Cottage holiday rentals in Winchester

Ultra luxury, newly refurbished country retreat

Newly extended and refurbished countryside cottage re-opened after HUGE 2025 refurbishment! One acre garden with countryside views. Three bedrooms, three luxury bathrooms! Extra special bespoke quadruple bunk bed room with slide! Lots of toys provided to keep kids entertained! Hot tub, daybed, the ultimate relaxation spot! Large decking area adjoining the hot tub with lots of comfortable garden furniture. This cottage is situated on our private country estate consisting of 7.5 acres.

Family · Value · Decor

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.

Value · Family · Hospitality

Gorgeous CountryCottage overlooking Windsor Castle

The Victorian Lodge (1876) is a charming & quintessentially English country cottage on a private estate once owned by King Henry 8th. It sits right beside Windsor Great Park, at the entrance of a long driveway to Little Dower House, where the owners of the Lodge live. The private gardens and stunning view at the Victorian Lodge provide the perfect setting for a small intimate wedding. Whilst the romantic gardens within the Little Dower House estate provide an ideal venue for larger weddings.

Family · Location · Decor

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.

Value · Location · Kitchen

Charming 16th century cottage in rural setting

Dating from the 16th century, Stable Cottage adjoins the rest of the property but has its own front door and is a completely private and self contained space. Downstairs has an entrance hall, sitting room, with original beams and kitchen; upstairs there are 2 bedrooms, one double and one single, bathroom and separate shower room. Perfect for 2/3 adults (3 adults max) or for a family with a baby/child. Close to Salisbury and the New Forest, it's the place to explore Wiltshire.

Location · Family · Hospitality

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.

Family · Location · Layout

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.

Location · Value · Quiet

Cottage in beautiful Hampshire village

Relaxing and comfortable country cottage. Village pubs and lovely walks nearby. Fully equipped. Superking or twin beds in both bedrooms, 2 bathrooms, sitting room with log burner, dining room and kitchen. Secluded, peaceful garden with seating. Access to hot-tub by prior arrangement. Linen, towels, toiletries, wifi and welcome pack included. Off-road parking for 1 car, other cars by arrangement. Unsuitable for young children or people with mobility challenges.

Family · Value · Barbecue

Beautiful Luxury Cottage in the New Forest

Rose Cottage is set within the grounds of a private estate. The New Forest National Park where the animals roam freely, is just outside of our gate. Enjoy watching deer, rabbits, birds, and an abundance of other forest wildlife visit the grounds. You will also notice that the New Forest ponies, donkeys, and pigs are regular visitors. This self-catering Luxury Cottage has all the comfort needed to enjoy a fantastic holiday within the New Forest National Park.

Family · Location · Walkability

Entire Country Cottage in Hampshire's Test Valley

This stunning country cottage is located in the heart of the Test Valley with its own patio and garden looking out to the fields behind. It is nestled in a lovely rural setting, with beautiful walks from the house, pubs and village amenities within walking distance. The cottage has luxury fittings, a wood burner and provides a haven for couples whatever age to getaway in an idyllic part of rural England. We are happy to host one well behaved pet.

Value · Location · Cleanliness

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!

Value · Location · Barbecue

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!

Family · Location · Check-in