Cheltenham holiday rentals

We found 805 holiday rentals — enter your dates for availability
Discover a selection of 251 homes, 164 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:8 Jan - 15 Jan

what's not to like - it can be difficult to get up!!
Living area
fabulous farmhouse style kitchen with AGA
Huge oversize Oak porch with OLive Trees on guard to welcome you.
Exceptional
(11 reviews)

Cotswolds luxury family friendly oak framed cottage with fab interior style

Tewkesbury

23% off
AU$3,375
for 7 nights, 1 cottage
AU$482 per night
includes taxes & fees
Cotswolds luxury family friendly oak framed cottage with fab interior style
Christmas fairy lights and a stocked log basket awaits you from November toApril
The beautiful Winchcombe Almshouses. The Feathered Nest backs onto these cottage
The cosy sitting room inside the cottage. Large fireplace with woodturning stove
The beautiful fully equipped kitchen.
Exceptional
(76 reviews)

Charming Victorian Wool Cottage on the Cotswold Way in Winchcombe.

Cheltenham

8% off
AU$1,503
for 7 nights, 1 home
AU$215 per night
includes taxes & fees
Charming Victorian Wool Cottage on the Cotswold Way in Winchcombe.
Property grounds
Exterior
Living area
Room
Exceptional
(61 reviews)

5* Gold Award Barn Conversion at the Heart of The Cotswolds

Cheltenham

18% off
AU$6,125
for 7 nights, 1 home
AU$875 per night
includes taxes & fees
5* Gold Award Barn Conversion at the Heart of The Cotswolds
One of the double bedrooms
Exterior
One of the views from the cottage
Dining room open plan to sitting room
Exceptional
(30 reviews)

Cotswold Cottage in historic village of Stanton with views over open fields

Broadway

9% off
AU$4,107
for 7 nights, 1 cottage
AU$587 per night
includes taxes & fees
Cotswold Cottage in historic village of Stanton with views over open fields
Sitting room and kitchen beyond.
The Almshouses of Winchcombe
The kitchenette - combination microwave oven, dishwasher, single hob and fridge.
The driveway to Sudeley castle
Exceptional
(65 reviews)

The Vine - A Luxurious Cotswold Escape for Two.

Cheltenham

8% off
AU$1,202
for 7 nights, 1 apartment
AU$172 per night
includes taxes & fees
The Vine - A Luxurious Cotswold Escape for Two.
Christmas magic
Lou’s View
Welcome.
Exterior
Wonderful
(32 reviews)

Cotswold Detached Hillside Cottage packed with Quirky Character

Cheltenham

9% off
AU$1,889
for 7 nights, 1 cottage
AU$270 per night
includes taxes & fees
Cotswold Detached Hillside Cottage packed with Quirky Character
dining area and stable door
A warm welcome always awaits in Winchcombe
Terrace/patio
Living area
Exceptional
(114 reviews)

Traditional Cotswold Stone Cottage, Winchcombe, Cotswolds Way.

Cheltenham

5% off
AU$2,119
for 7 nights, 1 cottage
AU$303 per night
includes taxes & fees
Traditional Cotswold Stone Cottage, Winchcombe, Cotswolds Way.
Entrance hall, with cloakroom (w.c. and washbasin)
The butchers shop in Northleach
Bedroom 1
Courtyard garden from top of steps to sitting room french doors
Exceptional
(21 reviews)

Cotswold Holiday Accommodation in beautiful Northleach

Cheltenham

5% off
AU$2,581
for 7 nights, 1 home
AU$369 per night
includes taxes & fees
Cotswold Holiday Accommodation in beautiful Northleach

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Why visit Cheltenham

  • Regency Architecture: Discover Cheltenham's stunning Georgian and Regency buildings that reflect its rich historical heritage.
  • Cheltenham Racecourse: Experience the excitement of horse racing at one of the UK’s premier racecourses, famous for its annual events.
  • Cultural Festivals: Attend renowned events like the Cheltenham Literature Festival, showcasing local and international authors.
  • Beautiful Parks: Enjoy leisurely walks in expansive parks, perfect for family outings and outdoor activities.
  • Charming Town Centre: Stroll through the vibrant town centre filled with friendly locals, shops, and cafes.

