Holiday rentals in Cheltenham

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Top-rated holiday rentals in Cheltenham

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Flat in Gloucestershire

4.93 out of 5 average rating, 148 reviews

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.

30 Nov – 7 Dec

$186 SGD per night

Guest favourite

Home in Gloucestershire

5.0 out of 5 average rating, 157 reviews

Delightful Coach House - Great Location - 5.0*

A highly rated , stylishly converted, detached 2-Bed Coach House. Perfectly located in the popular Leckhampton district of Cheltenham, just a stone’s throw away from the trendy Bath Road area of the town. Conveniently located for the town centre and within a pleasant 10 minutes stroll to the Montpellier & Suffolk’s areas of Cheltenham, famed for vibrant bars, cafés, restaurants, specialist shops, Regency buildings and Parks. Newly refurbished & equipped to high specification throughout.

13–20 Jun

$243 SGD per night

Guest favourite

Home in Gloucestershire

4.98 out of 5 average rating, 109 reviews

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.

23–30 Oct

$196 SGD per night

Guest favourite

Cottage in Gloucestershire

4.94 out of 5 average rating, 109 reviews

Cheltenham - Cosy Bath Road Cottage

A beautifully presented cosy and welcoming, newly refurbished, 2 bedroom Georgian cottage located just off the desirable Bath Road. The local area has plenty of great shops, restaurants and pubs. In addition, trendy Montpellier is a short walk away. The historical spa town of Cheltenham, in the centre of the Costwolds, has a buzzing atmosphere and hosts many events throughout the year, with the famous racecourse is only a 10 minute drive away.

2–9 Oct

$171 SGD per night

Guest favourite

Flat in Gloucestershire

4.93 out of 5 average rating, 224 reviews

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

$85 SGD per night

Guest favourite

Apartment in Gloucestershire

4.97 out of 5 average rating, 149 reviews

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.

22 Feb – 1 Mar

$139 SGD per night

Guest favourite

Guest house in Cheltenham

4.97 out of 5 average rating, 235 reviews

Private Annexe - double bedroom with en-suite

A detached annexe in Cheltenham with double bedroom and en-suite bathroom, this newly refurbished self-contained property has a private entrance via side gate and free on road parking. There are tea and coffee making facilities, mini fridge, flat screen smart TV and free Wi-Fi. 5 mins walk from Cheltenham train station - on race days there is a free shuttle from the station to the racecourse. Prices vary depending on time of year.

25 Jun – 2 Jul

$112 SGD per night

Guest favourite

Apartment in Gloucestershire

4.88 out of 5 average rating, 220 reviews

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. 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.

5–12 Jun

$117 SGD per night

Guest favourite

Guest house in Cheltenham

4.96 out of 5 average rating, 153 reviews

Mulberry is our self contained small town house

Located a short walk from the centre of Cheltenham, this small town house has its own entrance, a ground floor living space with discreetly concealed kitchen and a first floor double bedroom with an en suite luxury shower room. We have enhanced our cleaning routine and thoroughly disinfect all the property between visitors. We closely follow the AIRBNB and GOVERNMENT guidelines for the safety of us all.

26 Aug – 2 Sep

$175 SGD per night

Guest favourite

Flat in Gloucestershire

4.97 out of 5 average rating, 170 reviews

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.

18–25 Jun

$132 SGD per night

Guest favourite

Guest house in Cheltenham

4.87 out of 5 average rating, 454 reviews

Self-contained unit, parking & 3 mins walk to town

Period apartment with own private access, feature fireplace with wood-burning stove and black beams in ceiling. Modern kitchen and ensuite wet room. Fully equipped with all necessary kitchen equipment and toiletries. Use of private courtyard garden with table and chairs. Off street parking on drive. At end of quiet cul-de-sac next to beautiful park. Very peaceful with no traffic noise. Very comfy bed!

16–23 Sep

$149 SGD per night

Guest favourite

Flat in Gloucestershire

4.95 out of 5 average rating, 111 reviews

Gorgeous Georgian Cheltenham Flat

Ensuite bedroom and large living room dining area. Free Parking, on a private driveway. 15 mins walk to Cheltenham Town Hall. The house was built in 1835 and converted in 2017. This basement flat is in a great location, just off Bath Road. The property offers excellent modern accommodation with open plan lounge, dining room & full working kitchen. Separate double bedroom and ensuite bathroom.

22–29 Jul

$136 SGD per night