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Family-friendly vacation rentals in Winchester

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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.

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Top guest favorite
A light-filled living area features a comfortable gray sofa adorned with patterned cushions. A small, cozy armchair sits nearby, and a wooden coffee table is positioned in front. Natural light streams through the window, highlighting a light blue wall and decorative shelf.
Condo in Winchester

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

4.96 out of 5 average rating, 188 reviews
Top guest favorite
A well-appointed room features a spacious bed with plush bedding. Light wood flooring complements the seating area with a circular table and two upholstered chairs. Skylights and decorative lamps provide soft lighting. A mirror adds depth, and a hairdryer is available on the wall.
Guesthouse in Winchester

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 spacesAmenities

4.92 out of 5 average rating, 159 reviews
Superhost
An open living area features a large grey sofa adorned with colorful cushions, complemented by a vibrant floral area rug. A dining table with wooden chairs sits adjacent to a modern kitchen, illuminated by soft ceiling lights.
Townhouse in Winchester

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 spacesKitchenEV charging

4.86 out of 5 average rating, 168 reviews
Top guest favorite
Apartment in Winchester

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.

FamilyIndoor spacesBreakfast

4.92 out of 5 average rating, 331 reviews
Top guest favorite
Two distinct entrances are visible, each framed by elegant archways. A decorative black iron railing separates the front door area from the sidewalk, while light green planters with small shrubs add a touch of greenery to the scene. Large windows allow natural light to fill the interior.
Guest suite in Winchester

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.

KitchenIndoor spacesCheck-in

4.97 out of 5 average rating, 467 reviews
Guest favorite
A spacious living area is showcased, featuring a large screen displaying the Netflix logo. Comfortable seating is arranged with two armchairs and a sofa, complemented by a coffee table. A decorative plant and wall clock enhance the room's atmosphere, with natural light illuminating the space.
Home in Winchester

4 Bed City House with Private Garden and Parking

Discover our beautifully decorated four-bedroom home in Winchester's historic city centre. Enjoy the convenience of two rare parking spaces and a courtyard garden to unwind in. Indulge in the city's amenities that are just a stone's throw away, from artisan coffee shops to chic restaurants. Winchester Cathedral is only a leisurely five-minute stroll away! Whether for leisure or business, our spacious home offers comfort and convenience. Experience Winchester's charm and book your stay today!

KitchenIndoor spacesCleanliness

4.93 out of 5 average rating, 110 reviews
Top guest favorite
A polished silver bowl filled with ice displays several bottles of champagne. Fresh lilies and elegant candelabras are positioned nearby, adding a touch of sophistication to the setting. The arrangement creates a celebratory atmosphere.
Apartment in Winchester

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.

KitchenIndoor spacesCondition

5.0 out of 5 average rating, 110 reviews
Guest favorite
The bedroom features a spacious bed dressed in soft grey bedding, complemented by decorative cushions. Light streams through the window, softened by sheer curtains. A bedside table with literature adds a functional touch, while a wall-mounted mirror enhances the overall brightness.
Home in Winchester

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 spacesFamilyLayout

4.95 out of 5 average rating, 779 reviews
Top guest favorite
The lounge area features a comfortable sofa adorned with colorful cushions and a light rug underfoot. A small armchair adds seating options, while natural light filters through the large windows, illuminating the room. A round coffee table rests in the center, enhancing the cozy atmosphere.
Apartment in Winchester

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.

Indoor spacesFamilyBackyard

4.95 out of 5 average rating, 429 reviews
Guest favorite
The living room features a light and airy design, showcasing a two-seater sofa and a separate sofa bed. A dining table for four is centered in the space, complemented by a fireplace and a wall-mounted TV. Decorative plants enhance the welcoming atmosphere.
Condo in Winchester

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.

KitchenIndoor spacesWifi

4.92 out of 5 average rating, 264 reviews
Guest favorite
A modern living space is visible through open bi-fold doors, blending indoor and outdoor areas. A sleek seating arrangement is placed outside on a patio, complemented by soft lighting. Inside, a light-filled room showcases a comfortable sofa and dining area, enhancing the welcoming atmosphere.
Tiny home in Winchester

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 spacesKitchenSleep quality

4.95 out of 5 average rating, 307 reviews
Top guest favorite
The Cottage features a charming exterior with a textured roof and a modern patio area. Surrounded by greenery, a spacious seating arrangement is set on a stone surface, offering a tranquil spot for relaxation. Nearby structures exhibit a contemporary architectural style.
Cottage in Winchester

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!

