Family-friendly vacation rentals in City of Winchester

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Popular amenities for City of Winchester family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
A traditional shepherd's hut is positioned on a grassy area, surrounded by a lush garden. The exterior is clad in dark corrugated metal, featuring a large window for natural light. Scenic valley landscapes extend in the background, contributing to the secluded ambiance.
Shepherd’s hut in Salisbury
4.95 out of 5 average rating, 856 reviews

Shepherd's Hut with large hot tub near Stonehenge

LauraRating, 5 stars2 weeks ago
An absolutely dreamy escape for two! complete with scenic views, and enough special touches to feel at home. Fiona made everything so comfortable and we look forward to coming back!
Guest favorite
A charming two-story cottage is set within a large, green garden, surrounded by trees and planted areas. The building features multiple glass doors opening to the outdoors, with a spacious outdoor dining table visible on the patio. A small, separate structure complements the main residence.
Home in West Sussex
4.97 out of 5 average rating, 166 reviews

Luxury Rural Retreat with Hot Tub set in 3 acres

JordanRating, 5 stars2 weeks ago
We enjoyed our stay at Andy & Rosie's thanks to the great location and beautiful surroundings. We used it as a base for Goodwood, which was a short drive away. The local golf club being so close was also a bonus. The accommodation itself was well furnished and spacious and check in was made simple with the clear instructions and Andy's welcoming greeting on arrival.
Top guest favorite
A spacious living area features exposed wooden beams and warm lighting. A large bed adorned with decorative pillows is visible alongside a cozy seating arrangement. A dining table and chairs are positioned near a storage unit, while an inviting rug adds a touch of comfort.
Home in Sandleheath
4.97 out of 5 average rating, 279 reviews

Orchard Barn Spa, exclusively for you, New Forest

AlessandroRating, 5 stars1 day ago
Orchard Barn Spa is a peaceful retreat for those looking to escape the city. We stayed there with our four month old and Chris was very accommodating, providing a baby bath etc. It provides the perfect base to explore all that the new forest has to offer, has ample parking space, is very clean and sits in a private plot. Thanks again Chris for a great stay and for your great communication throughout our trip.
Guest favorite
A charming cottage is set amidst a well-maintained garden, featuring a lush green lawn and various flowering plants. The stone exterior is complemented by wooden accents, and large windows invite natural light. A peaceful environment contributes to the serene atmosphere of the property.
Cottage in Niton
4.79 out of 5 average rating, 102 reviews

Cosy coastal cottage

AlexaRating, 5 stars3 weeks ago
Amy’s cottage was very cosy! Great location with the Buddle inn nearby for a delicious dinner. The cottage was more than big enough for our family of five and we had a hugely restful and enjoyable stay. We’ll be back!
Guest favorite
A charming 1960s British Bedford horsebox is shown parked on a wooden deck. The exterior features deep green and brown wood planks, illuminated by soft outdoor lighting. Surrounding greenery adds to the tranquil setting, with fields visible in the background under a gentle evening sky.
Home in East Meon
4.89 out of 5 average rating, 397 reviews

Betty the Bedford + Outdoor Jacuzzi Bath!

LauraRating, 5 stars3 weeks ago
Beautiful, secluded weekend getaway! Saw lots of wildlife within the fields and the accommodation was lovely. Outside bath was extra special.
Superhost
A bright dining area features a round glass table surrounded by white chairs, and is adorned with a vibrant orchid centerpiece. Large windows open to a private deck with a hot tub and views of lush greenery, enhancing the natural light within the space.
Chalet in Pitt
4.8 out of 5 average rating, 110 reviews

5 Star, 2 Bedroom Scandinavian Lodge with Hot Tub

David MRating, 5 stars2 months ago
So nice to unwind, listen to the birds and decompress. Exactly what was needed with our hectic lives and schedules. Loved the quiet location and that our dogs could walk around the golf course and woods. Only recommendation we would make is a little freshen up and updating in some areas, like sealant around the bath (which was great by the way after a long day!) Having milk when we arrived was well appreciated, if there was a complimentary starter pack of some small jams/butter and scones - I'd give you 5* here! But a great stay nonetheless. Really comfortable.
Top guest favorite
A private annex is set against a backdrop of landscaped gardens, featuring a hot tub and distant trees. The blue swimming pool reflects the clear sky, with sun loungers positioned nearby. Lush greenery surrounds the area, creating a serene outdoor atmosphere.
Guesthouse in Kirdford
4.92 out of 5 average rating, 291 reviews

