Winchcombe holiday lettings

We found 1,129 holiday rentals — enter your dates for availability
Select from 15 homes, 53 cottages and other holiday rentals in Winchcombe to find one that's perfect for your trip. Whether you're staying in a holiday rental with friends, family or even just your pets, you'll find the amenities that you need and want, which might include a garden and pool. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Winchcombe

Showing deals for:5 Feb - 12 Feb

Image gallery for Charming Victorian Wool Cottage on the Cotswold Way in Winchcombe.

View from the front of the cottage. (left hand front door)
10 out of 10, Exceptional, (76 reviews)
Exceptional
(76 reviews)

Charming Victorian Wool Cottage on the Cotswold Way in Winchcombe.

Cheltenham

8% off
Price is £774
for 7 nights, 1 home
£111 per night
includes taxes & fees
Charming Victorian Wool Cottage on the Cotswold Way in Winchcombe.

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Why visit Winchcombe

  • Historic Landmarks: Discover the rich heritage of Winchcombe through its iconic sites, including the stunning Sudeley Castle and local churches.
  • Scenic Trails: Enjoy the breathtaking views along the Winchcombe Way, perfect for outdoor enthusiasts and nature lovers.
  • Cultural Experiences: Visit the Winchcombe Museum to immerse yourself in the town's history and local culture.
  • Charming Atmosphere: Stroll through the picturesque streets, enjoying the quaint shops and inviting cafés that define Winchcombe.
  • Family-Friendly Activities: Engage in various activities that cater to families, ensuring a fun-filled visit for all ages.

Popular types of accommodation in Winchcombe

Discover the charm of Winchcombe, a picturesque town nestled in the heart of the Cotswolds. Known for its rich history and stunning landscapes, Winchcombe offers a delightful array of attractions, including the iconic Sudeley Castle and the serene gardens of Winchcombe Abbey. Whether you're seeking a cosy cottage, a private holiday home, or a modern apartment, our selection of Winchcombe accommodation ensures a perfect base for exploring this enchanting locale.

  • Cottages: These charming, often traditional dwellings are the most sought-after option for a delightful stay in Winchcombe.
  • Houses: Enjoy the comfort and privacy of a fully-equipped home, making it the second favourite choice for visitors.
  • Apartments: Modern and convenient, apartments offer a great alternative for those seeking a central location.
  • Cabins: Rustic and cosy, cabins provide a unique escape into nature for your holiday.
  • Caravan Parks: Ideal for a more adventurous stay, caravan parks allow you to experience the outdoors while enjoying essential amenities.**

Top attractions in and around Winchcombe

Winchcombe, located in Cheltenham, England, is a delightful destination for outdoor enthusiasts and culture lovers alike. Visitors can explore the historic Winchcombe Museum, delve into its rich heritage, and admire stunning architecture at local churches and galleries. This charming town offers a perfect blend of family-friendly activities and cultural experiences, making it an ideal spot for a memorable getaway.

  • Belas Knap: This ancient long barrow offers a unique glimpse into Neolithic burial practices, surrounded by tranquil countryside. Its historical significance and serene atmosphere make it a fascinating visit for history enthusiasts.
  • Sudeley Castle: Nestled close to Winchcombe, this stunning castle boasts beautiful gardens and rich Tudor history, ideal for a romantic stroll. Explore its intriguing exhibitions and enjoy the picturesque views.
  • The Promenade: A charming street in Cheltenham, perfect for leisurely shopping and dining. Experience lively city vibes while enjoying the elegant architecture and vibrant atmosphere.

Things to do recommended for couples

Winchcombe offers a delightful escape for couples. Explore charming streets hand-in-hand, visit the historic Sudeley Castle, and enjoy a leisurely stroll through the beautiful Cotswold countryside. Don’t forget to savour a romantic dinner at a local bistro, making unforgettable memories together.

Things to do recommended for families

Families will delight in exploring the enchanting Sudeley Castle, with its beautiful gardens and fascinating history. The nearby Winchcombe Railway offers scenic train rides, perfect for all ages, while the surrounding Cotswold countryside invites delightful walks and picnics.

Things to do recommended for groups

Experience the thrill of motor racing at Prescott Speed Hill Climb, just 3km from Winchcombe, or venture 24km to Shakespeare County Raceway for more adrenaline-fuelled excitement. Both venues offer a fantastic atmosphere for group travellers seeking adventure and sports vibes.

