Cheltenham holiday lettings

We found 679 holiday rentals — enter your dates for availability

Discover a selection of 271 homes, 180 apartments and other holiday rentals in Cheltenham that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll find the amenities that you need and want, such as Wi-Fi and cable TV. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Cheltenham

Showing deals for:7 Nov - 14 Nov

Image gallery for Ivy Cottage - Charming 18th Century Detached Cottage in Cotswold's area, UK

Sitting Room
9.6 out of 10 rating
Exceptional
(20 reviews)

Ivy Cottage - Charming 18th Century Detached Cottage in Cotswold's area, UK

Tewkesbury, Gloucestershire

22% off
Price is £2,553
£365 per night
includes taxes & fees
Ivy Cottage - Charming 18th Century Detached Cottage in Cotswold's area, UK

Find spaces that suit your style

Find out more about Cheltenham

Find out more about Cheltenham

Why visit Cheltenham

  • Rich history: Discover Cheltenham's historic houses, churches, and modern colleges that showcase its cultural heritage.
  • Beautiful parks: Enjoy the picturesque scenery in Cheltenham's exquisite parks, perfect for leisurely strolls and picnics.
  • Cheltenham Spa: Relax and rejuvenate at the famous Cheltenham Spa, renowned for its soothing waters and wellness facilities.
  • Outdoor adventures: Engage in various outdoor sports and activities, catering to both thrill-seekers and nature lovers.
  • Diverse accommodation: Choose from charming cottages, private holiday homes, and stylish apartments for a comfortable stay.

Popular types of accommodation in Cheltenham

If you're seeking the perfect getaway in Cheltenham, you're in the right place. Our most popular types of accommodation include charming cottages, private holiday homes, and stylish apartments. Whether you're looking for delightful Cheltenham cottages or spacious bedroom houses, we have a variety of options to suit your needs. Enjoy a memorable stay with a range of accommodation choices that promise comfort and convenience in this lovely town.

  • Cottages: Cottages are the top choice for holidaymakers in Cheltenham, offering a charming and homely retreat.
  • Houses: Ideal for families or groups, private homes provide ample space and privacy.
  • Apartments: Convenient and centrally located, apartments cater to those seeking a modern living experience.
  • Cabins: Perfect for a rustic getaway, cabins offer a cosy escape in picturesque surroundings.
  • Motels: A practical option for budget-conscious travellers, motels provide basic amenities and easy access.**

Top attractions in Cheltenham

Cheltenham offers a delightful mix of adventure and culture, making it perfect for outdoor and sports enthusiasts. Visitors can explore a variety of attractions, including historic houses, churches, and modern colleges. The area's points of interest cater to families and those seeking enriching experiences, ensuring there's something for everyone to enjoy during their stay.

  • Sudeley Castle: Nestled in the heart of Cheltenham, Sudeley Castle boasts stunning architecture and lush gardens, offering a romantic atmosphere steeped in history and culture.
  • Cheltenham Town Hall: A modern civic building, this venue serves as a hub for business and community events, showcasing impressive architecture and a vibrant atmosphere.
  • Cotswold Countryside Collection: This engaging museum presents the rich cultural heritage of the Cotswolds, featuring exhibits that celebrate local history and rural life.

Things to do recommended for couples

If you're seeking romance in Cheltenham, consider a visit to the luxurious Spiers and Hartwell Jubilee Stadium, just 8.1km away, or indulge in the enchanting atmosphere at Woodchester Valley Vineyard and Winery, located 9.3km away. Both offer unforgettable experiences for couples.

Things to do recommended for families

During your family vacation in Cheltenham, enjoy the lively atmosphere at Kingsholm Stadium, navigate the playful Dragonfly Maze, and unwind in the serene Crickley Hill Country Park, perfect for relaxation and wellness, all while creating memorable experiences together.

Things to do recommended for groups

Explore the vibrant Gloucester Quays for shopping and dining, then rev up the excitement at Prescott Speed Hill Climb for a thrilling motorsport experience. Finally, unwind at the Everyman Theatre, where you can enjoy captivating performances in a charming setting perfect for groups.

