Winslow vacation rentals

We found 156 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Winslow that are perfect for your trip. Whether you're staying in a vacation rental with your kids or with friends, you'll find the best amenities for hanging out with the people that matter most, such as air conditioning and a TV. You'll be sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Winslow

Showing deals for:Jan 9 - Jan 16

Image gallery for Sunset Chalet Lakefront Hot Tub Game Room

Relax by the water at Sunset Chalet. With a canoe ready for adventure and a chair just waiting for you, enjoy the perfect spot to unwind and take in the serene views of the lake and surrounding nature.
10 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)

Sunset Chalet Lakefront Hot Tub Game Room

Belgrade, ME

8% off
Price is $397
$2,777 for 7 nights
All fees included
Sunset Chalet Lakefront Hot Tub Game Room

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Find out more about Winslow

Find out more about Winslow

Why visit Winslow

  • Outdoor Adventures: Enjoy a variety of outdoor activities, from hiking to kayaking in the scenic landscapes surrounding Winslow.
  • Rich History: Discover historical sites and local heritage, offering a glimpse into the area's past.
  • Charming Neighborhoods: Explore picturesque streets filled with quaint shops and beautiful views, perfect for leisurely strolls.
  • Romantic Getaways: Experience Winslow's serene environment, ideal for couples seeking a cozy retreat.
  • Diverse Accommodations: Choose from cozy cabins, quaint cottages, or spacious apartments to suit your vacation needs.

Popular types of accommodation in Winslow

Planning your getaway to Winslow? Discover the charm of this beautiful destination with a variety of vacation rental options. From cozy houses and quaint cottages to rustic cabins, you'll find the ideal spot to unwind. If you're considering a longer stay, explore spacious apartments in Merrimack County, perfect for families or groups. With so many choices, your perfect Winslow retreat is just a click away.

  • Houses: The top choice for visitors to Winslow, offering spacious and comfortable lodging for families, friends, or couples seeking a home-like atmosphere.
  • Cottages: A delightful second option, these quaint and cozy retreats provide a charming escape for those looking to unwind.
  • Cabins: Ranked third, these rustic lodgings immerse you in nature, perfect for outdoor enthusiasts.
  • Apartments: Affordable and convenient, these units are ideal for solo travelers or couples wanting a central location.
  • Chalets: These stylish mountain-style homes offer a unique blend of comfort and scenic views, making them a popular fifth choice.**

Top attractions near Winslow

Winslow, Maine, is perfect for outdoor enthusiasts and those seeking a romantic getaway, offering stunning scenery and rich history. Visitors can explore historic colleges and universities, serene lakes, and picturesque rivers. The area caters to travelers looking for cultural experiences and a taste of city life, making it an ideal destination for a diverse range of activities and adventures.

  • Colby College: A historic college located 2 miles from Winslow, Colby College boasts beautiful architecture and a rich cultural atmosphere. Visitors can enjoy art exhibits, scenic walking paths, and the vibrant campus life, making it a great spot for exploration.
  • Kennebec River: Just 0.4 miles away, the Kennebec River offers stunning views and outdoor activities like kayaking and fishing. The serene environment is perfect for a relaxing day surrounded by nature.
  • Waterville Opera House: Located 0.4 miles from Winslow, this historic venue hosts a variety of performances, providing a blend of culture and entertainment. The charming atmosphere makes it a wonderful place for a romantic evening out.

Things to do recommended for couples

For a romantic getaway in Winslow, indulge in a scenic ski experience at Quarry Road Trails, only 3 miles away. Then, savor delightful wines at Tree Spirits, just 4 miles from town. Don’t miss the adventure and cozy vibes that these local gems offer for couples.

Things to do recommended for families

Your family can enjoy ice skating at Kennebec Ice Arena, located 19 miles from Winslow. This venue offers a fun atmosphere filled with sports and adventure, making it a perfect spot for kids to glide on ice and create lasting memories together.

Things to do recommended for groups

Experience a round of golf at Natanis Golf Course, just 9 miles away, or hike the scenic Kennebec River Rail Trail, located 18 miles from Winslow. For some shopping and entertainment, visit Turnpike Mall, 19 miles away, perfect for a fun day with your group.

