Photo by mick finn

Winslow holiday rentals

We found 333 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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Why visit Winslow

  • Historic charm: Winslow boasts a rich history, with beautiful architecture and historic landmarks that reflect its heritage.
  • Cultural experiences: The Winslow Centre offers a vibrant cultural atmosphere, perfect for leisurely exploration.
  • Community spirit: Enjoy the friendly local atmosphere while wandering through quaint neighbourhoods.
  • Outdoor activities: The nearby Chilterns provide opportunities for scenic walks and outdoor adventures.
  • Family-friendly attractions: Winslow features various activities suitable for all ages, ensuring a memorable visit for families.

Popular types of accommodation in Winslow

Discover Winslow, Buckingham, England – a charming town steeped in history and local allure. Explore Winslow holiday rentals, from cosy apartments to unique private holiday homes and picturesque cottages. Wander through traditional streets, admire historic landmarks, and experience authentic local culture. Whether visiting Winslow Hall or immersing yourself in the town’s rich heritage, our selection of holiday rentals in Winslow offers the perfect base for your British escape.

  • Apartments: A highly sought-after choice, these self-contained spaces offer convenience and comfort for travellers in Winslow.
  • Private Holiday Homes: Ideal for families or groups, these homes provide a homely atmosphere and ample privacy during your stay.
  • Cottages: Charming and often situated in picturesque settings, cottages offer a unique and cosy retreat for visitors.
  • Chalets: These quaint lodgings combine rustic charm with modern amenities, perfect for a relaxing getaway.
  • Villas: Spacious and luxurious, villas are perfect for those seeking an upscale experience with beautiful surroundings.**

Top attractions near Winslow

Winslow in Buckingham, England offers a rich blend of family-friendly and cultural experiences. Visitors can explore historic houses, motor racing events, and historic sites, each echoing the local charm and heritage. Whether you're interested in outdoor adventures or cultural excursions, Winslow provides a unique opportunity to immerse yourself in its storied past and vibrant present.

  • Silverstone Circuit: Experience the thrill of motor racing with a sporty, adventurous atmosphere, just 18km from Winslow.
  • Bletchley Park: Immerse yourself in rich cultural heritage at this historic site, located 11km away from Winslow.
  • Waddesdon Manor: Discover the elegance of a historic house with deep cultural roots, also 11km from Winslow.

Things to do recommended for couples

Experience a romantic escape in Winslow, Buckingham. Enjoy quaint local cafes, scenic walks by the river, and a charming countryside picnic. Discover hidden gems in this delightful haven for couples seeking authentic British charm.

Things to do recommended for families

Families visiting Winslow can enjoy a delightful day exploring local parks and countryside walks, as well as engaging in interactive exhibitions at nearby historical sites. A perfect outing for children and parents alike.

Things to do recommended for groups

Groups visiting Winslow can experience the thrill of motor racing at Silverstone Circuit, just 18km away, or embark on an adventurous zipline course at Go Ape in Wendover Woods, located 21km away. Motor Racing Live, 29km from Winslow, offers more adrenaline-pumping excitement.

*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

Whether you're journeying with a group, as a family, accompanied by your pets, or seeking extended stays, be sure to apply the appropriate filters. Here are some Stayz booking tips for you.

  • Traveling to Winslow with a group: Consider the number of bedrooms required, along with facilities like a fully-equipped kitchen or an outdoor area for group gatherings. Fortunately, you can refine your search for these and many other features on Stayz.
  • Traveling to Winslow with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, alongside ensuring access to 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, a family holiday isn’t truly fulfilled without their furry companion by their side. If this resonates with you, take a look at Stayz properties that welcome pets. Most 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 seeking holiday lets offering discounts for stays of one month or more, you’ve come to the right place. With the appropriate filter, you can effortlessly find and secure savings on monthly rentals. You might also consider including a parking space, a well-equipped kitchen or a private pool in your search.

Where to stay near Winslow

Discover Winslow, a charming village in Buckingham, England, where history meets modern family-friendly comforts. Explore the Winslow Centre, the heart of the village, and soak in the cultural ambience of its central streets. Enjoy leisurely strolls through the quaint neighbourhoods and experience the friendly local atmosphere, all set against the backdrop of the nearby Chilterns. Winslow offers a perfect blend of historical allure and relaxed, community spirit for a memorable holiday.

  • Milton Keynes: Milton Keynes is a vibrant city situated 13km from Winslow. It offers a rich blend of family, culture, and entertainment experiences. Visitors can enjoy a variety of activities including theatre performances, motor racing events, and shopping at a bustling mall centre. The city is also famed for its local landmarks such as a stadium, sports facility, and historic sites that reflect its diverse heritage, making it an appealing destination for those seeking both modern amenities and a touch of history.
  • Great Horwood: Great Horwood is a charming village located 3km from Winslow. It is particularly popular with travellers looking for business, sports, and adventure experiences. In this quaint setting, water sports and motor racing provide an exciting backdrop, while the nearby stadium offers a glimpse into the local sporting culture. The village's close proximity to Winslow makes it an inviting spot for a brief excursion, combining the allure of rural tranquillity with spirited recreational activities.
  • Swanbourne: Swanbourne is a delightful village also positioned 3km from Winslow, ideal for those seeking family-friendly, romantic, and outdoor adventures. The area boasts a theatre that enriches its cultural scene, while attractions such as a stadium, park, and lake offer ample opportunities for leisure and exploration. With its scenic surroundings and inviting outdoor spaces, Swanbourne is a perfect destination for a relaxed day out, blending natural beauty with cultural experiences.

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 March to April and July, while off-peak times, like February and November to December tend to have fewer bookings and better deals.

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

Booking with Stayz is a breeze

Looking to cut costs on your upcoming adventure? Try being flexible with your travel dates, as prices can vary. Moreover, booking a longer stay often leads to significant savings. To locate the ideal Stayz property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Stayz’s innovative Trip Board offers you a dedicated space to start new journeys, pick up where you last left off, or review and organise your plans. Any properties you have previously saved or booked are now conveniently grouped under Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.stayz.com.au/trips

**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? Stayz 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 Stayz 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 Stayz. 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, Stayz 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 Stayz, 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 Stayz 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.