Vacation rentals in Headley Down

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Top-rated vacation rentals in Headley Down

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Guest favorite

Farm stay in Headbourne Worthy

5.0 out of 5 average rating, 233 reviews

A Unique Farm Retreat

There’s something magical about The Granary. Set in acres of farmland with spectacular sunrises and sunsets, The Granary brims with rustic charm. A dreamy hideaway with an outdoor copper bath and wood fired hot tub. An idyllic get-away-from-it-all yet only 3 miles to historic Winchester. Soak amid hot water, steam and fresh air surrounded by nature and birdsong, enjoy magnificent sunsets from the ‘Sundowner’ or cosy up toasting marshmallows over the fire pit - a perfect escape to unwind.

Feb 26 – Mar 5

G$43,552 GYD per night

Guest favorite

Guest suite in Liphook

4.88 out of 5 average rating, 282 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.

Dec 4 – 11

G$19,993 GYD per night

Guest favorite

Guesthouse in Holybourne

4.97 out of 5 average rating, 117 reviews

Private, peaceful Annexe in rural Hampshire

Ground floor annexe located in the picturesque countryside village of Holybourne, near Alton. The entire self-contained annexe is for your use for the duration of your stay. It is attached to the main house and has its own front door for private use by guests. It is spacious and bright with a private garden for guests to enjoy. The perfect base to explore glorious Hampshire countryside with its many walking routes and cycle paths, or visit the nearby Watercress Line and Jane Austen’s House.

Oct 7 – 14

G$27,906 GYD per night

Guest favorite

Cottage in Hampshire

4.96 out of 5 average rating, 380 reviews

The Garden Cottage at Oakhanger Farmhouse .

Close to Jane Austen's House in Chawton 10 mins, Situated in the S.D.National Park,Alice Holt Forest (5 mins), Gilbert Whites House (5 mins)The Watercress Steam Railway, West Wittering Beach (50 mins), Chichester 30 mins fab theatre! and Goodwood 35mins. The cottage has been completely refurbished and beautifully designed down to the last detail,comfortable and with all mod cons. With so much to do in the area it's a great place for anyone who wants a lovely break from their everyday life.

Oct 21 – 28

G$34,705 GYD per night

Guest favorite

Tiny home in Headley

4.87 out of 5 average rating, 223 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.

Nov 6 – 13

G$22,160 GYD per night

Guest favorite

Shepherd’s hut in Passfield

5.0 out of 5 average rating, 287 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!

Jul 7 – 14

G$32,899 GYD per night

Guest favorite

Guesthouse in Hampshire

4.94 out of 5 average rating, 656 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.

Aug 25 – Sep 1

G$30,997 GYD per night

Guest favorite

Tiny home in Grayshott

4.97 out of 5 average rating, 244 reviews

The Look Out @ Stable Yard

The Look Out @ Stable Yard is set in an elevated position amongst the trees overlooking the valley. It's a self contained one bedroom boutique house set within our pretty English country garden. The fridge will be stocked with continental breakfast goodies on the first day of arrival. The property has its own access and outdoor space. Ideal for those looking for a place to stay within walking distance to the award winning village. The property does have low ceilings throughout.

Jun 29 – Jul 6

G$22,922 GYD per night

Guest favorite

Tiny home in Surrey

4.99 out of 5 average rating, 110 reviews

Unique Tiny Woodland Home With Log Burner

Relax and unwind in our beautifully secluded, unique tiny home set in its own little woodland complete with outside bath tub, overlooking neighbouring fields. Bright open plan living with projector, log burner, and rainfall shower. Ideally located within a short walk of Weyhill and the quintesentially british market town of Haslemere and train station. Situated a short drive to the A3 and many attractions such as Goodwood, Devils Punchbowl, and many walking and cycling routes.

Apr 12 – 19

G$43,798 GYD per night

Guest favorite

Shepherd’s hut in Headley

4.99 out of 5 average rating, 162 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.

Aug 14 – 21

G$43,395 GYD per night

Guest favorite

Condo in Hampshire

4.97 out of 5 average rating, 172 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 banks 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.

Dec 16 – 23

G$18,212 GYD per night

Guest favorite

Guesthouse in Oakhanger

4.84 out of 5 average rating, 364 reviews

Beautiful Blossom Bothy(self contained)

Bijou, comfortable single room garden cabin ( 1 superking bed or twins ) with kitchenette, excellent WiFi,TV and adjoining ensuite shower and WC, set in the middle of an SSSI within the South Downs National Park and accessed by an unmade bumpy track. Please note this is not a village location though pubs are about a 5 minute drive ( walkable with good footwear and a map ! ) A car or bicycles are favourable although we have accommodated hikers overnight.

May 23 – 30

G$12,925 GYD per night