Vacation rentals in Upleadon

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Upleadon

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

A cozy exterior view of the annexe surrounded by greenery features a small table with two chairs. Stone and brick walls are complemented by mature plants, creating a peaceful setting. An inviting entranceway leads into the main living space.

Guest suite in Ledbury

4.98 out of 5 average rating, 286 reviews

The annexe at Glenberrow

Recently refurbished, fully self-contained, one-bedroom annexe in large grounds in a beautiful, rural location at Hollybush in the foot of the Malvern Hills. The local countryside is great for walking, road or mountain biking. Within 10 minutes are the pretty market town of Ledbury, Eastnor Castle, and the wedding venue Birtsmorton Court. Great Malvern and the Three Counties Show-ground are 20 minutes and Cheltenham - home of the Gold Cup and literature and jazz festivals - is around 30 minutes.

Top guest favorite

A stone coach house is framed by lush green grass and trees. Its warm wooden door and window accents complement the natural surroundings. A swing hangs from a nearby tree, inviting relaxation. The building's rustic charm is enhanced by the gentle play of dappled sunlight.

Cottage in Clifford's Mesne

4.95 out of 5 average rating, 243 reviews

Cosy and quiet coachhouse. Orchard. Private patio.

Converted coach house, ancient cruck beams and woodburner. Country village near Ross on Wye. Restful and quiet, ideal for couple. Open plan with mezzanine bedroom. Two loos, shower. Long views. Great pubs nearby. Own patio and fire basket in orchard. 3 friendly dogs, 2 horses. On May Hill with many walking opportunities . Seven counties visible from the top. On edge of Forest of Dean with excellent walking/cycling routes, and canoeing on the River Wye just 20 mins away. Cheltenham races 40 mins.

Top guest favorite

A spacious cobblestone courtyard is framed by manicured trees and lush green fields beyond. A central fountain adds a serene focal point, while charming red brick buildings provide a warm backdrop on either side. The scene is brightened by a clear sky scattered with clouds.

Barn in Newent

4.98 out of 5 average rating, 133 reviews

Beautiful Rural Apt;walk to award winning vineyard

The Courtyard is a stylish 1 bedroom unique apartment set in the grounds of an historic 1000 year old house & located within a stunning stable courtyard & fountain. Ideal for walkers, cyclists, visitors & close to the beautiful Wye Valley, Forest of Dean, counties of Glos, Worcs, Herefordshire and Wales. Explore the ancient market towns of Ledbury & Ross On Wye plus beautiful spa towns of Malvern & Cheltenham. Just a short stroll away from the award winning “Three Choirs Vineyard" & brassiere.

Top guest favorite

The exterior of Rectory Cottage showcases a charming brick facade with elegant timber accents. The garden features a manicured lawn and assorted flowering plants. A spacious terrace with outdoor seating provides a welcoming spot for relaxation, surrounded by wooden fencing and lush greenery.

Home in Tibberton

5 out of 5 average rating, 108 reviews

Rectory Cottage - Luxury Gloucestershire Retreat

Rectory Cottage is a former coach house newly converted to a luxury 2 bedroom cottage. In summer enjoy a BBQ and a glass of wine on the terrace. In winter keep toasty with its log burner and underfloor heating. Connect to the Sonos sound system. Situated in the pretty village of Tibberton, nestled in beautiful countryside with wonderful walks and cycle rides from the door to delight both walkers and keen cyclists. Dogs are welcome and will enjoy the fully fenced garden and outdoor dog shower.

Top guest favorite

The exterior of a charming two-story house is featured, showcasing whitewashed walls and a slate roof. A large garden with manicured grass and various plants surrounds the property, while a small pathway leads to the separate entrance of the Stable Cottage annexe.

Cottage in Ledbury

4.98 out of 5 average rating, 164 reviews

The Stable Cottage - cosy, quiet self catering

Horseshoe Inn House was once the village pub, but now provides quiet and relaxing self catering accommodation in The Stable Cottage, an annexe to the main house. Situated in the hamlet of Brooms Green, on the Gloucestershire and Herefordshire borders, 4 miles from the historic market town of Ledbury. There is plenty with walking, visiting historical places, local events such as an annual Poetry Festival, events at Eastnor Castle or visiting the towns of Hereford, Gloucester and Worcester

Top guest favorite

A shepherd's hut is nestled among trees, featuring a wooden deck at the entrance. The natural surroundings include a grassy area dotted with foliage, inviting a sense of tranquility and privacy in a rural setting.

