Cottage holiday rentals in Winchester

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Top-rated cottage rentals in Winchester

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Top guest favourite
A serene garden pond is surrounded by lush greenery and wildflowers, reflecting clear blue skies. A gazebo can be seen in the distance, complemented by wooden decking and seating that invites relaxation. Tall grasses frame the tranquil waters, creating a peaceful natural retreat.
Cottage
4.99 out of 5 average rating, 193 reviews

Pussy Mouse Rew, Idyllic Rural Cottage in 6 Acres

This accommodation has been specifically designed for couples looking for a tranquil break where quality and attention to detail are important factors. Ideal for romantic breaks or special occassions, surrounded by open countryside with an abundance of wildlife right outside your door. The quiet yet accessible location is a few minutes drive from various beaches perfect for cycling, walking, nature watching and exploring the IOW. See "Other details" for ferry discounts. EV charging at 40p KWH.

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, 154 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
Cottage
4.98 out of 5 average rating, 680 reviews

Stylish Hideaway with an amazing woodland view

Our hideaway offers the perfect getaway. Soak up the peace and quiet, take in the amazing view and relax surrounded by ancient woodland, only 50 miles from London. "Watching the birds fly overhead, from the comfort of a relaxing bed. Watching the trees in the winds sway, all my worries seem faraway. Listening to the beauty of the dawn chorus, whilst enjoying the views laid before us. Your woodland hideaway is just the place to fill the visitor's heart with grace." (A guest's poem)

Top guest favourite
A charming Georgian country house is set amidst lush greenery. The brick façade is complemented by a well-maintained garden featuring various trees and a spacious lawn. Outdoor seating arrangements are visible, creating an inviting outdoor space.
Cottage
4.98 out of 5 average rating, 168 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.

Top guest favourite
Cottage
4.97 out of 5 average rating, 355 reviews

Colindale Cottage, Nether Wallop

Located between the historic cities of Winchester and Salisbury ,Colindale Cottage is an ideal base for exploring the Test Valley and beyond. Stonehenge, Highclere Castle and the New Forest are close by. The coast is approx and hour away. Dogs are welcome. Nether Wallop is a pretty village in the heart of the Test Valley close to the small town of Stockbridge with its independent shops and eateries. Nether Wallop featured in the Miss Marple series starring Joan Hickson.

Top guest favourite
An open-plan living and kitchen area displays wooden flooring and modern furnishings. A gray sofa is positioned in the foreground, with a coffee table and a patterned rug. Dining chairs surround a wooden table, and a television is situated nearby, accompanied by a wood-burning stove.
Cottage
4.99 out of 5 average rating, 103 reviews

Gorgeous rural escape only 10 mins from Winchester

Nested in a conservation area and with a private garden, yet only a 10 minute drive from Winchester, this 2-bedroom Stables Conversion (overlooking our vineyard - Rose Charity Estate) has the modern comforts that make it perfect for those looking for an escape (incl. EV charging). From parents with young children, to romantic couples, to those wanting a base to explore Winchester, this offers something for everyone. BTW, stunning beaches are from only a short drive away...

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
4.97 out of 5 average rating, 179 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.

Top guest favourite
The image features a serene waterfront scene at dusk, with a pink and blue sky reflecting on the calm water. The weathered stone wall encloses a small harbor, while historic buildings are positioned nearby, contributing to the tranquil ambiance.
Cottage
4.98 out of 5 average rating, 274 reviews

Adventure Prospect - Historic Waterfront Cottage

Relax and enjoy your stay at this unique and tranquil getaway. 'Adventure Prospect' has recently been completely renovated and is steeped in military history. Formerly known as the "shifting house" it was first built in 1898-1899 to accommodate munitions workers changing into the special clothing that they wore when working on magazines. The cottage provides an ideal escape from everyday life and has direct access to the water.

Guest favourite
Cottage
4.96 out of 5 average rating, 626 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!

Guest favourite
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
4.83 out of 5 average rating, 133 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
4.99 out of 5 average rating, 202 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!

Top guest favourite
The exterior of the lodge features a charming wooden façade with distinctive double doors and a blue entrance door. Potted plants adorn the gravel pathway, adding greenery to the inviting atmosphere. A large tree provides shade in the background under a bright blue sky.
Cottage
4.98 out of 5 average rating, 258 reviews

Self-contained Lodge, Stockbridge

The Lodge has been newly renovated, giving 24sqm of self-contained studio style accommodation, with modern fitted kitchen and bathroom facilities. Located on the ever popular Stockbridge High Street with it's host of shops, pubs and restaurants, it also sits in the heart of the Test Valley with endless opportunities for those who love the outdoors.

Popular amenities for cottage rentals in Winchester

Quick stats about cottage rentals in Winchester

  • Total holiday rentals

    Explore 10 holiday rentals in Winchester

  • Nightly prices starting at

    Winchester holiday rentals start at £89 per night before taxes and fees

  • Verified guest reviews

    Over 680 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of Winchester holiday 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!

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