Photo by mick finn

Winslow holiday homes

We found 331 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Winslow to find one that's perfect for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll have the amenities that you expect and more, including parking and a TV. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
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  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

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Why visit Winslow

  • Historic charm: Explore Winslow's rich heritage through its quaint streets and historic landmarks that reflect the town's past.
  • Family-friendly attractions: Enjoy various engaging activities suitable for all ages, making it an ideal destination for families.
  • Picturesque town centre: Stroll through the charming town centre, filled with local shops and inviting cafés.
  • Relaxed atmosphere: Experience the friendly vibe and welcoming locals, perfect for leisurely exploration.
  • Outdoor activities: Take advantage of the beautiful surroundings for walks and outdoor pursuits, enhancing your visit.

Top attractions near Winslow

Winslow, Buckingham, England, offers a delightful mix of family-friendly and cultural experiences. Visitors can explore historic sites and charming landmarks that reflect the city's rich heritage. With opportunities for outdoor activities and engaging attractions, Winslow is perfect for those seeking a memorable city-themed holiday. Whether you're interested in history or simply enjoying the local atmosphere, there's something for everyone to savour in this quaint English town.

  • Silverstone Circuit: Experience exhilarating motor racing vibes at this renowned circuit, located 18km from Winslow. Embrace the thrill of sports and adventure, making it a must-visit for racing enthusiasts.
  • Bletchley Park: Discover rich culture at this historic site, situated 11km from Winslow. Immerse yourself in the stories of wartime codebreakers and marvel at the heritage preserved here.
  • Waddesdon Manor: Step into history at this stately manor, 11km from Winslow. Enjoy the elegant architecture and cultural exhibits that bring the past to life.

Things to do recommended for couples

Wander through Winslow's charming streets, exploring quaint shops and delightful cafés. Enjoy a leisurely picnic in the beautiful Winslow Park, or take a romantic stroll along the scenic countryside trails. Don't miss the local farmers' market for fresh produce and unique crafts, perfect for a couple's day out.

Things to do recommended for families

Explore Winslow's charming parks, where kids can play freely. Visit the Winslow Market for local treats, or take a family stroll through the historic town centre. Don't miss the nearby Claydon House for a glimpse of stunning architecture and gardens perfect for a picnic.

Things to do recommended for groups

Experience the thrill of motor racing at Silverstone Circuit, 18km from Winslow, and enjoy adventure activities with your group at Go Ape at Wendover Woods, 21km out, plus more excitement at Motor Racing Live, 29km 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 in Winslow

When planning your trip—whether you're travelling with a group, family, pets, or seeking extended stays—it's important to prioritise your preferences. Here are some helpful tips for booking on Vrbo.

  • Traveling to Winslow with a group: Consider how many bedrooms you'll need, along with features such as a fully equipped kitchen or an outdoor area for group gatherings. Luckily, you can filter for all these options—and more—on Vrbo.
  • Traveling to Winslow with young kids: Traveling with young ones can be demanding. You must prioritise their comfort and safety, along with ensuring access to age-appropriate facilities like a private swimming pool. It’s also wise to consider how close you are to family-friendly attractions.
  • Taking your pets with you to Winslow: For many, a family holiday isn’t complete without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties offer feeding bowls and beds, ensuring everyone feels right at home.
  • Planning for a long term stay visiting Winslow: If you’re after holiday rentals offering discounts for month-long stays, you’ve come to the right spot. With the proper filter, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Winslow

Winslow, a charming village in Buckinghamshire, offers a delightful blend of historical charm and modern amenities. Visitors can stroll through its picturesque town centre, explore local shops, and enjoy family-friendly attractions. The friendly atmosphere and relaxed vibe make it a perfect base for those seeking a cultural experience. Whether you're wandering the quaint streets or enjoying a leisurely meal, Winslow promises a memorable holiday filled with warmth and welcoming locals.

