House vacation rentals in City of Winchester

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Popular amenities for City of Winchester house rentals

House rentals with a pool

Guest favorite
The image captures the serene outdoor pool, reflecting the surrounding greenery and part of the cottage. Attractive seating arrangements can be seen in the background, framed by lush hedges, creating an inviting area for relaxation.
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 favorite
An outdoor swimming pool is surrounded by sun loungers and vibrant flower beds filled with red and purple blooms. Clear blue skies provide a bright backdrop to the serene scene, enhancing the sense of relaxation and leisure by the poolside.
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
A scenic view is presented from the expansive decking area, featuring a rainbow arching over the tranquil Solent and Bay. The landscape includes soft, grassy fields that stretch toward the water, framed by gentle hills in the distance.
Home in Isle of Wight
5 out of 5 average rating, 5 reviews

Starfish Lodge Discounted ferry sailings available

Ms Gemma RoseRating, 5 stars3 weeks ago
We had the most wonderful stay at this lodge on the beautiful Isle of Wight. Tucked away in a peaceful caravan park just a stone’s throw from the sea, it offered the perfect mix of relaxation and seaside charm. The location couldn’t be better—waking up to the beautiful sea view and being able to stroll down to the beach in just minutes was absolute bliss. The on site pool and playground were the perfect end to a day exploring for our kids, all the staff here were friendly, helpful and couldn’t do enough to help. The accommodation itself was spotless, stylish, and incredibly comfortable. Everything we needed was there, from towels, a well-equipped kitchen to cozy beds and a lovely lounge area with the most stunning uninterrupted sea views . It felt more like a boutique coastal retreat than a lodge! Can’t recommend this place highly enough—whether you’re after a romantic escape, a quiet solo retreat, or a family break by the sea, this gem has it all. Thank you Rob :)
Top guest favorite
A modern caravan is set on a grassy area, featuring a spacious front deck with white railing. Two black chairs are positioned on the deck, providing an outdoor seating option. Large windows allow natural light into the interior space.
Home in Hillway
5 out of 5 average rating, 31 reviews

Rosie’s Isle of Wight Caravan - Whitecliff Bay

NARating, 5 stars5 days ago
Our time in Rosie’s caravan was truly enjoyable. The space was spotless and well-organized, making it feel immediately welcoming. The shower had excellent pressure and consistently hot water, which was a real treat. We had no issues with the TV reception, and everything worked smoothly. The king-size bed was incredibly comfortable, complemented by soft, supportive pillows. The kitchen was impressively well-equipped—everything we needed was right at our fingertips. Rosie herself was a fantastic host—warm, quick to respond, and full of helpful local tips that really enhanced our trip. We will come back again!
Superhost
A spacious indoor pool area is featured with large windows that provide abundant natural light and views of the surrounding gardens. Comfortable lounge seating is visible along one side, complementing the serene atmosphere of the heated pool.
Home in Bosham
4.91 out of 5 average rating, 240 reviews

Luxury Cedar House - Private Garden, Pool & Spa

TomRating, 5 stars4 weeks 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.
Top guest favorite
Home in Hampshire
4.98 out of 5 average rating, 86 reviews

Eden Cottage, your home away

JoannaRating, 5 starstoday
My husband & I and our husky spent 3 night’s at Eden Cottage and really enjoyed our stay! Kevin & Debbie were super helpful before and during our stay, with clear info on getting there, facilities available, and local recommendations, and were really lovely people to chat with. Their 3 Labradors were adorable! The cottage was very comfortable and clean, with all we needed for a relaxing stay, a comfy bed, great shower and well equipped kitchen, with some welcome treats! It’s set in a lovely large garden, which we and our dog enjoyed spending time in. The pool was a fab bonus; clean, warm and with towels provided. Kevin’s book ‘Reckless’ is well worth a read! The cottage is a 3-min walk to the Spread Eagle pub, which does a fantastic Sunday roast, and 10 mins walk into Liss is Turtle Bean cafe, serving tasty lunches; both places are dog friendly, and there’s a lovely IPC church 5 mins walk away. All in all, a great weekend and we will definitely visit again! Thank you, Kevin & Debbie!
Guest favorite
The exterior of a static home is presented, situated on stilts with a spacious white deck adorned with lights. The structure features a light blue exterior, and steps lead up to the entrance, while neighboring homes can be seen partially in the background.
Home in Hillway
4.91 out of 5 average rating, 11 reviews

Beautiful and spacious 4-6 berth luxury caravan

OlgaRating, 5 stars3 weeks ago
We enjoyed our stay at this house a lot. It is very well stocked with things you might need, which are usually unavailable in caravans, eg, an iron, a vacuum cleaner, lots of books, puzzles, DVDs, and games for kids and parents. Our kids were entertained with the games and books for quite some time. The house is spotless and cozy. It is within walking distance to the center of the caravan park, at the same time, the house is on a quiet road with a beautiful sunset view. Crystal was very helpful and friendly. She sent clear instructions and helped us get a good deal for the ferry ride. When we had a change of plans, Crystal was very supportive; she replied quickly, even late in the evening, and made the whole stay perfect. Thank you very much, Crystal! I would highly recommend staying at this house, particularly working with Crystal. It was a pleasure!
Guest favorite
A spacious outdoor area is seen featuring a heated private pool, surrounded by modern landscaping. A large umbrella provides shade over comfortable seating, while lush greenery and a distant sea view enhance the tranquil atmosphere.
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.