Popular types of accommodation in Cheltenham

Welcome to Cheltenham, a charming spa town in England known for its Regency architecture and vibrant cultural scene. Here, you can explore stunning parks, visit the historic Pump Room, or enjoy the annual Cheltenham Literature Festival. When it comes to accommodation, you’ll find a variety of options including cosy cottages, private holiday homes, and stylish apartments, ensuring a perfect stay in this delightful destination.

  • Cottages: Charming and quaint, cottages offer a quintessentially British experience, perfect for a relaxing getaway.
  • Private Holiday Homes: Enjoy the comforts of home with spacious private residences that provide flexibility and privacy.
  • Apartments: Modern and convenient, apartments are ideal for travellers seeking a stylish base in the heart of Cheltenham.
  • Cabins: Nestled in nature, cabins offer a rustic retreat, perfect for those who appreciate the great outdoors.
  • Caravan Parks: For a unique experience, caravan parks provide a blend of fun and adventure, suitable for families and groups.**

Top attractions in and around Cheltenham

Cheltenham offers visitors a delightful blend of culture and adventure, featuring historic houses, charming churches, and expansive urban parks perfect for family outings and outdoor exploration. The city's rich heritage is complemented by experiences such as the renowned Cheltenham racecourse and the celebrated Cheltenham festival, ensuring a memorable holiday filled with scenic beauty and local tradition.

  • Sudeley Castle: Nestled in Cheltenham, this historic castle charms visitors with its rich cultural legacy and romantic aura, perfect for history enthusiasts.
  • Gloucester Cathedral: Located 13km from Cheltenham, this magnificent cathedral offers a profound cultural experience steeped in centuries of heritage.
  • Cotswold Countryside Collection: Situated within Cheltenham, this museum celebrates local culture, providing insights into the rural traditions of the region.

Things to do recommended for couples

Experience Cheltenham romantically with a leisurely walk through the historic town centre, hand in hand along scenic pathways, and intimate afternoons in cosy tearooms. Discover local charm tailored for couples seeking a delightful escape.

Things to do recommended for families

Families visiting Cheltenham can enjoy a delightful day at the picturesque Cheltenham Spa, explore the fascinating interactive exhibits at the Science Centre, and have fun at the local playgrounds like Montpellier Gardens, perfect for a relaxing family outing.

Things to do recommended for groups

Visitors to Cheltenham can experience the thrill of local motorRacing at the Prescott Speed Hill Climb, where sports and adventure await groups seeking an unforgettable day out.

*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 Cheltenham

Whether you’re travelling with a group, as a family, with your pets, or seeking extended stays, be sure to prioritise the right filters. Here are some Stayz booking suggestions 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 space for group gatherings. Thankfully, you can easily filter for all of these options and more on Stayz.
  • Traveling to Cheltenham with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, it’s wise to think about your closeness to attractions that are family-friendly.
  • Taking your pets with you to Cheltenham: For many, a family holiday wouldn’t be complete without their four-legged companion. If this resonates with you, take a look at Stayz properties 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 Cheltenham: If you're in search of holiday rentals with discounts for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly accommodations. Don't forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Cheltenham

Explore Cheltenham's vibrant town centre, where the blend of charming streets and friendly locals creates a warm welcome. Enjoy leisurely strolls through scenic parks and engaging cultural hubs, perfect for both family-friendly adventures and budget-conscious travellers. With a range of neighbourhood experiences and a relaxed atmosphere, Cheltenham promises an ultimate getaway filled with local choice and inviting vibes.