*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 Winslow

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

  • Traveling to Winslow with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Winslow with young kids: Traveling with young kids can be a bit tough. It's important to prioritize their comfort and safety, along with finding amenities that are suitable for their age, like a private pool. Additionally, it's wise to think about how close you are to attractions that are fun for families.
  • Taking your pets with you to Winslow: For many families, a trip isn't truly complete without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winslow: If you're in search of vacation rentals that offer great deals 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 consider adding features like a parking space, a well-equipped kitchen, or a private pool to enhance your search.

Where to stay in Winslow

Winslow, Maine, offers a delightful blend of outdoor adventures and scenic beauty, perfect for a romantic getaway or family-friendly vacation. Explore the charming neighborhoods nearby, where you can enjoy quiet streets and picturesque views. Excursions to historical sites and recreational activities await, ensuring a memorable experience in this prime location. Whether you’re seeking relaxation or adventure, Winslow and its surroundings provide the ideal backdrop for your exploration.

  • Waterville: Nestled along the banks of the Kennebec River, Waterville is not only the heart of the region but also a gateway to outdoor adventures. Located just a stone's throw from Winslow, this vibrant city offers stunning scenery and a plethora of activities for nature lovers. Explore the hiking trails or hit the ski fields during winter months. Don't miss a visit to the historic college university, where you can immerse yourself in local culture. The nearby national state park and picturesque lake provide perfect spots for picnicking or relaxation, making Waterville a must-visit destination for those seeking both adventure and tranquility.
  • Oakland: A charming city located five miles from Winslow, Oakland is renowned for its romantic ambiance and outdoor experiences. Known for its beautiful lake and inviting beach, this area is perfect for couples looking to enjoy scenic walks or a leisurely day by the water. Golf enthusiasts will appreciate the local courses, while winter visitors can take advantage of the nearby ski fields. With its quaint surroundings and proximity to a historic college university, Oakland offers a delightful blend of education, relaxation, and recreation, making it an ideal stop on your vacation.
  • Fairfield: Just three miles from Winslow, Fairfield is a picturesque city that captivates visitors with its stunning landscapes and romantic vibe. Outdoor enthusiasts can explore the scenic hiking trails or engage in winter sports at the ski fields. The area is rich in natural beauty, with a nearby lake and a national state park inviting exploration and relaxation. The historic college university in Fairfield adds an educational twist to your visit, offering a glimpse into the region's culture and history. Fairfield promises a serene escape with plenty of opportunities for adventure and connection with nature.

Best time to go to Winslow

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January19.8°F (-6.8°C)Light RainMostly SunnyModerately LowSlightly Low
February21.6°F (-5.8°C)Light RainMostly CloudyAverageAverage
March29.8°F (-1.2°C)Light RainMostly CloudyAverageSlightly Low
April42.1°F (5.6°C)Light RainMostly CloudyAverageSlightly Low
May54.0°F (12.2°C)Light RainMostly SunnyAverageSlightly High
June61.9°F (16.6°C)Light RainMostly SunnyModerately HighAverage
July68.9°F (20.5°C)Light RainMostly SunnyModerately HighSlightly High
August67.6°F (19.8°C)Light RainMostly SunnyAverageSlightly High
September60.6°F (15.9°C)Light RainMostly SunnyModerately HighAverage
October49.3°F (9.6°C)Light RainMostly SunnyAverageAverage
November36.9°F (2.7°C)Light RainMostly SunnyModerately LowAverage
December27.0°F (-2.8°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is a breeze

Are you eager to save on your upcoming adventure? Consider being flexible with your travel dates, as this can lead to better prices. Additionally, booking a longer stay can also result in considerable savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your full booking. It truly benefits you to take on the planning role. When you join our travel rewards program, One Key, you’ll gain access to exclusive discounts and accumulate OneKeyCash on eligible bookings. Sign up today and start enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board is designed to help you plan your travels seamlessly. It provides a dedicated area where you can start new trip plans, manage your existing bookings, or review your travel arrangements. Your saved or reserved properties are conveniently categorized into Potential, Upcoming, or Current Trips, making it easier for you to stay organized. To explore the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Delight in the riverside landscape of Winslow

Enjoy the history and other features of Winslow. This scenic city allures visitors with its riverfront and bird watching. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Winslow

