Family-friendly holiday rentals in Winchester

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Winchester family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in West Sussex
4.97 out of 5 average rating, 165 reviews

Luxury Rural Retreat with Hot Tub set in 3 acres

JordanRating, 5 stars1 week 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.
Guest favourite
Shepherd’s hut in Salisbury
4.95 out of 5 average rating, 855 reviews

Shepherd's Hut with large hot tub near Stonehenge

HelenRating, 5 stars1 week ago
we had a superb getaway, ideal for timeout and a recharge. everything was as described and the mattress was so comfortable. is now on our favourites lists to return back to.
Top Guest favourite
Home in Sandleheath
4.97 out of 5 average rating, 278 reviews

Orchard Barn Spa, exclusively for you, New Forest

GRating, 5 stars2 weeks ago
The property was perfect, the pictures are lovely and they reflect the quality. The property once there is outstanding and very peaceful. It’s one of those hidden Gem AirBnBs, we loved the stay and will hopefully return.
Guest favourite
Home in East Meon
4.89 out of 5 average rating, 396 reviews

Betty the Bedford + Outdoor Jacuzzi Bath!

JessRating, 5 stars2 weeks ago
Could not have asked for a better staycation! Betty had everything we needed and more. Whilst we had the most amazing time in Betty, we also had a fantastic time on the curated ‘kissing gate walk’ which allowed us to explore the beautiful countryside around Betty!
Superhost
Home in Owslebury
4.79 out of 5 average rating, 200 reviews

Boxwood, Owslebury, Winchester

KateRating, 5 stars3 weeks ago
We spent a lovely long weekend in the house catching up with friends. The kids enjoyed the hot tub, and the room with twin beds was perfect for our 7 year olds. There is a patch of grass to play on, but by where you park the cars, not next to the house. Wasn’t a problem for us as we went out during the day, but in case that’s a necessity for you.
Top Guest favourite
Guesthouse in Kirdford
4.92 out of 5 average rating, 290 reviews

Private Annex with Hot Tub

ChloeRating, 5 stars1 week 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
Top Guest favourite
Apartment in Shanklin
4.96 out of 5 average rating, 146 reviews

Little Gem in Old Village - Up to 25% off ferry!

MichelleRating, 5 stars3 weeks ago
What a lovely place and lovely hosts. The bed was so comfortable we slept more than usual, unless it was the lovely relaxing hot tub that tired us. The welcome food and treats and wine was very generous and very welcome. It was a very quiet and relaxing area. We stayed for 6 nights and would highly recommended
Top Guest favourite
Cottage in Baughurst
4.96 out of 5 average rating, 369 reviews

Luxury rural thatched cottage with cedar hot tub.

ZoeRating, 5 stars2 weeks ago
Wow - Beautiful and tranquil place to stay with absolutely stunning gardens. Perfect place to stay to purely relax with the enjoyment of a private hot tub to use throughout , firepit and loungers in the gardens to use. Our dog loved this place and had so much to explore , the house supplies dog treats / and a dog bed , all the little touches were all noticed to make our stay as comfortable as possible! Keith / Jean were very communicative, and helpful during check in. The beds were very comfortable, each room pristine and decorated to a high standard , even provide slip on shoes and gowns to access the hot tub which was really handy! the continental breakfast supplied was lovely . We would love to come back and stay again , would recommend to anyone it is pure bliss, inside and outside , thank you!

Family- and pet-friendly home rentals

Top Guest favourite
Apartment in Pamber Green
4.92 out of 5 average rating, 144 reviews

Self Contained Annex

V MRating, 5 stars1 day 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 favourite
Cottage in Fittleworth
4.98 out of 5 average rating, 601 reviews

Stylish Hideaway with an amazing woodland view

HeatherRating, 5 stars1 day ago
A lovely short stay in this forest hideaway with a simply outstanding view. Didn’t realise in advance that it was on two levels with all the facilities of home in terms of kitchen and bathroom. Upstairs - en suite bedroom with balcony - is warm and sunny. Downstairs - living + dining room and kitchen - stays cool. If you like your birds, you will particularly enjoy watching the plethora of species that come from the forest to the feeder - courtesy of the hosts who provide a generous tin of bird seed.
Top Guest favourite
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 favourite
Cottage in England
4.88 out of 5 average rating, 132 reviews

The Forge

NedahRating, 5 stars5 days ago
We had a wonderful stay at The Forge. This was our first time staying in an Airbnb and we really enjoyed the experience. The cottage was very clean with good sized rooms and the kitchen had everything we needed for meal times. Particularly great for our young children with the books and toys available and a lovely outdoor space with a seesaw. Maxine answered all our questions and was a great host.
Guest favourite
Townhouse in Beaulieu
4.95 out of 5 average rating, 349 reviews

