthrop features quaint shops and eateries, which add to the charm of the stay.
Where are the best Winthrop ski resort rentals?
For the best ski resort rentals near Winthrop, Maine, travellers should focus on the vicinity of the nearby ski areas such as the Big Rock Mountain. In the Winthrop area, you can find a range of accommodations from cosy cabins to spacious lodges that cater to both families and groups. Many of these properties come with amenities such as fully equipped kitchens, wood-burning stoves, and outdoor decks, ideal for enjoying the tranquil mountain surroundings after a day on the slopes.

The area around Winthrop is also known for its picturesque landscapes and access to various outdoor activities. Rentals often feature rustic charm, with some offering additional perks like hot tubs, fire pits, and game rooms, superb for unwinding in the evenings. Moreover, the close-knit community provides a warm atmosphere, with local shops and restaurants just a short drive away for convenience.

For those interested in exploring beyond skiing, the surrounding region is rich in opportunities for snowshoeing, snowmobiling, and even ice fishing.
What is the most popular type of holiday rental accomodation in Winthrop?
In Winthrop, holiday houses are the most popular type of holiday rental, with around 39 available in the area. These properties often feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor areas, making them ideal for families or groups looking to enjoy the natural beauty of Maine. Alongside these, there are approximately 24 cottages and 18 cabins, which provide a cozier, rustic experience, typically set in serene locations close to lakes and forests. While there are several apartments and villas available, the majority of visitors tend to favour the larger holiday houses and cabins for their ample space and home-like amenities.
Are there any family house rentals in Winthrop?
In Winthrop, Maine, there are numerous family-friendly house rentals available, with around 23 options throughout the area. This charming town has an inviting space for families, featuring spacious homes that often include fully equipped kitchens, comfortable living areas, and outdoor spaces for children to enjoy. Many properties are situated near local attractions, such as the scenic Maranacook Lake, superb for swimming and picnicking.

Visitors can also discover nearby parks that provide playgrounds and ample space for outdoor activities. With the added conveniences of Wi-Fi and air conditioning commonly found in these homes, families can easily unwind after a day of exploration.
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 house rentals available, offering a comfortable stay for travellers with furry companions. The area features diverse properties, ranging from charming lakeside cottages to spacious family homes, many of which come equipped with amenities such as fully equipped kitchens, outdoor spaces, and laundry facilities. These rentals typically provide a friendly space for families or groups, with cosy living areas and sometimes even fenced yards for pets to enjoy.

Winthrop is close to beautiful natural surroundings, including the scenic Maranacook Lake, which offers opportunities for outdoor activities such as hiking and fishing. This lake area often has trails and picnic spots that are great for enjoying with pets. Additionally, the nearby conservation areas provide more options for exploring the outdoors, ensuring that both guests and their pets have plenty of space to roam and enjoy the fresh air.
Are there any remote work holiday rentals in Winthrop?
In Winthrop, Maine, there are numerous options for remote work holiday rentals, with around 87 available throughout the area. These properties are well-suited for those looking to combine work and leisure, often equipped with reliable internet access through third-party services and Wi-Fi available in both rooms and public areas. Many accommodations provide comfortable workspaces, allowing for productivity during your stay.

The charming town of Winthrop is surrounded by beautiful natural scenery, making it an ideal setting for remote work. You can expect amenities such as fully equipped kitchens for preparing meals, spacious living areas for relaxation after work, and sometimes outdoor spaces to enjoy the fresh air. 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 holiday rental amenities include well-equipped kitchens, allowing guests to prepare their own meals, along with coffee and tea makers for a warm beverage to start the day. Many properties feature decks or patios, providing a lovely outdoor space to relax and enjoy the surroundings. Onsite parking is commonly available, making it convenient for travellers with vehicles.
When is the best time to visit Winthrop for a holiday rental?
The best time to visit Winthrop for a holiday rental is during the peak season from June to August, with July standing out as the most popular month. This vibrant period attracts families and outdoor enthusiasts who are eager to partake in various activities, such as hiking, fishing, and exploring the beautiful scenery of the surrounding area.

During these summer months, temperatures typically range from 15 to 25 degrees Celsius, providing a comfortable climate for sightseeing and outdoor adventures. Visitors can enjoy the charm of Winthrop's picturesque Main Street, with its unique shops and local eateries, all while soaking in the stunning natural beauty that defines this region.

For those looking for a more budget-friendly option, consider planning your trip in December. While this is the low season, it offers a magical winter wonderland atmosphere, superb for cosy getaways and enjoying the peaceful surroundings.
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, Maine, visitors can enjoy a range of attractions that showcase the area's natural beauty and local charm. The picturesque Maranacook Lake is a central feature, offering opportunities for swimming, kayaking, and fishing during the warmer months, while in winter, it transforms into a popular spot for ice fishing and snowmobiling.

The nearby Mount Pisgah provides hiking trails with stunning views of the surrounding landscape, making it a favourite for outdoor enthusiasts. For those interested in local history, the Winthrop Historical Society offers insights into the region's heritage, and the quaint downtown area features charming shops and eateries, superb for leisurely strolls.

Additionally, the annual Winthrop Lakes Region Chamber of Commerce events, including the Winthrop Summer Festival, highlight local arts, crafts, and food, drawing in both locals and visitors alike.
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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