Holiday houses in Medstead

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Top-rated holiday rentals in Medstead

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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
4.81 out of 5 average rating, 114 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 a recently renovated recording studio is shown, featuring dark wooden cladding and yellow-framed windows. A welcoming front door is prominently displayed, while neatly landscaped planters add a touch of greenery. The historic church spire is visible in the background.
Home in Petersfield
4.96 out of 5 average rating, 187 reviews

Spacious and Stylish Home in Heart of Top Village

A stylish and spacious recently renovated recording studio, which has been finished to a high spec with exposed timber beams, brickwork and a stunning log burner perfect for relaxing after exploring all that Hampshire and West Sussex have to offer. There is a large double bedroom with king sized bed and ensuite bathroom, and an open plan living area with sofa beds and log burner that can accommodate up to 3 further guests. There are 3 fantastic pubs within walking distance - one only 50m away!

Guest favourite
The image captures a uniquely designed tiny home with vibrant green and wooden accents. A vintage yellow sports car is positioned prominently in front, while a spacious deck features comfortable seating and potted plants, creating an inviting outdoor area.
Hut in Medstead
4.99 out of 5 average rating, 269 reviews

Lotus Car Spa & Horse Hut

Yes, that is a hot tub in a Lotus Elan! On the outskirts of Medstead village, in the corner of a field where shire horses once roamed, you’ll find a tiny home like no other. Once hauled to and fro for Polo and Shire shows, The Horse Hut has been lovingly transformed into a luxury holiday stay—while maintaining its horsey heritage. Whether you're soaking in the Lotus Spa or sitting back on the verandah, take in the beautiful vista of the Hampshire countryside and Hattingley Valley.

Guest favourite
The exterior of the studio flat features red brick walls accented with green climbing plants. A white door with a simple handle is framed by a small shrubbery, while a window with white trim is visible above, contributing to the charming appearance.
Condo in Monk Sherborne
4.92 out of 5 average rating, 140 reviews

Stunning studio flat in countryside setting

We live in a quiet and tranquil village surrounded by beautiful fields and countryside. Our studio flat is recently refurbished and is separate to our family home with its own access. There are many pretty walks around the area and several pubs in easy proximity. We have a village shop, and both Basingstoke and Tadley are 10 minutes by car. Basingstoke hospital and the railway station are also a 10 minute drive. We offer private parking (off road) for 1 car.

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 Itchen Valley
4.97 out of 5 average rating, 154 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!

Guest favourite
The modern barn conversion features a combination of wooden and brick exterior, showcasing tall windows that provide natural light. A hedge surrounds the building, adding greenery to the landscape, while the roof has metal accents, emphasizing its contemporary design.
Barn in Overton
4.92 out of 5 average rating, 129 reviews

Hazel - Heath Row Barn

Hazel is one of two self-catering flats, within a modern barn conversion. Situated in a rural location, near the village of Overton. First floor flat, with two bedrooms and a spacious living area, it is perfectly situated to enjoy country walks while close enough to Overton which has a large range of independent shops, pubs, restaurants and takeaways. A great place to get away from it all and enjoy the countryside, while still being close to amenities.

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 in Upper Wield
4.97 out of 5 average rating, 138 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.
Apartment in Medstead
4.92 out of 5 average rating, 161 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.

Guest favourite
A couple relaxes in a bubbling outdoor hot tub, holding glasses, with a scenic view of lush green fields and trees in the background. A champagne bottle sits in an ice bucket beside them, enhancing the tranquil atmosphere.
Shepherd’s hut in Chessington
4.98 out of 5 average rating, 346 reviews

The Ultimate Couples Retreat | 30 Mins from London

This countryside retreat is the perfect romantic escape, just a 35 minute taxi/train ride minutes from London. Unwind in your private luxury hot tub, sip on a complimentary bottle Champagne under the stars, and wake up to breathtaking views of rolling fields and wildlife. Our handcrafted shepherd’s hut blends rustic charm with modern comfort, offering a king-sized stargazing bed, a cozy fire-lit deck, and a luxury bathroom, all set in a peaceful meadow.

Top Guest favourite
The exterior of Butler's Rest cottage is presented with a charming red brick facade. Large windows with gray frames provide a glimpse into the inviting interior. A cobbled pathway leads towards the entrance, bordered by a gravel courtyard and green foliage.
Cottage in Hyde
4.98 out of 5 average rating, 154 reviews

Romantic cottage set in walled garden, New Forest

Situated in the grounds of an impressive country house, Butler's Rest is a stylishly renovated, quirky 19th Century cottage. Perfect for a romantic escape. In an unspoiled part of the New Forest, deer roam through the gardens, a short walk from three wonderful pubs and the open forest itself. It's a great setting from which to explore, although with a well equipped kitchen and cosy woodburner, you may not venture anywhere!

Top Guest favourite
Barn in Chiddingfold
4.97 out of 5 average rating, 718 reviews

Beautiful Barn nr Haslemere in a gorgeous setting

The Barn is situated half a mile up a track in the Surrey Hills, next to the Serpent Trail and a couple of 100 metres from the South Downs National Park. It feels like it is in the middle of nowhere, yet guests can walk to the centre of Haslemere in 30 minutes. Whether you are looking for great walks, visiting friends or relatives, or just want to escape it all, we hope you will love this place as much as we do.

Top Guest favourite
A stylish barn exterior showcases a mix of wooden and brick elements. French doors open to a bright interior with a bed visible inside. Two deck chairs are positioned on the terrace, and a chiminea stands to the side, all set against a landscaped garden.
Cottage in Privett
4.96 out of 5 average rating, 600 reviews

The Barn @ North Lodge -Soho Farmhouse-esque Cabin

Inspired by Soho Farmhouse. A stylish converted barn set in the grounds of a Georgian Lodge within the South Downs National Park. Conveniently located close to the picturesque market towns of Alresford, Petersfield, Alton and historic Winchester, it is an ideal base to both explore Hampshire and kick back and relax in luxury. Take a look at the Barn on ‘Escape to the Country’ series 25, Episode 10 on iPlayer!

Popular amenities for Medstead holiday rentals

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