Winslow vacation rentals

We found 157 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:Sep 12 - Sep 19
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Find out more about Winslow

Find out more about Winslow

Why visit Winslow

  1. Scenic Lakes: Enjoy the picturesque beauty of nearby lakes, perfect for outdoor activities and relaxation.
  2. Historic Sites: Explore notable civic buildings and historic college campuses that reflect Winslow's rich heritage.
  3. Outdoor Adventures: Engage in various outdoor activities, making it ideal for both families and romantics.
  4. Charming Accommodations: Choose from a variety of vacation rentals, including cozy apartments and rustic cabins.
  5. Proximity to Culture: Visit nearby cities like Waterville and Augusta for cultural experiences and historical exploration.

Popular types of accommodation in Winslow

If you're planning a getaway to Winslow, you've got some fantastic accommodation options to consider. From cozy cabins to spacious houses and inviting apartments, there's something for everyone. Explore the best Winslow apartments, find your favorite views, and enjoy a comfortable stay in this charming destination. Start your adventure by discovering the perfect apartment in Winslow that suits your needs!

  • Cabins: The top choice for visitors in Winslow, offering a rustic escape surrounded by nature.
  • Houses: A favored option for families and groups, providing spacious and comfortable accommodations.
  • Apartments: A convenient choice for those seeking a more urban experience with easy access to local attractions.
  • Cottages: These quaint and charming dwellings offer a cozy atmosphere for a relaxing getaway.
  • Caravan Parks: Ideal for budget-conscious travelers looking for a fun and communal camping experience.**

Top attractions in Winslow

Winslow, Maine, is a charming destination perfect for outdoor enthusiasts, romantics, and those seeking scenic beauty. Visitors can explore picturesque lakes, historic college campuses, and notable civic buildings. Whether you're traveling solo, with family, or as a couple, Winslow offers a delightful mix of culture and outdoor experiences that make for a memorable vacation.

  1. Colby College: A historic institution located 2 miles from Winslow, Colby College boasts beautiful architecture and a vibrant cultural atmosphere. Visitors can explore the stunning campus and appreciate its artistic offerings, including galleries and exhibitions.
  2. Waterville Opera House: Situated 0.4 miles away, this charming opera house is a hub for culture and entertainment. It hosts a variety of performances, making it a romantic spot for an evening out in the city.
  3. Kennebec River: Just 0.4 miles from Winslow, the Kennebec River offers breathtaking scenery and outdoor activities. Enjoy kayaking, fishing, or simply relaxing by the water's edge to soak in the natural beauty.

Things to do recommended for couples

Looking for a romantic getaway in Winslow? Enjoy a day of skiing at Eaton Mountain, just 15 miles away, perfect for adventure. Later, unwind with a visit to Tree Spirits, a charming winery only 4 miles from town, offering a delightful mix of entertainment and romance.

Things to do recommended for families

Families can enjoy ice skating at Kennebec Ice Arena, located 19 miles from Winslow. This fun spot offers a blend of sports and adventure, making it a perfect outing for kids and parents alike!

Things to do recommended for groups

Enjoy a round of golf at Natanis Golf Course, hike the scenic Kennebec River Rail Trail, or shop and dine at Turnpike Mall for a fun-filled group vacation experience in Winslow, Maine.

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

When planning your trip—whether you're traveling with a group, your family, pets, or seeking extended stays—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. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Winslow with young kids: Traveling with young kids can be quite a task. It's important to prioritize 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 family-friendly attractions.
  • Taking your pets with you to Winslow: For many families, a vacation isn't truly fulfilling without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that all members of your family feel at home.
  • Planning for a long term stay visiting Winslow: If you're searching for vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can quickly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

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 excursions. Explore nearby cities like Waterville and Augusta, rich in culture and history, or visit the charming coastal town of Old Orchard Beach for picturesque views. With its inviting atmosphere and vibrant college town vibe, Winslow is an ideal base for experiencing the best of Central Maine's charm and adventure.

  • Oakland: Located 5 miles from Winslow, Oakland offers a delightful blend of outdoor activities and scenic views. Visitors seeking romance can enjoy peaceful strolls along the picturesque lake or spend a day at the beach. For the adventurous, the nearby ski fields provide winter thrills, while golf enthusiasts can hit the local courses. The area is also home to an historic college university, adding a touch of culture and education to your visit. Oakland's charm lies not only in its attractions but also in its tranquil environment, making it a perfect getaway.
  • Fairfield: Just 3 miles away from Winslow, Fairfield is a haven for nature lovers and outdoor enthusiasts. With its stunning hiking trails and proximity to a national state park, visitors can immerse themselves in Maine's breathtaking landscapes. The area also features a serene lake, perfect for relaxation or recreational activities. Fairfield's educational opportunities, including those offered by its local institutions, make it a great spot for exploring the region's history and ecology. Whether you're looking for adventure or a romantic escape, Fairfield has something for everyone.
  • Benton: Situated 4 miles from Winslow, Benton is a city that captivates with its rich cultural offerings and beautiful scenery. Visitors can explore local theaters and entertainment facilities, providing a vibrant night out. The proximity to a historic college university adds an educational aspect to your stay. Nature enthusiasts will be drawn to the nearby lake and national state park, where outdoor activities abound. With its combination of artistic venues and natural beauty, Benton is an ideal destination for those looking to unwind and explore.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January19.8°F (-6.8°C)Light RainMostly SunnyModerately LowSlightly Low
February21.6°F (-5.8°C)Light RainMostly CloudyAverageSlightly Low
March29.8°F (-1.2°C)Light RainMostly CloudyAverageSlightly Low
April42.1°F (5.6°C)Light RainMostly CloudyAverageAverage
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 SunnyAverageAverage
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 LowSlightly High
December27.0°F (-2.8°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is simple