  • Cotswolds: Nestled 13km away from Cheltenham, the Cotswolds offers a captivating escape into nature with its scenic beauty and adventurous spirit. This area invites travellers to explore vast nature reserves and national parks, perfect for outdoor enthusiasts seeking adventure and stunning vistas. The region is dotted with recreational areas, shopping centres, and a variety of local attractions including recognised national parks and notable monuments, ensuring a memorable blend of natural splendour and cultural history.
  • Bourton-on-the-Water: Located within the vicinity of Cheltenham, Bourton-on-the-Water is a charming village celebrated for its quintessential English appeal. This village is a haven for those in search of outdoor adventures and picturesque landscapes. Visitors can enjoy leisurely strolls through scenic settings and explore nearby recreational spaces and shopping centres. The local landmarks, including national parks and historical monuments, add to the village's allure, offering a delightful mix of heritage and natural beauty.
  • Gloucester: Situated 13km from Cheltenham, Gloucester is a vibrant city that caters to family, urban, and business experiences alike. The city boasts excellent shopping centres and educational venues, making it an ideal destination for diverse interests. Its proximity to national parks, historic sites, and recognised state parks provides an enriching backdrop that combines modern city life with a rich tapestry of history and culture, perfect for day trips and extended explorations.

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.

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 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 Stayz is simple

