Family-friendly holiday rentals in City of Winchester

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!

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.

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.

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.

Beautiful, secluded weekend getaway! Saw lots of wildlife within the fields and the accommodation was lovely. Outside bath was extra special.

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.

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

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!

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.

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.

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!

lovely, clean cosy studio that was surprisingly spacious. Lots of little extras that were really appreciated. Good base for exploring the island.

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!

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.

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!

Would highly recommend....amazing accommodation, great location and a friendly & welcoming host in Hilary. We'll certainly be back again!

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.

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!

Highly recommended! Superb host. Thank you.

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.

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!

We had a perfect stay at Tara’s place — it was relaxing, comfortable, and we were surrounded by beautiful countryside. We especially loved sitting out on the deck in the sunshine, taking in the views, and listening to the peaceful sounds around us. Tara was a fantastic host — so friendly and welcoming, and she instantly made us feel at home. It was also such a treat to meet her beautiful dog, Sula! We really enjoyed spending time in the hot tub and at the tennis court, and it was even warm enough to have a little swim in the pool. The walk through the fields to the local pub was stunning and made our stay even more special. Thank you for the idillic stay!

We absolutely loved our stay. The caravan was gorgeous, clean, and in a great location to watch the sea and squirrels. We did not want to leave, a perfect cozy home by the sea.

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.