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

4.98 out of 5 average rating, 169 reviews

Beautiful basement flat. Leckhampton, Cheltenham

Beautiful self contained basement flat with own entrance. Open plan living area with pull down ‘Murphy bed’ (please ask when booking if you would like to use this bed as it requires host assembly). Full kitchen-dishwasher,oven,microwave & washing machine. Bedroom with wardrobe, dressing table and king size bed- can be separated into 2 singles on request at time of booking. Wet room with shower. Shampoo,conditioner,shower gel and towels provided. Tea,coffee,milk and breakfast items provided.

11–18 Jun

£90 per night
Guest favourite

Flat in Gloucestershire

4.93 out of 5 average rating, 140 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.

24 Apr – 1 May

£114 per night
Guest favourite

Apartment in Cheltenham

4.98 out of 5 average rating, 303 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.

5–12 Nov

£94 per night

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

4.97 out of 5 average rating, 170 reviews

Self-contained basement flat in regency home

3–10 Apr

£81 per night
Guest favourite

Guest house in Cheltenham

4.97 out of 5 average rating, 223 reviews

Private Annexe - double bedroom with en-suite

28 Jun – 5 Jul

£69 per night
Superhost

Home in Gloucestershire

4.84 out of 5 average rating, 169 reviews

Cosy House Centre of Cheltenham Parking & Garden

17–24 Feb

£100 per night
Guest favourite

Cabin in Gloucestershire

4.98 out of 5 average rating, 105 reviews

A luxury Cabin within a private garden

26 Feb – 5 Mar

£119 per night
Guest favourite

Home in Gloucestershire

4.95 out of 5 average rating, 101 reviews

Centrally situated house plus off road parking.

22–29 Sept

£102 per night
Guest favourite

Flat in Cheltenham

4.98 out of 5 average rating, 126 reviews

Garden flat close to town centre and Montpellier

13–18 Jun

£108 per night
Guest favourite

Home in Cheltenham

4.99 out of 5 average rating, 140 reviews

Detached Cotswold Stone Coach House

2–9 Aug

£82 per night
Guest favourite

Home in Charlton Kings

4.99 out of 5 average rating, 138 reviews

Comfortable and homely, 2 Ensuite Bedrooms Parking

12–19 Apr

£96 per night
Superhost

Apartment in Cheltenham

4.84 out of 5 average rating, 240 reviews

Apartment in the heart of Cheltenham/ Parking

19–26 Jun

£92 per night
Guest favourite

Apartment in Gloucestershire

4.98 out of 5 average rating, 62 reviews

Entire flat town centre - quiet

24 Jun – 1 Jul

£92 per night
Guest favourite

Flat in Gloucestershire

5.0 out of 5 average rating, 31 reviews

Charming Apartment in the heart of Montpellier

11–18 May

£118 per night
Guest favourite

Flat in Gloucestershire

5.0 out of 5 average rating, 85 reviews

Rosebank - Stunning apartment in Montpellier.

18–25 Oct

£117 per night

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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