House holiday rentals in Winchester

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Popular amenities for house rentals in Winchester

House 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 stars2 weeks 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
Home in Hampshire
4.91 out of 5 average rating, 252 reviews

NewForest Cottage alongside Limewood Lyndhurst

JohnRating, 5 stars1 week ago
We were looking for somewhere in the New Forest area to celebrate our wedding anniversary with family. This house was perfect for us all, 8 adults and 5 grandchildren. The house is in a beautiful, quiet location which is exactly what we wanted. The house has everything you need and more, fully fitted kitchen with massive island and dinning table. All rooms were spotless as well as the many toilets and bathrooms. We stayed in the master bedroom which is very tastefully decorated. The swimming pool was a big bonus, perfect size and depth for our Grandchildren and very warm. It also had a padlocked gate to keep the little ones out when playing in the garden. Our host Katie was brilliant from start to finish keeping us updated on the stay and very responsive to messages. She provided a welcome food pack of sausages, bacon, bread and essentials which was really appreciated. Katie even took the time to let our grandchildren help her feed her horses. Can’t wait to return!
Guest favourite
Home in Downton
4.9 out of 5 average rating, 153 reviews

Coastal, New Forest 3 Bed Home Facilities Included

EmmaRating, 5 stars1 week ago
We stayed at Sam’s place to celebrate my husbands birthday. From the start Sam was responsive, friendly, answered questions and gave some fab advice. When I made a request she did everything she could to make it happen. The caravan itself is in a lovely peaceful part of the park with easy walking distance to the woods for the dog to have a run and also to the beach where we wandered to the pub and then back for an ice cream. Sam clearly explained how everything worked, where everything was & what she was doing to make things perfect for her guests. Her guide for things to do was really helpful so our days were filled and never dull. I would call this caravan a proper family home, it does everything it’s suppose to so you can just relax and enjoy your holiday. When I had some sad family news, Sam went out of her way to make sure we were ok and that we didn’t need to rush out the caravan on check out, so if you want a proper family home from home that does what it says - visit here! 🩷
Guest favourite
Home in Hampshire
4.9 out of 5 average rating, 158 reviews

Arnewood Rise, a holiday home in New Forest & pool

AmyRating, 5 stars3 weeks ago
We hired this for a few days with family to celebrate my nans 70th birthday. Absolutely beautiful house and gardens and the facilities are amazing. We live locally so knew about the area but loved having a swimming pool, tennis courts and snooker table for all of us to enjoy. The lounge was bigger than we thought and comfortably sat all of us. We also received a helpful guide a few days before our stay which gave us all the information we needed. Overall a really lovely stay, thank you!
Guest favourite
Home in Somerford Keynes
4.85 out of 5 average rating, 125 reviews

Dog friendly stay with hot tub & 4 swimming pools

LauraRating, 5 stars2 weeks ago
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!
Superhost
Home in Somerford Keynes
4.86 out of 5 average rating, 158 reviews

Natures Retreat - HM99 - HOT TUB - Lakeside Spa

DarrenRating, 5 stars2 weeks ago
Thank you for a great stay. Nice relaxing weekend.
Superhost
Home in Oxfordshire
4.87 out of 5 average rating, 226 reviews

Barn conversion, Henley-on-Thames

AndrewRating, 5 stars6 days ago
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.
Superhost
Home in Somerford Keynes
4.89 out of 5 average rating, 142 reviews

43 Clearwater, Lower Mill Estate + Pools + Spa

TracyRating, 5 stars6 days ago
absolutely wonderful place, very spacious, big and catered for all our needs. peaceful & beautiful area, amenities little over priced. kids loved the pool, had fun, lovely location, feel very safe. Thank you

Weekly house rentals

Top guest favourite
Home in Bishop's Waltham
4.95 out of 5 average rating, 20 reviews

Barn Retreat in South Downs (Free EV Charging)

EmmaRating, 5 starstoday
We booked the barn for a weekend getaway with our dogs, so we could enjoy and explore the local area with them. The barn is spotlessly clean, easy to find and so peaceful! We had beautiful weather and enjoyed the open space and secure garden, the dogs loved having the freedom to be in and out as they chose. Charlotte hadn’t just left the usual bathroom toiletries you get with most stays, she had considerately left tea, coffee and sugar, washing liquids, cereals and much more! The smart tv in the living area is ideal, the sofa is super comfy and the dogs slept peacefully in their beds at our feet. All in all, we would 100% recommend this stay to anyone looking to explore the local area, especially if you have dogs too as there’s lots of lovely walks nearby. Thanks Charlotte!
Guest favourite
Home in Hampshire
4.93 out of 5 average rating, 27 reviews

House in the heart of Winchester

AnnetteRating, 5 stars2 weeks ago
Lovely house right in the centre of town yet surprisingly peaceful. We came by train and it was a very easy walk from the station and straight forward to find and get in. Kitchen was very well equipped. Unfortunately the weather wasn't nice enough to use the garden but great to have the outdoor space. Beds very comfortable. Considering coming back again later in the year.
Guest favourite
Home in Hampshire
4.89 out of 5 average rating, 36 reviews

South Downs Comfy Getaway

AbbieRating, 5 stars3 weeks ago
The photos looked good but in person this listing was even better. Lots of space, clean and homely. Very close to a wedding venue (The Barn at Avington) that we attended over the weekend which was super helpful too. Felt very safe, and a lovely location, garden and grounds. Jonathan’s communication was brilliant and we were even able to check in a little earlier which was super helpful too. Thank you for a fuss free, friendly stay. We would definitely consider staying again if we wanted to visit Winchester.
Top guest favourite
Home in Lepe
4.98 out of 5 average rating, 66 reviews

