Family-friendly holiday rentals in Winchester

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Top-rated family-friendly rentals in Winchester

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Bungalow in Eastleigh

4.93 out of 5 average rating, 385 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.

Guest favourite

Guest house in Winchester

4.95 out of 5 average rating, 276 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.

Guest favourite

Guest house in Hampshire

4.93 out of 5 average rating, 194 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.

Guest favourite

Rental unit in Winchester

4.91 out of 5 average rating, 318 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.

Guest favourite

Home in Hampshire

4.96 out of 5 average rating, 604 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.

Guest favourite

Guest house in Winchester

4.97 out of 5 average rating, 485 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!

Guest favourite

Cottage in Hampshire

4.97 out of 5 average rating, 288 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.

Guest favourite

Tiny home in Winchester

4.82 out of 5 average rating, 453 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!

Guest favourite

Cottage in Winchester

4.81 out of 5 average rating, 269 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.

Guest favourite

Barn in Midhurst

4.97 out of 5 average rating, 586 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.

Guest favourite

Rental unit in Hampshire

4.87 out of 5 average rating, 280 reviews

** Stylish, clean and modern apartment **

Clean, wonderfully modern and ideally located en-suite maisonette within close proximity to the following: * Peppa Pig World / Paultons Park (15 minute drive) * Marwell Zoo (20 mins) * Southampton Airport (5 mins) * Winchester (15 mins) * Southampton Cruise Terminal (20 mins) * The New Forest (20 mins) A great and comfortable apartment with all you need for a relaxing stay.

Guest favourite

Home in Hampshire

4.98 out of 5 average rating, 373 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!