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.

Guest favourite
Flat in Gloucestershire
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.
25 Nov – 2 DecIndividual Host,
£114 per night
4.93 out of 5 average rating, 140 reviews
Superhost
Home in Gloucestershire
Cosy House Centre of Cheltenham Parking & Garden
Cosy house tucked away on a quiet residential road in the town centre. Fantastically convenient for Cheltenham town centre (less than 5 minutes walk to the town hall), this 2 bed house with a south facing garden is light and bright whilst being cosy and homely. Both bedrooms have king size beds, with an additional small sofa bed in the lounge. There is a downstairs bathroom with walk-in power shower, large dining area and lovely sitting out garden space for when the sun shines! Pets welcome!
23–30 JanIndividual Host,
£100 per night
4.84 out of 5 average rating, 170 reviews
Guest favourite
Apartment in Cheltenham
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.
17–24 AprIndividual Host,
£94 per night
4.98 out of 5 average rating, 302 reviews

Popular amenities for Cheltenham holiday rentals

Stay near Cheltenham's top sights

Cheltenham Racecourse284 locals recommend
Pittville Park157 locals recommend
Everyman Theatre124 locals recommend
Montpellier Gardens56 locals recommend
The Brewery Quarter55 locals recommend
Sandford Parks Lido62 locals recommend

Other great holiday rentals in Cheltenham

Guest favourite
Flat in Gloucestershire
Beautiful basement flat. Leckhampton, Cheltenham
3–10 SeptIndividual Host,
£89 per night
4.98 out of 5 average rating, 168 reviews
Guest favourite
Flat in Cheltenham
Garden flat close to town centre and Montpellier
5–12 AugIndividual Host,
£96 per night
4.98 out of 5 average rating, 126 reviews
Guest favourite
Apartment in Cheltenham
Beautiful Two Bedroom Apartment
26 Feb – 5 MarIndividual Host,
£144 per night
4.98 out of 5 average rating, 450 reviews
Guest favourite
Flat in Cheltenham
Self contained studio apartment close to town
4–11 JanIndividual Host,
£40 per night
4.83 out of 5 average rating, 283 reviews
Superhost
Apartment in Gloucestershire
A self contained apartment on the Bath Road
9–16 JunIndividual Host,
£82 per night
4.89 out of 5 average rating, 268 reviews
Guest favourite
Flat in Gloucestershire
Self-contained basement flat in regency home
12–19 AprIndividual Host,
£81 per night
4.97 out of 5 average rating, 170 reviews
Guest favourite
Cabin in Gloucestershire
A luxury Cabin within a private garden
2–9 AprIndividual Host,
£119 per night
4.98 out of 5 average rating, 104 reviews
Guest favourite
Flat in Cheltenham
Luxury spacious Two Bedroom Apartment, Montpellier
20–27 FebIndividual Host,
£133 per night
4.92 out of 5 average rating, 187 reviews
Guest favourite
Apartment in Gloucestershire
Entire flat town centre - quiet
25 Aug – 1 SeptIndividual Host,
£92 per night
4.98 out of 5 average rating, 61 reviews
Guest favourite
Flat in Gloucestershire
Rosebank - Stunning apartment in Montpellier.
6–13 NovIndividual Host,
£116 per night
5.0 out of 5 average rating, 85 reviews
Guest favourite
Flat in Gloucestershire
Charming Apartment in the heart of Montpellier
9–16 AprIndividual Host,
£130 per night
5.0 out of 5 average rating, 30 reviews
Guest favourite
Holiday home in Gloucestershire
Spacious 1 bedroom apartment with free parking
13–20 JulIndividual Host,
£68 per night
4.98 out of 5 average rating, 84 reviews

Quick stats about holiday rentals in Cheltenham

Total rentals

1.6K properties

Wifi availability

1.6K properties include access to wifi

Rentals with dedicated workspaces

560 properties have a dedicated workspace

Pet-friendly rentals

280 properties allow pets

Family-friendly rentals

760 properties are a good fit for families

Total number of reviews

44K reviews

Your guide to Cheltenham

Welcome to Cheltenham

As a well-to-do town with one foot in the countryside, Cheltenham offers the best of both worlds. This attractive urban hub, best known for its internationally acclaimed festivals and immaculate Regency architecture, fizzes with culture and fine dining, with the rural idylls of the Cotswolds close by.

Mineral springs discovered in the early 18th century built Cheltenham into an early tourist spa town in the style of Bath; it became popular in the 18th and 19th centuries, when latter-day hipsters came to sip the curative waters that bubble up here. Exquisite parks and promenades developed during that era still add to its appeal, including Pittville Park, home to a boating lake, and the magnificent Pittville Pump Room, now an events space and cafe, adorned with fluted Ionic columns and housing the original marble water pump.

In town, leafy shopping districts around the Promenade, Montpellier, and the Suffolks — a square of colourful Georgian townhouses — feature independent stores, bars, cafes, and the Wilson Art Gallery and Museum.


The best time to stay in a holiday rental in Cheltenham

With plenty to see and do indoors, Cheltenham is pleasant at any time of year. The nearby Cotswold villages get packed in summer, so if you want to avoid crowds, dodge Bank Holiday weekends and peak school holiday periods at Easter and in May, July, and August when booking one of Cheltenham’s apartments. A wide range of major festivals also draw many visitors to Cheltenham. Among the big ones are the Cheltenham Literature Festival in October, the Jazz Festival in May, a Science and a Food and Drink festival in June, and the Cricket Festival, held in July in the manicured grounds of Cheltenham College. Others cover film, poetry, and hot air ballooning. Also fun are the regular Sunday street markets and annual fairs of the shopping districts.


Top things to do in Cheltenham

Holst Birthplace Museum

Go back in time to see a typical 19th-century domestic setting at this home of the famous composer. The piano on which he composed his best-known seven-movement suite is still in the music room.

Sandford Parks Lido

The bathing suits may have changed, but the nostalgic design of this 1930s lido is little altered. A 50-metre heated outdoor swimming pool backed by lawns is accompanied by a children’s pool with slides and a paddling pool. In summer it hosts outdoor movie screenings, with deckchairs for the top seats. The main summer period usually runs from May to October, but there are cold-water swimming sessions for hardcore swimmers during the winter.

Sudeley Castle

To the northeast of the city, Sudeley Castle is one of the closest Cotswolds attractions, and an absolute stunner with 10 distinct gardens bursting with flowers. A millennia of history is packed into the castle’s crenellated walls, and Katherine Parr, the last wife of King Henry VIII, is buried in the grounds.

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