
Family-friendly holiday rentals in Winchester
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Top-rated family-friendly rentals in Winchester
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Popular amenities for Winchester family-friendly rentals
Family-friendly home rentals with a hot tub

Superb Farmhouse with pool, hot tub and fast wifi
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!

Shepherd's Hut with large hot tub near Stonehenge
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!

Cosy coastal cottage
We had a lovely stay at Greenbank. The house was spacious, tidy and clean, and we appreciated the extras provided by the host (towels, toiletries, tea and coffee). The property is just a short walk away from a playground , shop, pharmacy and local places to explore, which we enjoyed investigating. Our 4-year-old loved reading the children's books from around the house and the garden was a lovely spot to play in. We paid to have the hot tub, which we found easy to use and great fun. Thank you to Amy for a lovely stay.

Betty the Bedford + Outdoor Jacuzzi Bath!
Beautiful, secluded weekend getaway! Saw lots of wildlife within the fields and the accommodation was lovely. Outside bath was extra special.

5 Star, 2 Bedroom Scandinavian Lodge with Hot Tub
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.

Boxwood, Owslebury, Winchester
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.

Private Annex with Hot Tub
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

Little Gem in Old Village - Up to 25% off ferry!
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
Family- and pet-friendly home rentals

Self Contained Annex
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.

Thatched cottage, Wherwell, Test Valley Hampshire
We had a wonderful relaxing time, lovely local walks and some great pubs nearby.

The Forge
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.

Honeysuckle Cottage - East Meon
Honeysuckle Cottage is on the main road through East Meon but once inside it is quiet. All the furnishing and equipment are good quality and although the cottage is small, there is plenty of storage and it has everyone needed for a relaxing weekend. As others have said the second bedroom is very small but our son and his girlfriend slept comfortably and had enough space for their clothes. The garden is secure, so perfect for our dog. It’s also a sun trap so we were able to enjoy relaxing outside even though it wasn’t particularly hot weather. There are many excellent walks on the doorstep with stunning views. We were able to eat at The George on a couple of evenings and didn’t use our cars all weekend, which was just perfect. We did not park our cars on the main road but there’re plenty of places to park in the village, including the car park.

New Forest, Seaview
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.

Pagham Beach House, sea views,
We absolutely loved Joanna's place and had a great weekend. It was extremely comfortable and in the perfect position to enjoy the beach and everything around us. Our dogs were also very happy and the garden was safe and secure for them with a bit of grass. The house is well laid out. The bedroom was comfortable and the linen first class. Joanna was helpful and welcoming and available at all times. Highly recommended!

Stunning listed stable conversion, Wiltshire
The home is beautiful, exactly as pictured, in excellent condition and perfectly clean. The location is picturesque and quite private. Hermione is an excellent host and was extremely helpful during our stay, providing recommendations for food, things to see and do as well as support for any issues we had. We would absolutely stay here again, it was an exemplary experience!

Funtington Village B and B - Annexe sleeps 4+
A great stay .Perfect location. The annex was perfect everything you would need for a holiday break. Nice and clean , comfy bed. Super shower and fluffy towels. Plenty of condiments ,tea,coffee ,sugar etc. Anthony left us some little extras in the fridge. Wonderful cooked breakfast from Anthony. Felt spoilt. The garden is beautiful and my little dog loved it. I would recommend the fox and hounds pub great food and only a 5 min stroll. Thank you Anthony for a lovely stay and warm welcome We will be back. Christine ,Paul and Bonnie
Family-friendly home rentals with a pool

Breathtaking sea views from this light, cosy lodge
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.

Dog friendly stay with hot tub & 4 swimming pools
We spent 6 days at Rob’s place with our 3 children. The weather was not our friend but the onsite swimming pool meant we still had a fabulous time. The hot tub was a great addition to the property. The cottage had plenty of room for us all & the spa facilities were fantastic. Great location as well, we had a lovely morning wandering around Cirencester. Rob was super helpful. We used 2 of the recommended places to eat & both were fantastic options. Lovely stay!

Beautiful S.Downs Cottage, pool and tennis
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!

Pennyroyal Lodge - HM31 - Lakeside Spa Property
Calm place and well maintained, we enjoyed the stay.

5* waterside luxury boathouse - pool & log-burner
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.

Barn conversion, Henley-on-Thames
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.

The Beach Huts: tranquil home, pool & tennis court
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!

Bucks Green Place Beautiful Converted Barn
Great place exactly as described! Rebecca is very responsive and made me feel very welcome.
Quick stats about holiday rentals that are family-friendly in Winchester
Total rentals
140 properties
Nightly prices starting at
₹4,327 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
Wifi availability
140 properties include access to wifi
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- New Forest national park
- Bournemouth Beach
- Kimmeridge Bay
- Paultons Park Home of Peppa Pig World
- Oxford University
- Boscombe Beach
- Goodwood Motor Circuit
- Stonehenge
- Windsor Castle
- Hampton Court Palace
- Southbourne Beach
- Lower Mill Estate
- Chessington World of Adventures Resort
- West Wittering Beach
- Thorpe Park Resort
- Arundel Castle
- Highclere Castle
- RHS Garden Wisley
- Goodwood Racecourse
- Winchester Cathedral
- The Tank Museum
- Marwell Zoo
- Worthing Pier
- Highcliffe Beach