Are you searching for things to do in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Winslow a one-of-a-kind vacation spot. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Belgrade Lakes Golf (13 mi / 20.9 km)
  • Natanis Golf Course (9.3 mi / 14.9 km)
  • Eaton Mountain (15.2 mi / 24.5 km)
  • Quarry Road Trails (3.1 mi / 4.9 km)
  • Tree Spirits (4.1 mi / 6.6 km)
  • Samantha Smith (17.7 mi / 28.5 km)

Exploring the natural features in Winslow

Whether you're an adventurous traveler or just want to spend some time taking in the scenery, Winslow is a great place to get outside. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Kennebec River (0.4 mi / 0.7 km)
  • Belgrade Lakes Chain (10.8 mi / 17.4 km)
  • Sandy Pond (15.7 mi / 25.2 km)
  • St George Lake (18 mi / 29 km)
  • Lovejoy Pond (7.7 mi / 12.4 km)
  • Kennebec River Rail Trail (17.9 mi / 28.8 km)

Traveling to and around Winslow

Fly into Waterville, ME (WVL-Robert Lafleur), the closest airport, located 3 mi (4.8 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Augusta, ME (AUG-Augusta State), which is 17.9 mi (28.8 km) away.

Frequently asked questions

What is the best area to stay in Winslow when booking a vacation rental?
When planning a vacation in Winslow, Maine, a fantastic area to consider for your rental is near the charming downtown district. This vibrant neighborhood offers easy access to a variety of local shops, cafes, and restaurants, great for experiencing the local culture. One of the highlights in this area is the beautiful Kennebec River, which provides picturesque walking paths and opportunities for outdoor activities like fishing and kayaking.

Another great option is the area surrounding the Winslow Historical Society and the nearby Fort Halifax Park. This region not only offers a peaceful, scenic atmosphere but also rich historical significance. As for vacation rentals, you can find a diverse range of options in both neighborhoods—many charming homes and cozy cottages that cater to different group sizes and preferences. This makes it an ideal spot for both families and couples looking to explore the beauty and history of Winslow.
How much does it cost to rent a vacation home in Winslow?
Prices for vacation rentals in Winslow 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 Winslow 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 Winslow vacation house rentals?
You can find great discounts on house rentals in Winslow 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.
Can I find long-stay vacation rentals in Winslow?
A long-stay vacation rental in Winslow 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 any Winslow vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winslow 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.
When is the best time to visit Winslow for a vacation rental?
The most popular time to visit Winslow is during the peak season from July to September. This vibrant period attracts travelers looking to enjoy the warm summer weather while exploring the beautiful surroundings of central Maine. With temperatures typically ranging from the mid-60s to low 80s Fahrenheit, visitors can comfortably engage in a variety of outdoor activities, including hiking, biking, and kayaking along the scenic Kennebec River.

July stands out as the pinnacle month for tourism in Winslow, when the local community hosts various festivals and events that celebrate the region's rich culture and history. This lively atmosphere is great for travelers, with plenty of opportunities for sightseeing and engaging with the local arts scene.

For those considering a more budget-friendly option, December offers a unique charm with its peaceful ambiance and lower rental rates. While the weather can be chillier, with temperatures often falling into the 20s and 30s Fahrenheit, it's a wonderful time to experience Winslow's winter activities, such as snowshoeing or cozying up in a local café with a warm drink.

Ultimately, your choice of when to visit Winslow can depend on whether you prefer the bustling summer vibe or the tranquil winter wonderland.
How early should I book a Winslow vacation rental?
Book your Winslow 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 Winslow?
In Winslow, visitors can explore a variety of attractions that showcase the area's natural beauty and cultural heritage. The historic downtown area features charming shops and local eateries, providing a quaint atmosphere for leisurely strolls. Nearby, the picturesque Kennebec River offers opportunities for kayaking and fishing, making it a great spot for outdoor enthusiasts.

For those interested in history, the Winslow Historical Society and Museum provides insights into the local heritage and artifacts from the region. The surrounding area also includes scenic parks, such as the nearby Quarry Road Recreation Area, which is great for hiking, biking, and enjoying the outdoors.
Can I change or cancel my Winslow home rental booking on Vrbo?
To find Winslow 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.
Are all fees included in the Winslow 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.

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