Holiday houses in Medstead

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Top-rated holiday rentals in Medstead

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Top Guest favourite
The exterior of a modern brick annexe is showcased, featuring a pitch roof and a welcoming dark door. Two outdoor chairs are positioned beside the entrance, with potted plants adorning the entryway. A small barbecue unit is visible, bordered by lush greenery.
Guest suite in Hartley Wintney
4.98 out of 5 average rating, 247 reviews

Private Annexe in Hartley Wintney

Our modern Annexe is located at the rear of our home, it has its own private access and gated parking to the front. Just on the outskirts of the beautiful village of Hartley Wintney & a 10 minute walk to the centre, there is a Tesco Express, restaurants, takeaways, cafes and 2 local pubs, one situated on the edge of the Cricket Green. Easy access to the M3 & M4 motorway and close to Fleet, Farnborough and Hook. With the village and local walks on your doorstep this is the perfect getaway!

Top Guest favourite
A polished silver bowl filled with ice displays several bottles of champagne. Fresh lilies and elegant candelabras are positioned nearby, adding a touch of sophistication to the setting. The arrangement creates a celebratory atmosphere.
Apartment in Winchester
5 out of 5 average rating, 101 reviews

The Sky Penthouse, City Centre Luxury

Positioned right in the heart of charming historic Winchester The Sky Penthouse offers luxury modern comfortable 5 star accommodation . Private parking for one car . Positioned an easy level 300 meter walk from the main High Street within the City Centre , 400 meters from Winchester Cathedral and 500 meters from Winchester train station. Great location with a garden. Guests can choose the bed configuration of both the double bedrooms, either 6ft wide super king luxury beds or single beds.

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, 777 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 wooden exterior wall showcases a large unframed window that reflects the surrounding greenery, providing views of the trees and hills beyond. The area in front is filled with lush foliage, contributing to the tranquil woodland setting.
Cottage in Fittleworth
4.98 out of 5 average rating, 659 reviews

Stylish Hideaway with an amazing woodland view

Our hideaway offers the perfect getaway. Soak up the peace and quiet, take in the amazing view and relax surrounded by ancient woodland, only 50 miles from London. "Watching the birds fly overhead, from the comfort of a relaxing bed. Watching the trees in the winds sway, all my worries seem faraway. Listening to the beauty of the dawn chorus, whilst enjoying the views laid before us. Your woodland hideaway is just the place to fill the visitor's heart with grace." (A guest's poem)

Guest favourite
An aerial view captures a dark-stained tiny house situated on a grassy expanse, surrounded by rolling hills and lush greenery of the South Downs National Park. The sky above features scattered clouds, and the landscape reveals a serene and expansive countryside.
Tiny home in Froxfield
4.88 out of 5 average rating, 168 reviews

Hilltop Cabin |Picture-Window Views of South Downs

In The Guardians Top 10 Best UK Off-Grid Retreats Escape to a romantic off-grid cabin overlooking the rolling hills of the South Downs. Designed for slowing down and reconnecting with nature, the cosy tiny home has a wood burner, king-size bed, ensuite shower and simple kitchen. Large windows frame beautiful countryside views, perfect for sunrise coffee and stargazing at night. Enjoy peaceful walks from the cabin and visit nearby villages and pubs around Petersfield. Pet friendly.

Top Guest favourite
A modern guest lodge is showcased, featuring a distinctive curved roof and large glass windows that enhance the natural light. The surrounding outdoor area is paved, including a pool with a cover and seating arrangements for relaxation.
Place to stay in Rogate
4.99 out of 5 average rating, 103 reviews

The Pool House (for 2 Adults & 2 Children)

This unique, Architect designed self contained building, has a style all of its own. With an open plan kitchenette and island unit, including an oven, microwave, hob and fridge freezer, you can dine in or go out to the Market Town of Petersfield. The lounge area has a 72" TV with a full sky package and spare HDMI leads. There is a walk in shower wet room and a separate cloakroom. The bedroom is cosy, with a king size bed. There is a separate area with bunkbeds, for smaller children.

Top Guest favourite
A spacious living area features a comfortable sofa and two armchairs, oriented towards arched glass doors that provide ample natural light. A coffee table sits in the center, with decorative items arranged neatly. The wooden floor and neutral walls create a welcoming atmosphere.
Cottage in Funtington
4.99 out of 5 average rating, 186 reviews

Quiet location. Close to Coast, Downs & Goodwood

Situated in the grounds of our Victorian family home, the newly converted 'Garden Rooms' occupy a separate self-contained building, furnished to a high standard, and perfect for coupes wishing to enjoy walking, cycling & sailing in the South Downs National Park. The annex has its own driveway and self check-in is via a key box. The Garden Rooms are located in the pretty downland village of West Ashling. There are three local pubs & a restaurant, all within walking distance.

Top Guest favourite
A modern cottage exterior is surrounded by lush gardens featuring various flowering plants. The building showcases a mix of wood paneling and large windows, reflecting natural sunlight. A spacious patio area can be seen, providing an inviting space to enjoy the peaceful outdoor setting.
Home in Beauworth
4.98 out of 5 average rating, 111 reviews

Stable Cottage Beauworth Southdowns Hampshire

Welcome to Stable Cottage, your idyllic getaway. Our newly built cottage is designed to the highest standard for your comfort and enjoyment. The cozy atmosphere is enhanced by super-insulated walls and a log-burning stove that keep you warm during colder months. In summer, the sliding patio doors let in sunshine and stunning views of the Hampshire countryside. Stay connected with super-fast fibre broadband and a Smart TV. Your stay at Stable Cottage will be unforgettable.

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 in Shalden
5 out of 5 average rating, 255 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.

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.

Top Guest favourite
A cozy sitting room is featured, showcasing a comfortable armchair and a large coffee table adorned with various books and decorative items. A warm fire burns in the fireplace, and built-in shelving lines one wall, filled with a diverse selection of books.
Cottage in Warfield
4.98 out of 5 average rating, 324 reviews

Luxury 2 bedroom cottage

Luxury Cottage at Hayley Green A charming, character-filled retreat for up to 4 guests in a peaceful semi-rural setting. Designed for comfort and relaxation, it’s ideal for couples, families, or friends. Enjoy a well-stocked library if you prefer to stay in. Perfectly located: 6 mins to Lapland Ascot 9 mins to Legoland 11 mins to Ascot 16 mins to Windsor & Wentworth 30 mins to Henley-on-Thames Under 1 hour by train to London via nearby Bracknell station

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, 598 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

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