House vacation rentals in Winchester

Find and book unique houses on Airbnb

Top-rated house rentals in Winchester

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

%{current} / %{total}1 / 1
Guest favourite
The exterior of The Joinery reveals a modern two-story structure with a combination of brick and wood accents. Large glass doors open to a private terrace area surrounded by greenery. The property is framed by fencing and features a gravel pathway leading to the entrance.
Home in Owslebury
4.87 out of 5 average rating, 261 reviews

The Joinery, Owslebury, Winchester

The Joinery is on the edge of Owslebury, a picturesque village just south of Winchester. It is light and airy and offers 4 bedrooms on ground floor level, two with ensuite shower and a family bathroom. Upstairs is a large open plan area with kitchen, dining table and sofas for relaxing and enjoying the views of the surrounding countryside.There is also a snug room with TV. There are steps down to the main entrance so not suitable for people with mobility issues. The garden area is not enclosed.

Top guest favourite
The exterior of a recently renovated recording studio is shown, featuring dark wooden cladding and yellow-framed windows. A welcoming front door is prominently displayed, while neatly landscaped planters add a touch of greenery. The historic church spire is visible in the background.
Home in Hampshire
4.97 out of 5 average rating, 175 reviews

Spacious and Stylish Home in Heart of Top Village

A stylish and spacious recently renovated recording studio, which has been finished to a high spec with exposed timber beams, brickwork and a stunning log burner perfect for relaxing after exploring all that Hampshire and West Sussex have to offer. There is a large double bedroom with king sized bed and ensuite bathroom, and an open plan living area with sofa beds and log burner that can accommodate up to 3 further guests. There are 3 fantastic pubs within walking distance - one only 50m away!

Top guest favourite
A flint-built hideaway is shown, featuring arched windows and a slate roof. The private garden is surrounded by lush green grass, with a small outdoor table and chairs visible. A tree partially frames the scene, adding to the peaceful atmosphere.
Home in Meonstoke
5 out of 5 average rating, 180 reviews

The Piggery: with tennis court and games barn

The Piggery is a secluded flint built hideaway, with lots of period charm, set in the grounds of a manor house. Converted to a high standard it has it’s own private garden, access to the owners tennis court & a large barn with table tennis, table football & pool, wider house grounds including an island, surrounded by the river Meon. Numerous walks direct from The Piggery and a number of local vineyards are nearby. 5/10mins walk away are two super pubs and the very well stocked village shop.

Guest favourite
A rustic oak-framed barn is nestled among trees, showcasing a sloped roof and large windows. Gravel pathways lead to the entrance, framed by potted plants. The structure is surrounded by open space, offering a serene rural setting.
Home in Winchester
4.94 out of 5 average rating, 372 reviews

Oak Framed Barn with Tennis Court

A stylish secluded, two storey, oak framed barn with tennis court, 4 miles from Winchester. Homely space with two bedrooms plus a sofa bed (upon request) and ground floor open plan living area. Super fast WiFi. The Barn adjoins the Watercress Way and stands separately in the grounds with views over open Hampshire fields. Nearest neighbour c.1 mile away but there is loads to do in the area with an abundance of country pubs, one or two within walking distance and beaches within 50 minutes

Top guest favourite
A comfortable living area features a gray sofa adorned with cushions, complemented by a wooden dining table surrounded by four chairs. Floral curtains frame the bright windows, allowing natural light to illuminate the space, which includes a decorative fireplace along one wall.
Home in Chandler's Ford
4.99 out of 5 average rating, 194 reviews

Homely and Comfortable in a quiet location

A pretty, well-equipped and homely two bedroom terraced property situated in a quiet and lovely area of Chandler's Ford. Marwell Zoo, the New Forest, Paulton's Park/Peppa Pig World, Beaulieu, Isle of Wight ferry links and south coast beaches are a short drive away with excellent motorway and rail links. Ideal for contractor/business stays as well as families, couples and friends. Walk to the local shops and take a stroll to the beautiful Hiltingbury Lakes and local nature reserve.

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 in Hampshire
4.86 out of 5 average rating, 665 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.

Guest favourite
The bedroom features a spacious bed dressed in soft grey bedding, complemented by decorative cushions. Light streams through the window, softened by sheer curtains. A bedside table with literature adds a functional touch, while a wall-mounted mirror enhances the overall brightness.
Home in Hampshire
4.95 out of 5 average rating, 702 reviews

Quiet Winchester One Bedroom Home with own parking

Welcome to your lovely detached one bedroom home in a quiet leafy private road on the edge of St Giles Hill - just above medieval Winchester and on the edge of beautiful the South Downs Way. Your self-contained home includes parking on the drive, a stylish double bedroom, shower room, living area (with full double-width sofa bed) incorpoating a full kitchen/washing machine. Its an easy 10 minute downhill stroll across the park (lovely for a sunset picnic) to historic Winchester.

