Cottage holiday rentals in Winchester

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Top-rated cottage rentals in Winchester

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Top guest favourite

Cottage in Warfield

4.98 out of 5 average rating, 282 reviews

Newly refurbished luxury 2 bedroom cottage

Luxury cottage at Hayley Green that accommodates up to 4 people. Newly refurbished in semi-rural setting. Full of character with all the amenities you need for a luxurious comfortable stay. The perfect relaxing getaway for couples, family and friends. The cottage is located 16 minutes to Windsor, 30 minutes to Henley on Thames, 11 minutes to Ascot, 9 minutes to Legoland, 6 minutes drive to Lapland Ascot.We are also close to Bracknell train station where you take a train to London under 1 hour.

Superhost

Cottage in Shawford

4.83 out of 5 average rating, 140 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

Cottage in Droxford

4.92 out of 5 average rating, 149 reviews

Gorgeous Country Escape 5 Bedroom House & Annex

Family run, our pretty 5 bedroom detached house & separate annexe set in a rural location surrounded by the idyllic Meon Valley & South Downs Park The large garden is a haven, providing a perfect setting for alfresco dining with friends & family. With no direct neighbours you'll feel like you have the countryside all to yourselves Many beautiful cities on our doorstep, including Winchester, Chichester, Petersfield & Southsea Pool table • table football • X Box • Wii We welcome your dog 🐶

Guest favourite

Cottage in Haslemere

4.94 out of 5 average rating, 706 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.

Guest favourite

Cottage in Bishop's Waltham

4.98 out of 5 average rating, 153 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 in Hampshire

4.97 out of 5 average rating, 101 reviews

New England Coach House with a boutique hotel feel

The cosy Coach House at Ava Cottage is a new building nestled in an easy to reach rural area. The area has been described as a "pocket of tranquillity". In front of the coach house is a large recreational ground complete with cricket wicket and clubhouse. There are country views everywhere you look. Located just 1hr 20 mins from Gatwick and Heathrow airports. There are plenty of south coast attractions including Goodwood, Portsmouth Historic Dockyard, Gun-wharf and Spinnaker Tower.

Top guest favourite

Cottage in Hampshire

4.97 out of 5 average rating, 321 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

Cottage in Salisbury

4.99 out of 5 average rating, 268 reviews

Lower Mews - Beautiful setting near Salisbury

A cosy, rural retreat in the beautiful Chalke Valley, just a 10 minute drive from the Cathedral City of Salisbury. Located in the grounds of a family owned country house set within an Area of Outstanding Natural Beauty. Perfect for getting away from it all and exploring the local countryside, Salisbury Cathedral, Stonehenge and much more. See the Location section for more details including our guidebook for the surrounding area.

Guest favourite

Cottage in Privett

4.96 out of 5 average rating, 555 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

Cottage in Winchester

4.99 out of 5 average rating, 160 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!

Superhost

Cottage in Swanmore

4.83 out of 5 average rating, 141 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

Cottage in Hampshire

4.98 out of 5 average rating, 185 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.