Weekly house rentals

Top guest favorite
The exterior of the barn showcases a blend of black wooden paneling and traditional stonework. Large glass doors invite natural light, and the surrounding greenery adds to the serene atmosphere. A gated entrance leads to a spacious parking area.
Home in Bishop's Waltham
4.95 out of 5 average rating, 20 reviews

Barn Retreat in South Downs (Free EV Charging)

EmmaRating, 5 stars1 day 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 favorite
A modern kitchen is featured with light grey cabinets and a stylish backsplash. A central island with seating for four is adorned with a bowl of fresh fruit. Natural light enters through a window, illuminating the workspace and appliances.
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 favorite
A spacious living area is presented with two comfortable sofas, adorned with decorative cushions. A wooden coffee table sits in the center, complemented by a flat-screen television mounted on the wall. Natural light filters in through small windows, highlighting the soft carpeted flooring.
Home in Hampshire
4.89 out of 5 average rating, 37 reviews

South Downs Comfy Getaway

adamRating, 5 stars4 days ago
Great Airbnb for the price. It is a well decorated house located near the owners house. It had a nice lawn with kids swings and toys available to use. plenty of space for a family of 5 (could of slept 2 couples and 2 kids. Easy drive into Winchester town centre or to the science centre
Superhost
A dining table is set with a light-colored plate and a glass of water. Fresh pastries and strawberries are arranged on a round dish. A vase of flowers adds color beside a French press. Bright light filters through the window with blinds.
Home in Shirley
4.87 out of 5 average rating, 76 reviews

Lovely, comfortable 5** home for HOSPITAL & CITY

EstefaniaRating, 5 stars1 week ago
The stay was as described, and the check-in process was smooth as the communication with the host was straightforward. Overall, it was a functional and practical place to stay. Everything was what we needed for the specific purpose. I will book again this place in the future if needed! :)
Guest favorite
The stable conversion presents a charming exterior surrounded by lush greenery. A wooden picnic table sits in the foreground amidst wildflowers, offering a serene spot for outdoor meals. The building features a welcoming entrance, complemented by decorative plants and a rustic wooden fence.
Home in Chichester
4.93 out of 5 average rating, 144 reviews

Delightful 1 Bed Lodge In South Downs Village

JulieRating, 5 stars2 weeks ago
Had a lovely stay at the Lodge. It was very clean and comfortable. Commuication from the owner was excellent. It is in a very peaceful location and has 2 pubs within walking distance. It is also within a short driving distance of so many varied places to visit or walk. We went to Bosham, Wealdon Downland museum, Fishbourne Roman palace, and the nature reserve at Kingley Vale and will be back again to do more. Would definitely recommend. Thank you
Guest favorite
A charming red-brick house is set against a bright blue sky, overlooking the serene River Itchen. Lush greenery and colorful garden plants surround the property, enhancing its tranquil riverside location. The gentle flow of the river complements the peaceful atmosphere.
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.
Guest favorite
A spacious living area features a large brown leather sofa, complemented by a circular coffee table. The room is bathed in natural light from expansive glass doors, leading to a private outdoor space with views of the garden. Wooden paneling adds warmth to the interior.
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
Top guest favorite
A well-lit bedroom features a spacious bed covered with white linens, accentuated by dark towels. A dresser and mirror are positioned to one side, with a kettle and coffee machine on top. A small rug adds comfort to the wooden floor, while a large window is draped with black curtains.
Home in Southampton
4.94 out of 5 average rating, 34 reviews

En-suite bed; private access

DanielRating, 5 stars3 weeks ago
Fantastic place to stay. Even though we didn't see Naomi we had regular contact with her and she was very helpful and responsive even when I lost the check in details. Great location,brilliant local bars. We can highly recommend this as a great place to stay. A1.

