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

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.

Jun 5 – 12

G$22,321 GYD per night
Guest favorite

Apartment 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.

Nov 7 – 14

G$29,002 GYD per night
Guest favorite

Condo 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.

Nov 5 – 12

G$23,501 GYD per night

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

4.98 out of 5 average rating, 450 reviews

Beautiful Two Bedroom Apartment

Sep 10 – 17

G$38,018 GYD per night
Guest favorite

Apartment in Gloucestershire

4.97 out of 5 average rating, 170 reviews

Self-contained basement flat in regency home

Apr 3 – 10

G$20,624 GYD per night
Guest favorite

Cabin in Gloucestershire

4.98 out of 5 average rating, 105 reviews

A luxury Cabin within a private garden

Feb 26 – Mar 5

G$30,306 GYD per night
Guest favorite

Home in Cheltenham

4.99 out of 5 average rating, 140 reviews

Detached Cotswold Stone Coach House

Aug 19 – 26

G$20,656 GYD per night
Superhost

Home in Gloucestershire

4.84 out of 5 average rating, 169 reviews

Cosy House Centre of Cheltenham Parking & Garden

Feb 12 – 19

G$24,886 GYD per night
Guest favorite

Home in Gloucestershire

4.95 out of 5 average rating, 101 reviews

Centrally situated house plus off road parking.

Feb 28 – Mar 7

G$25,403 GYD per night
Guest favorite

Apartment in Cheltenham

4.98 out of 5 average rating, 126 reviews

Garden flat close to town centre and Montpellier

Jun 13 – 18

G$27,305 GYD per night
Superhost

Condo in Cheltenham

4.84 out of 5 average rating, 240 reviews

Apartment in the heart of Cheltenham/ Parking

Aug 22 – 29

G$24,316 GYD per night
Guest favorite

Home in Charlton Kings

4.99 out of 5 average rating, 138 reviews

Comfortable and homely, 2 Ensuite Bedrooms Parking

Apr 12 – 19

G$24,158 GYD per night
Guest favorite

Apartment in Gloucestershire

5.0 out of 5 average rating, 31 reviews

Charming Apartment in the heart of Montpellier

May 11 – 18

G$29,335 GYD per night
Guest favorite

Condo in Gloucestershire

4.98 out of 5 average rating, 62 reviews

Entire flat town centre - quiet

Jun 24 – Jul 1

G$23,158 GYD per night
Guest favorite

Apartment in Gloucestershire

5.0 out of 5 average rating, 85 reviews

Rosebank - Stunning apartment in Montpellier.

Oct 18 – 25

G$28,579 GYD per night

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 townhouse rentals with a dedicated workspace in Cheltenham?

    Yes! Work meets play with ease at over 40 townhouse rentals in Cheltenham featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in guesthouse rentals in Cheltenham?

    Experience the best of Cheltenham with our guesthouse rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Destinations to explore

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