Vacation rentals in Headley

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Top-rated vacation rentals in Headley

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

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Top guest favorite
A spacious bedroom features a large double bed with a neutral-colored bedspread. Natural light fills the room through two slanted skylights. A small dresser is positioned opposite the bed, and a textured area rug adds warmth to the space.
Guesthouse in Rushmoor
4.95 out of 5 average rating, 116 reviews

The Corner House Guest House - stunning location!

The Guest House is spacious, comfortable and has loads of amenities. It is the perfect place to have a break and unwind. Enjoy being in the heart of the stunning Surrey countryside and walk around the lakes, forests, heathlands and hills right on your doorstep. You are surrounded by The Flashes, Frensham Common and Hankley Common which are simply beautiful. You can swim at Frensham Great Pond, bring the bikes, walk the dog/s, explore the local area and the excellent pubs. Just relax and enjoy!

Guest favorite
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 in Haslemere
4.94 out of 5 average rating, 766 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 favorite
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, 618 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.

Top guest favorite
The entrance of the cabin is framed by greenery, featuring a wooden door flanked by two small potted plants. Two chairs are positioned on a stone patio, providing a welcoming outdoor space. A small sign reads 'Kwet Cabin' above the door.
Tiny home in Headley
4.89 out of 5 average rating, 258 reviews

Log cabin. Quiet, private, cosy + breakfast

Cosy log cabin with kingsize bed and ensuite bathroom. The residence has its own private front door and is set in a village location with stunning walks and cycling routes. Parking available in the drive and in the summer, outdoor seating available. Village gem of a pub, The Crown & green is 100 yards from the property and it’s a short drive to Ludshott Common, Waggoners Wells and The Devils Punchbowl. 1.5 miles or a 4 minute drive from the wedding venue Cain Manor. Easy access to the A3.

Top guest favorite
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 in West Horsley
4.94 out of 5 average rating, 369 reviews

Unique Dome | Glamping | Hot Tub | Surrey | Adults

Olive Pod, is a the ultimate cozy, private picturesque geo dome home. Located on a fruit farm in Surrey, in its own private field hidden behind tall fir trees with no other pods or tents! Olive Pod has become a firm favourite adults only retreat with guests booking for proposals, anniversary's, birthdays and honeymoons - we can also decorate the place for your arrival ✨ Olive Pod is the ultimate escape to unwind and recharge in a tranquil natural setting. Perfect for couples or friends.

Top guest favorite
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, 658 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)

Top guest favorite
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 out of 5 average rating, 420 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 favorite
A charming detached cottage features dark wooden panels and a traditional red-tiled roof. The front door is surrounded by bright flowers and lush greenery, with a stone pathway leading to the entrance. Clear blue skies add to the inviting atmosphere.
Guesthouse in Hampshire
4.94 out of 5 average rating, 789 reviews

The Old School House Liphook - hot tub & tennis ct

The Old School House is a traditional and cosy one bedroom detached cottage in the grounds of our home on the western edge of Liphook village in Hampshire. Easy car access, just off the A3 and south of the Hindhead tunnel. The village has a train station. Situated in the South Downs National Park and ideally located for the market towns of Haslemere, Farnham, Petersfield and Alton, it is only 25 minutes from Goodwood. Great countryside and lots on offer locally for holiday or break.

Top guest favorite
A stylish living area features a light-colored sofa adorned with patterned cushions. Two armchairs are positioned nearby, and a rustic coffee table holds magazines and a floral arrangement. The kitchen cabinetry, painted in a soft green, complements the space, while natural light enters through two windows.
Barn in Passfield
4.92 out of 5 average rating, 115 reviews

The Artist’s Barn. A unique and rustic retreat.

Beautiful, unusual & stylish 2 bedroom, 2 bathroom, ( 1 en suite ) renovated and arty barn. In a tranquil, yet accessible countryside setting, overlooking fields with 2 ponies/stable yard. A comfortable, friendly & rustic place to unwind. It also stays cool, even on hot days but warm and toasty in the winter. Numerous nearby attractions including Jane Austen’s Museum, The Watts Gallery and Uppark House. DM if you’d like an art lesson. Can sketch ponies/portraits or landscapes!

Guest favorite
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, 268 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.

Top guest favorite
Tiny home in Surrey
4.99 out of 5 average rating, 230 reviews

Tiny Home Escape: Log Burner, Projector & BathTub

Escape to our secluded, one-of-a-kind tiny home nestled in a private woodland, complete with an outdoor bathtub overlooking peaceful fields. Enjoy bright, open-plan living featuring a log burner, projector, and luxurious rainfall shower. Perfectly located within walking distance of Weyhill and the charming market town of Haslemere with its train station. Just a short drive from the A3, Goodwood, Devil's Punchbowl, and countless walking and cycling trails. A tranquil getaway awaits!

Top guest favorite
A charming wooden structure is surrounded by lush greenery, set on a spacious, well-maintained lawn. The sky is partly cloudy, illuminating the natural landscape. A private hot tub is situated nearby, enhancing the secluded atmosphere of this tranquil retreat.
Shepherd’s hut in Headley
5 out of 5 average rating, 219 reviews

Shepherd's Hide, Hampshire with wood-fired hot tub

A truly luxurious ‘in touch with nature’ experience. Situated in it’s own private paddock in beautifully secluded yet accessible surroundings. Nestled between the Surrey Hills and the South Downs National Park, Shepherd's Hide provides a peaceful and tranquil retreat in the country. On the Hampshire/Surrey border surrounded by National trust woodlands and commons, the area offers access to many outdoor spaces, ideal for walking, cycling, riding, fishing or just relaxing.

Popular amenities for Headley vacation rentals

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