Holiday houses in Winsor

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Top-rated holiday rentals in Winsor

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Top Guest favourite
A modern one-bedroom bungalow is presented with a brick façade, complemented by a paved driveway that accommodates two vehicles. Lush greenery and well-maintained shrubs surround the property, which is situated in a quiet residential street under a partly cloudy sky.
Bungalow in Totton West
4.96 out of 5 average rating, 141 reviews

Refurbished bungalow on the edge of the New Forest

Located: just off junction 2 of the M27, 10 minutes drive from Peppa Pig World and perfect for trips all over the New Forest and Southampton, with Winchester, Salisbury, Stonehenge, Bournemouth and Portsmouth all less than an hour away.

 A modern self-contained one bedroom bungalow with off road parking for two vehicles. Situated in a quiet residential neighbourhood. Recently refurbished throughout in 2018/9 and offering a comfortable living space providing a great place to relax and unwind.

Top Guest favourite
Cabin in Winsor
4.99 out of 5 average rating, 100 reviews

New Forest Cabin with Stunning View

The Old Dairy is a beautiful hand-built cabin situated on a working farm on the edge of the New Forest National Park. We are ideally positioned for visiting the many beautiful villages, cosy forest pubs and fabulous country walks. Peppa Pig World is a 5 minute drive. There is a kingsize bed with an ensuite shower room and two single beds that can be made up in the spacious open-plan lounge, kitchenette area. The large decking area boasts spectacular views and is a great spot for a sundowner.

Top Guest favourite
An outdoor patio area is visible, featuring a dining table surrounded by eight chairs. A large umbrella provides shade. The barn's rustic wooden exterior contrasts with the neatly laid stone tiles. Lush greenery and trees form a backdrop, under a partly cloudy sky.
Home in Whiteparish
4.99 out of 5 average rating, 365 reviews

Stride’s Barn

A newly restored and beautifully refurbished oak framed barn conversion bordering the New Forest National Park . With spectacular far reaching views Stride’s Barn is situated 9 miles from the Cathedral City of Salisbury and 15 miles from Southampton . An ideal base to explore the local areas including many walks, pubs , restaurants, golf clubs and other tourist attractions such as Stonehenge and Paultons Park/Peppa Pig World . Can be rented with additional listing ‘The Cowshed’ (sleeps 2) .

Top Guest favourite
Farm stay in New Forest, Hampshire
4.98 out of 5 average rating, 234 reviews

Granary Grain Store with Oak Beams

Self check-in (key on inside of door) Free parking adjacent to granary. Welcome to our cosy oak beamed granary surrounded by fields on the edge of the National Park. Lyndhurst & Brockenhurst are nearby where you can see ponies, donkeys & cattle roaming on the Forest. Both have lovely tea rooms and shops. Lymington is a coastal town with unique shops and cafes as well as scenic walks along the Quay. Beaulieu is also a must to visit with very scenic walks from Beaulieu River to Bucklers Hard.

Top Guest favourite
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, 631 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.

Guest favourite
An inviting outdoor courtyard is illuminated by sunset hues and string lights. A hot tub is positioned nearby, alongside a fire pit with flames flickering. A dining table is set for meals, with a barbecue grill ready for use against the rustic brick backdrop.
Farm stay in Hampshire
4.99 out of 5 average rating, 158 reviews

Bluebell Copse Cottages New Forest with Hot Tub

Bluebell Copse Cottage is a stunning barn conversion on our 70 acre working farm. Fully renovated from the ground up in 2020 and opening in 2021 you will find all the modern conveniences you need as well as characterful design. There is space for you to explore a games room for family games and an on-site treatment room for relaxation. Bluebell Copse Cottage is more than just a holiday cottage it is an escape from the hustle & bustle of your busy life. Find us on all social media platforms

Top Guest favourite
A charming cabin is nestled among lush greenery, featuring large glass doors that allow natural light to fill the interior. The surrounding area includes a well-maintained lawn, with trees providing shade and a rustic fence delineating the space.
Barn in Winsor
4.92 out of 5 average rating, 113 reviews

The L'il Cat House

On the site of what was the Ritz Carlton of catteries in The New Forest we have created a luxury cabin for you to curl up in front of the log burner and to use a base for exploring this beautiful part of the world. The L'il Cat House is a 20 minute drive from the beautiful beach of Lepe, that faces The Isle Of Wight; 5 minutes from Peppa Pig World (Paultons Park). In the grounds behind the owners’ house, the cabin is secluded & discreet, but with your friendly hosts close at hand if needed.

Guest favourite
A spacious cabin interior features a kingsize bed adorned with textured cushions. A freestanding bath is positioned under a tree, while green walls create a calming effect. A dining table is set with dishes and glassware, enhancing the inviting space.
Cabin in Southampton
4.96 out of 5 average rating, 403 reviews

New Forest Luxury Couple Retreat Eling Tree Cabin

A beautiful open plan cabin ideal for couples looking for a relaxing getaway. Kingsize bed and freestanding bath under your very own tree,as well as a private toilet with rain shower. The cabin has underfloor heating to keep you warm all year round. We supply bedding and fluffy towels as well your essentials. The kitchen is equipped with oven/hob, microwave, fridge-freezer and dishwasher. You also have BBQ Smart TV and Wifi. Check out our sister cabin. airbnb.com/h/ivycottageappletreecabin

Top Guest favourite
The curved structure of The Farley Hangar is set amidst open fields, flanked by a solitary tree providing shade. A clear blue sky enhances the sense of tranquility, while the landscape offers a peaceful rural atmosphere.
Hut in Braishfield
4.99 out of 5 average rating, 382 reviews

The Hangar - countryside views, seclusion & peace.

The Farley Hangar is a peaceful space with far reaching views of Hampshire's woodlands and the Isle of Wight. Located on our family farm and private airstrip in the Test Valley. Winchester, Romsey and Stockbridge are just 20 mins away. On the doorstep of numerous cycle routes and footpaths including the Claredon Way (Sals-Win). King size bed & full-size bath with rain shower. From your private deck with log burner you will see various wildlife species and watch the stars at night.

Top Guest favourite
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, 285 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 favourite
A charming cottage is showcased with traditional timber framing and red brickwork. The front is adorned with white windows, and a wooden gate leads to a gravel pathway. Wood storage is neatly arranged beside the entrance, framed by lush greenery.
Cottage in Downton
4.97 out of 5 average rating, 348 reviews

Charming 16th century cottage in rural setting

Dating from the 16th century, Stable Cottage adjoins the rest of the property but has its own front door and is a completely private and self contained space. Downstairs has an entrance hall, sitting room, with original beams and kitchen; upstairs there are 2 bedrooms, one double and one single, bathroom and separate shower room. Perfect for 2/3 adults (3 adults max) or for a family with a baby/child. Close to Salisbury and the New Forest, it's the place to explore Wiltshire.

Top Guest favourite
Home in Romsey
5 out of 5 average rating, 225 reviews

John's Barn

Beautiful architect designed barn set in private woodland of over 50 acres. John's Barn was the result of a conversion of an existing barn. With 3 bedrooms, 2 bathrooms and an open plan kitchen / living / dining area. The natural woodland, fields, lake and river give the chance to get back to nature and is ideal for children to explore. The wildlife includes herds of deer that you will see up close. The barn is situated 2 miles from the New Forest Park national park.

Popular amenities for Winsor holiday rentals

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  4. Hampshire
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