If you’re aiming to cut costs on your upcoming journey, consider adopting a flexible approach to your travel dates, as fares can vary. Additionally, opting for a longer stay can often result in significant savings. To discover a Stayz property that fits your budget, simply utilise our filters to refine your search by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz’s Trip Board offers a user-friendly area for you to plan new trips, continue from where you last stopped, or review and manage your travel arrangements. You can easily find the properties you've saved or booked, sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.stayz.com.au/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)
  • The Vale Golf and Country Club (17.7 mi / 28.5 km)
  • Morgan Motor Company (18.4 mi / 29.6 km)
  • Crocodiles of the World (22.6 mi / 36.4 km)
  • Chipping Norton Golf Club (24.1 mi / 38.8 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'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, a popular area to stay is the town centre, which offers a vibrant setting and easy access to a variety of attractions. This area is home to a delightful mix of shops, cafes, and restaurants, making it an ideal base for exploring the town. Just a short stroll away, you can visit the beautiful Pittville Park, which features picturesque gardens and a lovely lake, great for leisurely walks or picnics.Another excellent choice is the Montpellier district, renowned for its elegant Regency architecture and charming streets. Here, you can enjoy the boutique shops and exquisite dining options, as well as the stunning Montpellier Gardens, which host various events throughout the year. The area has a good selection of holiday rentals, providing a range of options from cosy apartments to spacious homes.Finally, the Suffolks is a charming neighbourhood known for its unique character and vibrant community. This area features an array of independent shops and eateries, along with the impressive Cheltenham Art Gallery and Museum, showcasing fascinating exhibitions and local history.
What is the most popular type of holiday rental accomodation in Cheltenham?
In Cheltenham, cottages are the most popular type of holiday rental, with approximately 1,424 available throughout the area. These charming properties are typically situated in picturesque neighbourhoods, allowing visitors to enjoy the town's Regency architecture and beautiful gardens. Most cottages feature fully equipped kitchens, cosy living areas, and often a garden or outdoor seating area, superb for relaxing after a day of exploring.Holiday houses are also a significant option, with around 900 available. These homes tend to offer more space, boasting multiple bedrooms and amenities such as private gardens and BBQ facilities, making them ideal for families or groups. Additionally, there are about 560 apartments scattered across Cheltenham, providing a more modern stay with conveniences like laundry facilities and communal spaces.
Are there any family house rentals in Cheltenham?
In Cheltenham, there are numerous family-friendly house rentals available, with around 442 properties to choose from. This lovely town, known for its Regency architecture and vibrant cultural scene, offers various accommodations that cater to families. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and safe outdoor spaces where children can play. Additional amenities often include Wi-Fi and laundry facilities, ensuring a comfortable stay.Families can easily explore nearby attractions, including the picturesque Pittville Park, which boasts playgrounds and beautiful gardens, or the Cheltenham Racecourse, famous for its horse racing events.
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 10 options to choose from. This charming spa town, known for its Regency architecture and vibrant cultural scene, offers a range of neighbourhoods where these properties can be found. For instance, the area near Pittville Park is home to lovely residences with gardens and private pools, ideal for families or those looking to relax in a serene environment.Travellers can expect amenities such as outdoor hot tubs, spacious living areas, and fully equipped kitchens, which provide everything needed for a comfortable stay. Find your rental in Cheltenham with a pool or a hot tub.
Are there pet-friendly house rentals in Cheltenham?
In Cheltenham, there are numerous pet-friendly house rentals available, with options exceeding 369 properties. This charming spa town offers a variety of accommodations that cater to pet owners, ensuring a comfortable stay for both guests and their furry companions. Many of these rentals feature amenities such as enclosed gardens, spacious living areas, and fully equipped kitchens, making them ideal for families or groups.The town is also conveniently located near several parks and green spaces, such as Pittville Park and Montpellier Gardens, which are great for leisurely walks with pets. Additionally, Cheltenham's vibrant culinary scene includes several pet-friendly cafes and pubs, allowing visitors to enjoy dining out without having to leave their pets behind. See all pet-friendly rentals in Cheltenham.
Are there any remote work holiday rentals in Cheltenham?
In Cheltenham, there is a substantial selection of remote work holiday rentals available, with approximately 2,688 options to choose from. This charming town in England offers a variety of accommodations that cater well to remote workers. Many properties provide essential amenities such as high-speed Wi-Fi, desks in private rooms, and free public area Wi-Fi, ensuring that guests can work efficiently during their stay.Cheltenham is known for its beautiful Regency architecture and vibrant cultural scene, with attractions such as the Cheltenham Racecourse and the picturesque Montpellier district nearby. The town also boasts lovely parks and gardens, great for taking breaks or enjoying a leisurely stroll after work hours. With a range of cafes and restaurants in the vicinity, remote workers can easily find a suitable spot to unwind or grab a bite to eat. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Cheltenham?
In Cheltenham, popular holiday rental amenities include well-equipped kitchens, allowing guests to prepare their own meals with ease. Many properties also feature onsite parking, which is particularly convenient for those travelling by car. For pet owners, there are options that permit pets, alongside provisions for service animals. Additionally, a number of rentals come with gardens, providing a pleasant outdoor space to relax and enjoy the surroundings.
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 vibrant period coincides with the Cheltenham Festival, attracting numerous visitors eager to experience top horse racing and lively festivities. The atmosphere is electric, and the town comes alive with a variety of events and activities that cater to diverse interests.During these months, the weather in Cheltenham begins to warm up, typically ranging from 5 to 13 degrees Celsius. This mild climate makes it ideal for outdoor activities, such as leisurely strolls through the picturesque parks or enjoying the charming architecture of the Regency town centre. The beautiful gardens and historic sites are superb for sightseeing and offer plenty of opportunities to soak up the local culture.For those looking for a more budget-friendly experience, consider visiting in December. During this time, the festive spirit is palpable, with charming Christmas markets and seasonal events that create a delightful atmosphere. You'll find that this time of year allows for a more relaxed exploration of Cheltenham's attractions.Ultimately, your choice of when to visit Cheltenham will depend on whether you prefer the bustling excitement of the peak season or the serene charm of the winter months.
What are the top attractions in Cheltenham?
In Cheltenham, visitors can explore an array of attractions that highlight the town's rich history and cultural significance. The Promenade, lined with elegant Regency architecture, offers a pleasant stroll with shops, cafes, and the iconic Neptune Fountain. The nearby Pittville Park is great for leisurely walks and picnics, featuring picturesque lakes and the impressive Pittville Pump Room, a historic spa building that hosts events and concerts.The Cheltenham Art Gallery and Museum showcases a diverse collection of art and local history, making it a must-visit for culture enthusiasts. For those interested in literature, the town hosts the annual Cheltenham Literature Festival, attracting authors and book lovers from all over.The Montpellier district is known for its vibrant setting, with a variety of independent shops and eateries, creating a lively hub for both locals and visitors. Additionally, the Everyman Theatre offers a fantastic programme of performances, ensuring that there's always something entertaining to experience.
Are all fees included in the Cheltenham 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 Cheltenham holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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 Cheltenham holiday homes?
You can find great discounts on holiday homes in Cheltenham 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 Cheltenham holiday home booking on Stayz?
To find Cheltenham 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 Cheltenham?
A long-stay holiday home 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 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 Cheltenham holiday home?
Book your Cheltenham 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 Cheltenham?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Cheltenham 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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