Cottage vacation rentals in City of Winchester

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Top-rated cottage rentals in City of Winchester

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Guest favorite

Cottage in Droxford

4.93 out of 5 average rating, 120 reviews

Gorgeous Country Escape 5 Bedroom House & Annex

Family run, our pretty 4 bedroom detached house & separate 1 bedroom annexe enjoys a rural location surrounded by the idyllic Meon Valley & South Downs Park. The large garden is a haven, providing a perfect setting for alfresco dining with friends & family. With no direct neighbours you'll feel like you have the countryside all to yourselves! There are many beautiful cities on our doorstep, including Winchester & Chichester. Pool table & table football & X Box We also welcome your dog 🐶

Feb 10 – 17

R19,578 ZAR per night

Superhost

Cottage in Shawford

4.83 out of 5 average rating, 114 reviews

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.

Apr 14 – 21

R4,397 ZAR per night

Guest favorite

Cottage in Hampshire

4.96 out of 5 average rating, 380 reviews

The Garden Cottage at Oakhanger Farmhouse .

Close to Jane Austen's House in Chawton 10 mins, Situated in the S.D.National Park,Alice Holt Forest (5 mins), Gilbert Whites House (5 mins)The Watercress Steam Railway, West Wittering Beach (50 mins), Chichester 30 mins fab theatre! and Goodwood 35mins. The cottage has been completely refurbished and beautifully designed down to the last detail,comfortable and with all mod cons. With so much to do in the area it's a great place for anyone who wants a lovely break from their everyday life.

Dec 20 – 27

R2,938 ZAR per night

Guest favorite

Cottage in Romsey

4.99 out of 5 average rating, 132 reviews

Beautiful Winterberry Barn ,With Hot tub

WinterBerry Barn is a gorgeous 1 bedroom cottage with everything you could possibly need for a cosy country getaway. It has a beautiful wood fired hot tub .Every aspect of the property is finished to the highest standard. Oak finish throughout with raw natural beams flowing through the property to really give it that warm country feel. Close to all the wonderful local amenities such as the beautiful market town of romsey only a 5 minute drive! Also the beautiful historic city of Winchester.

Mar 18 – 25

R4,375 ZAR per night

Guest favorite

Cottage in Wherwell

4.93 out of 5 average rating, 221 reviews

Cottage in beautiful Hampshire village

Relaxing and comfortable country cottage. Village pubs and lovely walks nearby. Fully equipped, superking or twin beds in both bedrooms, 2 bathrooms, sitting room with log burner, dining room and kitchen. Secluded, peaceful garden with seating & gas BBQ. Access to hot-tub, and 4 bicycles, by prior arrangement. Linen, towels, toiletries, wifi and welcome pack included. Off-road parking for 1 car, other cars by arrangement. Unsuitable for young children or people with mobility challenges.

Mar 4 – 11

R3,522 ZAR per night

Guest favorite

Cottage in Bishop's Waltham

4.98 out of 5 average rating, 122 reviews

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.

Oct 27 – Nov 3

R2,338 ZAR per night

Guest favorite

Cottage in Downton

4.96 out of 5 average rating, 438 reviews

The Coach House with walled garden

Our converted coach house offers a cosy corner in the busy village of Downton from which to visit the historic cathedral city of Salisbury and the open spaces of the New Forest. Parts of the property date back to 1475 with links to the Bishops of Winchester. There is plenty on offer in and around the village, with local shops, gardens, pubs, walks and bicycle rides along the River Avon. Bournemouth beaches are not far away. We welcome dogs for a fee of £20 for up to 2 dogs per stay.

Sep 22 – 29

R2,351 ZAR per night

Guest favorite

Cottage in Hampshire

4.97 out of 5 average rating, 252 reviews

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.

Apr 11 – 18

R1,674 ZAR per night

Guest favorite

Cottage in Winchester

4.82 out of 5 average rating, 248 reviews

Beggar's Lane Cottage-3 beds in Central Winchester

Beggar's Lane cottage is Grade II listed and built circa 1720 and retaining many original features. Two similar sized bedrooms with great views of Winchester Cathedral and a downstairs bathroom. There is a small courtyard back garden. The WiFi is fast. There will be fresh towels, dressing gowns, tea and coffee for you on your arrival. A short walk to the City centre, with it's many bars, shops, restaurants and other attractions. Located in an elevated and quiet street.

Feb 12 – 19

R3,644 ZAR per night

Guest favorite

Cottage in Hambledon

4.92 out of 5 average rating, 158 reviews

Private cottage in a quiet countryside location.

Nestled in a peaceful South Downs hamlet, Courtyard Cottage is perfectly situated for a leisurely or active break in the country with easy access to the coast. The area is popular with walkers and cyclists due to the many footpaths and country lanes in the vicinity. There are also plenty of family attractions and sightseeing opportunities in the area. Guest will enjoy the privacy of the cottage with its own secluded courtyard garden. We are dog friendly!

Nov 5 – 12

R2,644 ZAR per night

Guest favorite

Cottage in Hampshire

4.98 out of 5 average rating, 144 reviews

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.

Dec 22 – 29

R3,856 ZAR per night

Guest favorite

Cottage in Hampshire

4.97 out of 5 average rating, 147 reviews

Self-contained Lodge, Stockbridge

The Lodge has been newly renovated, giving 24sqm of self-contained studio style accommodation, with modern fitted kitchen and bathroom facilities. Located on the ever popular Stockbridge High Street with it's host of shops, pubs and restaurants, it also sits in the heart of the Test Valley with endless opportunities for those who love the outdoors.

Oct 15 – 22

R2,831 ZAR per night