FamilyIndoor spacesParking

4.99 out of 5 average rating, 224 reviews

Popular amenities for Winchester family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
Condo in Winchester

Stable Apartment with Hot Tub near Winchester

Indoor spacesKitchenBreakfast

4.92 out of 5 average rating, 287 reviews
Guest favorite
Cottage in Sutton Scotney

Ultra luxury, newly refurbished country retreat

KitchenIndoor spacesHot tub

4.88 out of 5 average rating, 511 reviews
Guest favorite
A private deck features a luxurious hot tub surrounded by lush greenery. A round glass table with six cushioned chairs offers a space for dining or relaxation. A neatly folded towel is placed on the deck, enhancing the inviting outdoor setting.
Chalet in Pitt

Luxury 3 Bedroom, Scandinavian Lodge with HOT TUB

Indoor spacesFamilyCheckout

4.91 out of 5 average rating, 106 reviews
Superhost
A rustic cabin with a dark metal roof and timber exterior is surrounded by trees. Smoke gently rises from a chimney. The front porch, featuring large glass doors, leads to a welcoming seating area. A pathway of stepping stones guides the way through the lawn.
Farm stay in Headbourne Worthy

A Unique Farm Retreat

KitchenIndoor spacesHospitality

4.95 out of 5 average rating, 385 reviews
Top guest favorite
A riverside log cabin is nestled among trees, featuring a spacious deck and seating area overlooking the water. Lush greenery surrounds the outdoor space, creating a natural setting that invites relaxation. The cabin’s wooden structure blends harmoniously with its peaceful environment.
Cabin in Reading

Riverside Log Cabin+Luxury Hot Tub Spa+Copper bath

KitchenFamilyHeating

4.98 out of 5 average rating, 467 reviews
Guest favorite
An outdoor space features a hot tub in the foreground, with jets gently bubbling. A swimming pool is visible in the background, surrounded by a stone patio and outdoor furniture. Lush greenery and a sunset sky create a serene backdrop.
Place to stay in Stroud

The Pool House: Contemporary country escape

KitchenIndoor spacesBreakfast

4.97 out of 5 average rating, 235 reviews
Top guest favorite
A serene natural landscape showcases a tranquil pond surrounded by lush green foliage and tall grasses. Reflections of trees and cloudy skies are visible in the still water, enhancing the peaceful ambiance of the wooded area.
Cottage in Salisbury

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

KitchenIndoor spacesLayout

4.99 out of 5 average rating, 170 reviews
Top guest favorite
A cozy lounge area features a teal sofa, beanbag, and a rustic wooden coffee table. A brick fireplace with a log burner adds warmth, while a dining table is positioned nearby. A ladder leads to a mezzanine sleeping space, decorated with fairy lights.
Farm stay in Cadnam

A cosy farm cottage, with lots of character.

Indoor spacesKitchenAmenities

4.99 out of 5 average rating, 245 reviews

Family- and pet-friendly home rentals

Top guest favorite
A two-story black wooden building features a sloped roof and large front windows, surrounded by a gravel pathway. A blooming pink tree stands in the front garden, complemented by decorative potted plants. Lush greenery provides a serene backdrop.
Cottage in Sparsholt

The Old Tractor Barn - Rural holiday accommodation

FamilyIndoor spacesLocation

4.94 out of 5 average rating, 232 reviews
Top guest favorite
A charming brick and flint building is surrounded by neatly trimmed bushes and a well-maintained garden. Two wooden chairs and a small table are set outside, inviting guests to enjoy the tranquil rural setting under clear skies.
Guesthouse in Winchester

Idyllic Hideaway Ham Green Cottage near Winchester

FamilyIndoor spacesBackyard

4.97 out of 5 average rating, 602 reviews
Guest favorite
A rustic oak-framed barn is nestled among trees, showcasing a sloped roof and large windows. Gravel pathways lead to the entrance, framed by potted plants. The structure is surrounded by open space, offering a serene rural setting.
Home in Winchester

Oak Framed Barn with Tennis Court

FamilyIndoor spacesAmenities

4.94 out of 5 average rating, 412 reviews
Top guest favorite
The Watch House is viewed from a garden path lined with blooming flowers, leading down to the beach. The white exterior of the cottage is highlighted against a clear blue sky, while the tide is low, revealing a sandy shore.
Home in Lepe

Iconic Beach Front Stay | The Watch House, Lepe

Indoor spacesFamilyAmenities

4.98 out of 5 average rating, 154 reviews
Guest favorite
A spacious apartment complex is surrounded by lush greenery and trees, with well-maintained gardens showcasing a neat arrangement of colorful flowers. A paved driveway leads to the entrance, providing access to the residences, amidst a tranquil countryside setting.
Guesthouse in Hawkley

Daily Red Kite Feed & Pool - Countryside Apartment

Indoor spacesFamilyComfort

4.96 out of 5 average rating, 291 reviews
Guest favorite
The sitting room features high ceilings with exposed wooden beams and large skylights providing ample natural light. Comfortable seating arrangements include a blue couch and a cream sofa, complemented by a small wooden table. A bookshelf filled with books and a small television are visible along one wall.
Guest suite in Houghton

Peaceful barn conversion in rural location.

