Holiday houses in Cheltenham

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Top-rated holiday rentals in Cheltenham

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Guest favourite

Apartment 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.

6 – 13 Sept

$1,505 AUD total

Guest favourite

Condo in Cheltenham

4.98 out of 5 average rating, 306 reviews

Footsteps from the town & parks (+ hamper/parking)

Little Portland is a central 700 sq ft self-contained Grade-II apartment moments from the heart of town & Pittville Park (a historic area, with two lakes, cafes and a kids' play area). If you're coming to visit the town, races, festivals or Cotswolds, it's ideal. Parking centrally can be tricky so we offer guests 2 free parking permits. You'll also receive a food hamper with beer or cider, nibbles, brioche, fruit, milk & juice. The apartment has a cooling system for the summer months.

7 – 14 Nov

$1,238 AUD total

Guest favourite

Condo in Gloucestershire

4.97 out of 5 average rating, 230 reviews

MontpellierCourtyard Apt,parking for 1 car.Sleeps4

Our courtyard apartment is set right in the heart of beautiful Regency Montpellier. Home to countless restaurants, bars and boutiques, there is something for everyone. Located directly behind the vibrant Suffolk Parade, with its eclectic mix of Independent shops, galleries and bars. It 's a 2 minute walk to Montpellier Gardens, home of some of the Festivals that Cheltenham is renowned for. Imminently approaching is The Food & Drink Festival, followed by The Jazz Festival in early July.

11 – 18 Sept

$2,028 AUD total

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

$1,540 AUD total

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.

12 – 19 Oct

$1,412 AUD total

Guest favourite

Apartment 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

$91 AUD per night

Guest favourite

Condo in Gloucestershire

4.97 out of 5 average rating, 150 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.

21 – 28 Feb

$1,126 AUD total

Guest favourite

Guesthouse 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.

4 – 11 Dec

$947 AUD total

Guest favourite

Condo in Gloucestershire

4.88 out of 5 average rating, 222 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.

16 – 23 Jan

$851 AUD total

Guest favourite

Apartment in Cheltenham

4.83 out of 5 average rating, 294 reviews

Self contained studio apartment close to town

This self contained studio flat is close to the town centre, racecourse, restaurants, nightlife, and countryside. There is off road private parking, a small but fully equipped kitchen and a shower-bathroom. It is ideal for couples, solo adventurers, and business travellers, especially those working on contracts in the area. I provide tea,coffee, milk etc there are also all the basics. Iron and hairdryer are also provided.

17 – 24 Apr

$531 AUD total

Guest favourite

Apartment in Gloucestershire

4.97 out of 5 average rating, 171 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.

12 – 19 Aug

$1,075 AUD total

Guest favourite

Guesthouse 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!

29 July – 5 Aug

$1,236 AUD total