Cottage holiday rentals in Winchester

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Top-rated cottage rentals in Winchester

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Superhost
An open plan living, kitchen, and dining area is depicted, featuring a dining table with wooden chairs and a patterned tablecloth. The kitchen includes a stainless steel refrigerator, stove, and ample cabinetry. Soft seating is arranged in the living area, enhancing a comfortable environment.
Cottage
4.83 out of 5 average rating, 145 reviews

The Nest

This charming 3-bed cottage with private parking and garden is situated in Shawford, near to the historic town of Winchester. Walks along the River Itchen, swimming, fishing and picnic spots are on your doorstep. Local pub in Shawford and pubs in nearby village of Twyford. Winchester is also accessible by foot ( 45 mins) or a short 5 minute train or bus away. London is an hour by train and other local attractions include Marwell Zoo, Peppa Pig World, South Coast, Portsmouth and New Forest.

Top guest favourite
The exterior of the lodge is captured, featuring a brick facade with white-framed windows. A spacious lawn is visible in front, along with a small patio area equipped with outdoor seating and a table. Tall trees frame the background, enhancing the tranquil setting.
Cottage
4.98 out of 5 average rating, 161 reviews

Beautiful garden house, edge of town & South Downs

Beautiful self-contained lodge in the glorious garden of a Georgian Country House. Five minutes walk to the small market town of Bishops Waltham, with shops, restaurants and pubs. Surrounded by stunning countryside, on the edge of the South Downs, with wonderful walks from the house. Open plan kitchen-dining area & lounge, 2 bedrooms and a bathroom upstairs plus separate downstairs shower room. Sunny patio area with table and chairs & Weber bbq, perfect for watching the sun go down.

Guest favourite
A charming thatched cottage is framed by a white picket fence, surrounded by vibrant garden flowers. The distinctive curved roof and upper window are highlighted against a clear blue sky, emphasizing the cottage's historic character and inviting setting.
Cottage
4.91 out of 5 average rating, 127 reviews

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 a picture-perfect Hampshire village full of thatched cottages and surrounded by gorgeous walks it is the perfect country retreat!

Guest favourite
A quaint stone cottage is depicted against a clear blue sky, with a lush green hillside in the background. The structure features whitewashed walls, multiple chimneys, and a well-maintained hedge, creating a charming appearance near the water's edge.
Cottage
4.97 out of 5 average rating, 154 reviews

Quaint Cosy Cottage in East Meon

Quaint Cosy Cottage in East Meon with access to Pubs, Shops, Historic Church and lots of country walks and access to South Downs National Park. It has public transport to both Petersfield and Winchester. This cottage benefits from 2 bedrooms, downstairs shower room/ toilet, kitchen and lounge with wood burning stove. With a view to a stream to the front and beautiful countryside to the rear. It has off road parking, lockable storage for bikes, small paved cottage garden.

Guest favourite
A cozy sitting room is featured, showcasing a comfortable armchair and a large coffee table adorned with various books and decorative items. A warm fire burns in the fireplace, and built-in shelving lines one wall, filled with a diverse selection of books.
Cottage
4.98 out of 5 average rating, 302 reviews

Luxury 2 bedroom cottage

Luxury Cottage at Hayley Green A charming, character-filled retreat for up to 4 guests in a peaceful semi-rural setting. Designed for comfort and relaxation, it’s ideal for couples, families, or friends. Enjoy a well-stocked library if you prefer to stay in. Perfectly located: 6 mins to Lapland Ascot 9 mins to Legoland 11 mins to Ascot 16 mins to Windsor & Wentworth 30 mins to Henley-on-Thames Under 1 hour by train to London via nearby Bracknell station

Top guest favourite
A vibrant garden borders the side of the annexe, featuring colorful flowers in various hues, including pink, yellow, and white. This lush area is complemented by a gravel pathway and the wooden exterior of the annexe, creating a welcoming outdoor setting.
Cottage
4.98 out of 5 average rating, 123 reviews

Adorable Detached 1 bedroom Annexe with hot tub

Pet friendly self contained annexe with hot tub available in Denmead, Hampshire. Walk across the road for a stroll in the Forest of Bere or wander into Denmead for a choice of pubs. Pop next door to Furzeley golf club for a round of golf or round the corner to the fisheries, saddle up for a ride in the South Downs or hop in the car and visit Portsmouth Historic Dockyard or Goodwood. 1 kingsize bedroom (can be made into twin). Netflix and Broadband

