
Holiday rentals in Medstead
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Top-rated holiday rentals in Medstead
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Rivers stays with hot tub
Our unique river stay offers a one-of-a-kind experience, combining modern comfort & nature. This charming space features panoramic windows that invite the soothing sounds of the flowing water and stunning views of the surroundings right into your living area. Enjoy your morning on the private deck while watching the sunrise, or unwind in the evening with a glass of wine as you listen to the gentle rustle of leaves. Perfect for couples, solo adventurers, or anyone looking to reconnect with nature

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.

One bedroom cottage escape
Relax and make yourself at home in our charming 1-bedroom bungalow — the perfect retreat for a restful getaway. Featuring a super king-size bed with White Company bedding, a well-equipped kitchen and a bright and comfortable living room with stunning views of the garden. The modern restroom includes a walk-in shower and Rituals toiletries for a luxury experience. Enjoy your morning coffee on the patio or take advantage of the hammocks on the pond both with views of the surrounding garden.

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.

"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!

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.

Historic 16th Century thatched cottage, Hampshire
Right in the middle of Jane Austen country, this famous chocolate box 16th Century Grade II listed cottage, the oldest house in the village, is chocca-block full of history. It was home to the Archbishop of Canterbury, Queen Victoria's right-hand man, who not only christened and crowned the Queen but then went on to marry her Prince Albert. Set in the picture-perfect Hampshire village full of thatched cottages and surrounded by gorgeous walks it is the perfect country retreat!

The Woodshed
The Woodshed is right in the heart of the South Downs National Park, between the villages of Warnford and Exton, a secluded and peaceful space surrounded by a working farm. The Woodshed has a view of Old Winchester Hill that is magic. Activities in the area include biking, hiking, and angling, and three of the best pubs in Hampshire are within a 5 mile radius. As we are a little distance from the main track, I am happy to come and collect guests from Exton if walking.

Stylish Barn in Rural Hampshire
Beautiful barn space in the heart of the Hampshire countryside situated on the edge of a village. On the first floor there is a UK Superking bed which can be split into twin beds at £15 extra cost, a table for two people and shower room. Breakfast items such as fruit, yoghurt, bread for toast, jams, honey, marmite are provided along with tea and 'real' coffee. ** Although there is a small kitchenette, there are no cooking facilities for hot food preparation **

The Glade at Ladyhill Vineyard near Winchester
Nestled on the edge of an ancient wood in South Downs National Park and with fantastic views over Ladyhill Vineyard and the Hampshire countryside The Glade has a cosy A-Frame to grab a good night sleep, a separate shower room with flushable loo to keep you fresh and a kitchen equip-for-easy glamping. Relax and admire the views, BBQ on the fire pit, spot deer and hare or stroll down the river Itchen to The Bush gastro pub. You’ll return home totally refreshed!

Luxury Cabin with Outdoor Bath, Sauna & Fireplace
Set on the edge of the South Downs National Park, this luxurious cedar cabin offers complete privacy, stillness and refined comfort. Soak beneath the stars in your private outdoor bathtub, unwind in your exclusive sauna, or rest beside the indoor wood burner fireplace. Designed by a fellow traveller for deep rest and reconnection, every detail is intentional — inviting calm, closeness to nature and a quiet sense of renewal that lingers long after you leave.

Lovely one bed flat with free parking on premises
A small but perfectly formed one bedroom flat in a rural location. The Annex has a small kitchen with hob, cooker and microwave. There is a table for eating. One double bed and a shower room. We have good broadband and there is parking on the property. The village has a great pub within walking distance and plenty of lovely walks. We are about 11 miles from Winchester and 3 miles from Jane Austen's Chawton. Our stairs into the flat are steep and narrow.
Popular amenities for Medstead holiday rentals
Other great holiday rentals in Medstead

Farm Cottage, Hay Barn Drill Bits

Artist studio with outdoor bath and field views

Forest Cabin & IR Sauna near Goodwood & Cowdray

Charming village spot, cottage garden, sleeps 5

The Cottage at Lupton House, Froxfield Petersfield

Wyck Annex

A Unique Farm Retreat

Stunning converted Coach House.
Destinations to explore
- New Forest National Park
- Wembley Stadium
- Covent Garden
- Kings Cross
- Paddington
- Hampstead Heath
- Bournemouth Beach
- St Pancras International
- London Bridge
- Brighton Seafront
- West Wittering Beach
- Tower Bridge
- Paultons Park Home of Peppa Pig World
- Clapham Common
- University of Oxford
- Goodwood Motor Circuit
- Buckingham Palace
- Stonehenge
- Thorpe Park Resort
- South Downs National Park
- Chessington World of Adventures Resort
- Big Ben
- Windsor Castle
- LEGOLAND® Windsor Resort