Private house rentals

Guest favorite
A spacious living area features a beige sofa with decorative pillows and a glass coffee table. Natural light fills the room, highlighting the plants and inviting decor. A dining area is visible in the background, complemented by large windows that provide views of the outdoor space.
Home in Curdridge
4.91 out of 5 average rating, 47 reviews

Annex@Capers End

ValerieRating, 5 stars2 weeks ago
We only stayed at The Annex for two nights while attending a nearby friend's birthday party so we didn't explore local places/restaurants but it was ideal for our requirements. It is quite a concealed entrance to the property so we missed it first time round but, once inside, we were warmly greeted by Sara and very impressed with our lovely accommodation. We immediately felt at home and both had excellent nights' sleep in our separate double bedrooms with Duck Down Duvets and Pillows. Bliss!! We would definitely recommend The Annex at Capers Lane and hope to return again one day.
Top guest favorite
A vibrant wildflower meadow bursts with colors, featuring a variety of blossoms in yellow, purple, and red. In the background, a charming cottage with large windows and a covered terrace is visible, complemented by lush greenery and a clear blue sky.
Home in Exton
5 out of 5 average rating, 24 reviews

Allens Cottage, Exton.

CourteneyRating, 5 stars1 week ago
We had a picture perfect stay at Guy’s gorgeous home in Exton. The home features beautiful bedrooms and bathrooms, two separate living spaces, an ideal kitchen and the backyard is stunning with loads of space, a trampoline that backs up to horses and blooming wild flowers. It is one of our favorite Airbnb properties to date.
Top guest favorite
A charming brick cottage combines traditional architecture with modern features. The facade is adorned with flowering plants and a trellis. Two distinct entrances, framed by greenery, enhance the inviting appearance. Rooftop skylights and a clean slate roof complement the well-maintained structure.
Home in Hampshire
4.94 out of 5 average rating, 34 reviews

No 3

TimRating, 5 stars4 weeks ago
Lovely village location, quiet with access to a good pub and walking from the front door. Perfect location for exploring the countryside. House clean, well-equipped and spacious enough for 6 people. Good social space particularly. Lovely views out back. Loved the welcome cake and wine - very thoughtful. Would recommend!
Top guest favorite
The Watch House is viewed from a garden path lined with blooming flowers, leading down to the beach. The white exterior of the cottage is highlighted against a clear blue sky, while the tide is low, revealing a sandy shore.
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 favorite
A detached house is set in a well-landscaped front yard, with manicured shrubs framing the entrance. The brick facade is complemented by a classic arched doorway and a large bay window. Bright sunlight highlights the home's inviting exterior features.
Home in Southampton
4.9 out of 5 average rating, 49 reviews

Douglas House

LauraRating, 5 stars1 day ago
Stayed with 2 small children, husband and my mum. Great house, travel cot and highchair were missing, but we took our own anyway. Kitchen was well equipped, plenty of crockery and cutlery (plus tea/coffee/sugar). 5* cleanliness and we would know crawling around the floor with 2 small children. Bathroom and kitchen were spotless. Garden was lovely, sat outside both evenings, it does need some tlc though. Fab host brought us a fan while we were staying due to the heatwave. Much appreciated. Lovely area. Quiet, and quick walk to local shops, takeaways and pub. Would 100% stay again.
Guest favorite
A spacious living area is showcased, featuring a large screen displaying the Netflix logo. Comfortable seating is arranged with two armchairs and a sofa, complemented by a coffee table. A decorative plant and wall clock enhance the room's atmosphere, with natural light illuminating the space.
Home in Hampshire
4.95 out of 5 average rating, 79 reviews

4 Bed City House with Private Garden and Parking

AlexRating, 5 stars5 days ago
We stayed at this property for two nights before a cruise from Southampton. The location in the centre of Winchester is amazing! Everything is very close by and accessible. The property suited our needs perfectly having a well stocked kitchen, a large dining area, a comfortable living room. The parking space is excellent, even for a large car - safe and off road plus there is use of a garage too. There are two bathrooms - one en-suite - which are modern and spotlessly clean. The beds are COMFY! Three large King beds with superb mattress toppers. There is also a single bedroom. The hosts are absolutely brilliant! Really communicative and they went extra mile to ensure we were happy and comfortable. We will definitely be staying in this property again - highly recommended!
Guest favorite
A framed artwork displaying the number '122' in bold black typography contrasts against a textured brick wall. To the right, vertical white radiator fins add a sleek, modern element to the space.
Home in Hampshire
4.91 out of 5 average rating, 32 reviews

Beautiful townhouse in central Winchester

MaryRating, 5 stars3 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!
Guest favorite
A Scandinavian-style property features a striking peaked roof and expansive glass windows, allowing ample natural light. The landscaped surroundings include well-kept trees and shrubs, while a gravel driveway leads to the main entrance, providing a serene and inviting approach.
Home in Shedfield
4.85 out of 5 average rating, 13 reviews

Coachmans Lodge

ChristianeRating, 5 stars4 weeks 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 City of Winchester

  • Total rentals

    870 properties

  • Total number of reviews

    28K reviews

  • Family-friendly rentals

    410 properties are a good fit for families

  • Pet-friendly rentals

    200 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    380 properties have a dedicated workspace

Destinations to explore

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  2. United Kingdom
  3. England
  4. Hampshire
  5. City of Winchester
  6. House rentals