Photo by Andrew Meade

Winslow vacation rentals

We found 20 vacation rentals — enter your dates for availability

Nestled on the breathtaking Bainbridge Island, Winslow beckons with its picturesque beaches, lush state parks, and vibrant downtown filled with unique shops and art galleries. Perfect for families and friends seeking adventure, the area offers an array of outdoor activities from hiking to water sports, along with easy access to the urban excitement of Seattle just a ferry ride away. With a variety of cozy cabins and stylish condos, vacation rentals provide the comfort and space needed for an unforgettable getaway.

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Winslow

Why visit Winslow

  • Stunning waterfront views: Enjoy breathtaking scenery along the shores of Bainbridge Island, perfect for relaxation and photography.
  • Outdoor activities: Explore urban parks, beaches, and marinas, ideal for hiking, biking, and water sports.
  • Charming neighborhoods: Stroll through Winslow’s quaint streets, experiencing its friendly locals and vibrant culture.
  • Family-friendly atmosphere: Discover attractions and activities suitable for visitors of all ages, making it a great getaway for families.
  • Diverse accommodations: Choose from cozy apartments, spacious vacation homes, and comfortable condos to suit your stay.

Popular types of accommodation around Winslow

If you're exploring vacation rentals in Winslow, you're in luck. Our most sought-after accommodations include houses, cozy apartments, and comfortable condos. Whether you're looking for apartments in Winslow, a spacious bedroom apartment, or rentals near Winslow, we have a variety of options to suit your needs. Enjoy a seamless stay with transparency and savings in mind.

  • Houses: The top choice for travelers in Winslow, offering spacious and comfortable accommodations ideal for families, groups, or couples seeking a home-like experience.
  • Apartments: A popular option for those looking for modern amenities and convenience, perfect for both short and extended stays.
  • Condos: Stylish and often located in vibrant areas, these provide a blend of luxury and comfort for your vacation.
  • Cottages: Quaint and cozy, these charming rentals offer a delightful escape, often nestled in picturesque settings.
  • Cabins: Ideal for nature lovers, these rustic retreats provide a tranquil getaway surrounded by scenic beauty.**

Top attractions near Winslow

Winslow, Bainbridge Island, is perfect for outdoor enthusiasts and romantic getaways, offering stunning scenery and diverse attractions. Visitors can explore urban parks, beautiful beaches, and marinas, making it an ideal spot for those seeking culture, adventure, and a vibrant city experience. Whether you're traveling solo, with family, or as a couple, Winslow has something special for everyone to enjoy during their vacation.

  • Seattle Waterfront: A vibrant harbor offering stunning beach views and scenic vibes. Enjoy waterfront dining, shops, and beautiful sunsets along the waterfront promenade, making it a perfect spot for relaxation and exploration.
  • Space Needle: An iconic modern tower with breathtaking views of Seattle and the surrounding mountains. Experience the thrill of ascending to the observation deck for panoramic city views, especially captivating at sunset.
  • Bainbridge Island Ferry Dock: A charming marina perfect for outdoor adventures. Experience the joy of ferry rides, beach walks, and the vibrant atmosphere, making it an ideal starting point for exploring Bainbridge Island.

Things to do recommended for couples

For a romantic getaway in Winslow, enjoy a concert at Showbox SoDo for an entertaining evening. Visit Bainbridge Island Vineyards & Winery for a charming wine tasting experience. Cap off your day with a ride on the Seattle Great Wheel, taking in stunning views together.

Things to do recommended for families

Families visiting Winslow can enjoy a thrilling day at T-Mobile Park, just 9 miles away, for a sports experience. Fay Bainbridge State Park, 5 miles away, offers a serene escape for relaxation, while the Bremerton Ice Center, 6 miles away, provides fun ice skating adventures for everyone.

Things to do recommended for groups

Groups visiting Winslow can experience the vibrant atmosphere of Pike Place Market, just 8 miles away, and enjoy shopping and entertainment at Westlake Center, located 9 miles from Winslow. For a more local adventure, rent bikes at Bike Barn Rentals, conveniently located only 0.4 miles away.

*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 around Winslow

If you're traveling with a group, with family, bringing your pets, or seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful booking tips for using Vrbo.

