House holiday rentals in Cheltenham

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Top-rated house rentals in Cheltenham

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Guest favourite

Home in Gloucestershire

4.98 out of 5 average rating, 245 reviews

5* Luxury Modern Two Bedroom Townhouse

The house has been newly refurbished with contemporary décor and furnishings to create a cosy luxurious space. Décor and artwork reflect themes of nature and natural materials have been used as much as possible as well as recycled furnishings. Located in the heart of Cheltenham and with a dedicated parking space the property is perfectly suited for couples singles young families or the business traveler looking to have good walking access to the town, festivals the theatre or buses to the Races.

24–29 Jun

$291 SGD per night

Guest favourite

Home in Boddington

4.98 out of 5 average rating, 100 reviews

Stunning Victorian Mill, 3 BDR

Oriri presents Boddington Mill, a stunning countryside retreat steeped in history and rural charm. Multiple levels intersect the original mill parts for a generous and sociable living space. A south-facing garden includes alfresco dining, wood-fired hot tub, and large lawn, home to fruit-bearing trees and wildlife. Bedrooms feature luxury bedding; vaulted, oak-beamed ceilings; and period windows. Guests will enjoy fine comforts, modern media, and a kitchen fit for the highest culinary ambitions.

12–19 Apr

$833 SGD per night

Superhost

Home in Gloucestershire

4.87 out of 5 average rating, 107 reviews

Unique luxury boutique Cheltenham town centre

Experience refined living at Milton House, a chic, 2-bedroom, 2-bath oasis in Lansdown Walk, Cheltenham. Enjoy an open-concept space with floor-to-ceiling doors leading to a stunning terrace, designed by top London and Cotswolds designers. The loft is furnished with high-quality decor, Egyptian cotton linens, and luxurious White Company toiletries. Steps away from upscale shopping, nightlife, and renowned festivals, Milton House also provides easy access to the picturesque Cotswolds countryside!

27 Nov – 4 Dec

$494 SGD per night

Guest favourite

Home in Woodmancote

4.98 out of 5 average rating, 126 reviews

The Cotswold Holiday Home.

Innisfree was built in 1907 from local Cotswold stone, recently extended and renovated to a high standard with modern contemporary fittings making for a very warm and comfortable holiday home. Bedrooms have been fitted with new beds for flexible accommodation of singles and superking size doubles. A single child’s bed and travel cot may be added to the master suite. A double garage provides parking for two cars. The house has large enclosed gardens with outside furniture and BBQ fireplace.

23–30 Oct

$218 SGD per night

Guest favourite

Home in Gloucestershire

4.98 out of 5 average rating, 149 reviews

Granley Road Beautiful Victorian House

A beautiful and spacious 2 bedroom Victorian family home perfectly placed on the edge of the beautiful Cotswolds, with on road free parking. Easy access to Cheltenham town centre via a bus ride or short walk. Ten minute walk to the train station. Great location for the Theatre, Shopping, Cheltenham Racecourse, Cheltenham Festivals, and for business commuters. Visit Gloucester for the Rugby and the Cathedral made famous by the Harry Potter Movies. Close to the Forest of Dean and Malvern.

24–31 Mar

$266 SGD per night

Guest favourite

Home in Gloucestershire

5.0 out of 5 average rating, 157 reviews

Delightful Coach House - Great Location - 5.0*

A highly rated , stylishly converted, detached 2-Bed Coach House. Perfectly located in the popular Leckhampton district of Cheltenham, just a stone’s throw away from the trendy Bath Road area of the town. Conveniently located for the town centre and within a pleasant 10 minutes stroll to the Montpellier & Suffolk’s areas of Cheltenham, famed for vibrant bars, cafés, restaurants, specialist shops, Regency buildings and Parks. Newly refurbished & equipped to high specification throughout.

20–27 Aug

$310 SGD per night

Guest favourite

Home in England

4.94 out of 5 average rating, 249 reviews

Cotswold Garden Accomodation near Racecourse/Univ

Home from home , self contained, modern airy accomodation close to Cheltenham. The park & ride bus is 500m from us provides easy travel into the town centre and direct to Cheltenham Railway Station, or leave your car in our parking space . A great base to explore the Cotswolds with all the bars and restaurants of the Regency town close by. Stretch your legs in the beautiful Pittville Park and Pump rooms about ten minutes stroll from, perfect base for cycling and walking in the Cotswolds.

12–19 Aug

$144 SGD per night

Guest favourite

Home in Gloucestershire

4.98 out of 5 average rating, 109 reviews

7 Diamond Jubilee, Cheltenham

Diamond Jubilee is a unique fully electric property located in a quiet little mews street but a short walk to the bars, shops, and restaurants of the vibrant area of The Suffolks and Montpellier. Cheltenham has a thriving cultural scene and hosts numerous festivals throughout the year such as the jazz, food and drink, literature, and science. Undoubtedly, the highlight of the year is the annual racing festival, The Gold Cup at Cheltenham Racecourse. Newly renovated bathroom.

23–30 Oct

$200 SGD per night

Guest favourite

Home in Amberley

5.0 out of 5 average rating, 145 reviews

Magical cottage set within a woodland glade

Badgers Bothy is set within a woodland glade in the grounds of the 16th century Amberley Farmhouse and provides the most unique and charming country escape. Our idyllic cottage is set on the edge of Minchinhampton Common (located in an AONB) and with miles of footpaths which are perfect for those wishing to explore the Cotswolds. This beautiful cottage exudes an aura of peace and tranquillity and a haven for those wishing to escape the hustle and bustle of a busy life.

24 Feb – 3 Mar

$221 SGD per night

Guest favourite

Home in Cheltenham

4.87 out of 5 average rating, 122 reviews

The Coach House, Back Montpellier Terrace,

Our delightful Coach House is set in a quiet location within the trendy area of Montpellier in the heart of Cheltenham just minutes from restaurants, bars, fashion shops, the Promenade and beautiful local parks. The Coach House is ideally situated for all the festivals for which Cheltenham is renowned. There is one parking space for a small/medium size car adjoining the Coach House. Sorry but the Coach House is not suitable for infants and children and pets.

20–27 Oct

$238 SGD per night

Guest favourite

Home in Prestbury

4.88 out of 5 average rating, 108 reviews

Cheltenham accommodation -self-catering-2 bedrooms

Welcome to Cheltenham and to our new beautiful extension! You will have a place of your own with 2 large bedrooms, kitchen, dining/living room looking over our large, beautiful garden with views of Cleeve hill and the Cotswold. You are also welcome to use our large garden to have meals, drinks, BBQ or just relax (while your kids running around, if any) All rooms have beautiful views.

4–11 Nov

$195 SGD per night

Guest favourite

Home in Leckhampton

4.89 out of 5 average rating, 159 reviews

A Unique, Spacious & Modern Cheltenham Hideaway

This quirky red brick 18th century coach house has been finished to a high standard, offering a luxurious hideaway on a quiet lane in Leckhampton. Just one street away from the bustling Bath Road high street, you can easily walk to the local cafes, shops, bars, boutiques and restaurants. The Coach House is a fabulous hidden retreat for those wanting to visit Cheltenham.

13–20 Oct

$162 SGD per night