
Vacation rentals in Cheltenham
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Top-rated vacation rentals in Cheltenham
Guests agree: these stays are highly rated for location, cleanliness, and more.

Charming Coach House, fab location, highly rated!
A beautifully converted 2-bedroom Coach House in the desirable Leckhampton district of Cheltenham offers stylish living with the added benefit of free on-street parking. Ideally situated near the fashionable Bath Road and just a short stroll from the lively Montpellier & Suffolk areas, guests can enjoy a vibrant atmosphere filled with bars, cafés, restaurants, and boutique shops. The interior boasts high-specification design, making it a perfect blend of comfort and elegance in a prime location.

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.

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).

Best located Flat in Cheltenham + Free Parking
Luxury, modern, 5* apartment in the heart of Montpellier, Cheltenham. Centrally located, just a minutes walk from Cheltenham’s prestigious shopping on The Promenade. Montpellier bustles with bars & restaurants including The Ivy and 131. The apartment is set back off Montpellier Street in The Courtyard so has more privacy. A huge benefit is the free of charge, private parking space. If you’re here for one of Cheltenham’s festivals Imperial Gardens and Montpellier Gardens are opposite the flat.

Rosebank - Stylish 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.

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.

Studio 77 Cheltenham
You will be very welcome to stay in our brand new and beautifully renovated compact and bijou tiny home which is in an easy walk of Cheltenham Town Centre and the Racecourse. We have created a gorgeous space to the rear of our family home that is completely self contained with its own entrance. Studio 77 comprises of a king size bed, kitchenette area, small seating arrangement and a good sized shower room. There is a small private patio area for guests to enjoy on a sunny evening.

Regency flat, private courtyard, free parking
A beautiful recently renovated Regency flat in a grade II* building. We are 5 minutes walk to the city centre and 25 minutes to the Racecourse. The flat has its own front door and private courtyard. Virgin VIP package and high speed broadband plus Sky & BT Sports. One kingsize bed with soft linen sheets, plus one sofa bed for additional guests (book for 3 if you want the sofa bed). Well equipped kitchen. Separate shower room (off living room). Free parking nearby. Nest heating.

Magical cottage set within a woodland glade
Badgers Bothy is set within a woodland glade in the grounds of the 16th century Amberley Farmhouse and provides the most unique and charming country escape. Our idyllic cottage is set on the edge of Minchinhampton Common (located in an AONB) and with miles of footpaths which are perfect for those wishing to explore the Cotswolds. This beautiful cottage exudes an aura of peace and tranquillity and a haven for those wishing to escape the hustle and bustle of a busy life.

Montrose Lodge Regency Apartment, free parking(x2)
A beautifully refurbished Regency-style apartment in a superb central location. With permit street parking included for 2 vehicles within zone 1, extended parking times are available on request. The accommodation has been renovated to a high standard, featuring high ceilings, elegant period detailing, and a spacious, light-filled interior. Just a short walk to Montpellier and the Imperial Gardens, the perfect base to explore wonderful Cheltenham and all it has to offer.

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.
Popular amenities for Cheltenham vacation rentals
Private vacation rentals in Cheltenham

Regency Coach House Cheltenham

Stunning Central 2 Bedroom Apartment with parking

The Mews, Garden Flat free gated parking

Chapel End

* HUGE WOW FACTOR CENTRAL CHELTENHAM ABODE *

Luxury spacious Two Bedroom Apartment, Montpellier

Townhouse luxury, central Grade 2 listed apartment

Cosy cottage style apartment - Cheltenham centre
Other great vacation rentals in Cheltenham

Stunning coach house with walled garden & parking

6 Garden Flat

The Atelier A Stylish Cheltenham Hideaway for 4

The Coach House at Pittville Park

Bright spacious private annex in a great location

Super Stylish 2 Bed House | Cheltenham Town Centre

Guest house close to station

Luxury Central Cheltenham Apartment
When is the best time to visit Cheltenham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$31,797 GYD | G$31,797 GYD | G$44,977 GYD | G$29,078 GYD | G$30,542 GYD | G$32,216 GYD | G$32,634 GYD | G$32,634 GYD | G$31,588 GYD | G$31,588 GYD | G$31,588 GYD | G$33,471 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$2,092 GYD per night before taxes and fees

Verified guest reviews
Over 58,810 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 310 rentals that welcome pets

Rentals with dedicated workspaces
560 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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