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Winslow holiday rentals

We found 321 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)
  • Oxfordshire Golf Club (15.8 mi / 25.4 km)
  • ZSL Whipsnade Zoo (15.9 mi / 25.5 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)
  • Dunstable Downs (15.6 mi / 25 km)
  • Chiltern Hills (18.7 mi / 30.2 km)
  • Island Pond Wood (10.7 mi / 17.1 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 best area to stay in Winslow when booking a holiday rental?
When considering a holiday rental in Winslow, a charming market town in Buckinghamshire, you might find the historic centre to be the most appealing area. This part of Winslow is steeped in character, with its quaint streets lined with traditional buildings and a variety of shops and cafes. A stroll through the centre could lead you to the delightful Winslow Hall, an exquisite example of 18th-century architecture, which often hosts events and exhibitions.Another popular area to consider is near the Winslow Railway Station, which provides convenient links to nearby towns and cities, making it an ideal base for exploring the wider region. This area offers a selection of properties, from cosy cottages to larger family homes, suiting different preferences and group sizes.In addition to the scenic surroundings, Winslow is also close to the beautiful countryside, great for walking and cycling enthusiasts.
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 May to July, with July being the most popular month. This vibrant period attracts many visitors eager to explore the charming streets, historic buildings, and lush countryside of this picturesque English town. With the warmer temperatures averaging between 15 to 25 degrees Celsius, it's an ideal time for outdoor activities such as walking tours and picnics in the local parks.During the summer months, Winslow hosts various community events and festivals, offering a lively option that enhances your experience. The long daylight hours allow for ample sightseeing and exploration of nearby attractions, making it a superb season for travellers.If you're looking for a more budget-friendly visit, consider planning your trip in February. While this is the low season, visiting during this quieter month can still be delightful. You can enjoy Winslow's tranquil charm without the crowds, and take advantage of potentially lower rental rates. Plus, the winter months often bring a unique beauty to the area, allowing for peaceful strolls through the quaint town.Ultimately, your choice will depend on whether you prefer the bustling energy of the peak season filled with activities or the calm and serene ambiance of the off-peak months.
What are the top attractions in Winslow?
In Winslow, visitors can enjoy a charming blend of history and countryside. One of the key attractions is the Winslow Hall, an impressive Georgian mansion surrounded by beautiful gardens, often hosting various events and exhibitions. The town centre features quaint shops and cafes that reflect its traditional character, making it a pleasant place to stroll.Nearby, the Winslow Market Square is lively on market days, offering local produce and crafts. For those interested in nature, the surrounding countryside provides picturesque walking paths, particularly along the nearby Ouse Valley Way, which showcases the area's scenic landscapes. The local church, St. Laurence's, is also worth a visit, boasting stunning architecture and a rich history.
Are all fees included in the Winslow holiday homes prices shown on Stayz?
Stayz 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.
Are there any Winslow holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Winslow holiday homes?
You can find great discounts on holiday homes in Winslow on Stayz, 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.
Can I change or cancel my Winslow holiday home booking on Stayz?
To find Winslow holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Winslow?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Winslow holiday home?
Book your Winslow holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Winslow?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Winslow to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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