Holiday rentals in Medstead

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Medstead

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

%{current} / %{total}1 / 1
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
4.81 out of 5 average rating, 121 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.

Superhost
A rustic cabin with a dark metal roof and timber exterior is surrounded by trees. Smoke gently rises from a chimney. The front porch, featuring large glass doors, leads to a welcoming seating area. A pathway of stepping stones guides the way through the lawn.
Farm stay
4.96 out of 5 average rating, 359 reviews

A Unique Farm Retreat

There’s something magical about The Granary. Set in acres of farmland with spectacular sunrises and sunsets, The Granary brims with rustic charm. A dreamy hideaway with an outdoor copper bath and wood fired hot tub. An idyllic get-away-from-it-all yet only 3 miles to historic Winchester. Soak amid hot water, steam and fresh air surrounded by nature and birdsong, enjoy magnificent sunsets from the ‘Sundowner’ or cosy up toasting marshmallows over the fire pit - a perfect escape to unwind.

Guest favourite
The exterior of The Old Bakery showcases a charming blend of wood and glass. Lush, round topiary trees are neatly arranged in decorative pots along a gravel path, with sunlight illuminating the scene under a clear blue sky.
Cottage
4.94 out of 5 average rating, 781 reviews

Idyllic Cottage in the heart of The South Downs

The Old Bakery is a luxurious self-contained cottage set in the heart of the beautiful South Downs National Park. It has been voted one of the best Air B&Bs in the UK in 2021! Guests can enjoy beautiful walks directly from the cottage or visit local villages such as Haslemere, Midhurst, Petworth, Arundel, the South Coast (West Wittering) and Goodwood. You will be spoilt for choices with some excellent pubs and restaurants in the area with the fabulous Duke of Cumberland pub a short walk away.

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
4.98 out of 5 average rating, 626 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
4.95 out of 5 average rating, 786 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
5 out of 5 average rating, 430 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!

Guest favourite
A charming thatched cottage is framed by a white picket fence, surrounded by vibrant garden flowers. The distinctive curved roof and upper window are highlighted against a clear blue sky, emphasizing the cottage's historic character and inviting setting.
Cottage
4.91 out of 5 average rating, 129 reviews

Historic 16th Century thatched cottage, Hampshire

Right in the middle of Jane Austen country, this famous chocolate box 16th Century Grade II listed cottage, the oldest house in the village, is chocca-block full of history. It was home to the Archbishop of Canterbury, Queen Victoria's right-hand man, who not only christened and crowned the Queen but then went on to marry her Prince Albert. Set in the a picture-perfect Hampshire village full of thatched cottages and surrounded by gorgeous walks it is the perfect country retreat!

Top guest favourite
An inviting living area features a textured tile floor and exposed wooden beams. A light blue sofa and a soft mauve armchair provide comfortable seating options. A wooden dining table and chairs are positioned nearby, along with a cabinet displaying white dishware. Natural light enters through multiple windows.
Barn
5 out of 5 average rating, 261 reviews

The Stables at Warren Farm. Rustic charm

Warren Farm is 2 miles from Alton, which is famous for the Watercress Line steam railway and the home of Jane Austen. We are also on the edge of the South Downs National Park and within easy reach of Winchester and the Historic Dockyards and ferry terminals in Portsmouth. The Stables has it's own entrance from the beautiful garden room which adjoins our barn. There are country views and footpaths if you are feeling energetic! We look forward to welcoming you.

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
4.97 out of 5 average rating, 155 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
A compact living space is depicted, featuring a small kitchenette with modern appliances and a television in an alcove. Light enters through a window, brightening the light-colored walls and pale flooring. The design emphasizes an open and functional atmosphere.
Loft
4.97 out of 5 average rating, 139 reviews

Lovely one bed flat with free parking on premises

A small but perfectly formed one bedroom flat in a rural location. The Annex has a small kitchen with hob, cooker and microwave. There is a table for eating. One double bed and a shower room. We have good broadband and there is parking on the property. The village has a great pub within walking distance and plenty of lovely walks. We are about 11 miles from Winchester and 3 miles from Jane Austen's Chawton. Our stairs into the flat are steep and narrow.

Top guest favourite
A spacious grassy area is seen from a small balcony, framed by greenery and trees. A playground structure and garden shed are visible in the background, while the sky displays soft, overcast lighting enhancing the serene countryside atmosphere.
Flat
4.92 out of 5 average rating, 166 reviews

A Discreet Hampshire Downs Retreat for Quiet Stays

Set within the rolling Hampshire Downs, this thoughtfully designed annexe offers rare privacy, calm and refined simplicity. Evenings invite slow living beside your wood burner, while mornings begin beneath the luxury outdoor hot-water shower, immersed in countryside stillness. Designed as I like to travel myself, every detail is intentional, understated and quietly indulgent — a discreet retreat for guests who value space, quality and uninterrupted rest.

Top guest favourite
An aerial view showcases the unique geo dome structure surrounded by lush greenery. A wooden deck leads to an outdoor seating area, fire pit, and hot tub. The tranquil setting emphasizes a peaceful retreat in nature.
Dome
4.94 out of 5 average rating, 377 reviews

Unique Dome | Glamping | Hot Tub | Surrey | Adults

Olive Pod is the ultimate cosy, private and picturesque geo dome retreat. Set on a fruit farm in Surrey, in its own secluded field behind tall fir trees, with no other pods or tents nearby. A firm favourite adults-only escape for proposals, anniversaries, birthdays and honeymoons - we can also decorate for your arrival ✨ The perfect place to unwind and recharge in a peaceful natural setting. Ideal for couples or friends. No infants, children or pets.

Popular amenities for Medstead holiday rentals

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