*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 Winchcombe

When travelling with a group, family, pets, or planning an extended stay, it’s important to filter your options based on what matters most to you. Here are some useful Vrbo booking tips to assist you.

  • Traveling to Winchcombe with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for socialising. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Winchcombe with young kids: Travelling with young children can be quite demanding. It’s important to prioritise their comfort and safety, along with 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 Winchcombe: For many, a family holiday isn't truly fulfilling without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winchcombe: If you're seeking holiday rentals with special offers 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 criteria.

Where to stay in Winchcombe

Winchcombe, nestled in the heart of the Cotswolds, offers a delightful blend of history and natural beauty. Explore the enchanting Winchcombe Way, where scenic trails lead you through stunning countryside vistas. Immerse yourself in the village’s rich heritage with its historic landmarks, and enjoy the welcoming atmosphere that makes it perfect for families and adventurers alike. Whether you're hiking through the beautiful Cotswolds or relaxing in a local café, Winchcombe promises a memorable getaway.

  • Cheltenham: Cheltenham is a vibrant city situated near Winchcombe, renowned for its Regency architecture and stunning parks. Visitors can indulge in shopping at the popular shopping centres and malls, or enjoy a round of golf in the picturesque surroundings. The city is a gateway to outdoor adventures, offering scenic landscapes and historic sites, including monuments and national parks. Whether you’re wandering through the picturesque streets or enjoying a local café, Cheltenham provides a delightful blend of culture and nature.
  • Cotswolds: The Cotswolds, located approximately 11km from Winchcombe, is an enchanting area celebrated for its rolling hills and charming villages. This region is perfect for outdoor enthusiasts seeking adventure amidst stunning scenery. Visitors can explore nature reserves and national parks, with ample opportunities for hiking and cycling. The local attractions, including monuments and recreational areas, provide a perfect backdrop for a relaxing day out. The Cotswolds is a true gem for anyone looking to experience the beauty of the English countryside.
  • Bourton-on-the-Water: Bourton-on-the-Water, a picturesque village about 16km from Winchcombe, is known for its idyllic waterways and quaint stone bridges. This charming location is popular among tourists seeking outdoor activities and scenic views. Visitors can enjoy recreational areas and explore local shops within the village. Nearby national parks and monuments enhance the area's allure, making it an ideal spot for leisurely strolls and exploration. Bourton-on-the-Water offers a quintessential English village experience that is sure to captivate any traveller.

Best time to go to Winchcombe

If you're planning a trip to Winchcombe, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January39.4°F (4.1°C)Light RainMostly CloudyAverageSlightly Low
February40.5°F (4.7°C)Light RainMostly CloudyAverageSlightly Low
March43.2°F (6.2°C)Light RainMostly CloudyAverageAverage
April47.1°F (8.4°C)No Rain (Dry)Mostly CloudySlightly HighAverage
May52.7°F (11.5°C)Light RainMostly CloudyAverageAverage
June58.3°F (14.6°C)Light RainMostly CloudyAverageAverage
July61.9°F (16.6°C)Light RainMostly CloudySlightly HighSlightly High
August61.2°F (16.2°C)Light RainMostly CloudyAverageSlightly High
September57.4°F (14.1°C)Light RainMostly CloudySlightly HighSlightly Low
October52.0°F (11.1°C)Light RainMostly CloudySlightly LowAverage
November45.3°F (7.4°C)Light RainMostly CloudySlightly LowAverage
December41.5°F (5.3°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is simple

Are you eager to save on your upcoming journey? It might be worthwhile to be flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's innovative Trip Board offers you a dedicated space to plan new journeys, pick up from where you last stopped, or manage and organise your travel arrangements. You can easily access the properties you've previously saved or booked, now categorised under Potential, Upcoming, or Current Trips. To explore the Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The historical city of Winchcombe awaits you

The area's history and museums are just some of the reasons to come on holiday to Winchcombe. One of the city's many top draws is its restaurants. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Winchcombe

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

  • Cotswold Farm Park (5.8 mi / 9.3 km)
  • The Model Village (10.4 mi / 16.8 km)
  • The Vale Golf and Country Club (13.6 mi / 21.8 km)
  • Broadway Golf Club (8.4 mi / 13.6 km)
  • Cotswold Falconry Centre (10.2 mi / 16.5 km)
  • Birdland Park and Gardens (10.6 mi / 17 km)

