Holiday houses in Upton Saint Leonards

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Top-rated holiday rentals in Upton Saint Leonards

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The stone barn features a spacious patio and garden, framed by well-maintained topiary. A large balcony is accessible from French doors on the upper level, while outdoor seating is arranged on the patio, providing an inviting area to enjoy the surroundings.
Barn in Cotswolds
4.92 out of 5 average rating, 189 reviews

C15th Quiet Cotswold Hillside Barn: stunning Views

A beautiful stylish 15th century south facing stone barn; tastefully refurbished on our organic farm. Quiet, spacious, comfortable & cosy (a wood-burner); bedroom balcony & garden terrace with far reaching views of the Cotswold valleys & village church Our farm was one of Henry VIII hunting lodges, backing onto ancient beech woods, ~ footpaths from the door. Easily accessible to Stroud's famous market, Cheltenham races, Roman villas, village pubs! (2 adults & 2 children under 12 are welcome)

Top Guest favourite
The charming stone cottage features a welcoming double door entrance, revealing an open-plan living area with a small kitchen. A large window allows natural light to fill the space, providing a glimpse of the surrounding greenery outside.
Tiny home in Cowley
4.88 out of 5 average rating, 620 reviews

Little Knapp on the Cotswold Way

Snug space ideal for relaxing getaways. Set in area of outstanding natural beauty. Perfect base for couples to explore the Cotswolds with direct access to Cotswold Way. It's a quirky small space. Intended as a great escape, there is WiFi but no TV. Dogs: 1 w-behaved dog welcome (+ £10). Sofabed: Please request bedding (+£10 charge) or bring own for free. Firepit & logs: By request (£10) NB Bathroom space limited, stairs tricky for less mobile, roof terrace is private & overlooked by our house.

Guest favourite
Home in Stroud
4.93 out of 5 average rating, 138 reviews

Peaceful Cotswolds Chapel Breathtaking 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.

Top Guest favourite
A stone building featuring a unique gabled roof and multiple windows, allowing natural light to enter. The exterior is surrounded by neatly trimmed bushes and a gravel area, with lush greenery and trees visible in the background.
Condo in Painswick
4.97 out of 5 average rating, 240 reviews

Stunning one bedroom Cotswold loft apartment

Charming apartment with stunning views over orchard and fields in perfect location for both Painswick - Queen of the Cotswolds - and the Slad valley, home to poet Laurie Lee. Award winning pubs nearby. In the grounds of seventeenth century Turnstone House, listen to the owls, watch the buzzards and spot the deer. Enjoy a drink as the sun sets behind the iconic Painswick church steeple. Delicious breakfast. Microwave/mini-fridge/hob. Additional bed, pets by arrangement - additional £15 pet fee.

Top Guest favourite
A charming Cotswold stone cottage is depicted, featuring a stone pathway leading to a warm, inviting entrance. Surrounding greenery enhances the rustic ambiance, while the exterior showcases original details and serene landscaping. Bicycles are securely parked nearby, indicating accessibility for outdoor activities.
Cottage in Painswick
5 out of 5 average rating, 185 reviews

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).

Guest favourite
A modern house is set in a lush green garden, surrounded by well-maintained plants and trees. Large glass windows allow natural light to fill the interior. The building features a sloped roof and is complemented by a tall tree alongside, creating a welcoming exterior.
Home in Painswick
4.94 out of 5 average rating, 225 reviews

Dove Lodge Painswick

A stunning little house in an area of outstanding natural beauty with rolling hills and a location only a mile from the 'queen of the Cotswolds' ( Painswick). The modern little house consists of a bedroom on the ground floor, a large open kitchen and tv lounge on the first floor and spectacular views throughout. The house all equipped and has plenty of free parking as well as a sharegarden which is free to roam. 1 pet is allowed during the stay. Check out is strictly no later than 11am.

Top Guest favourite
The exterior of a charming stone annexe is shown, featuring a pitched roof and a white door. Planters with colorful flowers add a welcoming touch, while surrounding gravel pathways and lush greenery create a serene rural setting.
Guest suite in Sheepscombe
4.99 out of 5 average rating, 335 reviews

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.

Top Guest favourite
The entrance to the Garden House is framed by a sturdy tree and vibrant potted plants, showcasing colorful flowers. A wooden table and shelf stand beside the door, enhancing the welcoming appearance of this independent annex.
Tiny home in Gloucestershire
4.93 out of 5 average rating, 722 reviews

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.

Guest favourite
A compact kitchenette area features a small table with two chairs, set with plates and bowls. A toaster and a kettle are visible. In the background, a comfortable sleeping area is seen with a pull-out sofa bed and natural light flooding in through the windows.
Guest suite in Hucclecote
4.88 out of 5 average rating, 226 reviews

Neunundzwanzig. Self contained private suite.

Neunundzwanzig Is a totally self contained purpose built studio apartment that is light warm and airy with private access. Off road parking and private rear courtyard. Based in the village of Hucclecote near Cheltenham and Gloucester in a quiet and pleasant location and on the doorstep to the Cotswolds. Ideal for those wishing to explore the area or business people needing easy access to Gloucester business park and on the ring road for easy access to GCHQ on the outskirts of Cheltenham.

Top Guest favourite
An outdoor garden area is featured, showcasing a stone patio with a large dining table surrounded by chairs. Potted plants and lush greenery create a natural setting, while the rustic wooden structures of the property provide a charming backdrop.
Guesthouse in Cranham
4.97 out of 5 average rating, 211 reviews

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

Top Guest favourite
The living room features a comfortable leather sofa set arranged around a central rug, with a log burner and wooden mantel as focal points. Large windows provide natural light, while framed photographs decorate the walls. A television is positioned for viewing convenience.
Home in Painswick
4.97 out of 5 average rating, 213 reviews

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.

Top Guest favourite
A charming studio is enveloped by greenery, featuring a gravel courtyard with a stone planter at its center. The exterior showcases a red-tiled roof and wooden siding, while a small table and chairs are positioned nearby next to a barbecue, inviting outdoor relaxation.
Guesthouse in Edge
4.89 out of 5 average rating, 311 reviews

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.

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