Holiday rentals 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
4.96 out of 5 average rating, 140 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
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
4.99 out of 5 average rating, 362 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
4.98 out of 5 average rating, 231 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
4.98 out of 5 average rating, 626 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
The motor yacht is docked at the marina, showcasing its sleek white exterior against a bright blue sky. A group of four people is situated on the bow, enjoying the sun and the scenic views of the surrounding cityscape.
Boat
4.93 out of 5 average rating, 221 reviews

Superyacht on 5* Town Quay Marina, Southampton

FULLY HEATED FOR WINTER! A wonderful opportunity to stay onboard a beautiful spacious motor yacht moored on the prestigious Town Quay marina, Southampton. Ideal for couples, families or friends looking for an exciting or romantic getaway. Up to 7 guests. 3 bedrooms with 3 bathrooms. Bespoke packages also available including champagne reception, birthdays/decorations, secure cruise parking/transfers etc. Please enquire for details. Our base price is based upon 2 guests, extra guests are £25pp

Top guest favourite
A neatly paved pathway leads to a wooden gate, surrounded by lush greenery and well-maintained shrubs. A small seating area with a table and chairs is positioned on a stone patio, providing a tranquil outdoor space. Sunlight filters through the trees, creating a serene atmosphere.
Bungalow
4.99 out of 5 average rating, 210 reviews

Bungalow in new forest

Peaceful detached property lovely views ,all on one level well equipped, oven, microwave, dishwasher, air fryer, fridge , freezer ,log burner ,private parking, has 2 bedrooms but can accommodate up to 6 persons as have bed settee, patio area with garden furniture outside back of property, seating area also on the front of property, 7 mins away from Paultons park Longdown dairy farm 10 mins drive Southampton 10 min drive Bournemouth 30 mins drive Check in 3.oclock Checkout 10.oclock

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
4.92 out of 5 average rating, 108 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
The studio cottage features a cozy sleeping area with a spacious bed adorned with soft linens. A rustic brick chimney breast is visible, accompanied by a kitchenette and dining space, complete with a table, chairs, and a small electric fire for warmth.
Place to stay
4.94 out of 5 average rating, 126 reviews

The Old Dairy in the New Forest

The Old Dairy is a quaint studio cottage in the New Forest. The one bedroom studio was once the old parlor room for the dairy. With lots of original features such as the old brick chimney breast and wooden beams. This is perfect for a couple who want to come away to explore the forest for a few days. Equipped with a kitchenette for small meals with fridge microwave and single induction hob it also has a shower room. Set on our 70 acre farm which you can explore with fresh farm eggs daily.

Top guest favourite
A charming semi-detached cottage is framed by lush greenery and a well-maintained garden. The pathway, lined with stone tiles, leads to the entrance. A thatched summer house is visible in the background, complementing the cottage's traditional red brick exterior and white window frames.
Cottage
4.95 out of 5 average rating, 327 reviews

Stride cottage 4 nights minimum stay.

Built in 1840 to house workers making bricks this charming extended semi-detached cottage has been lived by the same family of New Forest commoners for the last 50 years. Recently tastefully refurbished to a high standard, STRIDE Cottage is a much loved comfortable family home which maintains the character of the traditional New Forest cottage whilst offering spacious, modernised, comfortable living. Set in a colourful well established cottage garden including thatched open summer house

Guest favourite
The exterior of the property is shown, featuring a whitewashed building with a brick accent wall. A wooden gate leads to a private entrance, and a gravel pathway displays vibrant flowers along the edge. Utility poles and neighboring structures are visible in the background.
Home
4.86 out of 5 average rating, 698 reviews

Private" Garden" suite ,in Cadnam, New Forest

Private, spacious, garden room with king size bed, and lounge area , large modern shower room. own entrance. Recently re-furbished . We' re in the New Forest, as little as 4 mins on foot to fabulous forest walks and trails. There are pubs and restaurants within walking distance ( The White Hart, The Coach and Horses, Le Chateau Bistro.) 4 miles to Lyndhurst, Highcliffe castle beach, Steamer Point, Mudeford approx 30 mins drive. Southampton, Salisbury .Bournemouth all close by.

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
4.99 out of 5 average rating, 377 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.

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
4.99 out of 5 average rating, 275 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.

Popular amenities for Winsor holiday rentals

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  4. Hampshire
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