Holiday houses in Headley Down

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Top-rated holiday rentals in Headley Down

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

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Guest favourite
The cottage is surrounded by lush greenery and a well-maintained garden. A gravel path leads to the entrance, framed by neatly trimmed hedges. Large windows reflect natural light, while bicycles are casually positioned nearby, suggesting an inviting outdoor environment.
Cottage in Hampshire
4.93 out of 5 average rating, 218 reviews

Beautiful S.Downs Cottage, pool and tennis

The private gate takes you directly onto the South Downs. Close to the beach and city, Chichester, Portsmouth, Goodwood, Cowdray and Witterings beaches are close by while the train takes you to Waterloo in an hour. Ripsley is a place to get away from it all. Great for cyclists, walkers, couples and families. There are garden games, a tree swing, tree house, firepit and football to enjoy while the pool and tennis court are available from late May until the end Sept/early Oct, Mon- Sat 9am - 1 pm.

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Top Guest favourite
Guesthouse in Thursley
4.95 out of 5 average rating, 154 reviews

Stylish Surrey Hills Barn | Walks, Pubs & Outdoors

Just an hour from London, Weymoor Barn offers a peaceful escape in the heart of the Surrey Hills. Explore beautiful landscapes, charming market towns and cosy country pubs, with the Devil's Punchbowl and Frensham Ponds both within easy reach. Just as appealing is the chance to slow down and enjoy the countryside at your own pace. With walks from the doorstep, peaceful surroundings and private dining available by arrangement, it's an easy place to switch off and make the most of your time away.

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Guest favourite
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, 145 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!

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Top Guest favourite
The exterior of the spacious annex is set amidst a well-maintained garden, featuring lush green grass, varied shrubbery, and decorative landscaping. A patio area can be seen, complemented by outdoor seating options and natural sunlight filtering through the surrounding trees.
Guest suite in Liphook
4.9 out of 5 average rating, 464 reviews

Large guest house

The spacious annex has a separate guest entrance and off-street parking. Guests can use the private patio and there are facilities for breakfast of toast & cereal (included). Located down a private drive in the heart of Liphook within walking distance of many local amenities (3 pubs, supermarket, cinema, take aways). The train station is only a 7 minute walk away and a 2 minute walk from a bus stop. We are on the edge of the South Downs National Park with some stunning walks from the house.

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Top Guest favourite
Cottage in Churt
5.0 out of 5 average rating, 102 reviews

Couples•Walkers•Wildlife Haven•Badger Watching

You come here to slow down together. You wake to birdsong & woodland views. Curl up in the evening watching badgers emerge from the nearby sett or live on cctv from the comfort of the sofa. Spotlessly clean, cosy and peaceful, every detail carefully thought through so you don’t have to think at all. Step straight out into the beautiful Surrey Hills for quiet paths, open fields and woodland trails that you and your dog will love. You leave relaxed, restored and already planning your return.

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Top Guest favourite
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, 276 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.

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Superhost
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
5.0 out of 5 average rating, 451 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!

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Top Guest favourite
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, 832 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.

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Guest favourite
An aerial view captures the serene lodge nestled within a forest of vibrant autumn foliage. The surrounding trees display a mix of colors, emphasizing the lodge's peaceful location amidst nature, while distant hills fade into the horizon.
Cabin in Grayshott
4.95 out of 5 average rating, 186 reviews

Cosy forest lodge with wood-burner. Dogs welcome.

Forget your worries in this spacious and serene cabin opposite the forest. Throw open the doors, hear the birdsong and relax in comfort. Enjoy its convenient location to mainline train stations and the A3 whilst surrounded by woodland tranquility and National Trust walks. The villages of Grayshott and Churt lie within walking distance with their pubs, cafes, restaurants and characterful shops, whilst slightly further afield lie bustling Farnham, Haslemere, Midhurst and Petworth.

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Top Guest favourite
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
5.0 out of 5 average rating, 235 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.

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Top Guest favourite
A light-filled studio space features a spacious bed draped in a white coverlet and a cozy seating area with a soft couch and coffee table. A large window allows natural light to brighten the room, complemented by a wall-mounted television.
Condo in Hampshire
4.97 out of 5 average rating, 291 reviews

Studio Apartment set within a rural village

Liphook’s endearing village centre is a walkable 0.7 miles away and holds everything you could expect from local shops. From a Boutique Cinema and pharmacies to takeaways and florists, all your daily needs are catered for. For a larger shopping trip, Sainsbury’s superstore is only 1 mile away by car and provides all the variety and choice you would expect. Local towns such as Haslemere and Petersfield bring more variety to the region with big brands and familiar names.

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Top Guest favourite
Guesthouse in Grayswood
4.97 out of 5 average rating, 358 reviews

Grayswood Cowshed in stunning Grounds

A beautifully converted Cowshed in a rustic style with luxurious Super King bed in a studio suite with added double bunk room for up to four extra guests. Studio has a galley kitchen with hob and oven for basic cooking. Well fitted bathroom facilities including powerful shower and roll top bath and underfloor heating. Relaxing Sofa in main space with Flatscreen TV and wifi throughout. Underfloor heating throughout. Large french windows overlooking an orchard.

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Popular amenities for Headley Down holiday rentals