
Holiday rentals 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.

Stunning Regency flat with parking town centre
This Beautiful Regency 1 bed apartment with 1 parking spot (available from 4pm check in to 12 noon check out please) is suitable for adults only. House is situated within walking distance of Cheltenham racecourse, all shops, parks, restaurants and theatres. It has been recently been refurbished . Lovely new carpets and furniture throughout…. Sitting room, kitchen are on one floor with a fabulous double bedroom and a lovely luxury bathroom with shower and large bath tub on the top floor.

The Garden House in Kingsholm, Gloucester
The Garden House is a lovely single room annex with independent access, en-suite bathroom and shower. Light, cosy, and simply furnished, set in the garden of a residential home near the centre of Gloucester, it's a quiet space to relax or work. Driveway parking available. A two-minute walk to the famous Kingsholm rugby stadium and food shops, ten minutes to city centre, bus and train stations, cathedral, Quays shopping outlet, restaurants and historic docks. Easy bus route to Cheltenham.

Rosebank - Spacious apartment in Montpellier.
Welcome to Rosebank, a self-contained basement apartment with a spacious, homely and creative vibe. The bedroom has a king size sleigh bed. There is a private entrance at the front and access at the back to your own south facing courtyard. Where possible a free guest parking permit can be arranged. Montpellier is a vibrant and chic area with excellent restaurants, bars & boutique shops. Easy access to the outstanding cotswold countryside makes it the perfect location for holidays or work.

The Best address in Montpellier, Cheltenham
This wonderfully spacious apartment is situated in the heart of fashionable Montpellier where you will find an incredible array of Independent shops and prestigious eateries such as The Ivy ,Giggling Squid , The Daffodil and the renowned Michelin starred Le Champignons Savage,a new find is Kibousushi located about 200 metres from the apartment ,a new find for us and an amazing Japanese restaurant ,but you have to book in advance . The home of horse racing is just a 20 minute walk .

7 Diamond Jubilee, Cheltenham
Diamond Jubilee is a unique fully electric property located in a quiet little mews street but a short walk to the bars, shops, and restaurants of the vibrant area of The Suffolks and Montpellier. Cheltenham has a thriving cultural scene and hosts numerous festivals throughout the year such as the jazz, food and drink, literature, and science. Undoubtedly, the highlight of the year is the annual racing festival, The Gold Cup at Cheltenham Racecourse. Newly renovated bathroom.

Beautiful & Vast Central Apartment Free Parking
Welcome to my spacious apartment within Montpellier! This exceptional ground floor living space offers a comfortable and inviting atmosphere, providing you with the perfect place to call home. Located in a desirable neighborhood, this apartment is conveniently situated close to a variety of dining, shopping, and entertainment options. With easy access to major transportation routes, you'll have no trouble exploring the surrounding area and beyond

Central Regency basement flat with free parking
* Stylish, cosy and clean basement flat in a listed Regency townhouse * 5 minute walk to the heart of Cheltenham - The Prom * Great night’s sleep in a comfortable double bed * Living room with small dining table * Well-equipped kitchen * Separate bathroom with walk-in shower * Free wi-fi * Free parking right outside the flat * Sofa bed for 3rd guest if required (additional fee) * Ideal base for business/leisure, solo travellers or couples

The Garden retreat
The Garden room has its own front and back door, and access to a lovely south facing garden. It has a kitchenette and en suite. It has a very comfortable king-size bed. We are 10-15 minutes walk from the town centre and have views onto Cleeve Hill the highest point of the Cotwolds. There are good local pubs, a national award winning fish and chip shop and a supermarket all nearby. Perfectly situated for all Cheltenham festivals.

Entire quiet flat town centre - Free parking
First floor refurbished flat accessible with lift, ideally situated a few steps away from the High Street and all commodities pubs restaurants shops. Very quiet flat days and nights (facing backyard). Modern and stylish kitchen with dining area. Sleeping arrangements: -Double bed with built-in wardrobes. -Living room with best quality convertible sofa. Free Wifi, large TV in the living room and bedroom with Netflix & Prime.
Cheltenham Superb 2 Bed Townhouse, The Suffolks
Recently refurbished, Traditionally Modern Townhouse in the Suffolk’s area of Cheltenham ... an area often referred to as the Notting Hill of Cheltenham, with an eclectic mix of independent cafes, bars, restaurants and shops, all on your doorstep Virgin Media SuperFast Fibre Broadband throughout, ideal for streaming and home working purposes.

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

Stylish 1 Bed Flat in Central Cheltenham

Quiet town centre double bedroom with parking

Super Stylish 2 Bed House | Cheltenham Town Centre

Stylish, town centre apartment with free parking

St Marg’s Hideaway; Grade II listed luxury apartment in the heart of Cheltenham - gateway to the Cotswolds! Sleeps 4 - outdoor seating and free private parking!

Chic 1 Bed Apartment in Montpellier Free Parking

Lovely self-contained annexe with private entrance

Clean & comfy period house close to town centre.
When is the best time to visit Cheltenham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $171 SGD | $166 SGD | $256 SGD | $178 SGD | $187 SGD | $198 SGD | $200 SGD | $200 SGD | $194 SGD | $176 SGD | $181 SGD | $185 SGD |
| 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 1,600 holiday rentals in Cheltenham

Nightly prices starting at
Cheltenham holiday rentals start at $13 SGD per night before taxes and fees

Verified guest reviews
Over 55,020 verified reviews to help you choose

Family-friendly holiday rentals
750 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 300 rentals that welcome pets

Rentals with dedicated workspaces
570 properties have a dedicated workspace

Wifi availability
1,550 of Cheltenham holiday rentals include wifi 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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- Cotswolds AONB
- University of Oxford
- Blenheim Palace
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- Silverstone Circuit
- Lower Mill Estate
- Cheltenham Racecourse
- West Midland Safari Park
- Cadbury World
- Sudeley Castle
- Ludlow Castle
- Waddesdon Manor
- Bath Abbey
- No. 1 Royal Crescent
- Coventry Cathedral
- Puzzlewood
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- Hereford Cathedral
- Royal Shakespeare Theatre
- Dyrham Park
- Lacock Abbey
- Manor House Golf Club
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