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Holiday rentals in Medstead

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Top-rated holiday rentals in Medstead

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

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Guest favourite
A dark-stained tiny house is nestled in an expansive green field, overlooking the scenic South Downs National Park. Solar panels are visible on the roof, while the surrounding landscape features rolling hills and a bright blue sky filled with fluffy white clouds.
Tiny home in Froxfield
4.83 out of 5 average rating, 142 reviews

Romantic OffGrid Cabin | Stargazing & Valley Views

Featured in The Guardian and The Times Top 10 UK Off-Grid Stays. Wake to sunrise over the South Downs in this secluded hilltop off-grid cabin overlooking the whole of the South Downs National park. Experience total serenity under star-filled skies with the warmth of a wood-burning stove enhancing the peaceful ambiance. Our off-grid cabin offers tranquility whilst still being close to cosy pubs, historic towns and scenic walks. Dog Friendly. It’s the perfect place to disconnect and recharge.

Guest favourite
The exterior of the floating accommodation is illuminated at dusk, highlighting the modern design and large windows. A wooden walkway leads to the entrance, with outdoor seating visible on the private deck. Surrounding buildings can be faintly seen in the background.
Houseboat in Southampton
4.99 out of 5 average rating, 111 reviews

Rivers stays with hot tub

Our unique river stay offers a one-of-a-kind experience, combining modern comfort & nature. This charming space features panoramic windows that invite the soothing sounds of the flowing water and stunning views of the surroundings right into your living area. Enjoy your morning on the private deck while watching the sunrise, or unwind in the evening with a glass of wine as you listen to the gentle rustle of leaves. Perfect for couples, solo adventurers, or anyone looking to reconnect with nature

Top guest favourite
Guest house in North Boarhunt
4.99 out of 5 average rating, 111 reviews

One bedroom cottage escape

Relax and make yourself at home in our charming 1-bedroom bungalow — the perfect retreat for a restful getaway. Featuring a super king-size bed with White Company bedding, a well-equipped kitchen and a bright and comfortable living room with stunning views of the garden. The modern restroom includes a walk-in shower and Rituals toiletries for a luxury experience. Enjoy your morning coffee on the patio or take advantage of the hammocks on the pond both with views of the surrounding garden.

Top guest favourite
The Pigsty features a unique domed structure with a blend of dark and natural wood accents. A small outdoor seating area with a round table and two chairs is positioned at the entrance, surrounded by lush greenery and potted plants.
Hut in Winchester
4.98 out of 5 average rating, 642 reviews

The Pigsty

The Pigsty is Winchester's first luxury woodland hideaway, with beautiful views of Vale Farm. Less than 2.5 miles from the historic centre of Winchester, this peaceful retreat is perfect for those looking to visit the city, or escape for some peace. The Pigsty’s domed design with wooden interior has a roll top bath, cosy open plan living space and decking area to enjoy dinner with sunset views. Just a few minutes walk from the famous Clarendon Way, and a 30 minute walk to the city centre.

Guest favourite
A charming outdoor area features a cosy wagon, wooden barn, and saloon-style seating. Flower pots add greenery, while a gravel path connects the spaces. The surrounding trees provide a natural setting, creating an inviting atmosphere for relaxation and enjoyment.
Shepherd’s hut in Medstead
4.95 out of 5 average rating, 804 reviews

Wagon in the Woods & Wine Barrel Hot Tub

A cosy wagon and a hot tub in a giant wine barrel! Nestled in the Hampshire countryside. Features inside include a double bed, trap-door bath, toilet, and large ‘wagon wheel’ window with stunning views. Outdoors is the Wild Cherry Barn with chiminea fireplace and a saloon seating area with pizza oven and campfire with BBQ grill. The Wagon in the Woods is a bespoke, self-contained little place in the country with a private woodland, ideal for those wanting a tranquil and restful getaway.

Top guest favourite
A group of friendly alpacas roams in a grassy paddock surrounded by trees with fallen leaves. The handmade Shepherds Hut stands in the background, providing a charming retreat amidst nature.
Shepherd’s hut in Passfield
5.0 out of 5 average rating, 444 reviews

"Bumble" The Shepherd's Hut

This traditionally inspired, hand-made Shepherds Hut is nestled inside a paddock in the leafy county of Hampshire. It offers a tranquil retreat in a home away from home setting with a cosy open plan living space championed by the log burning stove. Enjoy cooking your own English Breakfast - of which eggs are graciously supplied by our chickens -amongst views and visits of our 17 strong Alpaca herd. Please let us know if you'd like to meet and feed the Alpaca - they'd like to meet you!

