
Holiday houses in Cheltenham
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Top-rated holiday rentals in Cheltenham
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Modern studio in the heart of Cheltenham
Enjoy your stay in this centrally located studio apartment on the top ( second ) floor. Ideally located for all the wonderful bars cafes and restaurants that Cheltenham has to offer, this easy living, modern studio apartment is on the doorstep to all the activity. You will see instructions for entry 48 hours before arrival. GL52 2SQ There is a secure side door for bike storage on ground floor. Cheltenham Racecourse is a 5 minute drive ( traffic dependent ) or a 30 minute walk from apartment.

Beautiful basement flat. Leckhampton, Cheltenham
Beautiful self contained basement flat with own entrance. Open plan living area with pull down ‘Murphy bed’ (please ask when booking if you would like to use this bed as it requires host assembly). Full kitchen-dishwasher,oven,microwave & washing machine. Bedroom with wardrobe, dressing table and king size bed- can be separated into 2 singles on request at time of booking. Wet room with shower. Shampoo,conditioner,shower gel and towels provided. Tea,coffee,milk and breakfast items provided.

Pittville Loft - 5* Free parking no cleaning fee
The hidden gem of hidden gems. Our beautiful apartment is nestled in a quiet private mews lane - close to all you need and want in central Cheltenham. Free Parking inc Pittville Loft is perfectly situated for couples, young families, small groups of friends and single people traveling for business or pleasure. Within easy walking distance to the festival sites and the racecourse. Quirky and unique, Pittville Loft combines all modern conveniences with stylish vintage style and industrial chic.

Annexe in the foothills
Kick back and relax in this calm, stylish space. A newly created annex nestled in the foothills of Leckhampton Hill. 2 minute walk to an Area of Outstanding Natural Beauty and 15 minute walk from the Cotswold Way. This beautiful, bijou annexe is self contained, with private entrance and off road parking, in a quiet, residential cul de sac. Finished to a very high standard throughout with double bed, sofa, smart TV, shower room, and kitchen with workspace. 30 minute walk into Regency Cheltenham.

Regency Apartment | Free Parking | Walk to Town
Ideally located within walking distance of Cheltenham town centre and the racecourse, this recently refurbished apartment offers a comfortable private living space within a large Regency house. Perfect for couples, the apartment sleeps 2, with space for up to 4 using additional single beds if required. Please contact us before booking if you would like the single beds prepared. I co-host with my son Patrick, husband John and daughter Rachel, and we’re always happy to help during your stay.

Charming house in the centre of town.
A centrally located charming house. Just a short walk from the trendy Montpellier area and High Street it’s perfect for a city break. The house has a spacious open plan living/dining area with separate kitchen, two spacious bedrooms, bathroom and courtyard garden. There is a comfy fold down king size Murphy bed in the living room. Included in your booking is a parking permit for one vehicle. Additional parking permit available for a small fee.

Natures Edge Cabin
Award-winning, adults-only retreat for two. Chemical-free hot tub, private sauna, cinema, fire pit, and four geodomes for dining, day napping, creativity, and spa treatments. Enjoy a pizza oven, Kamado BBQ, wild shower, cold plunge, mini golf, and lush, jungle-style gardens. Total privacy, no shared spaces. As featured in Country Living, Time Out & Airbnb’s Top 10 Proposal Spots. Romance, luxury, and nature—reimagined in every detail.

Stylish apartment in the heart of Cheltenham
A chic stylish one bedroom apartment in a Victorian townhouse in the centre of Cheltenham with FREE PARKING. Perfectly located to experience all Cheltenham has to offer. A short walking distance to festival locations and the most popular bars and restaurants in Montpellier, The Suffolks, Bath Road and the Promenade. The racecourse is a 25 minute walk or 10 minutes by road. An ideal base for those travelling for business or pleasure.

Self-contained basement flat in regency home
Refurbished basement flat in grade 2 listed regency terraced house. Central Cheltenham location, walking distance to all local festivals, shopping, pubs and restaurants. Modern, light and spacious accommodation with private access and patio terrace via the bedroom. Good size bathroom with bath and walk-in shower. There is no separate kitchen but an area containing a fridge, microwave, kettle & toaster.

Luxury Refurbished 2 Bedroom Regency Apartment
Superbly Appointed Regency Apartment Situated Along A Tree Lined Road Close To Cheltenham Centre Where You Will Find A Plethora Of Amazing Shops & Restaurants. With Its Own Private Entrance This Luxury Apartment Has Been Refurbished To A High Standard Throughout & Offers Spacious & Comfortable Living. It Is Suitable For Up To 4 Guests, Couples, Families Or Corporate Stays.

Cotswold lodge with amazing views and famous walks
Enjoying spectacular views this 2 bedroom, dog friendly lodge sits on the top of Leckhampton Hill, enjoying easy access to the famous ‘Cotswold Way’ walk and is a 5 minute drive from the town centre of regency Cheltenham. The Lodge also includes a 3.5m outdoor kitchen looking over The Malvern Hills. The kitchen includes a large built in BBQ, a pizza oven and sink.

