
Cottage holiday rentals in Winchester
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Top-rated cottage rentals in Winchester
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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.

Crestyl Cottage riverside barn for 2 with hot tub
Crestyl Cottage is a delightful self contained country cottage in Sarratt - providing the perfect place to relax, walk, cycle, birdwatch and fish for carp in our small private lake. We provide high end accommodation for 2 adults in an area which has plenty to offer in the heart of the stunning Chess Valley. Crestyl Cottage is a conversion of a redundant barn, originally used for watercress seed drying which has been converted into self catering holiday accommodation with wood fired hot tub.

Stylish Hideaway with an amazing woodland view
Our hideaway offers the perfect getaway. Soak up the peace and quiet, take in the amazing view and relax surrounded by ancient woodland, only 50 miles from London. "Watching the birds fly overhead, from the comfort of a relaxing bed. Watching the trees in the winds sway, all my worries seem faraway. Listening to the beauty of the dawn chorus, whilst enjoying the views laid before us. Your woodland hideaway is just the place to fill the visitor's heart with grace." (A guest's poem)

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.

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.

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...

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.

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!

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!

Secluded & Quiet Coach House
An original Coach House - in the heart of Ramsbury, a quintessential English village. 5 miles from Hungerford, Marlborough & M4 junction 14. The house is in our quiet garden, with your own private access from the street. It is spacious, light & recently decorated. Ramsbury is a stunning village on the river Kennet which is in an area of outstanding natural beauty.
Popular amenities for cottage rentals in Winchester
Cottage rentals with a hot tub

Cosy little country cottage with luxury hot tub

Holiday cottage With hot tub

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

Luxury New Forest Cottage, with hot tub & log fire

Wisteria Lodge, a self-contained unit with spa

Ultra luxury, newly refurbished country retreat

Cottage in beautiful Hampshire village

Detached and romantic cottage with hot tub.
Pet-friendly cottage rentals

Gardeners’ Cottage (Georgian stable conversion)

Corner Cottage, Limerstone, IOW, PO30 4AB

Honeysuckle Cottage - East Meon

Self contained, rural cottage, 2 double bedrooms

Stylish-Stays: Fleet, Patio, Pets, EV, Parking

Two bedroom rural retreat.

The Old Tractor Barn - Rural holiday accommodation

The Old Garage, Romsey Countryside Cottage.
Private cottage rentals

Lane End Cottage, Rural Annexe to the main house

Cosy Victorian cottage set in a country park

Thatched Grade ll property in Ashford Hill

The Old School House, Ascot, Berkshire

The Old Bakery At The Grange

Period cottage, cosy sittingroom individual host

Luxury 2 bedroom cottage

Beautifully renovated cottage - Prince's Forge
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 £91 per night before taxes and fees

Verified guest reviews
Over 680 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

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!
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- New Forest National Park
- Bournemouth Beach
- West Wittering Beach
- Paultons Park Home of Peppa Pig World
- University of Oxford
- Goodwood Motor Circuit
- South Downs National Park
- Stonehenge
- Thorpe Park Resort
- Longleat Safari Park
- Chessington World of Adventures Resort
- Windsor Castle
- LEGOLAND® Windsor Resort
- Southbourne Beach
- Bracklesham Bay
- Lower Mill Estate
- Hampton Court Palace
- Highclere Castle
- Boscombe Beach
- Mudeford Quay
- Goodwood Racecourse
- Winchester Cathedral
- The Tank Museum
- Ascot Racecourse





