
Cottage vacation 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.

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.

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!

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

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.

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

Adorable Detached 1 bedroom Annexe with hot tub

The Old Piggery, East Boldre, New Forest

Luxury New Forest Cottage, with hot tub & log fire

Wisteria Lodge, a self-contained unit with spa

Cottage with Covered Hot Tub Godshill New Forest

Cottage in beautiful Hampshire village
Pet-friendly cottage rentals

Beautiful, secluded, country cottage near to beach

Converted barn perfect for families and couples

Elm Cottage, Goodwood Studio

Manor Farm Cottage

New Forest retreat, cosy & pretty, 4 guests

Luxury Cottage near Stonehenge & Salisbury

Forest’s Edge - Ashurst

Luxury cottage in the heart of The New Forest
Private cottage rentals

The Bothy – Countryside Retreat in the New Forest

Watch the deer from your cosy barn near Goodwood

Beautiful S.Downs Cottage, pool and tennis

The Nestle House City Centre Luxury

The Cottage at Lupton House, Froxfield Petersfield

Lyndhurst - A New Forest Gem with Garden

The Coachman's Cottage

Modern Countryside Retreat with Stunning Views
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $232 CAD | $232 CAD | $225 CAD | $246 CAD | $242 CAD | $256 CAD | $255 CAD | $263 CAD | $255 CAD | $248 CAD | $241 CAD | $253 CAD |
| 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 vacation rentals
Explore 100 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at $42 CAD per night before taxes and fees

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

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

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
100 of Winchester vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, 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
- Goodwood Motor Circuit
- Paultons Park Home of Peppa Pig World
- Oxford University
- Stonehenge
- Windsor Castle
- Hampton Court Palace
- Boscombe Beach
- Winchester Cathedral
- Highclere Castle
- Bournemouth Beach
- Chessington World of Adventures Resort
- Twickenham Stadium
- Kimmeridge Bay
- Thorpe Park Resort
- Goodwood Racecourse
- Highcliffe Beach
- West Wittering Beach
- Worthing Pier
- The Tank Museum
- Southbourne Beach
- Wentworth Golf Club
- RHS Garden Wisley
- Poole Quay
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