
Vacation rentals in Cheltenham
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Top-rated vacation 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.

Elegant regency garden flat with parking
This property is located conveniently in the centre of Cheltenham Spa town, with one parking space. Available from 4pm check in. To 12 noon check out only. The location is very convenient for sight seeing and business trips alike. Two minutes walk to the town centre, restaurants and bars, but tucked away from noise. This property also benefits from spacious rooms and a secluded, private patio garden leading off of the master bedroom. The TV is connected by Wi-Fi to various apps and stations

New Town Centre Studio Flat
Whatever you’re in Cheltenham for, this newly renovated self-contained studio flat is the perfect location for your stay. 5 minutes walk from the high street and from the fantastic bars and restaurants of Montpellier. Round the corner from the hospital and with the beautiful Sandford Park Gardens and Lido on the doorstep. The studio is the ideal bolthole with permit parking available, key pad entry, kitchen area, newly fitted bathroom, bedroom area and sofa (sofa bed for an additional fee).

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 .

Stylish, town centre apartment with free parking
Fantastic location for a city centre stay. Beautiful, regency apartment, with original Georgian features, spacious rooms and luxury interior. Town centre location, 5 minute walk to John Lewis. Also walking distance to Cheltenham Racecourse. The apartment is fully equipped with Wi-Fi, fully heated and powerful water pressure! There are two bedrooms, a fully equipped kitchen, one bathroom, one luxury en-suite, This is a perfect base from which to explore Cheltenham and the Cotswolds.

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 Cosy Terraced Victorian 2 Bedroom Cottage
Enjoy easy access to everything from this perfectly located cottage. Set in the heart of Cheltenham, the property is ideally located to access all the Town has to offer. Within walking distance of the Town Centre, The Suffolks, Montpellier and Bath Road this is perfectly situated for shopping, dining and exploring. A perfect base for business guests or those wishing to explore Cheltenham and The Cotswolds.

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.
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 vacation rentals
Other great vacation rentals in Cheltenham

Private flat, close to town centre with parking

Central Regency basement flat with free parking

Charming house in the centre of town.

MontpellierCourtyard Apt,parking for 1 car.Sleeps4

Bright spacious private annex in a great location

Gorgeous Georgian Cheltenham Flat

Cosy Cheltenham Hideaway

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!
When is the best time to visit Cheltenham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$27,811 GYD | G$26,975 GYD | G$41,612 GYD | G$29,066 GYD | G$30,529 GYD | G$32,202 GYD | G$32,620 GYD | G$32,620 GYD | G$31,575 GYD | G$28,647 GYD | G$29,484 GYD | G$30,111 GYD |
| 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 vacation rentals in Cheltenham

Total vacation rentals
Explore 1,610 vacation rentals in Cheltenham

Nightly prices starting at
Cheltenham vacation rentals start at G$2,091 GYD per night before taxes and fees

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

Family-friendly vacation rentals
760 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 300 rentals that welcome pets

Rentals with dedicated workspaces
580 properties have a dedicated workspace

Wi-Fi availability
1,570 of Cheltenham vacation 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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