Shepherd’s hut in Poolhill

4.97 out of 5 average rating, 262 reviews

Hazels Hut

Get away from it all in a cosy shepherd’s hut amongst trees in a beautiful rural location. Hazels Hut has a luxury double bed, storage below and a compact kitchen unit with double gas hob, sink and fridge, pots, pans crockery and cutlery. Keep warm with a wood-burner and ready supply of wood, or underfloor heating. Outside, there is a table for al-fresco dining. A newly built, heated, shower room is close by along a short path adjacent to the hut. Just 3 miles from Newent and various pubs.

Top guest favorite

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, 696 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 favorite

A light-filled living area features a comfortable gray sofa and a wall-mounted television. Glass doors open to a private garden with a grassy area and outdoor seating, creating a seamless connection between indoor and outdoor spaces.

Guesthouse in Redmarley D'Abitot

4.95 out of 5 average rating, 121 reviews

Redmarley D'Abitot country lovers' retreat

This recently refurbished, ground level, self contained unit, is set in a rural location. The unit consists of a fully fitted, well equipped kitchen and living area, shower room and bedroom with a king size bed. Guests have their own designated parking space. Private entrance with keylock. The property also has a private, fully enclosed garden. Ideal for walkers or those just seeking a quiet getaway. Close to the market town of Ledbury. Ideal base for visiting the Malverns or Cotswolds.

Top guest favorite

A scenic landscape is framed by vibrant flowers in the foreground. Green fields stretch into the distance, leading towards gentle hills under a clear blue sky. Shadows from the flowers create interesting patterns on the grass, enhancing the serene rural setting.

Tiny home in Oxenhall

4.98 out of 5 average rating, 196 reviews

A newly Renovated and Exclusive Studio

A newly renovated and exclusive studio within a peaceful rural setting, sleeping two guests within easy reach of The Forest of Dean, Gloucester, Cheltenham and the Malvern Hills. Scenic walks and cycle routes surround. All on the ground floor with an open plan living space French doors lead to a private patio and seating area with spectacular uninterrupted views of the Cotswolds as far as the eye can see. Betula Views Apartment coming on line early 2026 - so bring your friends!

Top guest favorite

A scenic view captures a charming property surrounded by greenery. A gravel driveway leads to the house, framed by lush trees and well-maintained gardens. A horse is seen near the stables, adding to the tranquil rural atmosphere.

Loft in Redmarley D'Abitot

4.97 out of 5 average rating, 397 reviews

The Loft Apartment

Spacious first-floor furnished loft apartment (outside stairs, rather steep) above our garages in delightful quiet rural locality, good area to explore. Suit couple or couple with one child. Double bed, single bed, kitchenette, and separate shower/toilet room. Off road parking. Extra charges are applied for more than two people, and for pets. Separate (50m) from the main house, and therefore offers great privacy. Some access to the garden.

Top guest favorite

A contemporary garden studio is set against a lush backdrop, featuring a stone patio with a small table and chairs under a green parasol. A tranquil pond with water lilies reflects the surrounding greenery, enhancing the peaceful outdoor atmosphere.

Cottage in Wellington Heath

4.98 out of 5 average rating, 295 reviews

Wonderful cottage with glorious views

Uplands Garden Cottage is a luxury retreat with wonderful views across Herefordshire countryside. Located 1 mile from the market town of Ledbury and its independent shops and cafes, it is within striking distance of the Malvern Hills and the Wye Valley (Areas of Outstanding Natural Beauty). Festivals nearby are Ledbury Poetry, Hay, Longborough Opera, Cheltenham, Three Counties/Choirs. Piano & dedicated work station for those wanting to WFH.

Top guest favorite

The exterior of Daisie Cottage is presented, showcasing its white facade and distinctive roofline. A gravel pathway is visible, leading to the entrance, while wooden fencing provides privacy. Natural surroundings enhance the rural setting, offering a serene view of the countryside.

Cottage in Gloucestershire

4.94 out of 5 average rating, 170 reviews

Pretty 2 bedroom country cottage with rural views

Daisie cottage is a relaxing rural retreat near May Hill, just outside Newent , with lovely country views. It is light and airy - perfect for relaxing. Good for couples, solo adventurers, business travellers, families and dogs welcome too. With wonderful walks and trails right on the doorstep for either gentle strolls or for more serious ramblers. The Forest of Dean offers lots of activities from high ropes to cycling and canoeing.