  • Traveling to Winslow with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Winslow with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with having suitable amenities like a private pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Winslow: For many, a family vacation feels incomplete without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels at home.
  • Planning for a long term stay visiting Winslow: If you're in search of vacation rentals offering 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 amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Winslow

Your vacation in Winslow, Bainbridge Island, promises a delightful blend of outdoor adventures and romantic scenery. Explore charming neighborhoods with friendly locals, offering a family-friendly atmosphere perfect for relaxation. Don’t miss the stunning waterfront views and nearby attractions that showcase the island experience. Whether you’re wandering through Winslow’s quaint streets or enjoying the lush landscapes, this destination captures the essence of a memorable getaway in the Pacific Northwest.

  • Seattle: A bustling metropolis located 9 miles from Winslow, Seattle is a vibrant city that draws travelers for its outdoor activities, family-friendly attractions, and urban charm. Explore the iconic Pike Place Market, where you can savor fresh seafood and artisanal goods. The city's recreational areas offer stunning waterfront views and outdoor adventures, while local landmarks like the sports facilities and national state parks provide ample opportunities for exploration and enjoyment. Whether you're catching a game at a stadium or enjoying a scenic walk along the waterfront, Seattle promises an unforgettable experience.
  • Downtown Seattle: Situated 9 miles from Winslow, Downtown Seattle is a lively neighborhood that blends family fun with city excitement. Visitors can indulge in shopping at various boutique stores or visit the renowned Pike Place Market. The area is rich in culture, with historic places and sports facilities that highlight the city's heritage. Whether you're enjoying a meal at one of the many restaurants or taking a stroll through the vibrant streets, Downtown Seattle offers a dynamic urban experience that caters to all ages.
  • Bainbridge Island: Bainbridge Island is a beautiful city that embodies the charm of island life. Winslow, located within Bainbridge Island, serves as the main hub for visitors. Travelers flock to this scenic destination for its outdoor adventures, breathtaking views, and serene atmosphere. Explore the local markets and recreational areas, or take a leisurely walk in the nearby national parks and lakes. With its stunning natural beauty and welcoming community, Bainbridge Island is perfect for those seeking adventure and relaxation in a picturesque setting.

