Vacation rentals in Upton Saint Leonards

The Cottage, a cosy, peaceful, rural retreat

Nestled on the side of a hill within a small hamlet close to both Cheltenham and Gloucester and situated on the edge of the Cotswolds escarpment in an area of outstanding natural beauty the cottage annex offers peace, privacy and pretty views. It is an ideal place to stay for the Cheltenham Races and the local annual Cheese Rolling event, the Cotswold Way is on the doorstep, perfect for exploring the stunning countryside. With pretty enclosed gardens it is perfect for relaxing inside and out.

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.

Historic Cotswolds Farmhouse for Groups and Family

Impressive 16th-century Grade II listed Cotswolds farmhouse set within peaceful countryside, designed for landmark gatherings of families and friends staying 4–7 nights. Sleeping up to 14 across six bedrooms, the house offers generous living and dining spaces, two fireplaces, enclosed private garden with pond, and room for everyone to relax together. Guests enjoy fast fibre Wi-Fi, shared games room, landscaped grounds and easy parking. A historic country retreat created for meaningful escapes.

‘Shamba Barn’ Cotswolds Grade II Converted Barn

A beautifully renovated old Cotswold stone apple barn, Shamba Barn is nestled in an acre of lovely landscaped gardens belonging to Bond End Farm; a Grade II listed 400-year-old Timber Frame house where it's rumoured Henry VIII once stayed! Escape for a peaceful break to explore the Cotswolds and exclusively enjoy the beautiful garden with visiting deer and pheasants, orchard and tree swing, and cosy indoor fire-side evenings or beautiful sunsets on your private patio with a warming fire pit.

Quiet grade 1 listed entire cottage in Cotswolds

A bright and recently modernised grade 1 listed Cotswold stone cottage, 100 yards from the Cotswold Way with breathtaking views down the Stroud Valley, its own parking and secluded outdoor eating. Filled with natural light, it is very peaceful and extremely comfortable with luxury bedding (super king or twin bed) and kitchen. An idyllic spot for walking, cycling, exploring the local scenery or simply escaping the city Painswick is 10 minutes from Stroud ( 87 mins hourly train to London).

The Garden House in Kingsholm, Gloucester

The Garden House is a lovely single room annex with independent access, en-suite bathroom and shower. Light, cosy, and simply furnished, set in the garden of a residential home near the centre of Gloucester, it's a quiet space to relax or work. Driveway parking available. A two-minute walk to the famous Kingsholm rugby stadium and food shops, ten minutes to city centre, bus and train stations, cathedral, Quays shopping outlet, restaurants and historic docks. Easy bus route to Cheltenham.

Idyllic rural location in Sheepscombe village

A self contained annexe on a working small holding which has recently been refurbished to a high standard. It is overlooking the unique village of Sheepscombe with fantastic panoramic views over the village and surrounding National Trust beechwoods. This rural retreat is a walkers paradise, dog friendly with close access into the woods behind and near to the Laurie Lee way in the Slad Valley. Stroud, Cheltenham, Cirencester and Gloucester are a short drive away. An idyllic quiet get away.

Cheerful 3-bedroom Cottage in Rural Village.

Ground Floor: Living room: With electric fire and Smart TV. Dining room: With French doors leading to small courtyard. Kitchen: With breakfast area, electric oven, electric hob, microwave and coffee machine. Utility room: With fridge/freezer and washing machine. Bedroom 3: With double bed. Cloakroom: With toilet. First Floor: Bedroom 1: With kingsize bed. Bedroom 2: With double bed and en-suite with shower cubicle. Bedroom 3: With bunk beds. Bathroom: With shower over bath, and toilet.

The Organic Cotswolds Cowshed

The Organic Cotswolds Cowshed Set in the heart of The Cotswolds, one of the most beautiful areas in the UK, we are offering the most organic and toxic free environment that we can for our guests which may be important to you if you are allergic or intolerant to such things as added fragrance to laundry soap or the chemicals used in non-bio cleaning chemicals and sprays. I also have a shepherds hut on the property that sleeps two. See my other listing 1 DOG welcome. No other pets

Quiet Edwardian era House, Painswick

Welcome to our family owned Edwardian era house situated in Painswick. Renovated with hosting in mind, we'll have everything you need for a relaxing stay. Situated just off the Cotswold Way national trail, it's the perfect pit-stop for keen walkers (or runners!). If sight seeing is more your thing, the popular 18th Century Rococo Garden is just a 5 minute walk away. Ideally located for travel to Stroud, Cheltenham, Cirencester and Gloucester all within a 20 min drive.

Artist's studio in Edge in stunning countryside.

This is a well equipped studio in the Cotswolds. It's at the end of a singletrack no through road about 1/2 mile from the Cotswold way and at the junction of several footpaths. The nearest towns are Painswick,which is 1 mile away, and Stroud where there is a train station and supermarkets. The studio has a sleeping area with a king size double bed. It is separated by a bookcase from the main living area. where there is also a sofa.

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.