What do I need to keep in mind when booking a vacation in 'Cheltenham

If you're travelling with a group, enjoying a family getaway, bringing along your pets, or seeking extended stays, it's essential to filter your options based on your key priorities. Here are some helpful Vrbo booking tips tailored for you.

  • Traveling to Cheltenham with a group: Think about how many bedrooms you'll require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Cheltenham with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, as well as seek out suitable amenities, like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can greatly enhance your experience.
  • Taking your pets with you to Cheltenham: For many, a family holiday wouldn’t feel complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. The majority of pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Cheltenham: If you're in search of holiday rentals that offer discounts 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 accommodations. Don’t forget to consider adding features like a parking space, a well-equipped kitchen, or even a private pool to your search criteria.

Where to stay in and around Cheltenham

Cheltenham offers a delightful mix of adventure and relaxation, making it an ideal getaway destination. Explore the stunning Cheltenham Spa, enjoy the picturesque scenery in exquisite parks, and soak in the friendly atmosphere of this charming city. Whether you're seeking outdoor sports or a peaceful retreat, Cheltenham and its surrounding areas promise an unforgettable experience for every traveller.

  • Cotswolds: Nestled a mere 5.0km from Cheltenham, the Cotswolds is renowned for its picturesque rolling hills and charming villages. This Area of Outstanding Natural Beauty offers a plethora of outdoor adventures, from hiking through national parks to exploring nature reserves. Visitors can indulge in shopping at quaint local centres and enjoy recreational spaces perfect for picnics or leisurely strolls. Iconic landmarks such as ancient monuments and the stunning national park beckon nature enthusiasts and those seeking tranquil scenery, making it a must-visit for anyone looking to immerse themselves in the natural beauty of England.
  • Gloucester: Located also 5.0km from Cheltenham, Gloucester is a vibrant city steeped in history. Ideal for family outings and business trips alike, it boasts a variety of shopping centres and educational attractions. The city's historic places tell tales of its rich past, while modern amenities ensure a comfortable experience. Visitors can explore the majestic Gloucester Cathedral or catch a game at the local stadium. With a blend of city excitement and cultural significance, Gloucester offers an engaging experience for all types of travellers.
  • Bourton-on-the-Water: This enchanting village, situated within close proximity to Cheltenham, is often referred to as the Venice of the Cotswolds due to its charming waterways. Bourton-on-the-Water is a haven for outdoor enthusiasts and offers stunning scenery, perfect for leisurely walks or adventurous pursuits. Visitors can explore local shops and enjoy recreational areas that enhance the village's tranquil atmosphere. Notable attractions include monuments and the nearby national park, providing an idyllic backdrop for a memorable day out in the heart of the Cotswolds.

Best time to go to Cheltenham

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January39.4°F (4.1°C)Light RainMostly CloudyAverageSlightly Low
February40.5°F (4.7°C)Light RainMostly CloudyModerately HighSlightly Low
March43.2°F (6.2°C)Light RainMostly CloudyModerately HighAverage
April47.1°F (8.4°C)No Rain (Dry)Mostly CloudyModerately HighAverage
May52.7°F (11.5°C)Light RainMostly CloudyModerately LowAverage
June58.3°F (14.6°C)Light RainMostly CloudyAverageAverage
July61.9°F (16.6°C)Light RainMostly CloudyAverageSlightly High
August61.2°F (16.2°C)Light RainMostly CloudyAverageSlightly High
September57.4°F (14.1°C)Light RainMostly CloudyAverageSlightly Low
October52.0°F (11.1°C)Light RainMostly CloudyModerately LowAverage
November45.3°F (7.4°C)Light RainMostly CloudyAverageAverage
December41.5°F (5.3°C)Light RainMostly CloudyModerately LowSlightly High

Booking with Vrbo is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform to plan new journeys, continue from where you previously stopped, or manage your travel arrangements. You can easily find your saved or booked properties sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Why people love visiting cosy Cheltenham

The area's musicals and jazz are just some of the reasons to come on holiday to Cheltenham. Travellers to this welcoming city praise the sightseeing, local tours and hiking. 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.

