Holiday houses in Winsor

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Top-rated holiday rentals in Winsor

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

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Top Guest favourite
A well-equipped galley kitchen features sleek white cabinetry and a modern design. Natural light flows through the window, illuminating the space. Appliances include a built-in oven, microwave, and a sink. A dining area is visible at the end of the kitchen, showcasing a contrast of textures.
Bungalow in Totton West
4.97 out of 5 average rating, 144 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.

Guest favourite
A private hot tub is featured on an outdoor deck, surrounded by low walls and offering views of the river and distant lights. The softly illuminated water invites relaxation, while the tranquil night sky creates an intimate atmosphere.
Houseboat in Southampton
4.99 out of 5 average rating, 102 reviews

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

Top Guest favourite
A spacious decking area is featured, surrounded by gravel, with a wooden picnic table and chairs shaded by a large umbrella. A sun lounger is positioned nearby, providing a comfortable spot to relax. The rustic cabin exterior is seen in the background, adorned with multiple windows.
Cabin in Winsor
4.99 out of 5 average rating, 105 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
A light-filled open-plan living area showcases original oak beams and stone flooring. A spacious corner sofa invites relaxation, facing a wooden coffee table. A dining area with wooden chairs and a staircase leading to the mezzanine can be seen in the background, along with a well-equipped kitchen.
Home in Whiteparish
4.99 out of 5 average rating, 368 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
Hut in Winchester
4.98 out of 5 average rating, 634 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
4.98 out of 5 average rating, 160 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 secluded cabin is framed by lush greenery. Large glass doors provide a view of the outdoor area, where natural wood tones complement the gravel path. A seating area is visible, featuring stylish lounge chairs and a small table, inviting relaxation in the tranquil setting.
Barn in Winsor
4.92 out of 5 average rating, 114 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
An open plan cabin interior showcases a kingsize bed adorned with a textured gray coverlet. A freestanding bath sits beneath a tree, flanked by green cabinetry. Well-placed lighting creates a soft glow, enhancing the overall relaxing ambiance. Natural elements are integrated throughout the space.
Cabin in Southampton
4.96 out of 5 average rating, 407 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
A cozy bedroom features exposed oak beams and wooden flooring. A spacious bed is centered against the wall, complemented by light-colored bedding. Two nightstands with lamps are placed on either side of the bed, while a window with a blind allows for soft natural light.
Farm stay in New Forest, Hampshire
4.98 out of 5 average rating, 235 reviews

Romantic converted granary in the New Forest

Self check-in & parking space. Welcome to our beautiful converted oak beamed granary on a working farm surrounded by fields in the heart of the New Forest. Local pubs, countryside walks & cosy evenings make it perfect for couples. Lyndhurst is nearby and has independent shops, tearooms as well as ponies roaming on the forest. Brockenhurst has great cycling routes and woodland walks. Both have bike hire shops. Beaulieu has riverside walks, motor museum, palace & quaint village shops.

Guest favourite
Home in Hampshire
4.87 out of 5 average rating, 713 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
An inviting room features a king-size bed with a green and white headboard, flanked by bedside tables and lamps. A blue loveseat is positioned in front of the bed, with a small table displaying refreshments. Wooden walls offer a warm ambiance, enhanced by overhead lighting.
Hut in Braishfield
4.99 out of 5 average rating, 384 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
An aerial view captures Pine Lodge, nestled among lush trees, surrounded by serene water. The lodge features a spacious deck leading to a private lakeside area, ideal for outdoor relaxation. Green foliage frames the setting, creating a tranquil atmosphere.
Farm stay in West Wellow
4.9 out of 5 average rating, 503 reviews

Pine Lodge - Headlands Farm

🌲 Pine Lodge — Lakeside Retreat for Families & Friends ✨ Perfect for families of four, couples wanting extra space, or mixed groups seeking a peaceful countryside escape. Step outside to your child-friendly lakeside decking right on the water’s edge. Enjoy breakfast at our onsite coffee shop ☕, discounted fishing 🎣, plus sauna & cold plunge, padel, and massage & beauty treatments 🧘‍♀️🎾💆‍♀️. Dog friendly, with self check-in 🧼 — 5 more lodges available on Airbnb 💌

Popular amenities for Winsor holiday rentals

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