Exploring the natural features in Winchcombe

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Winchcombe is a great spot to appreciate mother nature. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Pittville Park (5.6 mi / 8.9 km)
  • Snowshill Manor and Garden (5.6 mi / 9 km)
  • Cotswold Way (10.3 mi / 16.5 km)
  • Batsford Arboretum (10.4 mi / 16.7 km)
  • Evesham Country Park (10.5 mi / 17 km)
  • Hidcote Manor Garden (12.9 mi / 20.8 km)

Travelling to and around Winchcombe

Fly into Oxford (OXF), the closest airport, located 29.4 mi (47.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Birmingham Airport (BHX), which is 35.7 mi (57.4 km) away.

Frequently asked questions

What is the best area to stay in Winchcombe when booking a holiday rental?
When considering a holiday rental in Winchcombe, the town centre is an excellent area to stay in, as it offers a charming blend of history and convenience. This picturesque market town is known for its beautiful Cotswold stone buildings and is surrounded by stunning countryside, making it a superb base for exploring the region.

In the centre, you'll find a variety of properties, ranging from quaint cottages to more spacious homes, providing ample choice for visitors. Staying here allows easy access to local attractions such as the magnificent Sudeley Castle, with its beautiful gardens and rich history, and the delightful Winchcombe Museum, which showcases the area's heritage. The vibrant high street is also a treat, featuring a selection of lovely shops, cafés, and traditional pubs where you can immerse yourself in the local culture.

Additionally, the surrounding areas, such as the scenic countryside leading to the Cotswold Way, offer fantastic walking opportunities, superb for those looking to explore the natural beauty of the Cotswolds.
How much does it cost to rent a holiday home in Winchcombe?
Prices for holiday rentals in Winchcombe 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 Winchcombe 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 Winchcombe holiday house rentals?
You can find great discounts on house rentals in Winchcombe 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.
Can I find long-stay holiday rentals in Winchcombe?
A long-stay holiday rental in Winchcombe 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.
Are there any Winchcombe holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Winchcombe 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.
When is the best time to visit Winchcombe for a holiday rental?
April is a fantastic time to visit Winchcombe, as the town begins to bloom with spring flowers and the weather becomes pleasantly mild. This month offers a wonderful opportunity for visitors to explore the charming Cotswold countryside, with temperatures typically ranging from 5 to 15 degrees Celsius. The scenic walking paths and historic sites, such as Sudeley Castle, are superb for outdoor activities and provide a delightful backdrop for sightseeing.

The peak tourist season in Winchcombe runs from July to September, attracting many visitors eager to enjoy the warm summer weather and vibrant local events. During these months, you can take advantage of various activities, including the Winchcombe Festival and the surrounding nature trails. However, if you prefer a quieter experience, April is ideal, as you can enjoy the beauty of the area without the larger summer crowds.

For those considering a more budget-friendly getaway, December presents a unique charm, with festive decorations and a serene atmosphere. Although it's the low season, the town is still lovely to explore, with opportunities to enjoy cosy local pubs and the winter landscape.

Ultimately, the best time to book a holiday rental in Winchcombe depends on your preferences—whether you wish to immerse yourself in the vibrant summer scene or relish the peacefulness of spring and winter.
How early should I book a Winchcombe holiday rental?
Book your Winchcombe 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 Winchcombe?
In Winchcombe, visitors can experience firsthand a charming blend of history and natural beauty. One of the top attractions is Sudeley Castle, a stunning historical site surrounded by beautiful gardens, which often hosts events and exhibits reflecting its rich heritage. The town itself features quaint streets lined with traditional Cotswold stone buildings, superb for leisurely strolls and discovering local shops and cafes.

Nearby, the Winchcombe Railway Station offers a glimpse into the area's railway history and provides scenic train rides through the stunning countryside. For those who enjoy outdoor activities, the Cotswold Way National Trail runs close by, presenting opportunities for hiking and enjoying breathtaking views of the Cotswold landscape.

The town also hosts the annual Winchcombe Food Festival, where visitors can explore local produce and enjoy various culinary delights, making it a delightful destination for food enthusiasts.
Can I change or cancel my Winchcombe home rental booking on Vrbo?
To find Winchcombe 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 Winchcombe 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.

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