
Family-friendly vacation rentals in Winchester
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Winchester

Total vacation rentals
Explore 160 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at ﺩ.ﺇ 220 per night before taxes and fees

Verified guest reviews
Over 7,620 verified reviews to help you choose

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
160 of Winchester vacation rentals include wi-fi 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!
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.
KitchenFamilySleep quality

Central, Quiet & Self-Contained
Incredibly central location. Only 150m from Cathedral & 200m to High St. Quiet: Set back from the street, double glazing, detached building. King size bed with luxury mattress & topper, hypoallergenic duvet & pillows, Egyptian cotton bedlinen and fluffy towels. Work space. Reading & soft lighting. Well Equipped: Tea & Coffee Facilities, Mini Fridge, TV (Netflix only) Iron+Board, Hairdryer, Toiletries & Fan. Secure parking subject to availability £20per night. NB. Access via external staircase.
FamilyIndoor spacesComfort

The Winchester Pad
The Winchester Pad is a spacious, modern townhouse ideally located within walking distance to the city centre and rail station to London. There is good road access in/out of the city and two free car parking permits are provided. Guests love it; with genuine accommodation all to themselves for 8 guests in 4 bedrooms and all the facilities required for an enjoyable stay. We welcome families, couples or 'professionals' from around the world seeking accommodation in this friendly, bustling city.
Indoor spacesFamilyHospitality

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 Everyone Active Winchester Sports Centre. The apartment is accessed via an external staircase and so may not suit those with mobility issues.
KitchenFamilyRiver

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.
Indoor spacesKitchenAccuracy

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.
FamilyKitchenGetting around

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.
Indoor spacesKitchenLayout

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!
KitchenFamilyBreakfast

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.
FamilyIndoor spacesWalkability

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.
FamilyIndoor spacesDecor

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
Indoor spacesFamilyParking

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

Ultra luxury, newly refurbished country retreat
KitchenIndoor spacesLayout

A Unique Farm Retreat
Indoor spacesFamilyLocation

Cedar House - Pool & Spa Complex
FamilyKitchenSleep quality

Luxury 3 Bedroom, Scandinavian Lodge with HOT TUB
FamilyIndoor spacesQuiet

The Pool House: Contemporary country escape
Indoor spacesKitchenBathroom

A cosy farm cottage, with lots of character.
Indoor spacesKitchenWalkability

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

A holiday home in New Forest with pool & hot tub
KitchenIndoor spacesBiking
Family- and pet-friendly home rentals

The Old Tractor Barn - Rural holiday accommodation
Indoor spacesKitchenBiking

Oak Framed Barn with Tennis Court
FamilyIndoor spacesGrill

The Nest
KitchenIndoor spacesCondition

The Annexe - Unique and Tranquil Getaway.
FamilyIndoor spacesComfort

Daily Red Kite Feed & Pool - Countryside Apartment
KitchenIndoor spacesPool

The Barn @ North Lodge -Soho Farmhouse-esque Cabin
KitchenFamilyBiking

Peaceful barn conversion in rural location.
Indoor spacesFamilyComfort

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

The Pool House (for 2 Adults & 2 Children)
FamilyKitchenLocation

Secluded Country Cottage
FamilyIndoor spacesWifi

Grayswood Cowshed in stunning Grounds
Indoor spacesFamilyGrill

Sandy Balls Holiday Village New Forest Hampshire
KitchenFamilyCheck-in

Charming cottage with pool in the New Forest
Indoor spacesFamilyComfort

Comfortable 1-Bedroom Guest Suite in rural setting
Indoor spacesFamilyAccuracy

Delightful one bedroom barn with beautiful views
Indoor spacesFamilyBeach

Cottage Pye - Beautiful Barn In The New Forest
KitchenIndoor spacesPets
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 889 | ﺩ.ﺇ 815 | ﺩ.ﺇ 845 | ﺩ.ﺇ 944 | ﺩ.ﺇ 948 | ﺩ.ﺇ 984 | ﺩ.ﺇ 933 | ﺩ.ﺇ 1,058 | ﺩ.ﺇ 959 | ﺩ.ﺇ 889 | ﺩ.ﺇ 826 | ﺩ.ﺇ 933 |
| 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 |
Destinations to explore
- Condo rentals Winchester
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- Pet-friendly rentals Winchester
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- Cottage rentals Winchester
- House rentals Winchester
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- Family-friendly rentals Hampshire
- Family-friendly rentals England
- Family-friendly rentals United Kingdom
- New Forest National Park
- Bournemouth Beach
- West Wittering Beach
- Paultons Park Home of Peppa Pig World
- Longleat Safari Park
- Goodwood Motor Circuit
- University of Oxford
- Thorpe Park Resort
- Stonehenge
- Southbourne Beach
- South Downs National Park
- Windsor Castle
- LEGOLAND® Windsor Resort
- Boscombe Beach
- Lower Mill Estate
- Bracklesham Bay
- Hampton Court Palace
- Highclere Castle
- Mudeford Quay
- Chessington World of Adventures Resort
- The Tank Museum
- Winchester Cathedral
- Ascot Racecourse
- Bournemouth International Centre