Private Annex with Hot Tub

ChloeRating, 5 stars2 weeks ago
Me and my partner had a wonderful mid-week retreat at Tracy’s Annex! Welcomed with a bottle of Prosecco, the place was just lovely. We had access to the hot tub and the heated pool which was just amazing! It felt totally private, we were never disturbed but always just a message away if we needed anything- Tracy has some fab recommendations and knows the area so well. The walks around are beautiful and the wildlife we saw was brilliant! There’s so much I could say but my real highlight was Tracy’s 2 golden labs, they’ll come and say hello when out in the garden and they are such love bugs! Totally made my day as a dog lover! Would stay again and would recommend to others. X
Guest favorite
The image features a charming country cottage surrounded by a lush garden. Various trees and flowering shrubs create vibrant greenery. A broad lawn stretches out in front, with well-manicured hedges circling an ornamental bush. Dappled sunlight filters through the leaves creating a serene atmosphere.
Home in Wimborne Saint Giles
4.94 out of 5 average rating, 154 reviews

Charming Country Cottage

CarolineRating, 5 stars2 months ago
Definitely recommend Sam’s beautiful house. Immaculately kept garden with hot tub and huge trampoline which kept the children busy. All rooms with clean and had everything that we needed. Beds very comfortable and bathrooms were clean and showers etc all in good order. Thank you!

Family- and pet-friendly home rentals

Top guest favorite
The exterior of a charming cottage is shown, featuring a rustic facade with white walls and a red tiled roof. A gravel driveway leads to the entrance, and outdoor seating is arranged near the porch. Lush greenery and trees provide a natural backdrop.
Apartment in Pamber Green
4.9 out of 5 average rating, 146 reviews

Self Contained Annex

V MRating, 5 stars1 week ago
Thoroughly enjoyed our stay and will hopefully return. Our hosts were a delight and exceptionally helpful and friendly.. The location is amazing. We were watching red kites in flight and even heard a cuckoo. Lots of walking trails nearby too. Would definitely recommend a visit.
Top guest favorite
The entrance showcases a light blue door framed by two square windows. Hanging planters adorned with flowers embellish the door area. A white bench rests against the wall, flanked by stone planters filled with vibrant flowers, enhancing the cottage's welcoming exterior.
Cottage in Wiltshire
4.98 out of 5 average rating, 103 reviews

Duck Cottage self catering cottage

RobertRating, 5 stars4 months ago
We had a lovely time. Love the location. Perfect for walkers. Inside was light and airy. Bed was very comfortable. The animals were happy and friendly and the area has lots of wildlife. We enjoyed going for walks and visiting Hungerfords Elaine's for lunch. Look forward to visiting again.
Guest favorite
A rustic dining area features a wooden table surrounded by six chairs, with a view of exposed beams and stonework. A wood-burning stove is positioned in the corner, while a decorative vase and wine bottles add detail to the table.
Townhouse in Beaulieu
4.94 out of 5 average rating, 351 reviews

Entire Historic Cottage in Beaulieu/Parking/ Wi-Fi

AnjuRating, 5 stars1 week ago
Matthew's property was perfect for myself and 2 friends. It's lovely and full of character, as well as well stocked with everything we needed (including a hairdryer, fan for the warm nights and some toiletries that we forgot). We enjoyed chatting at the table overlooking the large well maintained and beautiful garden on the sunny evenings. It was easy to find, very central in the New Forest, off the high street in the lovely Beaulieu village. It was exactly what we were looking for. We constantly saw horses on our drive to and from the property which just felt magical. Definitely a place I'd come back to.
Guest favorite
A bright studio apartment features a spacious bed, a comfortable sofa, and a small table with two chairs. A wall-mounted TV is visible, along with a window allowing natural light to fill the room. The entrance door is also present.
Condo in Wootton Bridge
4.87 out of 5 average rating, 160 reviews

Station Location

JaneRating, 5 stars1 week ago
lovely, clean cosy studio that was surprisingly spacious. Lots of little extras that were really appreciated. Good base for exploring the island.
Guest favorite
A stone terrace features a wooden table surrounded by four light green chairs, creating an inviting outdoor dining space. Potted bamboo plants provide privacy, while a charcoal grill is visible in the foreground. Lush greenery and a well-maintained lawn are seen in the background.
Home in Fawley
4.94 out of 5 average rating, 181 reviews

