Vacation rentals in Stoke Orchard

Willow Cottage, A Luxury Cotswold Retreat

Willow Cottage is a self-contained annexe connected to Waterloo House, a 19th century farmhouse. Named after the Weeping Willow tree right outside the door and located in the beautiful semi-rural village of Stoke Orchard, this recently renovated cottage offers an excellent base from which to explore the Cotswolds. There are great walks and cycle routes straight out of the door, and with Cheltenham Racecourse and Cheltenham town only a short drive away the possibilities for exploring are endless!

Boddington Mill

Boddington Mill is a stunning countryside retreat in the heart of the Cotswolds, steeped in history and rural charm. The building retains industrial mill parts which intersect multiple levels for a unique and generous living space. Its south-facing garden includes outside dining, wood-fired hot tub, and large lawn, home to wildlife and fruit-bearing trees. Inside, the three king sized bedrooms feature luxury bedding beneath vaulted, oak-beamed ceilings and period windows. Sky TV, Sonos speakers.

Hobbit Hole, Shepherds Hut nr Cheltenham/Cotswolds

Enjoy the natural beauty surrounding this quiet shepherd's hut set in the grounds of a historic original Tudor Manor. 'Hobbit hole' is an ideal break for anything between one night and a week, or more. Only 5 minutes from junction 9 of the M5, it's set in a rural farming hamlet, 2 miles out of Tewkesbury, and 20 mins drive to Cheltenham and Gloucester. The 'Hobbit hole' enjoys free car parking, and sits in a gravel area overlooking a herb & veg garden with shady trees overlooking a young orchard

Architectural gem on an acclaimed Cotswold farm /1

Enjoy a luxurious 'Bantam House' on our award-winning conservation farm. Your every comfort catered for with a handmade super king bed, air-conditioning and superfast fibre broadband. Overlooking a conservation orchard, this house is immersed in nature. The farm has been named one of the top wildlife destinations in the UK (Iolo Williams, Spring Watch). Ten minutes' drive to the spa town of Cheltenham, our cotswold getaway has bountiful access to the outdoors and great road links via the A40.

Luxury Home 5 Bedrooms 4.5 Baths Jacuzzi/Swim Spa

Luxury detached home with stunning scenic views, 5 large bedrooms, 4 ensuite. Contemporary open plan kitchen diner with a feature island & bar stools, 2 sets of bi-fold doors leading out onto a raised deck area in an enclosed garden with a stream running through. You will find a Jacuzzi/Swim Spa, bbq, dinning and seating areas to relax and unwind whilst soaking up the gorgeous views. Lounge has a 60 inch TV, Log burner, bi-fold doors & 3 sofas Master bedroom has a lounge area and ensuite.

Breathtaking Cotswolds Restored Chapel Valley View

Step into a rare and remarkable stay at ‘The Old Church’, a lovingly restored & renovated 1820s chapel nestled on the hillside in the idyllic Cotswolds village of Sheepscombe. This enchanting property blends timeless character & period charm with a relaxing contemporary feel. A truly unique picturesque countryside escape. Located in a tranquil woodland setting on the edge of Blackstable Nature Reserve with scenic valley walks, a rustic village setting, a playground & lovely pub down the lane.

Little Nook Cottage - Cosy & Large Garden

Located in the heart of Winchcombe with far reaching views over the rolling Cotswold hills, Little Nook Cottage is a charming bolt hole, perfect for couples or a small family from which to explore the Cotswolds. You will find beautifully crafted beams and original stone floors paired with all the luxuries you need for a relaxing break. Featuring a cosy living/dining room with wood burning fire, a super comfy double room and even a dedicated work space should you wish to work away from home!

Buttermilk Cottage, Stoke Orchard, Cheltenham

Welcome to Buttermilk Cottage - an exceptionally accessible, light and spacious property in a village location, situated approximately five miles north of the regency town of Cheltenham Spa. Step free access and a ground floor bedroom with a ceiling track hoist and an adjacent accessible wet-room ensures access for all . A further two double bedrooms and shower room are situated on the first floor. It is ideally situated for visiting Cheltenham racecourse and exploring the idyllic Cotswolds.

Harpe Cottage

Step into a storybook setting at this beautifully heritage cottage in the heart of Wilmcote, Stratford-upon-Avon. A beautiful cottage beaming with character, that blends original period features- stone walls, timber beams, and traditional craftsmanship, with thoughtful modern comforts to create a warm, inviting retreat. Whether you’re curling up by the fire, soaking in the freestanding tub, or enjoying a peaceful moment in the private garden, this is a place designed to slow down and savour.

Fresh & Modern Bungalow - Friends, Families &Pets

New bungalow completed in 2025, finished to a very high standard. Ideal for couples, friends or families. 10 min drive to Cheltenham town centre & racecourse. Directly opposite the local farm shop. Two bedroom (super king & double), one bathroom, separate toilet, large open kitchen and living space. Large, fenced garden and private parking. Cleaner available for longer term stays, extra charge. Please Note: our photos don't really do the place justice. New photos coming soon.

Cottage luxe in The Cotwolds

Wycke Cottage welcomes you with unequivocal charm and a little luxe at every turn. Hunker down in style in the picture-perfect Cotswold setting in the heart of Painswick. This 400-year-old cosy cottage, sits opposite the historic church. With stunning sunset views across to the church's beautiful spire and clockface, and its much storied 99 cloud-like yew trees, this stay offers the quintessential Cotswold experience.

Becketts Farm Shepherd’s hut

Set amongst the orchard on a small traditional working farm with good access for exploring Gloucestershire and the cotswolds and beyond! Our shepherd's hut is located just off the A38 right in the middle of Cheltenham, Tewkesbury and Gloucester making it a great base for seeing the sites. A fully equipped shepherd's hut complete with fridge, kettle, toaster, microwave, induction hob, bbq and wood fired hot tub.