
Guesthouse vacation rentals in City of Winchester
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Top-rated guesthouse rentals in City of Winchester
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Popular amenities for City of Winchester guesthouse rentals
Family-friendly guest house rentals

Manstone Cottage, Yattendon
Very helpful, beautiful location, peaceful, had a wonderful stay, didn’t want for anything. Lovely food in the surrounding pubs. Thank you for a great stay.

Converted Granary, South Downs nr Goodwood
The barn is a gorgeous place to stay - it is very well appointed and comfortable with many thoughtful touches. The breakfast of homemade granola was a real treat. I would recommend this place to anyone who wants to stay in the beautiful area. Natasha was extremely thoughtful and responsive to any requests.

Self contained studio near Marlborough and Avebury
Sheila was a great host! The studio is wonderful for a weekend getaway in the country. The place is quiet and has a beautiful setting, yet the town is really closeby if one fancies a nice outing at a restaurant. Highly recommended!

Funtington village B and B - Cartbarn Sleeps 5
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!

Garden Room
Fabulous location, friendly host and great accommodation

Idyllic Detached Lodge nr Salisbury Wiltshire
The Owl Lodge is amazing, the location is perfect if you are looking for rest and relaxation. Thoroughly enjoyed our stay and would recommend to others.

Idyllic Country Escape in Detached Oak Annexe
We stayed for 4 nights and this place was perfect. Location wise it was right in the middle between the historical cities of Winchester and Salisbury - making it great spot for exploring. The annexe itself was clean, spacious and had everything you would need for your stay! The extra touches of some essential items like milk and bread etc were very helpful for our first night after a long drive!

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
Guest house rentals with a patio

Studio 114- 1 bedroom guest house.
A great bolthole for two people! Sharon’s place is small but perfect for a few nights away. The studio had everything we needed and we loved the extra touches such as bread, milk, tea & coffee and even a birthday banner above the bed! The central location was ideal as everywhere we wanted to visit was a 15 minute drive away (Osborne House, Isle of Wight Donkey Sanctuary, Isle of Wight Steam Train). Carisbrooke castle is also a 10 minute walk. Highly recommend!

Comfortable Cabin
Always very quick to respond to online messages. Parking permit organised for us immediately. Cabin had everything we needed. Bed is slightly tricky to manoeuvre but that is made clear in the listing. Great location. Peaceful and quiet but close to town. Extra touches in kitchen much appreciated (milk, butter etc) Julia thought of everything!

Cabin in the Forest
The Cabin is lovely and cosy, just as shown in the photos. It has a pretty garden, perfect for relaxing after exploring the area. The location is perfect with a nice pub with good food just a couple of minutes walk away and the brewery right next door. Loved our stay here and looking forward to returning!

Self contained studio in Lower Bourne, Farnham
Loved our stay! Perfect location for the wedding we attended. The place is well furnished and has everything you need. The hosts were very responsive and kindly allowed us to move our check out.

The Gardeners
Beautiful, clean and such lovely decor. I always love a host that goes above and beyond and Emma does that and more. Easy check in and lots of lovely extras in the home to make the stay nicer (bread,coffee etc) thanks so much !!

Delightful boathouse overlooking Fishery Creek.
We really enjoyed our stay at the Boathouse - the sofa bed was comfy and set up for us on arrival, hosts were friendly and helpful when renting paddle boards from them and we were provided with a list of local recommended places to eat (fish and chips at the Dolphin nearby were great!)

The Author's Retreat New Forest
Cosy hideaway in a beautiful and incredibly peaceful location, with horses roaming on the adjacent village green, which was a lovely surprise. Very clean and an extremely comfortable bed! Lots of great touches, such as the pots of yoghurt, granola and honey. The garden is small but stunning, and the village couldn't be prettier, with a friendly pub over the road. Great hosts who always answered queries quickly. EV charging was a useful bonus too. Highly recommended!

Garden cottage in the South Downs National Park
Garden cottage was perfect for a quiet getaway, the host was really helpful and communicative and the room itself was fully stocked with everything you could possibly need and really thoughtfully done. Property was a bit difficult to find even though the instructions were great I still managed to drive past twice but thats very much because I’m useless 😂 Only downside was the tv reception was a bit intermittent but we enjoyed the terrace area with a drink and only wanted tv for some background noise in the evening. Would love to return and explore more of the area next time
Guest house rentals with a washer and dryer

Beautiful rural retreat, outskirts of Swanage
We had a wonderful weekend here and can highly recommend it. William and Charlotte were so welcoming to us and our dog! The welcome pack was fabulous, we could not have asked for more and the cottage is very well equipped and spotlessly clean. Walks directly from the property are stunning , we certainly plan another stay here one day soon. Just loved it.

The Old Stable
Janet’s place was great. Really comfortable and had everything you could need. It was very well designed and thought out, perfectly clean and really cosy. I would not hesitate to stay again if in the area and would recommend it to anyone. Thanks for a brilliant stay.

Walk to West Wittering Beach | Pass The Keys
Upon arrival we were greeted by Steve who kindly asked if we had everything we needed and let us know that they were available if we had any questions. The annex was exactly as described and was very clean and tidy. A peaceful stay in a quiet and beautiful setting.

Self-contained studio Wokingham
Perfectly located for our first day at Nirvana Spa - we were then in an easy 6 minutes! Arrived close to 11pm but directions were accurate and the access very well lit. Loved that Faizan & Hannah had kindly left some fresh milk and biscuits so we could have a cuppa on arrival. Also left a few other treats. Had a really good few nights sleep on a comfortable bed although we were woken early one morning by the dog barking but it was only for a minute or so. Clean property, lovely bathroom, good storage and power points( inc USB) - we will definitely book again if we’re in the area. Good value for money.

14th Century Dairy
I had a wonderful stay in this charming place. A place to totally relax and let go in the beautiful countryside. I would highly recommend staying in such a special place.

Lovely annex - a home away from home
This was our first time staying in an Air B+B and we were pleasantly surprised with the standard and quality of the premises. The online photos don't do the premises justice, as it is far nicer in person. The garden was lovely and our children loved feeding the fish in the magnificent pond. Lynne was a super host and we can't wait to return.

Beautiful studio with direct access to New Forest
Sarah and her Partner understand how to deliver a great Airbnb experience. The property is located in the most bucolic country scene, and we were surrounded by nature ( woodpeckers, squirrels and horses etc. The hosts are very generous, providing clean utensils, complimentary food and drinks and they really allow you to feel at home in their space. 10/10

Self contained Coach House with private parking
Beautiful space. Very nicely finished inside and out. The kitchen and bathroom are clear very new. The space is even better than the photos - high ceilings and skylights make it feel very spacious. Loved sleeping with the windows open and hearing the birds. We met Phil briefly and he was very friendly. We would have liked to chat more! Deborah and Phil are both fantastic hosts. Very responsive and very respectful of the space set aside for guests. Really hope to stay again - we had a family gathering nearby and this was such a great place for two of us as a base. Close to Woking town centre with a direct train to London. Thank you Deborah and Phil for a lovely stay!
Quick stats about guesthouse rentals in City of Winchester
Total rentals
150 properties
Nightly prices starting at
G$6,277 GYD before taxes and fees
Total number of reviews
9.9K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
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- New Forest national park
- Bournemouth Beach
- Kimmeridge Bay
- Paultons Park Home of Peppa Pig World
- Oxford University
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- Goodwood Motor Circuit
- Stonehenge
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- RHS Garden Wisley
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- Winchester Cathedral
- The Tank Museum
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