
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.

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.

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.

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

Adorable Detached 1 bedroom Annexe with hot tub
Pet friendly self contained annexe with hot tub available in Denmead, Hampshire. Walk across the road for a stroll in the Forest of Bere or wander into Denmead for a choice of pubs. Pop next door to Furzeley golf club for a round of golf or round the corner to the fisheries, saddle up for a ride in the South Downs or hop in the car and visit Portsmouth Historic Dockyard or Goodwood. 1 kingsize bedroom (can be made into twin). Netflix and Broadband

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.

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!

Country Cottage near Winchester, Hampshire
Tenacre Cottage is a cosy and quirky semi-detached cottage located in the outskirts of the rural village of Owslebury. Just a 5-mile drive from the medieval city of Winchester, Tenacre Cottage is situated in a prime location, perfect for a rural getaway or business stay. Secluded from the busy bustle of the city, yet a swift 10-minute drive, Tenacre Cottage is surrounded by acres of fields and beautiful views.

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!

Lane End Cottage, Rural Annexe to the main house
Perfectly situated in the Itchen Valley between the Georgian market town of Alresford and the Cathedral City of Winchester providing easy access to great shopping and historic venues with the benefit of being in a picturesque village. This lovely eighteenth century cottage has stunning walks right from the front door and a local riverside pub, the Bush Inn just a stone's throw away.

Honeysuckle Cottage - East Meon
Honeysuckle Cottage is a quaint 16th century cottage in the heart of the beautiful village of East Meon. With 2 great pubs within 200m walk and surrounded by the rolling countryside of the South Downs National Park, this recently renovated cottage is the perfect country getaway for a romantic retreat or up to 4 guests. Pets are welcome at Honeysuckle Cottage.

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.

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.
Popular amenities for Winchester cottage rentals
Cottage rentals with a hot tub

Cosy little country cottage with luxury hot tub

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

The Old Piggery, East Boldre, New Forest

Superb cottage edge of new forest near paultons

Wisteria Lodge, a self-contained unit with spa

Luxury New Forest Cottage, with hot tub & log fire

Cottage with Covered Hot Tub Godshill New Forest

Cottage in beautiful Hampshire village
Pet-friendly cottage rentals

Farthings - genuine Austen charm cottage & garden

Elm Cottage, Goodwood Studio

New Forest retreat, cosy & pretty, 4 guests

Forest’s Edge - Ashurst

Luxury cottage in the heart of The New Forest

A beautiful cottage set in magnificent grounds

Gorgeous Country 5 Bed Escape with Separate Annex

Colindale Cottage, Nether Wallop
Private cottage rentals

Gorgeous rural escape only 10 mins from Winchester

Watch the deer from your cosy barn near Goodwood

Beautiful S.Downs Cottage, pool and tennis

Fisherman's Loft A Unique Cottage By The Sea

The Nestle House City Centre Luxury

Lyndhurst - A New Forest Gem with Garden

A charming little wooden house by the sea

New England Coach House with a boutique hotel feel
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $256 AUD | $256 AUD | $248 AUD | $271 AUD | $267 AUD | $282 AUD | $281 AUD | $290 AUD | $281 AUD | $273 AUD | $265 AUD | $279 AUD |
| Avg. temp | 5°C | 5°C | 7°C | 9°C | 12°C | 15°C | 17°C | 17°C | 15°C | 11°C | 8°C | 5°C |
Quick stats about cottage rentals in Winchester

Total holiday rentals
Explore 100 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $46 AUD per night before taxes and fees

Verified guest reviews
Over 5,900 verified reviews to help you choose

Family-friendly holiday rentals
60 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
100 of Winchester holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Winchester rentals

4.9 Average rating
Winchester stays are highly rated by guests—averaging 4.9 out of 5!
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- New Forest national park
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