
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.

Spacious central 2 bedroom apartment+ free parking
A spacious family-friendly 2 double/twin bedroom first floor flat located in the lovely Hyde area of central Winchester. Provides easy access to the city centre with all that the city offers. Only 5 minutes stroll to the train station. This apartment is close to all the historical sites and wide variety of restaurants and cafes which you'll enjoy as well as the cathedral and its impressive grounds. Winchester Christmas market and the city's magical atmosphere should be on everybody's calendar.

Own Front Door
Welcome to the beautiful city of Winchester! I have self contained central accommodation comprising of a double bedroom with en-suite shower room, a lounge with fridge/tea/coffee making facilities and your own private front door accessed from the street at ground level. The accommodation has been part of a massive renovation of the main house, now fully completed. Dating from the 1850’s it still retains a Victorian feel with high ceilings and sash windows. It is a lovely light, airy space.

St Michael's Hall, City Centre
St Michael's Hall is a unique, newly renovated church hall in the heart of the historic city centre. A stone's throw from the Cathedral, College, buzzy high street and water meadows, it's the perfect base to explore everything Winchester and the surrounding area has to offer. Each bedroom has its own bathroom, meaning it's as suitable for two couples as it is for a romantic city break or four friends. One on-street parking permit is available, while the train station is a short walk away.

The Sky Penthouse, City Centre Luxury
Positioned right in the heart of charming historic Winchester The Sky Penthouse offers luxury modern comfortable 5 star accommodation . Private parking for one car . Positioned an easy level 300 meter walk from the main High Street within the City Centre , 400 meters from Winchester Cathedral and 500 meters from Winchester train station. Great location with a garden. Guests can choose the bed configuration of both the double bedrooms, either 6ft wide super king luxury beds or single beds.

Oak Framed Barn with Tennis Court
A stylish secluded, two storey, oak framed barn with tennis court, 4 miles from Winchester. Homely space with two bedrooms plus a sofa bed (upon request) and ground floor open plan living area. Super fast WiFi. The Barn adjoins the Watercress Way and stands separately in the grounds with views over open Hampshire fields. Nearest neighbour c.1 mile away but there is loads to do in the area with an abundance of country pubs, one or two within walking distance and beaches within 50 minutes

Beautiful stylish Garden flat 8 mins to Winchester
Unique and stylish, this very comfortable and relaxing space offers the peacefulness of countryside whilst being a stones throw from the beautiful city of Winchester - a very short drive or a beautiful walk away. You get the best of both worlds with the city's pubs, restaurants, cafes and historic sights close at hand as well as river walks by the Itchen & beautiful countryside straight from your door. Excellent transport links to London, M3, Southampton Airport and the New Forest.

Central Winchester 1 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.

Bright Bijou Studio in Central Winchester
A beautiful bright cosy studio apartment on one of the quietest streets in the centre of historic Winchester❤️. The breathtaking cathedral and other must-see sights are all within a flat 10 minute walk. Ideal for short stays or a weekend get-away. Just five minutes walk from train station/city centre, and 10 mins walk from the bus station. * Super-comfy double bed ✅ * Fast WiFi ✅ * Comfortable big chair and table for laptop working ✅ * Wide range of caf/decaf teas and coffees ✅

Central Winchester garden flat, permit parking
Winchester City Centre- Bijou, charming, characterful, homely, warm and cosy self contained one bedroom flat with free permit parking and luxuriously large bath tub with shower, private garden with patio for alfresco dining. Fully equipped galley kitchen for self - catering. Only a five minute level walk to the central High Street and Cathedral, with the world famous Christmas Market through November and December. Less than ten minutes walk from the Railway Station.

Stylish Apartment • Central Winchester
Situated in the heart of Winchester, this newly refurbished two-bedroom apartment with its own private entrance offers a stylish and comfortable stay for couples, friends and families. Modern décor and thoughtful design create a cosy space to relax after exploring the city’s historic streets, shops and cathedral. You’re just steps from the popular St James Tavern, a welcoming traditional pub serving excellent locally sourced food.

The Hidden house in Winchester
The Hidden House is a slice of modern luxury tucked away in the heart of Winchester. Detached and private, this space is perfectly placed for exploring Winchester and all it has to offer. Our guests also love hiding away and making use of the big TV setup and Hotel Chocolat Velvetiser! Don't take our word for it - check out our reviews. Winchester High Street/The Cathedral - 10 min walk Winchester Train Station - 5 min walk

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!
Popular amenities for Winchester family-friendly rentals
Family-friendly home rentals with a hot tub

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

The Joinery, Owslebury, Winchester

Cottage in beautiful Hampshire village

Cosy cabin in Annie’s meadow

Ultra luxury, newly refurbished country retreat

Riverside Log Cabin+Luxury Hot Tub Spa+Copper bath

Luxury hut on the River Arle

River Rose Retreat Shepherds Hut, view and hot tub
Family- and pet-friendly home rentals

Daily Red Kite Feed & Pool - Countryside Apartment

Adventure Prospect - Historic Waterfront Cottage

The Barn @ North Lodge -Soho Farmhouse-esque Cabin

The Old Stables, Derrydown Farm

Coach House in the heart of the test valley

The Annexe - Unique and Tranquil Getaway.

The Nest

Iconic Beach Front Stay | The Watch House, Lepe
Family-friendly home rentals with a pool

Panoramic Sea Views, quiet, relaxed, cliffs, Beach

Sandy Balls Holiday Village New Forest Hampshire

Unique, romantic luxury countryside retreat

Beautiful S.Downs Cottage, pool and tennis

The Pool House: Contemporary country escape

Delightful Chalet Bungalow with a Spa

The Guest House, Five Trees

The Hideaway Loft. Pool*, Sauna, Gym, Yoga classes
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £149 | £170 | £162 | £182 | £200 | £198 | £191 | £216 | £196 | £182 | £169 | £191 |
| Avg. temp | 5°C | 5°C | 7°C | 9°C | 12°C | 15°C | 17°C | 17°C | 15°C | 11°C | 8°C | 5°C |
Quick stats about holiday rentals that are family-friendly in Winchester

Total holiday rentals
Explore 150 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at £45 per night before taxes and fees

Verified guest reviews
Over 7,090 verified reviews to help you choose

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
150 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!
Destinations to explore
- Rentals with breakfast Winchester
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- Flat rentals Winchester
- House rentals Winchester
- Pet-friendly rentals Winchester
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- Rentals with outdoor seating Winchester
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- Rentals with a washing machine and dryer Winchester
- Apartment rentals Winchester
- Family-friendly rentals Hampshire
- Family-friendly rentals England
- Family-friendly rentals United Kingdom
- South Downs National Park
- New Forest National Park
- Paultons Park Home of Peppa Pig World
- University of Oxford
- Goodwood Motor Circuit
- Stonehenge
- Bracklesham Bay
- Windsor Castle
- Hampton Court Palace
- Highclere Castle
- Lower Mill Estate
- Boscombe Beach
- Bournemouth Beach
- Chessington World of Adventures Resort
- Thorpe Park Resort
- Winchester Cathedral
- Bournemouth International Centre
- Goodwood Racecourse
- The Tank Museum
- Kimmeridge Bay
- West Wittering Beach
- Highcliffe Beach
- Southbourne Beach
- Worthing Pier




