Cottage vacation rentals in Winchester

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Top-rated cottage rentals in Winchester

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Top guest favorite

A wooden treehouse is elevated among tall trees, surrounded by green foliage. Two children play on the ground, while one swings from a rope attached to the treehouse. Sunlight filters through the leaves, creating a natural, vibrant setting.

Cottage in Salisbury

4.99 out of 5 average rating, 100 reviews

80 acre Wood, Dutchtub, Lake, Treehouse & Zip-line

Escape to a private 80-acre woodland, just 10-15 minutes from the historic, and picturesque, city of Salisbury. Enjoy tranquil trekking trails, or relax by the secluded lake. Glide through the trees, from the fun kids treehouse, on our 100 ft zip-line, or wind down by immersing yourself in nature with a good soak in our wood-fired Dutch tub. We believe our guest cottage offers the perfect balance of natural and peaceful comfort; ideal for romantic escapes, family adventures, or digital detoxes.

Superhost

The sleeping area features a spacious bed with light bedding and two soft pillows. A light-colored blanket is neatly placed at the foot of the bed. Natural light floods the room through large, partially covered windows. A door leads outside, and minimal decor is present on the walls.

Cottage in Shawford

4.83 out of 5 average rating, 134 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 favorite

Cottage in Haslemere

4.95 out of 5 average rating, 680 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 favorite

A wood-fired hot tub is positioned within a gravel area, bordered by black wrought iron fencing. Nearby, a cozy seating arrangement is visible, with a small table and log storage. Lush greenery and trees can be seen in the background, contributing to a peaceful outdoor setting.

Cottage in Romsey

4.99 out of 5 average rating, 177 reviews

Beautiful Winterberry Barn ,With Hot tub

WinterBerry Barn is a gorgeous 1 bedroom cottage with everything you could possibly need for a cosy country getaway. It has a beautiful wood fired hot tub .Every aspect of the property is finished to the highest standard. Oak finish throughout with raw natural beams flowing through the property to really give it that warm country feel. Close to all the wonderful local amenities such as the beautiful market town of romsey only a 5 minute drive! Also the beautiful historic city of Winchester.

Top guest favorite

A wide open field filled with bright yellow dandelions spans the foreground, surrounded by lush green grass. Trees line the edges of the field, and a clear blue sky with fluffy white clouds creates a serene and natural landscape.

Cottage in Bishop's Waltham

4.98 out of 5 average rating, 149 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 favorite

A garden room is depicted, featuring a high vaulted ceiling with exposed wooden beams. Two comfortable armchairs are positioned around a small coffee table. A dining area with four wooden chairs is visible in the background, complemented by a lamp and decorative elements on the walls.

Cottage in Hampshire

4.97 out of 5 average rating, 308 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 favorite

Cottage in West Sussex

4.99 out of 5 average rating, 167 reviews

Quiet location. Close to Coast, Downs & Goodwood

Situated in the grounds of our Victorian family home, the newly converted 'Garden Rooms' occupy a separate self-contained building, furnished to a high standard, and perfect for coupes wishing to enjoy walking, cycling & sailing in the South Downs National Park. The annex has its own driveway and self check-in is via a key box. The Garden Rooms are located in the pretty downland village of West Ashling. There are three local pubs & a restaurant, all within walking distance.

Top guest favorite

A serene view of a meandering stream is captured, flanked by grassy banks and bordered by a stone wall. The scene includes a pathway alongside the stream, while the leafy backdrop adds a natural touch to the tranquil environment.

Cottage in East Meon

4.97 out of 5 average rating, 132 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.

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Cottage in Ropley

4.9 out of 5 average rating, 116 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. Not only is it mentioned in the Domesday Book, it was also 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. Full of quirky character yet updated and comfy it's the perfect retreat!

Top guest favorite

A private garden area features a small patio with a wooden table, three glasses of wine, and a bottle. Comfortable seating is arranged nearby, surrounded by potted plants. Floor-to-ceiling doors provide access to the interior, creating a seamless connection to the outdoor space.

Cottage in Pikeshill

4.98 out of 5 average rating, 294 reviews

Bramblings, New Forest cottage by the green

Bramblings is in a magical position, at the edge of Lyndhurst, on the green and just over the cattle grid. It is just a short walk in to Lyndhurst for restaurants, cafes and shopping and there are great walks and cycling direct from the house. Remember to keep the gate shut whenever you are coming and going as the ponies, donkeys and cows are free to meander just outside and they are always keen to help themselves to the greenery in the garden.

Guest favorite

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, 529 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 favorite

A spacious outdoor seating area is shown on a stone patio, featuring a large rectangular table surrounded by several light-colored benches. Lush greenery and flowering plants create a natural border, with large trees providing shade in the background under a clear blue sky.

Cottage in Winchester

4.99 out of 5 average rating, 141 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!