Winchcombe

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This 18th-century cottage has plenty of period charm, with low beamed ceilings, a traditional stone inglenook fireplace and bedrooms nestled under the eaves. While it may not suit taller guests, those who fancy an authentic Cotswolds stay will love the original features, as well as the garden with its rolling countryside views and unfenced pond. Winchcombe's high street is just a short walk away where you’ll find cosy country inns, restaurants and boutiques, while other Cotswolds gems like Stow-on-the-Wold, Chipping Campden and Cheltenham are easily reachable by car. 

The Green Hill

Instantly cosy, this characterful cottage is a true home away from home. With a log burner for winter months and a sunny courtyard come summer, you can enjoy every season here to the fullest. We love the traditional features, though there are low ceilings in the bedrooms and steep stairs – but hey, that's all part of the charm. One furry friend is welcome to tag along for a fee, and you'll find plenty of pup-approved walks (and pubs) in the local area. You're also not far from Bourton-on-the-Water, Stow-on-the-Wold, and Cheltenham when you're in the mood to explore.

Winchcombe Winner

Nestled in the grounds of a 15th-century castle, and fringing the charming village of Winchcombe, this dog-friendly cottage is one-of-a-kind. Make sure to discover the fascinating history of the estate, which you’ll have complimentary access to. Once home to King Charles I and his nephew, Prince Rupert, the castle has impressive royal connections. It’s worth noting that the downstairs living space is compact and will feel particularly cosy if you have two dogs in tow. But there’s a decked terrace to spill out onto that you’ll share with another two cottages. Location-wise, Winchcombe, with traditional inns, tearooms and honey stone houses aplenty is just a short amble away.

A Royal Guest

Situated on a historic estate in the Cotswolds, this cottage grants you free entry to the on-site castle and gardens. As a former engine house, this home has heaps of character with traditional windows and wood beams, though the ceilings are low on the ground floor. Two guests will sleep on the living room's sofa bed, but they'll have easy access to the downstairs bathroom for relaxing soaks in the tub. While these grounds have once hosted Tudor royalty, you'll now find country pubs and restaurants a short walk away in Winchcombe.

Queens & Castle

You’ll find this 17th-century Grade II-listed cottage in the centre of Winchcombe, on the doorstep of many fantastic restaurants, boutiques, and tea rooms. It’s also surrounded by countryside – perfectly positioned to explore both the quaint towns and picturesque walking paths of the Cotswolds. The home itself is quintessential of the area with wooden beamed ceilings, a log-burning fireplace and a charming country-style kitchen perfect for families or groups of friends. There’s also a sunny patio outside – it’s compact but just right for alfresco breakfasts in the fresh air.

Little Winchcombe

Charming and bright, this Grade II-listed cottage in the heart of Winchcombe is a beautiful mix of old and new. Retaining some of the original character –including beamed ceilings and stone walls – it has been modernised to make your stay comfortable. There's plenty of space here for eight, but if you need more, there's also a garden with an alfresco dining space. Given the central location, you're surrounded by boutiques, artisanal shops, cafes and more. You're also within walking distance of a pub for a quintessentially British experience. 

Castle Vale Cottage

Nestled into the Sudeley Castle Estate, fringing the charming village of Winchcombe, you'll find this Cotswold stone 18th Century farmhouse. Spread out over three floors, with a separate annex to spill into, this home is the perfect country escape for an extended family or group of friends. Climb the flight of stairs to discover luxurious bedrooms to sleep all fourteen of you, with crisp, white linens and many with en-suites. Back downstairs, the layout is set up for easy socialising with a spacious kitchen made for action and two dining spaces. But there are also cosy nooks to retreat to, with a separate playroom and snug complete with a crackling fire.  Outside, kids and furry friends alike can roam free on the immaculate lawns, all under the watchful gaze of the grown-ups from the raised deck terrace as you fire up the barbecue. And when it's time to get out and about, you're right on the edge of Winchcombe, with restaurants, shops, and bars just a stroll away, as well as easy access to the area's many breathtaking walking trails. Or call in on your neighbourhoods at Sudeley Castle (ten minutes on foot) – guests have complimentary entrance during the open season, don't you know.