New Forest, Seaview

NevileRating, 5 stars1 week ago
Wonderful house in a terrific, peaceful location. The house and gardens are idyllic, and we loved spending time in the hedged gardens in the evening sun after playing tennis. The house is within easy access of all the best landmarks of the New Forest and also bang on the coast. The interior of the house has great style and charm and is a great place to spend time in.
Guest favorite
The exterior of the Cartbarn is showcased, featuring a wooden structure with a sloped roof, situated under a flowering tree. A vehicle is parked nearby, and a staircase leads to the upper entrance. The surroundings include a gravel driveway and lush greenery.
Guesthouse in Funtington
4.94 out of 5 average rating, 342 reviews

Funtington village B and B - Cartbarn Sleeps 5

SarahRating, 5 stars1 month ago
Anthony was such a welcoming and generous host. The Cartbarn is a delightful - very well designed, immaculate and in the most beautiful and tranquil setting. Having a delicious, cooked-to-order breakfast delivered to the door each morning by Anthony was the icing on the cake!
Top guest favorite
A wooden lodge features natural, rustic siding and a pitched roof. Two windows allow in light, while a central door provides access. Potted plants sit on either side of the entrance, and gravel surrounds the front of the building, enhancing the countryside setting.
Guesthouse in Winterslow
4.99 out of 5 average rating, 285 reviews

Idyllic Detached Lodge nr Salisbury Wiltshire

PaulRating, 5 stars3 days ago
Hayley is a great host if you need any help or information where to get breakfast or the shop just ask . Great place to stay and relax , sunbathe, read .
Guest favorite
The cottage exterior features a blend of brick and wood cladding, with large windows allowing natural light. A small paved terrace is accessible, adorned with green foliage and a few potted plants. The surrounding gravel area provides ample space for outdoor seating.
Cottage in Ibworth
4.94 out of 5 average rating, 175 reviews

Self contained, rural cottage, 2 double bedrooms

HannahRating, 5 stars1 month ago
We stayed at The Twig whilst visiting family in the area and it was absolutely perfect for our needs. The cottage was spacious, clean and the animals were an added bonus especially for our 3 year old daughter. We will definitely be back when next visiting the area, thank you!

Family-friendly home rentals with a pool

Guest favorite
A wooden deck features a neutral-toned table surrounded by matching chairs, providing a seating area with panoramic views of Swanage Bay. The coastline can be seen in the distance, framed by lush greenery and a clear blue sky.
Chalet in Dorset
4.94 out of 5 average rating, 269 reviews

Breathtaking sea views from this light, cosy lodge

ValerieRating, 5 stars2 weeks ago
The views from Seascape are wonderful and added greatly to our holiday. From sunny breakfast on the deck to cosy evenings watching the sun set we found everything we needed and we felt at home straight away. The lodge was immaculate and Judith dealt quickly with the only issue we had when the oven had a fault, so our holiday was not impacted greatly. It's a 15 minute walk into Swanage with an uphill return or free 2 hrs parking next to the Co op if you spend £10 there. Altogether a perfect place to enjoy Swanage and explore the Isle of Purbeck.
Guest favorite
The cottage is surrounded by lush greenery and a well-maintained garden. A gravel path leads to the entrance, framed by neatly trimmed hedges. Large windows reflect natural light, while bicycles are casually positioned nearby, suggesting an inviting outdoor environment.
Cottage in Hampshire
4.94 out of 5 average rating, 196 reviews

Beautiful S.Downs Cottage, pool and tennis

CharlieRating, 5 stars2 months ago
If you are looking for a home from home or an upgrade from home, this is the place to stay. Arrived from Melbourne and immediately settled into the joy of living in the countryside. Although too cold to enjoy the pool, we did use the tennis court and shot some hoops. We walked to Old Thorns Golf and Country Club and can recommend Katie's Coffee bar. It's an easy walk amongst stunning scenery. We walked back via the Foley Estate from the Deers Hut pub. Liphook is so lucky to have not one but two stunningly beautiful golf courses. If their is a heaven on earth, we must have stayed in its guest house!
Superhost
An artistic illustration depicts the outline of a caravan nestled within a stylized representation of the Isle of Wight. The simple design showcases the caravan's shape and windows, suggesting a peaceful and inviting atmosphere amidst the natural landscape of the island.
Camper/RV in Shanklin
4.75 out of 5 average rating, 166 reviews

