Family-friendly vacation rentals in Winchester

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Top-rated family-friendly rentals in Winchester

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Guest favorite

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 11 – 18

G$26,099 GYD per night

Guest favorite

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 15 – 22

G$19,540 GYD per night

Guest favorite

Bungalow in Eastleigh

4.93 out of 5 average rating, 377 reviews

One bedroom home.

Relax and make yourself at home in this comfortable bungalow with sunny lounge, fully equiped kitchen/diner and bathroom. Situated in a quiet cul-de-sac in the village of Bishopstoke on the outskirts of Eastleigh. The M27 and M3 motorways and Southampton Airport are just a few miles away. The historic City of Winchester is an easy drive. Whether you are on your way to explore the South West, visiting family or friends or just wanting a short break, we offer a convenient home away from home.

Oct 14 – 21

G$16,081 GYD per night

Guest favorite

Cottage in Fordingbridge

4.98 out of 5 average rating, 411 reviews

Wisteria Lodge

This beautiful lodge is on the edge of the New Forest. A perfect retreat for those wanting a relaxing, peaceful getaway but also a great location for an active holiday and great for families, with lots of space around you and a host of opportunities nearby. The lodge is set in the garden of a lovely family home, it is surrounded by fields and private woodland to explore. You will have the entire lodge to yourselves. Tea, coffee and a delicious continental breakfast is provided on arrival.

Dec 17 – 24

G$24,354 GYD per night

Guest favorite

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 18 – 25

G$41,715 GYD per night

Guest favorite

Guesthouse in Winchester

4.97 out of 5 average rating, 462 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!

Aug 12 – 19

G$29,226 GYD per night

Guest favorite

Apartment in Winchester

4.91 out of 5 average rating, 287 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 6 – 13

G$20,692 GYD per night

Guest favorite

Cottage in Hampshire

4.97 out of 5 average rating, 251 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.

Nov 21 – 28

G$18,550 GYD per night

Guest favorite

Tiny home in Winchester

4.82 out of 5 average rating, 434 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!

Apr 10 – 17

G$17,792 GYD per night

Guest favorite

Cottage in Winchester

4.82 out of 5 average rating, 247 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 9 – 16

G$39,978 GYD per night

Guest favorite

Barn in Midhurst

4.97 out of 5 average rating, 550 reviews

The Cowshed, Midhurst

The Cowshed is within walking distance of the centre of Midhurst which lies at the heart of the South Downs National Park and is surrounded by beautiful countryside and a wealth of walking opportunities. Enjoy walking or mountain-biking on the South Downs Way (local bike hire available), explore the beautiful National Trust gardens at Woolbeding, Polo at Cowdray Park or the fantastic sandy beach at West Wittering. Goodwood is a short drive away.

Oct 17 – 24

G$24,376 GYD per night

Guest favorite

Home in Hampshire

4.98 out of 5 average rating, 330 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!

Oct 28 – Nov 4

G$27,035 GYD per night