The Crown & Chandelier

Overlooking the church, this dog-friendly apartment places adventurers just off Winchcombe's high street. In town, you'll be treated to boutique shops and countryside tearooms. From the flexible bed set-up in the main bedroom to the cosy living area upstairs, this home offers a lot to love. There's even a roof terrace to enjoy sunny spells, though the outdoor space is shared with your neighbours. But, with a staircase leading to the front door and steep steps inside, it won't be accessible to everyone.

Quaint Countryside

Dating back 300 years, this historic home has plenty of character and all the comforts you could need for a refreshing rural retreat. The rooms are set across the main house and an independent annexe – making this a great option for groups looking to stretch out and socialise. There is a beautiful orangery and an infrared sauna, while the garden is perfect playground for lazy summer afternoons. At full occupancy, two guests will be sleeping on the sofa bed in the snug, but this is ideal for kids. And for explorations further afield, follow hiking trails straight from the door or take the short drive to Cheltenham, Winchcombe or Broadway.

The Orangery

With a stone facade and chocolate-box windows, this cottage in the Cotswolds is as cute as can be. It’s in the ancient Anglo-Saxon market town of Winchcomb, a fifteen-minute drive from Cheltenham. In Winchcomb, you’ve got cosy, timbered inns, tea rooms, indie shops, galleries and a Michelin-starred restaurant, all on your doorstep. It’s also known as a walker’s paradise with traffic-free trails snaking across the countryside and pints by the fireside as a reward after. Speaking of firesides, it doesn’t get much better than settling by the wood-burning stove at the heart of this home, especially after a day on the trail. Bookshelves are stacked high with board games for quality time together and the solid wood dining table is perfect for family meals. The cottage blends right in with the historic feel of Winchcomb, with flagstone floors underfoot, exposed stone walls and timber beams on show inside. A little bonus is the conservatory-style hall at the back door, which has a monk seat as a sunny reading nook. Beyond this, the private garden has outdoor dining on the lawn, and a cute bistro set for two on the patio.  

Rambler's Reward

Only a mile from Winchcombe and Sudeley Castle, this pocket-sized hideaway is a perfect fit for two. We love how cosy and bright the living space is. Whether you're preparing breakfast in the mint green kitchenette, unwinding with a glass of wine on the comfy sofa or snuggling up in the sumptuous bed adorned with a William Morris duvet, you'll feel right at home here. And the views aren't too shabby, either. In the morning, savour a cup of tea and listen to the birdsong on the private patio, overlooking the tree-lined paddock. Evenings call for charcoal barbecues as the sun goes down, followed by glasses of wine under the stars. 

Ramblers will love this rural spot. Public footpaths lead through the rolling countryside towards the Cotswold Way and along the River Isbourne, and with pubs and restaurants in Winchcombe, you'll have everything you need just a stone's throw away. If it's the magic of the Cotswolds you're after, take an afternoon drive to Bourton-on-the-Water – it's twenty-five minutes away.

Cotswold Grace

To take the title of ‘Area of Outstanding Natural Beauty’, the environment has to be pretty spectacular. With The Cotswolds being one of only forty-six places awarded this coveted accolade, this lush countryside region certainly matches its description. But just as you thought it couldn’t get any more outstanding, how does staying on a castle estate sound? Just a twenty-one-minute drive from the bustling city of Cheltenham, this apartment offers a regal base to come home to after a day at the races.

While you could spend all day perusing Sudeley Castle and its ten gorgeous gardens (which you can do as much as you want, with free entry as a guest of the cottage), you’ve got history to discover closer to home. Your cottage is set in an old paper mill, where you can admire original timber beams and exposed stone walls throughout.

Within these cosy interiors, the lounge exudes a certain warmth that feels unique to rural England. Recline on a chequered chaise longue with a glass of champagne, or cook up Sunday roast to serve on the wooden dining bench. And make sure you put those fabulous sash windows to use – your river views offer the most calming Cotswolds scene.

The Canopy of the Forest

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