Cottages in The Cotswolds
Picture-perfect villages full of honey-coloured cottages, rolling fields lined with stone walls, dappled woodlands full of bird song and deer… The Cotswolds is a rather special place for a self-catering holiday. Our hand-picked collection of chocolate-box stone cottages and gorgeous converted barns is full of pretty homes to escape to, whether you’re looking for a cosy retreat for couples or a big and beautiful house for a fun-filled family gathering. Spanning Gloucestershire, Oxfordshire, Warwickshire, Wiltshire, Worcestershire, and Somerset, fill your days visiting honey-dipped market towns and exploring sweeping vistas, before returning to your welcoming abode for an evening by the wood burner. Lots of our holiday cottages are dog-friendly too, promising a wonderful stay for the whole family full of adventures throughout the Cotswolds. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 22 self catering cottages in The Cotswolds
7 nights from £804
2 Old Turnpike Cottages
58662 bedroom, dog friendly self catering cottage with hot tub near Chipping Norton.
Tucked away in the picturesque village of Middle Barton, just a short drive from Chipping Norton and the exclusive Soho Farmhouse lies this quintessential, dog-friendly Cotswold Co...
7 nights from £804
7 nights from £1168
The Yew Trees
58622 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 £726
Poppy Cottage
58502 bedroom, dog friendly self catering cottage in Stratford-upon-Avon.
Perfectly situated within walking distance of the historic town of Stratford-upon-Avon lies this stylish Victorian dwelling, Poppy Cottage. A beautiful characterful terraced home w...
7 nights from £726
7 nights from £565
Oak Tree Cottage
57412 bedroom self catering cottage near Burford.
Oak Tree Cottage is a delightful semi-detached barn conversion and is nestled next to its neighbour, The Gallery (5756). They can be booked together for larger gatherings. The acco...
7 nights from £565
7 nights from £530
The Gallery
57562 bedroom self catering cottage near Burford.
The Gallery is a super spacious, light and airy, semi-detached Cotswold barn. It has a fully equipped kitchen that leads through to an open plan sitting/dining-room, with a hugely ...
7 nights from £530
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
From £608 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 £608 per night
Weighbridge Barn
7 nights from £1282
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!
7 nights from £607
Stable End
56481 bedroom, dog friendly self catering cottage near Chippenham.
Located in Grittleton, a short drive from both Chippenham and Bath, just on the edge of the Cotswolds, an area of beautiful countryside and picturesque villages, come and discover ...
7 nights from £607
7 nights from £675
Weighbridge End
56471 bedroom, dog friendly self catering cottage near Chippenham.
This stunning barn located on the edge of the Cotswolds is a gem of a property just waiting to be discovered. Sympathetically converted with nods to its previous life as a working ...
7 nights from £675
Holidays in the Cotswolds
If you’re looking to escape to the English countryside, it doesn’t get much more quintessential than a holiday in the Cotswolds.
Prettiest towns and villages in the Cotswolds
Famed for its postcard-pretty towns and villages, the Cotswolds is something of a fairytale. From the Cotswolds’ very own Venice at Bourton-on-the-Water to the chocolate-box delights of Upper and Lower Slaughter, if you’re looking for a beautiful backdrop to your photos, you simply can’t beat the magical setting the Cotswolds provides. Chipping Campden promises listed buildings galore, while Stow-on-the-Wold invites you to immerse yourself in its historic setting, including pub stops at England’s oldest inn. Thought to be one of the prettiest sights in the Cotswolds, the picture-perfect setting of Arlington Row is unmatched, forming one of the most well-known streets in the UK.
Things to do in the Cotswolds
The Cotswolds is first and foremost a National Landscape, meaning it’s home to outstanding natural beauty, from tranquil woodlands to rolling countryside just waiting to be explored on foot. Throughout the undulating landscape, a number of beautiful gardens add a splash of colour to the honeyed tones of the countryside. The fabulous Rococo gardens at Painswick are utterly unique, while the dappled delights of the Westonbirt Arboretum promises a dog-friendly day out throughout the year. For a little slice of history, head to the famous Broadway Tower for panoramic views or Blenheim Palace for a royally good time. Families will love the Cotswold Water Park, which is packed with activities and wildlife-watching opportunities, while couples should head to Bath’s Spas for some luxurious pampering.
Places to eat in the Cotswolds
With such a bountiful natural larder on its doorstep, it’s of little wonder the Cotswolds is a beacon for foodies. Boasting numerous Michelin star restaurants and cosy pubs (many with breathtaking walks nearby), it’s deliciously easy to refuel in the Cotswolds. Visit tree-lined restaurants for stylish celebrations, toasty tearooms for giant slabs of cake, and fire-warmed pubs that have served visitors for generations. Farm shops pepper the rolling farmland, offering superb local ingredients from meats and cheeses to fresh bread and pies - perfect for filling up the cupboards in your holiday cottage or packing up for a lovely picnic surrounded by the sights and sounds of the Cotswolds.