Iconic Beach Front Stay | The Watch House, Lepe

JennyRating, 5 stars1 week ago
Echoing other reviews, this is an absolutely stunning place. I totally fell in love with it - so unique, full of character, beautifully done up, and with everything needed for a stay. Such fun being lulled to sleep by the sounds of the sea. Thanks for a truly fab stay.
Guest favourite
Home in Hampshire
4.97 out of 5 average rating, 33 reviews

Beautiful Views, Cosy Home from Home Dog Friendly

ClareRating, 5 stars2 weeks ago
The cottage is the most stunning location by the river. We stayed for 3 days everything was as described and we would definitely stay again. Paula is a great host and always responded quickly with any queries.
Guest favourite
Home in Hampshire
4.91 out of 5 average rating, 32 reviews

Beautiful townhouse in central Winchester

MaryRating, 5 stars2 weeks ago
We loved our stay at this adorable townhome in Winchester! It’s close to the train station and just a short walk to the town centre (maybe 15 minutes through the centre to the cathedral). Inside, the townhome is spacious, meticulously clean and comfortable, and charmingly decorated. We had everything we needed for a very enjoyable stay. Sarah was very responsive when I needed help with a minor thing, and she made sure we were comfortably settled. Wish we could’ve stayed longer!
Top guest favourite
Home in Hampshire
4.97 out of 5 average rating, 79 reviews

Stable Cottage Beauworth Southdowns Hampshire

AbigailRating, 5 stars3 weeks ago
We have had the most wonderful time, Sarah was a fantastic host and even left home made treats. She gave great restaurant suggestions, every one was delicious and left very clear information on local walks. The accommodation was even better than the photos. Finished to a really high standard with everything you could need. The bed was very comfortable. It’s is so tranquil and relaxing, we absolutely loved the view across the field of sheep. Honestly me and my husband had the best trip we will definitely be back again.
Guest favourite
Home in Hampshire
5 out of 5 average rating, 20 reviews

Stunning Beachhouse with Sea Views | Pass the Keys

JohnRating, 5 stars3 weeks ago
We had a fantastic stay during May half term with the kids - the house is stunning, even better than the photos and the view is spectacular. The house has a very high -end finish to it and had everything you could wish for in terms of amenities. We look forward to visiting again sometime soon

Private house rentals

Top guest favourite
Home in Woodgreen
5 out of 5 average rating, 31 reviews

Cottage in the New Forest

EsmeRating, 5 stars2 weeks ago
We had an amazing time, This house was lovely, just like the description, perfect for a holiday. The host was easy to communicate with and the instructions were very clear. The area is lovely, backing into a horse field with beautiful views. I would recommend this to anyone looking for a nice holiday in the new forest. Thank you for a lovely holiday and great memories.
Guest favourite
Home in Hampshire
4.95 out of 5 average rating, 62 reviews

Lovely 2 bedroom home

NicoleRating, 5 stars2 weeks ago
Great property, in a great location for where my team were working. Emma was very helpful and responded quickly when I sent her messages. Would recommend.
Top guest favourite
Home in Holt
5 out of 5 average rating, 12 reviews

5 The Mews, Holt nr. Bath. EV charger & parking

HannahRating, 5 stars2 days ago
We loved our stay at this Airbnb, would recommend to those looking for a getaway near Bath! Highly recommend!
Guest favourite
Home in Winchester
4.84 out of 5 average rating, 31 reviews

West Cottage

AnnaRating, 5 stars4 months ago
A fabulous stay, cosy yet spacious; hosts were lovely, very accommodating, and welcoming. We will definitely stay again! Bliss!
Top guest favourite
Home in Hampshire
4.95 out of 5 average rating, 74 reviews

Boutique Retreat in Central Winchester

KeithRating, 5 stars1 month ago
Crowder house is really an excellent home! We had a wonderful month there and would have happily stayed for another if we could. Some places just feel right. As soon as we arrived we felt settled. There was plenty of space to work and to relax, and the back garden was lovely during sunny days. It is a few minutes walk to town, and a great selection of pubs, restaurants and shops. The museums, river walks and Hampshire countryside are all easily accessible too. Would thoroughly recommend this home-from-home!
Guest favourite
Home in Winchester
4.97 out of 5 average rating, 36 reviews

Stylish house in Central Winchester

ThomasRating, 5 stars1 week ago
Highly recommended! A very nice holiday home. Winchester city is easily accessible on foot or by bus. Grocery stores and small shops are just a few minutes away. Thank you for letting us stay in your holiday home. We felt very comfortable.
Superhost
Home in Hampshire
4.84 out of 5 average rating, 32 reviews

Stunning City Centre House, 3BR, Parking 2 Cars

LisaRating, 5 stars1 month ago
We really enjoyed our stay! We appreciated the amount of space and privacy it offered us. Everything was nice and clean & well decorated. It's in a great location to explore Winchester without the need for a car if you don't have one. We were aware that it was next to a bar-and that did get a bit noisy at times-something to keep in mind if you are sensitive to that. The master bedroom was most affected by the noise as it borders it the most. It wouldn't deter me from booking again but it is important to note. We hope to stay again on future travels to the area!
Top guest favourite
Home in Stedham
5 out of 5 average rating, 65 reviews

Cosy cottage in stunning village

AmandaRating, 5 stars2 weeks ago
Beautiful spacious, clean and well equipped cottage in a pretty village. The garden is delightful and there is an opportunity to use the outdoor furniture. The indoor space is very comfortable and we enjoyed relaxing there after busy days sightseeing in the area. Would definitely return.

Quick stats about house rentals in Winchester

  • Total rentals

    130 properties

  • Total number of reviews

    6.1K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    130 properties include access to wifi

Destinations to explore

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  4. Hampshire
  5. Winchester
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