Beautiful Two Bedroom Apartment
A spacious, 1000 sq ft / 92 sqm, two double bedroom apartment, taking up the entire lower ground floor of a beautiful Grade II listed Villa in central Cheltenham. Self contained, it has its own entrance, two bedrooms, a separate kitchen, separate sitting room, and bathroom with shower. It also has super fast 150mb wifi broadband.
Popular amenities for Cheltenham holiday rentals
Other great holiday rentals in Cheltenham

The Promenade Cheltenham Luxury Apartment Number 1

Regency Coach House Cheltenham

Pear Tree Nook | Stylish Stay Near Races & Town

Margaret's Quattro by Fortuna Property Portfolio

Cottage luxe in The Cotwolds

Town Centre Stay with Cozy Balcony Retreat

Super Stylish 2 Bed House | Cheltenham Town Centre

Charming 1BR Cheltenham Apt,Sleeps 2, FREE parking
When is the best time to visit Cheltenham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $188 AUD | $182 AUD | $281 AUD | $196 AUD | $206 AUD | $218 AUD | $220 AUD | $220 AUD | $213 AUD | $213 AUD | $213 AUD | $226 AUD |
| Avg. temp | 5°C | 5°C | 7°C | 9°C | 12°C | 15°C | 18°C | 17°C | 15°C | 11°C | 7°C | 5°C |
Frequently Asked Questions
What are the best places to stay in Cheltenham?
Explore neighbourhoods like Montpellier, which has elegant Regency architecture, or The Suffolks, known for independent shops and cafes. Around Pittville Park also draws visitors for its green spaces and leafy atmosphere.
What are the best things to do in Cheltenham with kids?
Families often explore Pittville Park for its playgrounds and boating lake, visit the Wilson Art Gallery and Museum, or enjoy hands-on science at a discovery or activity centre. In summer, local lidos and splash pads frequently attract younger visitors.
What are some of the best things to do in Cheltenham?
Discover Regency-era buildings along the Promenade, stroll Montpellier Gardens, or explore local markets. Art lovers visit The Wilson Art Gallery and Museum, while the restored Pittville Pump Room highlights spa town heritage.
How is the weather in Cheltenham?
Cheltenham has cool winters, with January temperatures around 35–46°F (2–8°C), and mild, pleasantly warm summers reaching 55–73°F (13–23°C) in July. Rain occurs year-round, so a light raincoat or umbrella is often suggested.
When is the best time to visit Cheltenham?
Late spring through early autumn is often recommended, when gardens bloom and outdoor festivals contribute vibrant energy. Cooler months bring quieter streets and a relaxed pace for enjoying local cafés and indoor sites.
What are the best places to visit in Cheltenham?
Stroll the tree-lined Promenade, step inside the Pittville Pump Room, or enjoy Montpellier Gardens. The Wilson Art Gallery and Museum has changing exhibitions and local history collections.
What are some hiking trails in Cheltenham?
Ascend Cleeve Hill for panoramic views, or wander gentle paths across Leckhampton Hill with its distinctive geology. Parks like Pittville Park have accessible walking routes suitable for all ages.
What are some family activities we can do in Cheltenham?
Enjoy boating or picnicking in Pittville Park, explore art and history together at The Wilson Art Gallery and Museum, or splash in an open-air lido during warmer days. Local theatres sometimes host children’s performances and activities.
What are some of the best day trip ideas from Cheltenham?
Explore historic Cotswold villages, walk castle ruins, or visit gardens renowned for their English floral displays around the region. The area also has country parks and nature reserves for those looking to connect with local landscapes.
Are there any pet friendly accommodations available in Cheltenham?
Many Cheltenham rentals welcome pets, especially in areas near Pittville Park, The Suffolks, and Charlton Kings. Green spaces and walking trails make it easy to explore the outdoors with your companion.
What are some local tips for visiting Cheltenham?
Street markets pop up regularly for fresh produce and crafts—bring a reusable bag. Locals enjoy independent cafés in Montpellier, and walking shoes are useful for exploring gardens and hilly countryside nearby.
What is Cheltenham known for?
Cheltenham is well known for its Regency architecture, cultural festivals, and heritage as a spa town. Visitors often explore its lush gardens, independent shops, and vibrant arts scene.
What are the best hidden gems to explore in Cheltenham?
Discover winding lanes in The Suffolks, find local art studios tucked amid the Montpellier quarter, or relax in Sandford Park with its art deco lido. Independent bookstores and markets often give a glimpse into the town’s creative spirit.
What are the best foods to try in Cheltenham?
Cheltenham has locally sourced cheeses, Gloucestershire pies, and Sunday roasts commonly featured in traditional pubs. Bakeries and markets showcase scones, pastries, and artisanal cakes reflecting English and regional flavours.
What should I bring for a trip to Cheltenham?
A versatile wardrobe works well—include layers for mild or cool weather, sturdy shoes for garden strolls, and a raincoat. A reusable bag is helpful for market days and local shops.
What is the nightlife in Cheltenham like?
Cheltenham’s nightlife has independent bars, lively pubs, and occasional jazz or comedy venues, especially around Montpellier and the Brewery Quarter. Some venues feature local music or seasonal pop-up events.
What are the most popular events or festivals in Cheltenham?
Cheltenham hosts several widely celebrated festivals, including Cheltenham Literature Festival in autumn, Cheltenham Jazz Festival in late spring, and the Cheltenham Festival, a major horse racing event. Science and music festivals also draw visitors yearly.
Are there family friendly vacation rentals in Cheltenham?
Cheltenham has a range of family-friendly rentals, with many located near parks like Pittville Park or in residential neighbourhoods such as The Suffolks and Charlton Kings. These areas often have easy access to playgrounds and shops.
Quick stats about holiday rentals in Cheltenham

Total holiday rentals
Explore 1,610 holiday rentals in Cheltenham

Nightly prices starting at
Cheltenham holiday rentals start at $14 AUD per night before taxes and fees

Verified guest reviews
Over 57,620 verified reviews to help you choose

Family-friendly holiday rentals
760 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 300 rentals that welcome pets

Rentals with dedicated workspaces
580 properties have a dedicated workspace

Wi-Fi availability
1,570 of Cheltenham holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Cheltenham rentals

4.8 Average rating
Cheltenham stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Cheltenham's top spots, include Cheltenham Racecourse, Pittville Park, and Everyman Theatre
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