Top guest favourite
A bright and welcoming living area features a striped sofa and a small dining table set for two. A colorful area rug lies beneath a wooden coffee table. Natural light filters through sheer curtains, enhancing the cozy atmosphere of the space.
Home in Hampshire
4.99 out of 5 average rating, 136 reviews

One bedroom house in Waterlooville. An ideal base.

This is my small one bed house which is ideal for exploring SE Hampshire & W Sussex. The new king size bed, lounge, kitchen & bathroom provide an ideal base, located in a quiet suburban location. There is excellent access to the A3M & A27, so Portsmouth, Petersfield, Chichester and the South Downs lie within easy reach. I have a nice garden and car bay for my visitors and include broadband and gas central heating which I hope will make your visit relaxing, convenient and enjoyable.

Guest favourite
A charming garden stretches across the landscape, featuring lush greenery and a serene waterway. Two distinctive structures are visible: a traditional house and a converted mill, both surrounded by trees, creating a peaceful atmosphere by the River Meon.
Home in Hampshire
4.96 out of 5 average rating, 254 reviews

Romantic 17th Century Paper Mill on The Meon River

Enchanting converted 17th Century Paper Mill over the River Meon in Warnford, Hampshire. Quirky interior with original Japanese features. Trout anglers will have a ball. There are swans, herons, kingfishers and mallards and, if you're really lucky, you might see an otter. As you can see from the photo, the Mill is just by our cottage, but we're not always there so often you'd have the whole garden to yourself. My place is good for couples and solo adventurers.

Guest favourite
A charming detached property is surrounded by lush greenery, featuring a gravel driveway. The two-storey building includes a wooden balcony and a staircase leading to the upper level. Planters and trees add to the serene setting, enhancing the appeal of the outdoor space.
Home in Crawley
4.97 out of 5 average rating, 326 reviews

Secluded and peaceful home in beautiful village

A delightful detached two storey property in the grounds of Whitethorn cottage, in the picturesque village of Crawley near the historic city of Winchester. Secluded and quiet with pleasant garden views. Nicely furnished to a high standard throughout. Crawley is a beautiful classic English village with an excellent gastro pub, within easy walking distance. We will be available to offer help and advice on the many places to visit in the local area.

Superhost
The spacious bedroom features a wood-paneled accent wall and a large bed with light bedding and decorative pillows. A piece of wall art is displayed above the bed. Natural light enters through large windows adorned with floral curtains, providing a serene ambiance.
Home in Kings Worthy
4.78 out of 5 average rating, 206 reviews

The Granary Annex at Worthy Barn.

Ideal location for visiting the beautiful & historic Winchester in Hampshire. The Granary is 2 miles from Winchester, opposite a farm shop & lovely country pub is a 10 minute walk away. The main bedroom has a kingsize bed and views across watercress beds, the adjoining bedroom has bunk beds. The Granary is self contained with private 24 hour, access via key safe. There are many local walks and a variety of local food delivery options available.

Guest favourite
An open-plan living area features a plush couch adorned with decorative pillows, complemented by cozy armchairs. A wooden coffee table rests on a soft rug, and a fully equipped kitchen is visible in the background. Natural light floods the space through large windows, enhancing the inviting atmosphere.
Home in Funtington
4.83 out of 5 average rating, 121 reviews

Peaceful And Beautiful Barn In Downland Village

* Beautifully furnished barn in rural location * Close to Chichester, The South Downs and Goodwood * Free parking on premisies with access to EV charger Spend some time in this stunning barn furnished with the highest quality furniture and fabrics. This beautiful lodge offers luxury accommodation over two floors for four people looking for a peaceful retreat with restaurants, vineyards and country side on your doorstep.

Popular amenities for Winchester house rentals

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$161 CAD$160 CAD$155 CAD$171 CAD$180 CAD$178 CAD$162 CAD$185 CAD$176 CAD$168 CAD$164 CAD$178 CAD
Avg. temp5 °C5 °C7 °C9 °C12 °C15 °C17 °C17 °C15 °C11 °C8 °C5 °C

Quick stats about house rentals in Winchester

  • Total vacation rentals

    Explore 890 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at $14 CAD per night before taxes and fees

  • Verified guest reviews

    Over 32,560 verified reviews to help you choose

  • Family-friendly vacation rentals

    430 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 210 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    380 properties have a dedicated workspace

  • Wifi availability

    870 of Winchester vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winchester rentals

  • 4.8 Average rating

    Winchester stays are highly rated by guests—averaging 4.8 out of 5!

Destinations to explore

  1. Airbnb
  2. United Kingdom
  3. England
  4. Hampshire
  5. Winchester
  6. House rentals