Holiday rentals and lettings in Cheltenham

Table of Contents

• At a glance: What should you know about renting a holiday letting in Cheltenham?
• Holiday lettings in Cheltenham: find your perfect retreat
• Exploring Cheltenham: our top recommendations
• Activities: What are the top things to do and see in Cheltenham?

• Regency flats and cottages: Expect elegant Grade II apartments on the Promenade, garden cottages and townhouses with parking, most within walking distance of the town centre.
• Where to base yourself: Montpellier and the Promenade suit first-time visitors, Pittville favours families, and outlying villages give you the Cotswolds on the doorstep.
• Guests rate the location: Our best-reviewed Cheltenham lettings score 9.9+, with visitors praising free parking, quiet Regency streets and the short stroll into town.
• Timing your stay: March race week and the summer festivals fill the town and push prices up, while January and November stay calm and affordable.
• Things to do: Pittville Pump Room, the Cheltenham Festivals, Sandford Parks Lido, the Everyman Theatre and day trips to Sudeley Castle and Gloucester.

Cheltenham's Regency architecture shapes what you can book here. Most self-catering stays are apartments carved out of white stuccoed townhouses in Montpellier, Lansdown and around the Promenade, alongside garden cottages and family townhouses in Pittville and Leckhampton. Browse apartments for a central base, holiday cottages for a quieter village feel, or B&Bs for shorter festival trips. Amenities matter when you are staying in a busy spa town, so look for these:

• Off-street or permit parking, invaluable during race week
• Private gardens or Regency balconies for warm evenings
• Fully fitted kitchens for self-catering between festival events
• Hot tubs in townhouses and countryside cottages
• Pet-friendly rules for walks on Cleeve Hill

Book early for March and October, when the best-equipped properties disappear first.

What are the best areas to stay in Cheltenham?

Montpellier is the strongest all-round base, with boutiques, bars and the Promenade a few minutes' walk away. The table below details regions for specific interests:

What do our guests say?

Guests staying in Cheltenham consistently rate location above everything else: being able to walk home from a festival marquee or a Montpellier restaurant is what earns these properties their scores. Parking is the second most praised feature, since permit and off-street spaces are scarce in the Regency streets. The properties below all sit at 9.9+ on our platform, based on verified reviews left over the past year.

Here are our top-rated holiday lettings from the past year:

1. A Beautiful Grade II Regency Property with Parking - 9.9+: Guests highlight the period proportions and the rare private parking, a short walk from the Promenade in central Cheltenham.
2. Town Centre Penthouse with Hot Tub - 9.9+: A top-floor flat with a balcony and hot tub, praised for its central Cheltenham position and views across the rooftops.
3. Rural Hideaway Five Minutes from Cheltenham Centre - 9.9+: Reviewers repeatedly describe the same surprise: a quiet garden retreat that is still minutes from town.

Cheltenham sits in Gloucestershire on the western edge of the Cotswolds — a stunning Regency spa town beneath the Cleeve Hill escarpment!

✈️What is the best way to get to Cheltenham?

The direct train from London Paddington is the easiest option for most visitors. Here are the most common ways to get to the town:

• Train: Cheltenham Spa station is served by direct Great Western Railway trains from London Paddington in roughly two hours, and by CrossCountry services from Birmingham New Street in about 40 minutes and from Bristol Temple Meads in around 45 minutes. The station sits about a mile south-west of the centre, with a regular bus link and taxi rank outside; during race week extra shuttle services run to the racecourse.
• Car: Cheltenham is signposted from the M5 at junction 10 for the north of town and junction 11 for the centre and the A40 towards Oxford. From London the usual route is the M4 then the M5, around two and a half hours. Parking in the Regency streets is permit-controlled, so a property with off-street parking is worth prioritising; the town's car parks fill quickly in March.
• Plane: Bristol Airport is roughly 45 miles away and Birmingham Airport around 50, both about an hour and a half by car. Birmingham has the advantage of a direct rail link into Cheltenham Spa via Birmingham New Street, making it the simpler choice without a hire car. Gloucestershire Airport, between Cheltenham and Gloucester, handles private and training flights rather than scheduled services.

🥗Where to eat in Cheltenham?

According to Google Maps data and reviews, Prithvi is the best rated restaurant in Cheltenham. Below is a table showing the top 5 highly-rated restaurants hand-picked by our travel experts.

