
Vacation rentals in Headley
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Top-rated vacation rentals in Headley
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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!

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.

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.

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.

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.

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)

"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!

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.

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!

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.

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!

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
Other great vacation rentals in Headley

Waggoners Rest

Little Calluna

Forest Cabin & IR Sauna near Goodwood & Cowdray

Secluded Woodland Cabin with Outdoor Bath

Couples•walkers•wildlife haven•enclosed garden

Cosy/Private Studio Annexe, Hampshire Countryside

Wisteria Studio: rural retreat with private patio

Countryside Escape for Friends and Family
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