
Cottage vacation rentals in Winchester
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Quick stats about cottage rentals in Winchester

Total vacation rentals
Explore 10 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at G$25,135 GYD per night before taxes and fees

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Over 730 verified reviews to help you choose

Wi-Fi availability
10 of Winchester vacation rentals include wi-fi 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!
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.
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Romantic Thatched Riverside Garden Cottage Entire
Lovingly restored thatched cottage in beautiful countryside on the banks of the River Lambourn. Tranquil. Superfast broadband. Traditional comfortable. CAR NECESSARY as no shop or pub in the village itself. STEEP STAIRCASE! Unsuitable for disabled access. By car - M4 to London and Heathrow (1 hr) Oxford/Cotswolds, Hungerford, Wantage South facing garden to front of cottage (9m x 6m) Flower borders/lawn/table chairs. Loungers on request View onto river from cottage Good walks nearby
LocationKitchenWalkability

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.
LocationFamilyKitchen

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 picture-perfect Hampshire village full of thatched cottages and surrounded by gorgeous walks it is the perfect country retreat!
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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.
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Gorgeous rural escape only 10 mins from Winchester
Nested in a conservation area and with a private garden, yet only a 10 minute drive from Winchester, this 2-bedroom Stables Conversion (overlooking our vineyard - Rose Charity Estate) has the modern comforts that make it perfect for those looking for an escape (incl. EV charging). From parents with young children, to romantic couples, to those wanting a base to explore Winchester, this offers something for everyone. BTW, stunning beaches are from only a short drive away...
LocationFamilyComfort

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.
ValueFamilyWalkability

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
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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.
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Romantic cottage set in walled garden, New Forest
Situated in the grounds of an impressive country house, Butler's Rest is a stylishly renovated, quirky 19th Century cottage. Perfect for a romantic escape. In an unspoiled part of the New Forest, deer roam through the gardens, a short walk from three wonderful pubs and the open forest itself. It's a great setting from which to explore, although with a well equipped kitchen and cosy woodburner, you may not venture anywhere!
LocationFamilyBreakfast

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

Cosy little country cottage with luxury hot tub
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80 acre Wood, Dutchtub, Lake, Treehouse & Zip-line
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Adorable Detached 1 bedroom Annexe with hot tub
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Luxury New Forest Cottage, with hot tub & log fire
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Wisteria Lodge, a self-contained unit with spa
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Cottage with Covered Hot Tub Godshill New Forest
LocationFamilyPool

Cottage in beautiful Hampshire village
LocationFamilyNearby

Ultra luxury, newly refurbished country retreat
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Pet-friendly cottage rentals

Churchlands
LocationValuePets

Stylish Hideaway with an amazing woodland view
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Coach House in the heart of the test valley
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Gorgeous CountryCottage overlooking Windsor Castle
LocationFamilyHospitality

Cosy Sussex Cottage. South Downs National Park
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Two bedroom rural retreat.
LocationFamilyCleanliness

The Old Stables
FamilyLocationAccess

The Old Garage, Romsey Countryside Cottage.
FamilyLocationPool
Private cottage rentals

Lane End Cottage, Rural Annexe to the main house
ValueLocationComfort

2 Tudor Cottage - Cosy period cottage, West Sussex
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Beekeepers cottage, a cosy retreat by the stream
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Cosy Victorian cottage set in a country park
FamilyValueBackyard

The Old School House, Ascot, Berkshire
FamilyValueCheckout

The Cot, Characterful 400-year-old Cottage.
LocationFamilyCheck-in

Pussy Mouse Rew, Idyllic Rural Cottage in 6 Acres
FamilyLocationBathroom

The Cottage at Lupton House, Froxfield Petersfield
FamilyLocationOutdoor spaces
Destinations to explore
- Family-friendly rentals Winchester
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- Cottage rentals Hampshire
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- Cottage rentals United Kingdom
- New Forest National Park
- Bournemouth Beach
- West Wittering Beach
- Paultons Park Home of Peppa Pig World
- Goodwood Motor Circuit
- Longleat Safari Park
- University of Oxford
- South Downs National Park
- Thorpe Park Resort
- Chessington World of Adventures Resort
- Stonehenge
- LEGOLAND® Windsor Resort
- Southbourne Beach
- Windsor Castle
- Boscombe Beach
- Lower Mill Estate
- Hampton Court Palace
- Bracklesham Bay
- Mudeford Quay
- Highclere Castle
- Goodwood Racecourse
- Winchester Cathedral
- Ascot Racecourse
- The Tank Museum





