Family-friendly vacation rentals in Winchester

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Top-rated family-friendly rentals in Winchester

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Guest favourite

Guesthouse in Winchester

4.95 out of 5 average rating, 260 reviews

Water Meadows Lodge beside Winchester South Downs

"Riverside" Garden Lodge is separate, secure and sunny with a private garden and free parking in St Cross village Winchester, beside the Water Meadows and South Downs. Only 15 minutes walk from the centre via the famous Water Meadow paths or road's celebrated inns you have an ideal location to enjoy this historic city. Finished to high standards, the double bedroom, spacious living / dining room, kitchen, shower / loo have the essential luxuries. Plus Fast WiFi, 42" Smart TV and Laundry service.

Oct. 20 – 27

$180 CAD per night

Guest favourite

Guesthouse in Hampshire

4.92 out of 5 average rating, 176 reviews

Beautiful Self Contained Annex in South Downs NP

This brick and flint barn has been converted to a smart modern annex separate to our house. Set in the beautiful village of Meonstoke in the heart of the Meon Valley and the South Downs National Park. Ideal for visitors wanting a little luxury at the end of a day of outdoor pursuits. A really comfortable bed with blackout blinds and ensuite shower room. A spacious living area, with kitchen, dining area & log burning stove. Free wifi. Coffee (Nespresso machine) and tea, bread and jams included.

Jul. 20 – 27

$136 CAD per night

Guest favourite

Apartment in Winchester

4.9 out of 5 average rating, 304 reviews

Copper Beech, a secluded two bed apartment

Copper Beech is spacious & modern apartment in a semi-rural location close to Winchester. This apartment has two large king size bedrooms; both with ensuite bathrooms, large lounge/dining area and a well equipped kitchen. One of the bedrooms can sleep up to 4 guests with a daybed (with two full single size beds) plus kingsize bed. Parking is available for two standard-sized vehicles - one blocking in the other. There is a trampoline in a large shared garden for children to play on.

Sep. 26 – Oct. 3

$284 CAD per night

Guest favourite

Home in Hampshire

4.96 out of 5 average rating, 547 reviews

Quiet Winchester One Bedroom Home with own parking

Welcome to your lovely detached one bedroom home in a quiet leafy private road on the edge of St Giles Hill - just above medieval Winchester and on the edge of beautiful the South Downs Way. Your self-contained home includes parking on the drive, a stylish double bedroom, shower room, living area (with full double-width sofa bed) incorpoating a full kitchen/washing machine. Its an easy 10 minute downhill stroll across the park (lovely for a sunset picnic) to historic Winchester.

Aug. 19 – 26

$167 CAD per night

Guest favourite

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.

Jun. 25 – Jul. 2

$169 CAD per night

Guest favourite

Barn in Hampshire

4.98 out of 5 average rating, 304 reviews

Hay Loft - Barn

A spacious first floor suite with uninterrupted views across the fields. Enjoy indoor or outdoor dining. A super king bed aids restful sleep with a rain shower en-suite. It benefits from having a small self contained bunk room for the children giving space but having them with you. A very small but well equipped kitchen with essentials provided. If you need us we are on site but otherwise will leave you in peace to enjoy your stay. If the Hay Loft is full - look up the Cow Shed.

Nov. 15 – 22

$152 CAD per night

Guest favourite

Apartment in Winchester

4.91 out of 5 average rating, 290 reviews

The Loft with free off road parking

A self-contained studio by apartment with kitchen facilities, double bed, sofa and TV. En-suite toilet and shower room. Free off street parking on the doorstep. Situated 5-10 minutes walk from Winchester's historic city centre and even closer to the widely renowned Black Boy pub. Within 150 metres of the South Downs Way. Just a few minutes walk from the Winchester Sports Centre. The apartment is accessed via an external staircase and so may not suit those with mobility issues.

Jul. 28 – Aug. 4

$137 CAD per night

Guest favourite

Guesthouse in Winchester

4.97 out of 5 average rating, 463 reviews

Idyllic Hideaway Ham Green Cottage near Winchester

The Orchard Studio at Ham Green Cottage is a pretty brick and flint building tucked away in a corner of our truly English country garden. You are completely private. We are family-friendly and you can expect a comfortable stay and warm welcome. We are in a village close to the historic city of Winchester, however our setting is completely rural and quiet. We have a fantastic village pub or there are lots of places to chose from in Winchester itself - the best of both worlds!

Jan. 25 – Feb. 1

$207 CAD per night

Guest favourite

Cottage in Hampshire

4.97 out of 5 average rating, 254 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.

Jan. 19 – 26

$122 CAD per night

Guest favourite

Tiny homes in Winchester

4.83 out of 5 average rating, 435 reviews

Cosy rural hideaway, Hursley, near Winchester

Fantastic rural retreat! Gorgeous cosy space, very private with own secluded garden. Everything that you need for a relaxing break. Five miles from both Winchester and Romsey, a fifteen minute walk to the lovely village of Hursley with its two pubs and great walks! Perfect for IBM Hursley, Peppa Pig World/Paultons Park, the New Forest (25 minutes) and beaches (40 minutes). You can be in Southampton with cinemas, bowling, shopping etc in 20 minutes. A great exploring base!

Mar. 3 – 10

$123 CAD per night

Guest favourite

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.

Apr. 11 – 18

$280 CAD per night

Guest favourite

Home in Hampshire

4.98 out of 5 average rating, 334 reviews

Cozy 17th Century Cottage in Jane Austen's Chawton

A 17th century, beautiful cottage set in Chawton village, and a minute's walk from Jane Austen's house & museum. It has good access to London via train or car and is the perfect escape to a quintessential English village and countryside experience. We love the cottage for its unique charm and warmth, and we hope to extend that to you during your stay!

Jan. 20 – 27

$186 CAD per night