
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$25,066 GYD per night before taxes and fees

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Over 680 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

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.

Pussy Mouse Rew, Idyllic Rural Cottage in 6 Acres
This accommodation has been specifically designed for couples looking for a tranquil break where quality and attention to detail are important factors. Ideal for romantic breaks or special occassions, surrounded by open countryside with an abundance of wildlife right outside your door. The quiet yet accessible location is a few minutes drive from various beaches perfect for cycling, walking, nature watching and exploring the IOW. See "Other details" for ferry discounts. EV charging at 40p KWH.
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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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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.
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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.
ValueFamilyPets

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...
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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.
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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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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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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.
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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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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.
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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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Blashford Manor Farm - The New Forest Cottage
LocationFamilyHospitality

80 acre Wood, Dutchtub, Lake, Treehouse & Zip-line
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Adorable Detached 1 bedroom Annexe with hot tub
ValueFamilyParks

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

Stylish Hideaway with an amazing woodland view
LocationFamilyIndoor spaces

Coach House in the heart of the test valley
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Honeysuckle Cottage - East Meon
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The Boathouse waterside Yarmouth IOW
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Two bedroom rural retreat.
LocationFamilyBackyard

The Old Garage, Romsey Countryside Cottage.
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Entire Country Cottage in Hampshire's Test Valley
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Self-contained Lodge, Stockbridge
LocationFamilyTV
Private cottage rentals

The Old School House, Ascot, Berkshire
ValueLocationBiking

Gorgeous CountryCottage overlooking Windsor Castle
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Quiet location. Close to Coast, Downs & Goodwood
LocationValueBathroom

The Cot, Characterful 400-year-old Cottage.
LocationFamilyComfort

Stride Cottage in the heart of the new forest
FamilyValueHiking

Fisherman's Loft A Unique Cottage By The Sea
FamilyLocationParking

Luxury 2 bedroom cottage
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The Cottage at Lupton House, Froxfield Petersfield
LocationFamilyCheck-in
Destinations to explore
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- Cottage rentals Hampshire
- Cottage rentals England
- Cottage rentals United Kingdom
- New Forest National Park
- Bournemouth Beach
- West Wittering Beach
- Paultons Park Home of Peppa Pig World
- University of Oxford
- Goodwood Motor Circuit
- Stonehenge
- Thorpe Park Resort
- South Downs National Park
- Longleat Safari Park
- Chessington World of Adventures Resort
- Windsor Castle
- LEGOLAND® Windsor Resort
- Southbourne Beach
- Lower Mill Estate
- Bracklesham Bay
- Boscombe Beach
- Hampton Court Palace
- Highclere Castle
- Mudeford Quay
- Goodwood Racecourse
- Winchester Cathedral
- The Tank Museum
- Ascot Racecourse