Sightseeing in and around Cheltenham

Are you searching for top things to see and do in the city? Venture out of your cosy holiday rental and check out everything that Cheltenham has to offer. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Cotswold Farm Park (10.5 mi / 16.8 km)
  • The Model Village (13.7 mi / 22 km)
  • Cotswold Wildlife Park (20.1 mi / 32.3 km)
  • Crocodiles of the World (22.6 mi / 36.4 km)
  • Fairytale Farm (24.2 mi / 39 km)
  • Stratford Butterfly Farm (25.5 mi / 41 km)

Exploring the gardens and other natural features in Cheltenham

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Cheltenham is a great place to spend some time outside. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Pittville Park (0.6 mi / 1 km)
  • Snowshill Manor and Garden (11.5 mi / 18.5 km)
  • Minchinhampton Common (14.4 mi / 23.2 km)
  • Croome Park (14.6 mi / 23.5 km)
  • Evesham Country Park (15.4 mi / 24.8 km)
  • Batsford Arboretum (16 mi / 25.7 km)

Travelling to and around Cheltenham

The nearest airport is in Oxford (OXF), located 33 mi (53.1 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Coventry (CVT), which is 40.6 mi (65.4 km) away.

If you'd rather travel by train, make your way to Cheltenham Spa Station or Toddington Railway Station to see more of the city.

Frequently asked questions

What is the best area to stay in Cheltenham when booking a holiday rental?
When considering a holiday rental in Cheltenham, the Montpellier area is a fantastic choice. Known for its stunning Regency architecture and vibrant atmosphere, Montpellier offers a delightful blend of stylish boutiques, cafés, and restaurants. A must-visit nearby attraction is the Montpellier Gardens, which provides a lovely green space superb for leisurely strolls or picnics. The area is also close to the iconic Everyman Theatre, renowned for its excellent productions and cultural offerings.

Another excellent option is the town centre, which boasts a wide array of properties to choose from. Staying in the heart of Cheltenham allows easy access to popular attractions such as the Cheltenham Art Gallery and Museum, where visitors can appreciate an impressive collection of art and local history. The lively Promenade is also within walking distance, lined with shops and eateries, making it a convenient and enjoyable hub for your stay.

For those seeking a quieter environment, the Up Hatherley area is worth considering. This residential neighbourhood offers a peaceful retreat while still being just a short drive or bus ride from the town centre. Visitors can explore the beautiful nature trails and parks in the vicinity, such as the picturesque Hatherley Park.
How much does it cost to rent a holiday home in Cheltenham?
Prices for holiday rentals in Cheltenham 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 Cheltenham 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 Cheltenham holiday house rentals?
You can find great discounts on house rentals in Cheltenham 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.
What is the most popular type of holiday rental accomodation in Cheltenham?
In Cheltenham, cottages are the most popular type of holiday rental, with around 364 available across charming neighbourhoods close to the town centre and attractions like the Cheltenham Racecourse and the beautiful Imperial Gardens. These cottages often feature traditional interiors, fully equipped kitchens, and cosy living areas, making them great for a comfortable stay.
Are there any family house rentals in Cheltenham?
In Cheltenham, there are numerous family-friendly house rentals available, with around 416 properties to choose from. This charming town in the Cotswolds is known for its elegant regency architecture and vibrant cultural scene, making it an ideal spot for families. Many of these homes come equipped with spacious living areas, full kitchens for preparing family meals, and outdoor spaces great for children to play.