Guest favourite
A stylish barn exterior showcases a mix of wooden and brick elements. French doors open to a bright interior with a bed visible inside. Two deck chairs are positioned on the terrace, and a chiminea stands to the side, all set against a landscaped garden.
Cottage
4.96 out of 5 average rating, 576 reviews

The Barn @ North Lodge -Soho Farmhouse-esque Cabin

Inspired by Soho Farmhouse. A stylish converted barn set in the grounds of a Georgian Lodge within the South Downs National Park. Conveniently located close to the picturesque market towns of Alresford, Petersfield, Alton and historic Winchester, it is an ideal base to both explore Hampshire and kick back and relax in luxury. Take a look at the Barn on ‘Escape to the Country’ series 25, Episode 10 on iPlayer!

Superhost
A charming kitchen area features wooden cabinetry and modern appliances, including a microwave. A sofa with teal pillows provides seating in the inviting lounge space, complemented by a wooden coffee table. Exposed brick walls and warm wooden flooring enhance the rustic character of the cottage.
Cottage
4.82 out of 5 average rating, 117 reviews

Country Cottage near Winchester, Hampshire

Tenacre Cottage is a cosy and quirky semi-detached cottage located in the outskirts of the rural village of Owslebury. Just a 5-mile drive from the medieval city of Winchester, Tenacre Cottage is situated in a prime location, perfect for a rural getaway or business stay. Secluded from the busy bustle of the city, yet a swift 10-minute drive, Tenacre Cottage is surrounded by acres of fields and beautiful views.

Top guest favourite
The Cottage features a charming exterior with a textured roof and a modern patio area. Surrounded by greenery, a spacious seating arrangement is set on a stone surface, offering a tranquil spot for relaxation. Nearby structures exhibit a contemporary architectural style.
Cottage
4.98 out of 5 average rating, 173 reviews

The Cottage in Compton

Come and enjoy a stay in The Cottage, located in the grounds of our 17th Century converted Barn. Enjoy a unique location on the edge of Winchester with direct access to the countryside. The Cottage has been recently extended and refurbished with everything you will need to make your stay enjoyable. A perfect place for a break to explore all the wonderful things that Winchester has to offer!

Guest favourite
A charming eighteenth-century cottage is displayed, featuring a mix of flint and brick exteriors. The structure has a gabled roof and white window frames, surrounded by greenery and grass. Bright sunlight illuminates the scene, highlighting the peaceful village setting.
Cottage
4.93 out of 5 average rating, 206 reviews

Lane End Cottage, Rural Annexe to the main house

Perfectly situated in the Itchen Valley between the Georgian market town of Alresford and the Cathedral City of Winchester providing easy access to great shopping and historic venues with the benefit of being in a picturesque village. This lovely eighteenth century cottage has stunning walks right from the front door and a local riverside pub, the Bush Inn just a stone's throw away.

Superhost
A light and airy living space features two white sofas adorned with cushions in red and blue patterns. A round dining table with six chairs occupies one corner, while large glass doors lead to a private outdoor area framed by greenery.
Cottage
4.83 out of 5 average rating, 144 reviews

Village Location/Comfy 2 bed house/Pet friendly

Welsh Cottage is located in the centre of Swanmore with ample parking & green space around the village. The house is perfect for both weekend breaks & longer stays with 3 local pubs, shop & butchers within walking distance. Swanmore is within 25 minutes of Winchester, Portsmouth & Southampton with great tourist sites, eating & shopping to be had in all.

Top guest favourite
The exterior of the cottage features a charming red brick façade under a clear blue sky. Two large windows adorn the front, framed by greenery and manicured landscaping. A welcoming entrance is highlighted by a simple door and porch area, surrounded by soft grass.
Cottage
4.98 out of 5 average rating, 191 reviews

Cosy Victorian cottage set in a country park

Woodside Cottage was originally built in 1864 and formed part of the Royal Victoria Hospital. It is now nestled within the beautiful Royal Victoria Country Park on the edge of Southampton Water and popular coastal walks. This cosy cottage has recently been refurbished and furnished to a high standard with easy access to everything the park has to offer.

Popular amenities for cottage rentals in Winchester

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Quick stats about cottage rentals in Winchester

  • Total holiday rentals

    Explore 100 holiday rentals in Winchester

  • Nightly prices starting at

    Winchester holiday rentals start at £23 per night before taxes and fees

  • Verified guest reviews

    Over 5,900 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    100 of Winchester holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winchester rentals

  • 4.9 Average rating

    Winchester stays are highly rated by guests – averaging 4.9 out of 5!

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