Entire Historic Cottage in Beaulieu/Parking/ Wi-Fi

RogerRating, 5 stars1 week ago
Matthew’s place is the upper end of 5*. Pristine presentation, crisp linen, blankets and pillows. This is a boutique home. Matthew’s communication was regular, and with the right information at the right time. This is what you need to know now, and then next and next. Anyone who has not been to the New Forest, it is an eye opener. Absolutely stunning. Bieulieu is stunning with great walks and the New Forest is cycling Mecca!
Guest favourite
Condo in Wootton Bridge
4.87 out of 5 average rating, 159 reviews

Station Location

JaneRating, 5 starstoday
lovely, clean cosy studio that was surprisingly spacious. Lots of little extras that were really appreciated. Good base for exploring the island.
Guest favourite
Home in Fawley
4.94 out of 5 average rating, 180 reviews

New Forest, Seaview

MeghanRating, 5 stars1 month ago
This was our second stay. Everything was as nice as we remembered from our first visit. The flat is spacious and well-appointed, the location is private and quiet, and the hosts are friendly and responsive. What more could you ask for in an AirBnB?
Guest favourite
Barn in Funtington
4.9 out of 5 average rating, 320 reviews

Funtington Village B and B - Annexe sleeps 4+

Lyn & DavidRating, 5 stars1 week ago
Anthony was an excellent host who made us very welcome and provided us with a delicious breakfast! The spacious Annexe was clean comfortable and well equipped. The peaceful location was ideal surrounded by lovely countryside yet close to Chichester and the Witterings. We enjoyed our stay in Funtington.

Family-friendly home rentals with a pool

Guest favourite
Home in Christian Malford
4.97 out of 5 average rating, 184 reviews

Superb Farmhouse with pool, hot tub and fast wifi

CatherineRating, 5 stars1 week ago
Ann's place is incredible- stayed for two nights and there is everything you could possibly need or anticipate in the house. We had a great time - the pool and hot tub were very clean and the house was perfect! Ann was extremely responsive and helpful. Would absolutely book again!
Guest favourite
Chalet in Dorset
4.94 out of 5 average rating, 268 reviews

Breathtaking sea views from this light, cosy lodge

JaneRating, 5 stars2 weeks ago
Our second visit to this super property. Spotlessly clean throughout with everything you could need for your time away. The weather was great whilst we were staying so we were able to make good use of the decking overlooking Swanage Bay. Judith was very quick to respond when we had a question and she also recommended plenty of places for us to visit. Milk tea coffee and Dorset biscuits were left for us when we arrived which was a welcome treat when we arrived. Many thanks Judith and we will look forward to returning again next year.
Guest favourite
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!
Guest favourite
Villa in Isle of Wight
4.95 out of 5 average rating, 266 reviews

5* waterside luxury boathouse - pool & log-burner

BlakeRating, 5 stars3 days 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.
Superhost
Home in Oxfordshire
4.87 out of 5 average rating, 226 reviews

Barn conversion, Henley-on-Thames

AndrewRating, 5 starstoday
A beautiful barn conversion in lovely grounds with lots of facilities, with thoughtful and helpful hosts. It was a fabulous long weekend and we didn’t need to leave the grounds to be entertained throughout, from in the pool to playing pool, it was all we could ask for.
Top Guest favourite
Bungalow in Oving
4.96 out of 5 average rating, 161 reviews

The Beach Huts: tranquil home, pool & tennis court

JessicaRating, 5 stars6 days ago
We stayed at the Beach Huts for our mini-moon and it was absolutely wonderful. The apartment had everything we could need, and felt very private. The pool and tennis court are shared, but were always free when we used them. The location is quiet enough to be peaceful, but you still get all the deliveroo options from Chichester! We also enjoyed a walk across fields to Tangmere, where there was a useful coop and an interersting aviation museum. The kitchen was well-stocked, and we would highly recommend it to families and we hope to return in a few years time to enjoy it with others.
Top Guest favourite
Guesthouse in Rudgwick
4.94 out of 5 average rating, 234 reviews

Bucks Green Place Beautiful Converted Barn

GloeRating, 5 stars3 weeks ago
A home from home - ideal for either a short or long stay. Exceptionally well equipped, with everything you might need. Very clean and comfortable, in a delightful and secure and private setting. Rebecca was very welcoming and on hand if we needed anything. The best Airbnb we've stayed in and would definitely return when we are next in the West Sussex area.
Top Guest favourite
Farm stay in Guildford
4.97 out of 5 average rating, 135 reviews

The Luxury Cottage

AlfredRating, 5 stars2 weeks ago
Quiet, relaxing and in a great location .

Quick stats about holiday rentals that are family-friendly in Winchester

  • Total rentals

    140 properties

  • Nightly prices starting at

    $77 AUD before taxes and fees

  • Total number of reviews

    6.6K reviews

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    140 properties include access to Wi-Fi

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