⭐Our guests' recommendation: Our guest traveller Emma Wilson recommends the Purslane Restaurant in Cheltenham: a small Rodney Road dining room built around seafood and seasonal produce, ideal for a quiet dinner after a day at the festivals.

☀️When is the best time to visit?

May and September give you the best balance in Cheltenham: mild weather, open gardens and normal accommodation prices. Two periods change the picture entirely. March brings the four-day jumps racing festival, and the June to October festival season fills the town repeatedly, so both push prices up sharply and reduce availability. Book several months ahead if either date falls within your trip — you won't regret it!

Spring

• Best for: Racegoers in March, and garden walks in the Promenade and Imperial Gardens later in the season.
• Weather: Cool and changeable, warming to around 15°C by May with frequent bright spells.
• Atmosphere: Race week is the busiest of the year, after which the town settles into a quiet, blossom-filled spring.

Summer

• Best for: Festival-goers, families using Sandford Parks Lido and walkers heading up Cleeve Hill.
• Weather: Warm and generally settled, with highs around 22°C and long light evenings.
• Atmosphere: Lively and busy, with the jazz, science and music festivals and the balloon fiesta drawing large crowds.

Autumn and winter

• Best for: The October literature festival, Cotswolds drives and a calm, well-priced break from November onwards.
• Weather: Cooler and wetter, dropping towards 7°C by December, with early mist over the Severn Vale.
• Atmosphere: Busy during literature week, then genuinely quiet, with the Christmas market the only real crowd.

⭐Our Hosts' recommendation: Our Cheltenham local expert, Charlotte, of A Beautiful Grade II Regency Property with Parking recommends coming to visit Sudeley Castle near Winchcombe, about twenty minutes away by car. She suggests pairing the gardens and Katherine Parr's tomb with a walk on part of the Cotswold Way, then returning to Cheltenham for dinner in Montpellier. You can read more about local tips on Charlotte's page.

1. Take the waters at Pittville Pump Room
2. Catch a Cheltenham Festival
3. Swim at Sandford Parks Lido
4. Wander Montpellier and the Promenade
5. Head into the Cotswolds

1. Take the waters at Pittville Pump Room

   The grandest surviving building of Cheltenham's spa era stands at the top of Pittville Park, a colonnaded Greek Revival hall completed in 1830. You can still taste the alkaline spa water from the original pump, then walk the auditorium where the town's fashionable visitors once gathered. The surrounding park has a boating lake, aviary and wide lawns, making it an easy morning with children before heading back into town along the tree-lined avenues of the Pittville estate.

2. Catch a Cheltenham Festival

   Cheltenham runs one of Britain's densest cultural calendars. The Jazz Festival arrives in spring, Science and Music follow in early summer, and the Literature Festival takes over Imperial Gardens each October with hundreds of talks in temporary marquees. Separately, the March jumps racing festival draws enormous crowds to the racecourse below Cleeve Hill. Whichever you choose, book accommodation months in advance and expect the town's restaurants to be fully reserved.

3. Swim at Sandford Parks Lido

   One of the finest surviving 1930s open-air pools in the country, Sandford Parks Lido opens from late spring through the summer with a heated 50-metre main pool, a separate children's pool and lawns for sunbathing. The art deco frontage and clocktower are listed, and the atmosphere on a warm July afternoon is more seaside than landlocked Gloucestershire. Arrive early at weekends, as sessions sell out, and bring a picnic to use the surrounding gardens.

4. Wander Montpellier and the Promenade

   Montpellier is Cheltenham at its most Regency: caryatid figures supporting shopfronts, iron balconies and independent boutiques around a small green. From there the Promenade runs north past Imperial Gardens and the Neptune Fountain towards the Municipal Offices, a continuous terrace of stuccoed façades. The Everyman Theatre on Regent Street, designed by Frank Matcham in 1891, is a short detour and worth checking for an evening performance during your stay.

5. Head into the Cotswolds

   Cheltenham makes an unusually good base for the northern Cotswolds. Winchcombe and Sudeley Castle are twenty minutes away, the Gloucestershire Warwickshire Steam Railway runs heritage services from Toddington, and Tewkesbury adds a medieval abbey and half-timbered streets to the north. Southwards, Stroud and its five valleys reward a slower drive. Gloucester, with its cathedral cloisters, sits fifteen minutes west along the A40.