My Island Caravan - where memories are made ☺

KalinaRating, 5 stars1 month ago
Highly recommended! Superb host. Thank you.
Guest favorite
The converted boathouse is set among lush greenery, with large windows offering views of the water. A spacious patio extends towards the pool area, which is bordered by trees and features multiple seating options. The serene creek can be seen in the background.
Villa in Isle of Wight
4.96 out of 5 average rating, 267 reviews

5* waterside luxury boathouse - pool & log-burner

BlakeRating, 5 stars1 week ago
We loved staying in the boathouse. Ideal for a family with children. Wonderful location looking over the creek . We didn’t hear the ferry which is 5 minutes away. We liked the sound of children playing on the other side of the creek. The pool area was recently upgraded. The property is well equipped and comfortable. Catherine was an excellent host who looked after every detail professionally.
Top guest favorite
An indoor pool features clear blue water surrounded by large glass walls, allowing for ample natural light. The structure is accented by greenery on one wall and includes a comfortable seating area visible in the background, with views extending toward an outdoor tennis court.
Bungalow in Oving
4.96 out of 5 average rating, 163 reviews

The Beach Huts: tranquil home, pool & tennis court

HayleyRating, 5 stars1 week ago
Such a find - we absolutely loved this airbnb! Firstly the design was amazing, looks like beach huts and yet the inside was so spacious and filled with light that it was like a hidden gem. Amazing amenities - pool, tennis court and beautiful walks on the doorstep. The area was so lovely and quiet and I could immediately feel myself relaxing the moment we arrived. The property has everything that you could possibly need, a little home away from home and I loved all the little design touches - you could really tell that so much care had been taken to make the space welcoming. Everything was super clean and Helen was a lovely host, always responsive and friendly! I absolutely loved the digital guidebook which was so useful for our stay, especially finding the best pubs and restaurants in the area. We hope to be back soon!
Superhost
A modern, three-story building is shown with a mix of white and beige façades. Large windows allow natural light, and a central entrance is framed by a small balcony. A manicured garden with palm plants is situated in front, separated by a decorative fence.
Condo in Westbourne
4.94 out of 5 average rating, 18 reviews

The Palms Studio 6

NouriattRating, 5 stars9 months ago
My parents had an amazing one-month stay at Laura’s Airbnb! The apartment was exactly as described. Clean, comfortable, and well-equipped. The location was perfect, close to local shops, restaurants, and public transportation, which made exploring the area so easy. Laura was incredibly welcoming, quick to respond to any questions. I would highly recommend staying here to anyone looking for a pleasant and hassle-free experience! Thank you, Laura
Top guest favorite
A charming wooden guest house is surrounded by lush greenery. Featuring a wooden deck with seating and a private hot tub, the structure has large glass doors that invite natural light. Sun loungers are positioned nearby, creating a serene outdoor space.
Tiny home in Soberton
4.94 out of 5 average rating, 262 reviews

The Guest House, Five Trees

AaronRating, 5 stars1 day ago
Hard to put into words……Tara’s place was amazing, it was a few days away for my girlfriend’s birthday and I had even asked Tara to put up some birthday decorations in time for our arrival which was a nice touch. I can’t fault this place or the host what an amazing experience thank you and we’ll be back again. Check out The White Lion pub great food and drink and only a 10 minute walk away
Guest favorite
An L-shaped deck is visible, featuring a glass-topped table surrounded by four comfortable chairs. The deck offers expansive views of the sea and the surrounding landscape, with clear skies and a coastal town in the background.
Apartment in Swanage
4.8 out of 5 average rating, 184 reviews

Great Views from Our Modern Cosy Caravan

LilyRating, 5 stars1 week ago
We had a wonderful stay at Ann’s caravan, the views were really breathtaking and the caravan had everything we needed for the weekend. Ann sent over very detailed guidance before we arrived and everything was super easy from our arrival to departure.

Quick stats about vacation rentals that are family-friendly in City of Winchester

  • Total rentals

    1K properties

  • Nightly prices starting at

    G$2,092 GYD before taxes and fees

  • Total number of reviews

    34K reviews

  • Pet-friendly rentals

    340 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    520 properties have a dedicated workspace

Destinations to explore