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 Hyde
4.97 out of 5 average rating, 127 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, 150 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.

Guest favourite
The exterior of The Old Bakery showcases a charming blend of wood and glass. Lush, round topiary trees are neatly arranged in decorative pots along a gravel path, with sunlight illuminating the scene under a clear blue sky.
Cottage in Fernhurst
4.94 out of 5 average rating, 776 reviews

Idyllic Cottage in the heart of The South Downs

The Old Bakery is a luxurious self-contained cottage set in the heart of the beautiful South Downs National Park. It has been voted one of the best Air B&Bs in the UK in 2021! Guests can enjoy beautiful walks directly from the cottage or visit local villages such as Haslemere, Midhurst, Petworth, Arundel, the South Coast (West Wittering) and Goodwood. You will be spoilt for choices with some excellent pubs and restaurants in the area with the fabulous Duke of Cumberland pub a short walk away.

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 Bishops 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.

Superhost
A vibrant farm shop offers a variety of colorful flowers and plants displayed on wooden tables. Two buildings are visible, with a spacious greenhouse labeled 'Wildbunch' to the right. Natural light enhances the inviting atmosphere of this outdoor shopping area.
Cottage in Winchester
4.84 out of 5 average rating, 106 reviews

Winchester 3-Bed Cottage Next to 5-star Farm Shop!

Welcome to our 3-bedroom character cottage in Winchester. Cosy sitting room, separate dining room, fully equipped kitchen w/ Fridge Freezer, MW, DW, Washing machine & Dryer. Large family bathroom & big garden. A prestigious Farm Shop 50yds away with lovely Cafe serving food all-day, a bakery/cheese/deli counter, award winning butcher. Super Pub 10min walk. Approx 2 miles from the historic town center. Easy access by foot, bus, train, car M3/A34. The perfect town & country experience

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
4.91 out of 5 average rating, 129 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
The exterior of Colindale Cottage is depicted, showcasing a two-story structure with a light-colored façade. A garden room with glass panels is visible, along with well-kept flowerbeds and a lush green lawn. A large tree provides shade in the tranquil outdoor space.
Cottage in Nether Wallop
4.97 out of 5 average rating, 346 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
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
4.96 out of 5 average rating, 171 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
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 in Warfield
4.98 out of 5 average rating, 328 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
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 in Hampshire
4.98 out of 5 average rating, 260 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.

Top guest favourite
Cottage in Privett
4.96 out of 5 average rating, 603 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!

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, 193 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!

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 $127 SGD per night before taxes and fees

  • Verified guest reviews

    Over 610 verified reviews to help you choose

  • 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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