House holiday rentals in Winchester

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Popular amenities for Winchester house rentals

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, 253 reviews

NewForest Cottage alongside Limewood Lyndhurst

JohnRating, 5 stars2 weeks 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! 🩷
Superhost
Home in Somerford Keynes
4.81 out of 5 average rating, 142 reviews

Pennyroyal Lodge - HM31 - Lakeside Spa Property

Ashik MohammedRating, 5 stars2 weeks ago
Calm place and well maintained, we enjoyed the stay.
Superhost
Home in Oxfordshire
4.87 out of 5 average rating, 227 reviews

Barn conversion, Henley-on-Thames

MinchanRating, 5 stars4 days ago
We had a lovely time at Sarah's place. It's as the photos suggest and is in a very peaceful surrounding. The barn is next to Sarah's family home, but the way it is oriented means you get plenty of privacy. Thank you for letting us in to your home. We all had a lovely quality time with friends.
Superhost
Home in Bosham
4.91 out of 5 average rating, 240 reviews

Luxury Cedar House - Private Garden, Pool & Spa

TomRating, 5 stars1 month ago
Cedar House is simply stunning. Beautiful gardens and surroundings, very comfortable and spacious property with everything you need. The pool and spa are a delight and I couldn't recommend highly enough. Kelly as a host is great as well, good at responding and clear with information, nothing was too much trouble. Overall, a brilliant place, would definitely recommend.
Guest favourite
Home in Westbourne
4.97 out of 5 average rating, 76 reviews

Incredible sea views and heated outdoor pool

IanRating, 5 stars1 week ago
The house is exactly as advertised. Spotlessly clean. The rooms are spacious. The whole house is very well maintained. The location is superb. Absolutely nothing to complain about. I would thoroughly recommend it. Our hosts were very easy to contact and made sure we knew everything and had everything.
Guest favourite
Home in West Sussex
4.98 out of 5 average rating, 99 reviews

Spacious house and garden in Itchenor

TraceyRating, 5 stars3 days ago
An amazing long weekend and what a treat having the pool, particularly when the weather was so warm. Electric pool cover was very easy to operate. House so spacious and was perfect for 2 families of 4. Kitchen so well equipped. Garden was immense. And of course tennis court also such a treat. Maggie so responsive and so friendly, helped lots with advice around the local area. Highly recommend the walk to the Crown and Anchor in Chichester harbour….stunning views and a great lunch! A fab weekend for my husbands birthday….thank you Maggie!

Weekly house rentals

Top Guest favourite
Home in Hampshire
4.99 out of 5 average rating, 78 reviews

The Old Stables, Derrydown Farm

AmandaRating, 5 stars1 week ago
Such a lovely place to stay in beautiful peaceful surroundings. Very clean, comfortable and well equipped. Khalid was a helpful responsive host and when there was an issue with the water it was resolved very promptly. Had a delicious meal at the local pub, The George Inn and St Mary Bourne is an attractive village. Would definitely recommend a stay here.
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 stars4 days ago
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, 28 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.
Top Guest favourite
Home in Hampshire
4.95 out of 5 average rating, 74 reviews

Boutique Retreat in Central Winchester

KeithRating, 5 stars2 months 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!
Guest favourite
Home in Hampshire
4.97 out of 5 average rating, 33 reviews

Beautiful Views, Cosy Home from Home Dog Friendly

ClareRating, 5 stars3 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.
Top Guest favourite
Home in Hampshire
4.98 out of 5 average rating, 80 reviews

Stable Cottage Beauworth Southdowns Hampshire

EmilyRating, 5 stars3 days ago
We spent a wonderful week at Sarah's place with our small baby. She made sure we had everything we needed plus lots of toys and books too. She gave us great reccomendations of places to visit and was so helpful with any questions. We felt like it was our home for the week. The views and local area is beautiful (we were very lucky to have such great weather). Thank you for a fantastic stay...Sarah is the perfect host!

Private house rentals

Top Guest favourite
Home in Woodgreen
5 out of 5 average rating, 32 reviews

Cottage in the New Forest

EsmeRating, 5 stars3 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.
Superhost
Home in Hambledon
4.83 out of 5 average rating, 66 reviews

Vaulted Barn: Private Garden & Cozy Fireside Charm

KarlRating, 5 stars4 weeks ago
Great place to stay, beautiful little garden and walks to the nearby vineyard. We went with some of their local recommendations too, which was brilliant. Hambledon vineyard is well worth the short stroll for drinks or food.
Guest favourite
Home in Longparish
4.88 out of 5 average rating, 17 reviews

Stunning contemporary oak-framed village barn

NinaRating, 5 stars2 weeks ago
A lovely, comfortable stay in attractive surroundings. We were made to feel very welcome and our little dogs loved the beautiful walks right on the doorstep. The barn had everything we could possibly need to make our stay perfect. There is a nice pub very close by and we had a good lunch there one of the days. We enjoyed our stay so will definitely return very soon.
Top Guest favourite
Home in Weston Corbett
5 out of 5 average rating, 8 reviews

Peaceful Cottage, Hampshire

CliveRating, 5 stars6 months ago
As Super Hosts and owners of premium holiday accommodation in California and East Africa we know what great looks like and the effort that goes into hosting true 5 Star holiday rentals. Amanda and her cottage tick all the boxes. If you want a luxury rural retreat with all the trimmings of a 5 Star hotel, from linens to furniture to stunning artwork and gorgeous views, you’ve found it!
Top Guest favourite
Home in Broughton
5 out of 5 average rating, 18 reviews

Ashfield Barn - 2 Bedroom House in Broughton

LeslieRating, 5 stars2 weeks ago
Wow! Felt as good as home. Was an excellent place for exploring the area, which is fantastic. The two Greyhound pubs are great for food and drink. The local one accessed along a part of the Clarendon Way, a really nice walk. Such a comfortable place to be. Thank you 🤩
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 stars2 weeks 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 Romsey
5 out of 5 average rating, 21 reviews

Coombe Cottage

HannahRating, 5 stars2 weeks ago
We had a lovely weekend. The house is stunning and so spacious. Plenty of communal areas in the house. Plenty of parking, and private. Everything was clean and well equipped. We hope we can stay again some time
Guest favourite
Home in Shedfield
4.85 out of 5 average rating, 13 reviews

Coachmans Lodge

ChristianeRating, 5 stars1 month ago
Came here with friends over the bank holiday weekend and had a great time! Spacious and clean living area with two beds and two bathrooms, with lots of natural light and ample parking space (including an electric charging station). Really liked the modern furnishings and appliances (e.g. TV, sound system, induction stove) and the quiet, peaceful surroundings. Two things to point out - 1. Dishwasher wasn't working during our stay, which we only found out after cooking dinner. Thankfully Chelsea was responsive and provided some sponges the morning after even though it was a Sunday. 2. It would help to have some blinds / shades in the bedrooms, especially during summer when the sun rises early. Thank you Chelsea for the great stay and hope to visit again!

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

  • Wi-Fi availability

    130 properties include access to Wi-Fi

Destinations to explore

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  2. United Kingdom
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  5. Winchester
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