Vacation rentals in Cheltenham

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Top-rated vacation rentals in Cheltenham

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

Guest favorite
Apartment 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.
Aug 31 – Sep 7
ﺩ.ﺇ447 per night
4.93 out of 5 average rating, 140 reviews
Guest favorite
Apartment in Cheltenham
Stunning Regency Retreat; parking+heated pool
A peaceful and spacious 1200 sqft two bed apartment taking up the entire top floor of our eight bedroomed Regency Villa, on one of central Cheltenham's finest residential roads. Perfectly situated and providing the best of both worlds : a short stroll, 0.8 miles, to the shops, bars and restaurants of Cheltenham, combined with a relaxing private garden and heated swimming pool. The Cotswold Way, for walking trails, is close by. A great base for girls weekends, families, and couples.
Aug 19 – 26
ﺩ.ﺇ775 per night
4.93 out of 5 average rating, 275 reviews
Guest favorite
Condo 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.
Apr 21 – 28
ﺩ.ﺇ362 per night
4.98 out of 5 average rating, 302 reviews

Popular amenities for Cheltenham vacation 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 vacation rentals in Cheltenham

Guest favorite
Condo in Gloucestershire
Stylish apartment in the heart of Cheltenham
Dec 24 – 31
ﺩ.ﺇ354 per night
4.97 out of 5 average rating, 149 reviews
Guest favorite
Apartment in Gloucestershire
Beautiful Apartment close to town centre
May 30 – Jun 6
ﺩ.ﺇ618 per night
4.95 out of 5 average rating, 118 reviews
Guest favorite
Home in Cheltenham
Detached Cotswold Stone Coach House
Jun 3 – 10
ﺩ.ﺇ318 per night
4.99 out of 5 average rating, 140 reviews
Superhost
Home in Gloucestershire
Cosy House Centre of Cheltenham Parking & Garden
Nov 18 – 25
ﺩ.ﺇ382 per night
4.84 out of 5 average rating, 170 reviews
Guest favorite
Apartment in Gloucestershire
Luxury garden flat in the heart of Cheltenham
Apr 7 – 14
ﺩ.ﺇ412 per night
4.88 out of 5 average rating, 230 reviews
Guest favorite
Apartment in Cheltenham
Luxury spacious Two Bedroom Apartment, Montpellier
May 22 – 29
ﺩ.ﺇ515 per night
4.92 out of 5 average rating, 187 reviews
Guest favorite
Townhouse in Gloucestershire
Beautiful Townhouse Close to Montpellier, Sleeps 6
Sep 27 – Oct 4
ﺩ.ﺇ803 per night
4.96 out of 5 average rating, 251 reviews
Guest favorite
Apartment in Gloucestershire
Beautiful basement flat. Leckhampton, Cheltenham
Sep 3 – 10
ﺩ.ﺇ355 per night
4.98 out of 5 average rating, 168 reviews
Superhost
Apartment in Gloucestershire
Modern Artistic Apartment - Centre Of Cheltenham
Mar 21 – 28
ﺩ.ﺇ304 per night
4.83 out of 5 average rating, 163 reviews
Guest favorite
Apartment in Gloucestershire
Self-contained basement flat in regency home
Mar 20 – 27
ﺩ.ﺇ318 per night
4.97 out of 5 average rating, 170 reviews
Guest favorite
Apartment in Cheltenham
Studio apartment in Cheltenham .
May 20 – 27
ﺩ.ﺇ228 per night
4.97 out of 5 average rating, 68 reviews
Guest favorite
Apartment in Gloucestershire
Charming Apartment in the heart of Montpellier
Jun 8 – 15
ﺩ.ﺇ451 per night
5.0 out of 5 average rating, 30 reviews

Quick stats about vacation 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

Frequently Asked Questions

  • How is the weather in Cheltenham?

    Cheltenham experiences a temperate maritime climate with mild to warm summers averaging 70°F (21°C) and cool winters around 43°F (6°C). Expect the most rainfall in October and November.

  • What are some of the best things to do in Cheltenham?

    Visitors to Cheltenham can explore the Regency architecture, soak in the vibrant arts scene at the Everyman Theatre, or enjoy a day in the gardens of Cheltenham Spa. Other popular activities include discovering local wildlife at the Cotswold Wildlife Park and exploring the Gloucestershire Warwickshire Steam Railway.

  • What is the best time of year to visit Cheltenham?

    Cheltenham is often visited in March when it hosts the popular Cheltenham Festival, a four-day horse racing event. Additionally, the Cheltenham Literature Festival in October attracts many lovers of literature.

  • What are the best places to stay in Cheltenham?

    Montpellier is a popular area with its boutique shops and Regency architecture. Another favourite is Tivoli, known for its traditional pubs and Victorian houses. The centre of Cheltenham is ideal for those wanting to stay within walking distance of the main attractions.

  • What are the best places to visit in Cheltenham?

    Cheltenham has several popular places to explore. These include the Wilson Art Gallery and Museum, Cheltenham Town Hall, and the beautiful Montpellier District with its boutiques and cafes. Don't miss a stroll in the Pittville Park, home to the largest ornamental lake in Cheltenham.

  • What are some hiking trails in Cheltenham?

    Cheltenham is a gateway to the Cotswolds, offering a variety of hiking trails. The Cotswold Way is a 100 mile (160 km) long trail that winds through picturesque villages and countryside. Moreover, the Leckhampton Hill and Charlton Kings Common trail is a favourite among locals.

  • What are some family activities to do in Cheltenham?

    For family-friendly fun, the Cotswold Wildlife Park, the Jet Age Museum, and the Sandford Parks Lido, a heated outdoor swimming pool, are often recommended. Families also love exploring the interactive exhibits at the Wilson Art Gallery and Museum.

  • What are some of the best day trip ideas in Cheltenham?

    From Cheltenham, visitors can easily explore the quintessential English countryside. Day trips to the nearby Cotswolds, Bourton-on-the-Water, known as the Venice of the Cotswolds, and the Roman city of Bath are frequently suggested.

  • Are there house rentals with a dedicated workspace in Cheltenham?

    Yes! Work meets play with ease at over 230 house rentals in Cheltenham featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in bed and breakfast rentals in Cheltenham?

    Experience the best of Cheltenham with our bed and breakfast rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Destinations to explore

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  2. United Kingdom
  3. England
  4. Gloucestershire
  5. Cheltenham