Visitors can find accommodations in lovely neighbourhoods such as Pittville and Montpellier, both of which offer easy access to local parks, including Pittville Park with its picturesque lake and playgrounds. Additionally, the town centre is nearby, where families can explore a variety of shops, cafes, and restaurants, as well as attractions like the Cheltenham Art Gallery and Museum. See all family-friendly rentals in Cheltenham.
Can I rent a holiday home with a pool or hot tub in Cheltenham?
In Cheltenham, there are several holiday homes available for rent that feature pools or hot tubs, with around 13 options to choose from. This elegant town, known for its Regency architecture and beautiful parks, offers a range of neighbourhoods where these properties can be found, including the charming Montpellier area, which is renowned for its boutique shops and cafés, and the more residential locations like Leckhampton, offering a quieter retreat while still being close to the town centre. Find your rental in Cheltenham with a pool or a hot tub.
Can I find long-stay holiday rentals in Cheltenham?
A long-stay holiday rental in Cheltenham 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 pet-friendly house rentals in Cheltenham?
In Cheltenham, there are numerous pet-friendly house rentals available, with around 348 options to choose from. Many of these holiday homes can be found in residential areas that provide easy access to local parks and green spaces, making it convenient for pet owners to enjoy walks and outdoor activities.

Properties in Cheltenham typically offer amenities such as fully equipped kitchens, spacious living areas, and private gardens, which are ideal for families or groups. Some rentals may also feature outdoor seating areas or patios, allowing guests to relax in the fresh air with their pets. See all pet-friendly rentals in Cheltenham.
Are there any remote work holiday rentals in Cheltenham?
In Cheltenham, there are numerous options for remote work holiday rentals, with around 660 available in the area. This charming spa town in England offers a variety of accommodations suitable for those looking to balance work and leisure. Many properties feature dedicated workspaces, including desks and comfortable chairs, ensuring a productive environment. You can also expect amenities such as high-speed Wi-Fi and computer stations, which are ideal for remote professionals. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Cheltenham holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Cheltenham 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.
What are popular rental amenities in Cheltenham?
In Cheltenham, popular holiday rental amenities include fully equipped kitchens, which typically feature essential appliances such as refrigerators, ovens, microwaves, and cookware. These amenities are ideal for travellers who prefer to prepare their own meals during their stay. Additionally, many rentals provide comfortable living spaces that enhance the overall experience, making it easier for guests to relax after exploring the charming streets and attractions of this regency town.
When is the best time to visit Cheltenham for a holiday rental?
The best time to visit Cheltenham for a holiday rental is during the peak season from February to April, with March being particularly popular. This period marks the arrival of spring, bringing milder temperatures and blooming gardens that create a picturesque setting for exploration. Visitors can enjoy Cheltenham's renowned festivals, such as the Cheltenham Literature Festival, which attracts literary enthusiasts and offers a vibrant atmosphere filled with engaging events.

During these months, temperatures typically range from 7 to 12 degrees Celsius, making it comfortable for outdoor activities and sightseeing. Take the opportunity to stroll through the charming parks, visit the beautiful Regency architecture, and indulge in the local culinary scene. The lively atmosphere during this time is superb for those seeking both adventure and cultural experiences.

If you're looking for a more budget-friendly option, consider visiting in December. Although this is a quieter time, Cheltenham transforms into a festive wonderland, with Christmas markets and seasonal decorations creating a magical ambiance.
How early should I book a Cheltenham holiday rental?
Book your Cheltenham 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 Cheltenham?
In Cheltenham, visitors can explore a range of attractions that highlight its rich history and culture. The town is renowned for its stunning Regency architecture, particularly along the Promenade and in the Montpellier area, where charming cafes and boutique shops can be found. The Cheltenham Art Gallery and Museum, located near the town centre, offers a fascinating collection of art and historical exhibits.

The annual Cheltenham Literature Festival draws literary enthusiasts from all over, while the nearby Pittville Park provides a lovely green space for leisurely walks and picnics. For those interested in horse racing, the Cheltenham Racecourse, situated just outside the town centre, is famous for its prestigious events, especially the Cheltenham Festival held each March.
Can I change or cancel my Cheltenham home rental booking on Vrbo?
To find Cheltenham 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Cheltenham 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.

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