
Family-friendly vacation rentals in Winchester
Find and book unique family-friendly homes on Airbnb
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.

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 ✅

Stable Cottage Beauworth Southdowns Hampshire
Welcome to Stable Cottage, your idyllic getaway. Our newly built cottage is designed to the highest standard for your comfort and enjoyment. The cozy atmosphere is enhanced by super-insulated walls and a log-burning stove that keep you warm during colder months. In summer, the sliding patio doors let in sunshine and stunning views of the Hampshire countryside. Stay connected with super-fast fibre broadband and a Smart TV. Your stay at Stable Cottage will be unforgettable.

Room with a view
You’ll love sharing photos of this unique place with your friends. Room with a View is a cosy and bright studio room located in the outskirts of the rural village of Owslebury. Just a 5-mile drive from the medieval city of Winchester, Room with a View is situated in a prime location, perfect for a serene getaway or business stay. Secluded from the busy bustle of the city, yet a swift 10-minute drive, Room with a View is surrounded by acres of fields and beautiful views.

The Annexe at Longacre, near Winchester
The Annexe is a bright and airy self contained house separate from our home. The accomodation is over two floors with wonderful views out to the Hampshire countryside. We are on a quiet private country road 2 miles from the vibrant city of Winchester, 6 miles from Southampton Airport and 3 miles from IBM Hursley. Excellent transport links to London (1 hour from Shawford Station) and to Southampton. We live in the main house. Follow us on Instagram @longacreannexe

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.

Pretty self contained annexe
Pretty, self contained annexe with its own entrance, located between the historic city of Winchester & Southampton and on the doorstep of the New Forest National Park. Great travel links - M3/M27, Southampton Airport & Southampton Parkway station. Studio comprises double bed, kitchen with oven, hob, fridge & microwave. Breakfast bar, which doubles as a workspace, shower room and shared use of patio and garden. We also have a young, bouncy dog!

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

Modern Apartment Central Winchester
Situated in the heart of Winchester, this newly refurbished 2-bedroom apartment with its own private entrance and modern décor provides a well thought out space for friends, couples & families. This cosy home provides an excellent upmarket base to explore Winchester. A stone’s throw to the city’s favourite pub, St James Tavern, a warm welcoming traditional pub which serves excellent locally sourced home cooked food.
Popular amenities for Winchester family-friendly rentals
Family-friendly home rentals with a hot tub

Hacketts Annex, HotTub, Old Bursledon Hamble River

Adorable Detached 1 bedroom Annexe with hot tub

The Joinery, Owslebury, Winchester

The Annexe with Hot Tub Virgin TV, Sky & BT Sport

Cosy cabin with hot tub in peaceful location

Cosy cabin in Annie’s meadow

Rivermead Hut Retreat

Wagon & The Wigwam Hot Tub
Family- and pet-friendly home rentals

The Hayloft - Rural retreat very near Winchester

Oak Framed Barn with Tennis Court

The Nest

The Annexe @ Mandalay Lodge

Self-contained Garden Cottage in idyllic location

Stunning apartment in the heart of New Alresford

Studio in Abbots Worthy

Two bedroom rural retreat.
Family-friendly home rentals with a pool

Sandy Balls Holiday Village New Forest Hampshire

Cosy Shepherd's Hut with wood-fired hot tub

Chic Bungalow Retreat - Serene Garden, Pool & Spa

Beachside holiday home

Sea Views, Seaside, Quiet,Relaxing, Beach,Cliffs,

Beautiful S.Downs Cottage, pool and tennis

The Pool House: Contemporary country escape

Delightful Chalet Bungalow with a Spa
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $231 CAD | $225 CAD | $239 CAD | $264 CAD | $271 CAD | $274 CAD | $286 CAD | $289 CAD | $280 CAD | $267 CAD | $254 CAD | $261 CAD |
| 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 vacation rentals that are family-friendly in Winchester

Total vacation rentals
Explore 1,040 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at $28 CAD per night before taxes and fees

Verified guest reviews
Over 37,570 verified reviews to help you choose

Pet-friendly vacation rentals
Find 340 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
520 properties have a dedicated workspace

Wifi availability
1,000 of Winchester vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winchester rentals

4.7 Average rating
Winchester stays receive an average rating of 4.7 out of 5 from guests
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- Family-friendly rentals Hampshire
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- New Forest national park
- Goodwood Motor Circuit
- Paultons Park Home of Peppa Pig World
- Oxford University
- Stonehenge
- Windsor Castle
- Hampton Court Palace
- Boscombe Beach
- Winchester Cathedral
- Highclere Castle
- Bournemouth Beach
- Chessington World of Adventures Resort
- Twickenham Stadium
- Kimmeridge Bay
- Thorpe Park Resort
- Goodwood Racecourse
- Highcliffe Beach
- West Wittering Beach
- Worthing Pier
- The Tank Museum
- Southbourne Beach
- Wentworth Golf Club
- RHS Garden Wisley
- Poole Quay
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