Photo by Andrew Meade

Winslow holiday lettings

We found 21 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Winslow that are perfect for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include a pool and a washer and dryer. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to rent a holiday home in Winslow?
Prices for holiday 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 holiday 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.
Are there any Winslow holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Winslow 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.
Can I find long-stay holiday rentals in Winslow?
A long-stay holiday rental in Winslow 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.
When is the best time to visit Winslow for a holiday rental?
The best time to visit Winslow for a holiday rental is during the peak season from June to August, with July being the most popular month for travellers. This vibrant period attracts those eager to experience the charming coastal town, with plenty of opportunities for outdoor activities like hiking, kayaking, and enjoying the picturesque waterfront parks.

During these summer months, you can expect warm weather, typically ranging from 15 to 25 degrees Celsius, creating the great conditions for exploring the stunning scenery and local attractions. The lively option is complemented by community events and festivals, making it an ideal time for travellers.

If you're looking for a more budget-friendly option, consider visiting Winslow in December. This quieter month still offers a unique charm, with festive decorations and a chance to experience the local culture without the hustle and bustle of peak tourist traffic.

Ultimately, your choice of when to visit Winslow will depend on whether you prefer the energetic summer vibe, filled with outdoor fun and social gatherings, or a more serene escape during the winter months.
How early should I book a Winslow holiday rental?
Book your Winslow 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 Winslow, Washington, United States of America?
In Winslow, visitors can enjoy a variety of attractions that showcase the charm of this picturesque island town. The Bainbridge Island Museum of Art is a significant cultural highlight, offering rotating exhibitions that celebrate local artists and the region's artistic heritage. Close by, the waterfront parks like Waterfront Park and Bloedel Reserve provide stunning views and serene walking trails, superb for nature lovers.

The historic downtown area features quaint shops, local eateries, and the iconic Bainbridge Island Ferry Terminal, where visitors can catch scenic ferry rides to Seattle. Additionally, the nearby Winslow Way is lined with boutiques and cafes, making it a delightful spot for leisurely strolls.
Can I change or cancel my Winslow home rental booking on Vrbo?
To find Winslow 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 Winslow 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.

More holiday ideas