Top guest favourite
Home in Hampshire
4.98 out of 5 average rating, 129 reviews

Stable Cottage Beauworth Southdowns Hampshire

Nestled within the South Downs National Park, this charming countryside escape offers uninterrupted views across open fields where sheep graze. Wake up to breathtaking bedroom views, explore the surrounding countryside and historic Winchester, and in the winter, cosy up beside the crackling log burner. Thoughtfully equipped for families with babies and children, as well as couples seeking a peaceful getaway, it’s the perfect retreat to unwind and enjoy Hampshire’s beautiful landscape.

Top guest favourite
The exterior of a charming two-bedroom annexe is visible, featuring a well-maintained garden with lush green grass. A pathway leads to the entrance, framed by manicured shrubs and trees. The brick facade is complemented by large windows, allowing for natural light.
Guest suite in Alton
4.97 out of 5 average rating, 176 reviews

Quiet self-contained 4 guest annexe close to town

Lovely two bedroom annexe on a peaceful residential road in Alton, located just a short walk from the local amenities of this pretty market town including a Triple fff brewery pub and premium supermarkets. On the edge of the South Downs National Park Alton is surrounded by beautiful countryside ideal for cycling and walking. The house has it's own private entrance, driveway parking and fast wifi, kitchen, restful living room, bright airy bedrooms and a stylish shower room.

Guest favourite
A light-filled dining area features a large wooden table surrounded by six black chairs. Large glass doors with wooden frames open to a well-maintained garden, showcasing views of neatly arranged plants and greenery. Solid oak flooring complements the warm wood accents throughout the space.
Cottage in Petersfield
4.95 out of 5 average rating, 261 reviews

The Cottage at Lupton House, Froxfield Petersfield

Luxuriously comfortable and highly sustainable, the Cottage at Lupton House B&B, combines modern amenities with traditional character and charm. Situated on the owners' 3 acre small holding and surrounded by stunning countryside in the heart of the South Downs National Park. The ideal getaway to relax and unwind or to spend time with family or friends. All with the added bonus of a complimentary breakfast. Multiple night discounts, wedding party package available.

Top guest favourite
The spacious room features a plush bed dressed in crisp white linens, complemented by a soft green throw. A cozy armchair sits nearby, and a bedside table holds a stylish lamp. Natural light filters in through two windows, framed by subtle patterned curtains.
Flat in Medstead
4.94 out of 5 average rating, 232 reviews

Stylish Barn in Rural Hampshire

Beautiful barn space in the heart of the Hampshire countryside situated on the edge of a village. On the first floor there is a UK Superking bed which can be split into twin beds at £15 extra cost, a table for two people and shower room. Breakfast items such as fruit, yoghurt, bread for toast, jams, honey, marmite are provided along with tea and 'real' coffee. ** Although there is a small kitchenette, there are no cooking facilities for hot food preparation **

Guest favourite
An A-frame structure is framed by trees and surrounded by blooming bluebells. Light filters through the open front, illuminating the interior where a seating area is presented. The natural setting offers a serene escape, with vibrant flowers in the foreground enhancing the tranquil scene.
Hut in Ovington
4.97 out of 5 average rating, 172 reviews

The Glade at Ladyhill Vineyard near Winchester

Nestled on the edge of an ancient wood in South Downs National Park and with fantastic views over Ladyhill Vineyard and the Hampshire countryside The Glade has a cosy A-Frame to grab a good night sleep, a separate shower room with flushable loo to keep you fresh and a kitchen equip-for-easy glamping. Relax and admire the views, BBQ on the fire pit, spot deer and hare or stroll down the river Itchen to The Bush gastro pub. You’ll return home totally refreshed!

Top guest favourite
Cabin in Medstead
4.96 out of 5 average rating, 101 reviews

Luxury Cabin with Outdoor Bath, Sauna & Fireplace

Set on the edge of the South Downs National Park, this luxurious cedar cabin offers complete privacy, stillness and refined comfort. Soak beneath the stars in your private outdoor bathtub, unwind in your exclusive sauna, or rest beside the indoor wood burner fireplace. Designed by a fellow traveller for deep rest and reconnection, every detail is intentional — inviting calm, closeness to nature and a quiet sense of renewal that lingers long after you leave.

Popular amenities for Medstead holiday rentals

  1. Airbnb
  2. United Kingdom
  3. England
  4. Hampshire
  5. Medstead