  • Milton Keynes: Milton Keynes is a vibrant city located 13km from Winslow. It offers a rich blend of family-friendly attractions, culture-themed experiences, and dynamic entertainment. Visitors can enjoy a variety of activities including theatre performances, motor racing events, and extensive shopping at well-known retail centres. The city is also home to significant landmarks such as a major stadium, a dedicated sports facility, and historic sites that capture the region’s past. Whether you’re looking to immerse yourself in the local culture or enjoy a fun-filled day with the family, Milton Keynes provides a diverse travel experience.
  • Swanbourne: Swanbourne, a charming village positioned 3km from Winslow, is perfect for visitors seeking a mix of family, romantic, and outdoor adventures. This quaint locale offers intimate theatre experiences and is close to notable attractions including a stadium, a lovely park, and a scenic lake. It’s an ideal destination for those looking to enjoy a relaxed pace of life while exploring the natural beauty and local charm of the countryside.
  • Little Horwood: Little Horwood is a picturesque village also located 3km from Winslow. It appeals to travellers interested in family outings, outdoor pursuits, and city-themed experiences. The village is well-known for its shopping centre and mall, offering a blend of retail therapy and leisurely strolls. Nearby attractions include a contemporary gallery, a vast national park, and unique historic sites that provide a glimpse into the area’s rich heritage. Little Horwood is a perfect spot to experience a mix of modern conveniences and timeless charm.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January39.0°F (3.9°C)Light RainMostly CloudyAverage
February40.1°F (4.5°C)No Rain (Dry)Mostly CloudySlightly Low
March43.2°F (6.2°C)No Rain (Dry)Mostly CloudySlightly High
April47.3°F (8.5°C)No Rain (Dry)Mostly CloudySlightly High
May52.9°F (11.6°C)Light RainMostly CloudyAverage
June58.6°F (14.8°C)Light RainMostly CloudyAverage
July62.6°F (17.0°C)Light RainMostly CloudySlightly High
August62.1°F (16.7°C)Light RainMostly CloudyAverage
September58.1°F (14.5°C)No Rain (Dry)Mostly SunnyAverage
October52.3°F (11.3°C)Light RainMostly CloudyAverage
November45.3°F (7.4°C)Light RainMostly CloudySlightly Low
December41.4°F (5.2°C)Light RainMostly CloudySlightly Low

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can differ. Also, booking a longer stay can often result in significant savings. To find the ideal Vrbo property that suits your budget, take advantage of our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Here is the paraphrased text:Vrbo’s Trip Board provides a dedicated spot to start planning fresh adventures, pick up where you left off, or manage your existing bookings. Your saved or booked properties are now neatly categorised into Potential, Upcoming, or Current Trips. Visit https://www.bookabach.co.nz/trips to explore the Trip Boards.

**Based on Vrbo properties bookings.

The rustic city of Winslow awaits you

Enjoy the area's churches, entertainment and history with a rental holiday home in Winslow. This city is well-known for its cafes and football games. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Winslow

Are you looking for top things to see and do in the city? Venture out of your holiday home and check out everything that makes Winslow a fun spot to go on holiday. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Gullivers Land (9.7 mi / 15.6 km)
  • Woburn Golf Club (9.7 mi / 15.6 km)
  • Mead Open Farm (11.6 mi / 18.6 km)
  • Woburn Safari Park (12.9 mi / 20.7 km)
  • Bicester Golf and Country Club (14.2 mi / 22.9 km)
  • Oxfordshire Golf Club (15.8 mi / 25.4 km)

Exploring the natural landscape of Winslow

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Winslow is a great place to spend some time outside. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Bletchley Park (6.9 mi / 11.1 km)
  • Willen Lake (10 mi / 16.2 km)
  • Woburn Abbey (12.3 mi / 19.8 km)
  • Salcey Forest (14.6 mi / 23.5 km)
  • Dunstable Downs (15.6 mi / 25 km)
  • The Beach (15.6 mi / 25.1 km)

Travelling to and around Winslow

Fly into Oxford (OXF), the closest airport, located 20 mi (32.2 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into London (LTN-Luton), which is 21.9 mi (35.2 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Winslow?
The most popular types of holiday homes in Winslow are houses. Hoping for something different? Bookabach offers a variety of options to match our guests' needs, so you'll see properties in lots of shapes and sizes. The perfect home away from home is waiting for you — book yours today.
How much does it cost to rent a holiday home in Winslow?
Different factors influence what you'll pay for your holiday home in Winslow, like the season, length of stay and type of property. But, all Bookabach homes have something in common — excellent value. Just add 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 influence the cost of your beachside escape. Click on your Winslow travel dates to view your available options on Bookabach. Did someone just say "private pool"? Use our filters to choose the amenities and features you want in your holiday home.
What are popular home amenities in Winslow?
The most popular home amenities guests are looking for in Winslow include a fireplace, an electric car charging station and an oven. Whether you're on the road with family, buddies or even pets, Bookabach holiday homes come with the best amenities for making new memories with the people who matter most.
What are the top attractions for families in Winslow?
You'll find lots of fabulous things to do and see with the family in Winslow, such as:

  • Old Gaol Museum
  • Stowe House
  • Winslow Farmers Market

How old do you have to be to rent a holiday home in Winslow?
Age restrictions can differ between properties on Bookabach, so look at the rules of the holiday home in Winslow you're interested in. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Winslow for?
It all depends on the Winslow property. To view all available options offering extended stays, simply type your travel dates and number of guests into the Bookabach search page. You can enjoy having the whole place to yourself, as well as comforts such as a fully-equipped kitchen, air conditioning and an outdoor space where your little ones can play. Keep an eye out for any long-term stays that offer weekly or monthly discounts.