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.
Nov 25 – Dec 2
$122 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!
Jan 23 – 30
$104 per night
4.84 out of 5 average rating, 170 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 17 – 24
$98 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 Cheltenham
Beautiful Two Bedroom Apartment
Feb 26 – Mar 5
$160 per night
4.98 out of 5 average rating, 450 reviews
Guest favorite
Guesthouse in Cheltenham
Private Annexe - double bedroom with en-suite
Mar 24 – 31
$75 per night
4.97 out of 5 average rating, 220 reviews
Guest favorite
Apartment in Gloucestershire
Beautiful basement flat. Leckhampton, Cheltenham
Sep 3 – 10
$97 per night
4.98 out of 5 average rating, 168 reviews
Guest favorite
Apartment in Cheltenham
Garden flat close to town centre and Montpellier
Aug 5 – 12
$103 per night
4.98 out of 5 average rating, 126 reviews
Superhost
Condo in Gloucestershire
A self contained apartment on the Bath Road
Jun 9 – 16
$91 per night
4.89 out of 5 average rating, 268 reviews
Guest favorite
Cabin in Gloucestershire
A luxury Cabin within a private garden
Apr 2 – 9
$127 per night
4.98 out of 5 average rating, 104 reviews
Guest favorite
Apartment in Gloucestershire
Self-contained basement flat in regency home
Apr 12 – 19
$87 per night
4.97 out of 5 average rating, 170 reviews
Guest favorite
Apartment in Cheltenham
Luxury spacious Two Bedroom Apartment, Montpellier
Feb 20 – 27
$140 per night
4.92 out of 5 average rating, 187 reviews
Guest favorite
Condo in Gloucestershire
Entire flat town centre - quiet
Aug 25 – Sep 1
$97 per night
4.98 out of 5 average rating, 61 reviews
Guest favorite
Apartment in Gloucestershire
Rosebank - Stunning apartment in Montpellier.
Nov 6 – 13
$118 per night
5.0 out of 5 average rating, 85 reviews
Guest favorite
Apartment in Gloucestershire
Charming Apartment in the heart of Montpellier
Apr 9 – 16
$136 per night
5.0 out of 5 average rating, 30 reviews
Guest favorite
Vacation home in Gloucestershire
Spacious 1 bedroom apartment with free parking
Jul 13 – 20
$72 per night
4.98 out of 5 average rating, 84 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