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 months are August and August. Peak season runs in June, June to July, July to August and August, while off-peak times, like October, October to November, November to December and December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January41.0°F (5.0°C)Light RainMostly CloudyAverageSlightly Low
January41.0°F (5.0°C)Light RainMostly CloudyAverageSlightly Low
February41.0°F (5.0°C)Light RainMostly CloudyAverageSlightly Low
February41.0°F (5.0°C)Light RainMostly CloudyAverageSlightly Low
March44.4°F (6.9°C)Light RainMostly CloudyAverageSlightly Low
March44.4°F (6.9°C)Light RainMostly CloudyAverageSlightly Low
April48.7°F (9.3°C)Light RainMostly CloudyAverageAverage
April48.7°F (9.3°C)Light RainMostly CloudyAverageAverage
May55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
May55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
June60.8°F (16.0°C)Light RainMostly SunnyModerately HighSlightly High
June60.8°F (16.0°C)Light RainMostly SunnyModerately HighSlightly High
July66.9°F (19.4°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
July66.9°F (19.4°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
August67.5°F (19.7°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
August67.5°F (19.7°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
September61.3°F (16.3°C)Light RainMostly SunnyAverageAverage
September61.3°F (16.3°C)Light RainMostly SunnyAverageAverage
October53.1°F (11.7°C)Light RainMostly SunnyModerately LowAverage
October53.1°F (11.7°C)Light RainMostly SunnyModerately LowAverage
November45.0°F (7.2°C)Light RainMostly CloudyModerately LowAverage
November45.0°F (7.2°C)Light RainMostly CloudyModerately LowAverage
December40.1°F (4.5°C)Light RainMostly CloudyModerately LowAverage
December40.1°F (4.5°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that meets your budget, simply utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers an easy-to-use platform for planning your travels. You can start new trips, continue from where you last stopped, or organize your travel plans all in one place. Here, you'll see your saved or booked properties neatly organized into sections for Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Winslow?
In Winslow, vacation houses and condos are the most popular types of accommodations, with several options available in the area. These properties are often located in tranquil neighborhoods, providing a peaceful atmosphere for travelers. Many vacation houses typically feature multiple bedrooms, fully equipped kitchens, and outdoor spaces like decks or patios for enjoying the surrounding natural beauty. Condos tend to offer similar amenities, with comfortable living areas and convenient access to local attractions.
Are there any beach house rentals in Winslow?
In Winslow, several beach house rentals are available, offering a unique coastal experience. These properties are typically situated close to the waterfront, providing stunning views of Puget Sound and easy access to local beaches. Travelers can expect amenities such as fully equipped kitchens, spacious living areas, and outdoor decks or patios superb for enjoying the serene surroundings. Many rentals also feature multiple bedrooms, making them suitable for families or groups seeking a relaxing getaway.
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.
What are popular rental amenities in Winslow?
In Winslow, popular vacation rental amenities include balconies, fully equipped kitchens, and outdoor spaces such as decks or patios. Many properties also feature porches or lanais, providing additional areas for relaxation and enjoying the picturesque surroundings. Travelers can expect to find amenities like blenders in the kitchens, making it easy to prepare meals and beverages during their stay.
Can I find family house rentals in Winslow?
In Winslow, Washington, there are several family-friendly house rentals available, making it a suitable destination for groups seeking quality time together. The neighborhood offers charming properties that often feature spacious living areas, fully equipped kitchens for home-cooked meals, and outdoor spaces great for children to play. Many homes also come equipped with amenities like Wi-Fi and laundry facilities, ensuring a comfortable stay for families.Additionally, visitors can explore nearby attractions such as the scenic waterfront parks and local shops that showcase the town's unique character. Winslow's access to beautiful natural landscapes, including hiking trails and beaches, further enhances its appeal for families looking to enjoy a mix of relaxation and adventure.
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.
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.
When is the best time to visit Winslow for a vacation rental?
The best time to visit Winslow for a vacation rental is during the peak season from June to August, with July being the most popular month. This vibrant period attracts travelers eager to soak up the sun and enjoy outdoor activities along the picturesque waterfront. Visitors can expect warm temperatures ranging from the mid-60s to mid-80s Fahrenheit, superb for exploring the charming shops and local eateries or taking leisurely strolls along the beach.During these summer months, Winslow comes alive with events and festivals, making it an ideal destination for those looking to immerse themselves in the local culture while enjoying various recreational activities. The scenic beauty of the area, combined with a lively option, creates memorable experiences for families, couples, and solo travelers alike.If you're looking for a more budget-friendly option, consider visiting Winslow in December. While this month is outside the main tourist season, it offers a peaceful retreat with fewer crowds and the opportunity to enjoy the serene winter landscape. Cozy up in a vacation rental and take advantage of local holiday festivities or simply relax by the fireplace.Ultimately, your choice will depend on whether you prefer the energetic vibe of summer with its many attractions or the tranquil ambiance of winter for a serene getaway.
Are there any remote work vacation rentals in Winslow?
In Winslow, Washington, there are several vacation rentals suitable for remote work. Many of these properties are equipped with essential amenities, including high-speed internet and Wi-Fi to facilitate a productive work environment. You can expect accommodations to feature dedicated workspaces, such as desks and comfortable chairs, allowing travelers to set up their workspace comfortably.The charming neighborhood of Winslow offers a tranquil setting, superb for focusing on work while also being close to local attractions. The area is known for its beautiful waterfront, parks, and quaint shops, providing opportunities for breaks and relaxation after work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
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, Washington, United States of America?
In Winslow, visitors can explore a variety of attractions that highlight the charm of this picturesque island town. The waterfront area along Winslow Way is bustling with shops, cafes, and galleries, making it a great spot for leisurely strolls. Here, travelers can enjoy the scenic views of the Puget Sound and the Olympic Mountains.The Bloedel Reserve, located just a short drive from the town center, offers beautifully landscaped gardens and tranquil walking trails, ideal for nature enthusiasts. For a taste of local history, the Bainbridge Island Museum of Art showcases regional artists and provides insights into the island's cultural heritage.Additionally, the nearby Ferry Terminal offers a scenic route to Seattle, providing a unique opportunity for day trips.
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 cabin or a beach condo, 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 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.
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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively. Vrbo also offers support via live chat through our Help Center, 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 organizing 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.

More Vacation Ideas