Indoor spacesKitchenParks

4.93 out of 5 average rating, 198 reviews
Guest favorite
Cottage in East Hampshire

The Barn @ North Lodge -Soho Farmhouse-esque Cabin

Indoor spacesKitchenBiking

4.96 out of 5 average rating, 659 reviews
Top guest favorite
The exterior of the property displays a charming wooden facade with large glass doors, allowing natural light to fill the living space. A neatly landscaped garden features lush greenery, stone pathways, and patio seating, creating an inviting outdoor environment.
Guest suite in Lyndhurst

New Forest cottage by the green

FamilyKitchenHospitality

4.97 out of 5 average rating, 393 reviews

Family-friendly home rentals with a pool

Top guest favorite
A modern guest lodge is showcased, featuring a distinctive curved roof and large glass windows that enhance the natural light. The surrounding outdoor area is paved, including a pool with a cover and seating arrangements for relaxation.
Place to stay in Hill Brow

The Pool House (for 2 Adults & 2 Children)

KitchenIndoor spacesPool

4.98 out of 5 average rating, 120 reviews
Top guest favorite
A large heart-shaped sculpture is positioned on a circular wooden platform, surrounded by natural vegetation. The backdrop features rolling hills under a sky with varying cloud coverage, enhancing the scenic view of the surrounding landscape.
Holiday park in Hampshire

Sandy Balls Holiday Village New Forest Hampshire

KitchenIndoor spacesWalkability

4.99 out of 5 average rating, 218 reviews
Top guest favorite
Guesthouse in Grayswood

Grayswood Cowshed in stunning Grounds

Indoor spacesKitchenAccess

4.98 out of 5 average rating, 363 reviews
Top guest favorite
An indoor heated swimming pool is set against a backdrop of wooden beams and natural light streaming through large windows. The clear blue water is bordered by tiled flooring, and a stained glass window adds a colorful accent to the serene environment.
Cottage in Lyndhurst

Charming cottage with pool in the New Forest

KitchenIndoor spacesSleep quality

4.98 out of 5 average rating, 106 reviews
Top guest favorite
The semi-detached cottage features a charming exterior with a light-colored façade, complemented by vibrant greenery and climbing plants. Windows are adorned with traditional frames, and a well-defined entrance leads to the property. A gravel pathway is visible, enhancing the inviting approach.
Cottage in Isle of Wight

Rural Isle of Wight cottage with indoor pool use

Indoor spacesFamilyTV

4.99 out of 5 average rating, 141 reviews
Top guest favorite
Barn in West Sussex

Delightful one bedroom barn with beautiful views

KitchenFamilyDecor

4.94 out of 5 average rating, 162 reviews
Top guest favorite
A modern pool house features expansive glass walls surrounded by lush greenery. The indoor pool is visible, complemented by an outdoor lounging area with a sunbed and a vibrant garden showcasing various plants and flowers. A natural landscape of trees frames the property.
Place to stay in South Oxfordshire

Luxury Pool House set in an Oxfordshire forest

KitchenFamilyTV

4.97 out of 5 average rating, 104 reviews
Top guest favorite
A spacious bedroom features a comfortable bed dressed in light bedding. Large windows allow natural light to fill the room, with views of greenery outside. Artwork adorns the walls, and a cozy sitting area includes a chair and a television, enhancing the room's inviting atmosphere.
Guesthouse in West Sussex

Comfortable 1-Bedroom Guest Suite in rural setting

FamilyIndoor spacesBackyard

4.96 out of 5 average rating, 193 reviews

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 889ﺩ.ﺇ 815ﺩ.ﺇ 845ﺩ.ﺇ 944ﺩ.ﺇ 948ﺩ.ﺇ 984ﺩ.ﺇ 933ﺩ.ﺇ 1,058ﺩ.ﺇ 959ﺩ.ﺇ 889ﺩ.ﺇ 826ﺩ.ﺇ 933
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