Cottages in Cheltenham
An elegant town situated at the western edge of the Cotswolds, Cheltenham is a popular location for a weekend break. Find a self catering holiday cottage in Cheltenham, and spend a few days admiring the beautiful architecture, discovering the parks and gardens, and of course, indulging in a little retail therapy.
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 12 self catering cottages in Cheltenham
7 nights from £1168
The Yew Trees
58623 bedroom, dog friendly self catering cottage near Cheltenham.
This charming holiday cottage, nestled in the peaceful countryside just outside Cheltenham and the gorgeous Cotswolds, offers the perfect retreat for a tranquil getaway. Set in a r...
7 nights from £1168
7 nights from £840
Tower View
57352 bedroom self catering cottage in Broadway.
Situated in the highly desirable Cotswold village of Broadway, Tower View, a charming two bedroom annexe, is a delightful cottage and makes the perfect couple's retreat. Meticulous...
7 nights from £840
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40% off
22 Jun 2026 - 26 Jun 2026
£844.50 £506.70
7 nights from £653
Botloes Farm Barn
57112 bedroom, dog friendly self catering cottage near Newent.
This charming lodge style converted barn is beautifully styled to embrace the woodland that surrounds it and boasts a luxurious sauna in the garden. Botloes Farm Barn is situated w...
7 nights from £653
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30% off
23 Jun 2026 - 3 Jul 2026
From £1184.29 £829.00
7 nights from £2310
Wold House
56385 bedroom, dog friendly self catering cottage in Blockley
Beautifully situated in an elevated position overlooking the serene Cotswold village of Blockley, experience exquisite luxury and charm in this breathtaking five bedroom holiday ho...
7 nights from £2310
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £818 *
The Woodlands
61353 bedroom, dog friendly self catering cottage near Great Malvern.
A traditional bolthole with contemporary flair is just what you will find at The Woodlands. Cosseted in over two acres of gardens, this is a luxury retreat for families and friends...
7 nights from £818 *
7 nights from £556
The Farthings
56772 bedroom self catering cottage near Moreton-In-Marsh
If you are looking for a cosy Cotswold bolthole to escape to, then The Farthings won't disappoint. This pretty terraced cottage sits nestled amongst its neighbours and is located j...
7 nights from £556
7 nights from £588 *
Kettle Cottage
60262 bedroom self catering cottage in Chipping Campden.
Kettle Cottage is a charming two bedroom, two bathroom cottage tucked down a little cobbled alley and resting in the very heart of Chipping Campden, just a stone’s throw from the t...
7 nights from £588 *
7 nights from £924 *
Park Farm Cottage
4558Detached 4 bedroom, dog friendly holiday cottage near Malmesbury, Wiltshire
If uninterrupted countryside views enjoyed from a beautiful farmhouse with space for all the family sounds appealing, then look no further than Park Farm Cottage. This delightful, ...
7 nights from £924 *
7 nights from £394 *
The Gatehouse
60332 bedroom self catering cottage in Malmesbury.
If ever a property was the epitome of luxury town living, then The Gatehouse is it. Located in the historic market town of Malmesbury it provides the perfect base for couples or fa...
7 nights from £394 *
From £760 per night
King John's Palace
57306 bedroom self catering home near Burford
Stay in style at King John's Palace, where kings and queens resided before you. A beautiful historic home close to the quintessential Cotswold town of Burford. This unique hidden g...
From £760 per night
We’re here to help you find your perfect place to stay 7 days a week.
Open 7 days a week
Call our office on 01326 555555, email hello@classic.co.uk or click on the live chat button in the bottom right of the screen to talk directly to someone who can help with choosing your holiday. If you have any questions or need a hand with the booking process, we’re happy to help.
After booking your holiday with us, you’ll receive your holiday details two weeks before your holiday. This also includes our emergency out of hours phone number for when the office is closed, so we’re never more than a phone call away!
A number of fantastic festivals take place in the town; Cheltenham Literature Festival, Cheltenham Music Festival, and the Cheltenham Festival (to name just a few!). Shopping is a popular pastime here, with many independent boutiques and high street shops situated in the town centre. And we must also mention the wonderful selection of places to eat, with something to suit all palettes, from fine dining to street food.
There are many beautiful parks and gardens to explore if you fancy a slice of nature on your holiday. Pittville Park is a lovely place to spend an afternoon, being home to the grand Pittville Pump Room and a children’s play area. The Cotswolds is on your doorstep - ideal for exploring some of the many wonderful towns and villages, including Stow on the Wold and Moreton in Marsh. And if you’re looking for a little more inspiration, take a look at our guide to the best places to visit in the Cotswolds.
