Cottage holiday rentals in Winchester

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Top-rated cottage rentals in Winchester

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Top Guest favourite
The exterior of a brick building, showcasing a rustic charm, is surrounded by greenery. A wooden door is partially obscured by vines, and windows with white curtains allow for natural light. The pathway is lined with potted plants, enhancing the inviting atmosphere.
Cottage in Hampshire
4.97 out of 5 average rating, 122 reviews

Romantic barn with kingsize 4-poster, fire, bikes

If you are looking for a romantic escape in the New Forest, just a short walk from the pub and open forest, then look no further. Situated in the grounds of an impressive country house, the Goat Shed is the stylishly renovated ground floor of a 19th century barn, with a kingsize four poster bed, claw foot bath and woodburning stove. Deer roam through the gardens, and our wood burning stove makes nights in perfectly cosy. A great spot from which to explore the forest, or simply relax in comfort.

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 in Shawford
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 in Bishop's Waltham
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 in Ropley
4.9 out of 5 average rating, 126 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!

Top 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 in East Meon
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 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 in Privett
4.96 out of 5 average rating, 572 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 in Owslebury
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 in Winchester
4.98 out of 5 average rating, 172 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 in Ovington
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.

Guest favourite
A charming 16th-century cottage is depicted, showcasing a thatched roof and whitewashed exterior adorned with traditional timber framing. A well-kept garden surrounds the entrance, with lush greenery visible. The inviting red door and adjacent windows add character, while a quiet village road runs beside the property.
Cottage in East Meon
4.92 out of 5 average rating, 190 reviews

Honeysuckle Cottage - East Meon

Honeysuckle Cottage is a quaint 16th century cottage in the heart of the beautiful village of East Meon. With 2 great pubs within 200m walk and surrounded by the rolling countryside of the South Downs National Park, this recently renovated cottage is the perfect country getaway for a romantic retreat or up to 4 guests. Pets are welcome at Honeysuckle Cottage.

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 in Swanmore
4.83 out of 5 average rating, 143 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 in Hampshire
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 Winchester cottage rentals

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Avg. price$296 NZD$296 NZD$287 NZD$314 NZD$308 NZD$326 NZD$324 NZD$335 NZD$324 NZD$315 NZD$306 NZD$323 NZD
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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 $53 NZD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Winchester holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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