Are you aiming to cut costs on your upcoming journey? Keeping an open mind about your travel dates can lead to significant savings, as prices can vary. Additionally, opting for a longer stay often results in even greater discounts. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

When you reserve an eligible Vrbo for your group getaway, you'll receive OneKeyCash™ on the full booking amount. It truly benefits you to be the planner! Enroll in our One Key rewards program to unlock exclusive savings for members and accumulate OneKeyCash™ on qualifying stays. Sign up today and begin reaping the rewards!

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient area for you to plan new trips, refine your existing plans, or manage your bookings. All the properties you've saved or reserved are neatly categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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)
  • Eaton Mountain (15.2 mi / 24.5 km)
  • Samantha Smith (17.7 mi / 28.5 km)
  • Quarry Road Trails (3.1 mi / 4.9 km)
  • Tree Spirits (4.1 mi / 6.6 km)
  • Natanis Golf Course (9.3 mi / 14.9 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)
  • Kennebec River Rail Trail (17.9 mi / 28.8 km)
  • St George Lake (18 mi / 29 km)
  • Capitol Park (18.3 mi / 29.5 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 most popular type of vacation rental accommodation in Winslow?
Apartments are the most popular kind of vacation rental in Winslow, according to our data. Even if you’ve got something bigger or smaller in mind, Vrbo has vacation homes in all shapes and sizes. Browse our options to find your ideal fit.
How much does it cost to rent a vacation rental in Winslow?
Different things can affect the price of a vacation rental in Winslow, including the time of year, property type and length of stay. But, all our vacation homes have one thing in common — excellent value. Just enter your travel dates to find your ideal escape.
How much does it cost to rent a beach house in Winslow?
When you travel and the size and style of the property will help determine the cost of your beachside stay. Put in your Winslow travel dates to see all your options on Vrbo. Can’t live without a private pool? Use our filters to select the amenities and features you want in your vacation home.
Are there pet-friendly vacation rentals in Winslow?
Good news! Yes. You can choose from five vacation rentals that cater to pets in Winslow. Many of our pet-friendly vacation rentals even come with a backyard for your four-legged fur baby to have fun in, complimentary treats, special dog beds and proximity to parks or green space. Apply the “Pets allowed” filter to find a pad that’ll get tails wagging on Vrbo.
What are popular rental amenities in Winslow?
A nearby river, a garden and ski-in/ski-out facilities top the list of most popular rental amenities in Winslow. Whether you plan to travel on your own, with your other half or as a family group, Vrbo will help you find a vacation home that matches your tastes with all the extras you’re looking for.
Are there vacation rentals in Winslow that welcome kids?
Winslow has five family-friendly vacation homes to choose from. And finding a stay that welcomes kiddos is a breeze with our “Properties good for families” filter. In addition to having the entire place to yourselves, you’ll enjoy access to conveniences and perks like living rooms, full kitchens and yards.
Are there one-bedroom vacation rentals in Winslow?
Take your pick from two one-bedroom rentals in Winslow. Whether you want a secluded cottage or a condo, our one-bedroom properties are ideal if you don’t require tons of space. One of the perks of having your own place? You won’t ever need to share your adventure with strangers.
Are there vacation rentals with WiFi in Winslow?
Whether you want to stay in touch with world events, look over emails or update your social media accounts, there are three vacation homes with WiFi in Winslow. Check the “WiFi” box when searching on Vrbo and stay connected on your getaway.
How can I find vacation rentals with air conditioning in Winslow?
Pick your travel dates and then use our filters to look for vacation rentals with ac in Winslow on Vrbo. With three air-conditioned properties available, you can look forward to a comfy and cool stay.
How old do you have to be to rent a vacation rental in Winslow?
You’ll have to check with the Winslow vacation home you’re looking at on Vrbo as the age limit differs. However, it’s typically 16, 18 or 21.
How long can I rent a vacation rental in Winslow for?
It’s really down to the Winslow property. To browse a list of options offering extended stays, just type your travel dates and number of guests into Vrbo. Enjoy having the place to yourself, along with the comforts of home like air conditioning, a kitchen and outdoor spaces where the kids can burn off energy. Keep an eye out for any long-term stays that offer discounted weekly or monthly prices.
Does Vrbo offer discounts for vacation homes in Winslow?
Whether you’ve got your sights set on one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to score some incredible deals and discounts on Vrbo. From mini stays to extended vacations, we’ve got the ideal space for your next Winslow escape.

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