
Cottage holiday rentals in Winchester
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Top-rated cottage rentals in Winchester
Guests agree: these cottages are highly rated for location, cleanliness and more.

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.

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.

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.

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.

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

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!

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.

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.

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

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.

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!

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
Cottage rentals with a hot tub

Cosy little country cottage with luxury hot tub

Adorable Detached 1 bedroom Annexe with hot tub

Wisteria Lodge, a self-contained unit with spa

Luxury New Forest Cottage, with hot tub & log fire

Cottage in beautiful Hampshire village

Detached and romantic cottage with hot tub.

Luxury rural thatched cottage with cedar hot tub.

Delightful Cottage 15 Acre Estate + Pool + Hottub
Pet-friendly cottage rentals

Churchlands

Star Cottage - Arundel’s cosiest cottage!

Converted barn perfect for families and couples
Tranquil South Wiltshire Cottage with Views.

The Boathouse waterside Yarmouth IOW

Idyllic Thatched Cottage in heart of New Forest

Flintstone Cottage near Goodwood

Forest Lodge - Games Room & EV point, Dog friendly
Private cottage rentals

Lane End Cottage, Rural Annexe to the main house

The Old Bothy in the New Forest

A Hidden Gem

Sea Drift - a beautiful Fisherman’s Cottage

Quiet location. Close to Coast, Downs & Goodwood

The Cot, Characterful 400-year-old Cottage.

Deal Cottage - a cosy getaway for two

2 Bedroom Luxury Cottage (Secure & Quiet)
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!
Destinations to explore
- Rentals with a washing machine and dryer Winchester
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- Cottage rentals Hampshire
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- South Downs National Park
- New Forest National Park
- Paultons Park Home of Peppa Pig World
- University of Oxford
- Goodwood Motor Circuit
- Stonehenge
- Bracklesham Bay
- Windsor Castle
- Hampton Court Palace
- Highclere Castle
- Lower Mill Estate
- Boscombe Beach
- Chessington World of Adventures Resort
- Thorpe Park Resort
- Bournemouth Beach
- Winchester Cathedral
- Bournemouth International Centre
- Goodwood Racecourse
- The Tank Museum
- Kimmeridge Bay
- Southbourne Beach
- West Wittering Beach
- Highcliffe Beach
- Worthing Pier




