
Guesthouse holiday rentals in City of Winchester
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Top-rated Guesthouses in City of Winchester
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
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Popular amenities for City of Winchester guesthouses
Family-Friendly guesthouses

Converted Granary, South Downs nr Goodwood
Beautiful accommodation. An overnight stay with my daughter, spacious enough for the two of us and some beautiful restaurants near by with a lovely walk. The accommodation was as described and Natasha was very helpful. Would love to stay again

Garden Room
The most lovely host, and perfect stay. Forever grateful and would recommend 100x over.

The Chalet at Primrose Hill BH19 3EE
Fantastic little place to stay, central to an amazing area with loads to do. Home was exactly as described and clean and clutter free with essentials provided. Barbara was friendly and provided local recommendations within the guidance. Would stay again.

The Loft - Exceptional views, hot tub & balcony
Absolutely brilliant place. Nicola was a fantastic host. Breakfast was a lovely touch and very appreciated. Would highly recommend to anyone ! And the hot tub was a brilliant facility to have :) Would 100% stay again !!!

The Studio B&B Luxury Garden Room
Extremely happy with everything at this place. Kids loved the toys and enjoyed the garden. They wished they had stayed a little longer. We appreciate that there were options of breakfast included, never got that before in any other place, very kind gesture. Very cosy and spacious. Would highly recommend *****

Caister Cottage Barn
Had a lovely stay at Caister cottage. Hosts were very friendly and welcoming. Our accommodation was exactly as we had hoped. Lovely setting with walks straight from the house into the new forest. Easy to walk to several pubs and into Lyndhurst.

Perfect cycling, walking and star gazing base
Beautiful place at the side of Jenny’s house with a small enclosed garden area, Jenny has a beautiful enclosed larger garden which she let us use as and when we wanted with sheep and horses at the end to see. The house was like being at home, comfortable beds, clean and everything you need for your stay. We stayed with 4 dogs who all enjoyed their holiday. Location is peaceful but you will need to drive to anywhere you want to go. Would definitely stay again

Charming cottage in Shalford, in the Surrey Hills
Amanda and Ben couldn't have been more helpful, and the cottage was a lovely place to stay whilst visiting elderly family. The dogs were the icing on the cake for us!
Guesthouses with a patio

Studio 114- 1 bedroom guest house.
The perfect place to be able to rest for a few hours after my event, before the ferry home. Sharon was very communicative and accommodating, and I can’t thank her enough for giving me a place to stay. The studio is clean, cosy, and private. Just perfect Thank you. ❤️

Peaceful seaside stay in beautiful Bosham village
Emily's place is well equipped, well positioned and nicely decorated. The bedroom is light and airy. We very much appreciated the prosecco and milk left for us in the fridge. It was a shame we only had time to stay one night - it's a great spot!

Castle Hill Cottage
Lovely stay, location was perfect and private, especially with the resident animals we were able to see. Perfect getaway

Comfortable Cabin
I loved being in Julia’s cabin. It is a perfect little peaceful hideaway, yet within easy walking distance of the city amenities. It was indeed a comfortable cabin: compact, but with everything you might need. Sitting outside with breakfast, listening to the birds and the church bells then in the late afternoon sunshine with a drink was most enjoyable.

Self contained studio in Lower Bourne, Farnham
We really enjoyed our stay here. The annex is a lovely little space, very cosy and nicely decorated. Vanessa was helpful and communicated very clearly at all times. Would definitely recommend!

Peaceful one bedroom hideaway with hot tub
How often do we hear "If it looks too good to be true, it isn't true"? Well this is absolutely not the case here, because all we can do is echo all of the previous reviews that are saying what a truly fabulous place Chestnut Barn is. From the moment you pass through the gates you will be entranced by the beautiful surroundings, peace and the spotless accommodation with all the appointments that one could wish for. With the amenities of Midhurst a pleasant half hour's ramble away (why hurry?) and the delights of the West Sussex countryside on the doorstep, you are ideally placed to explore. The charming hosts Linda and Mike create a welcoming and helpful environment that complement the experience perfectly. We really thought we had visited some special Airbnb residences, but Chestnut Barn tops the lot - and more!

Large self-contained detached studio
Susan's place was perfect for me and what I needed. spotlessly clean and a really really lovely outside area to enjoy, especially in the morning sun. Gorgeous village and surrounding area. Will be back!

‘The Den’ Self contained one bedroom annexe.
The Den is a wonderful place to stay, with a wonderful garden and stream, and generous hospitality from Sue and her husband. With good wifi and immaculate decor, it's a perfect place to stay if you're on your way to the Army Flying Museum.
Guest house rentals with a washing machine and dryer

Daily Red Kite Feed & Pool - Countryside Apartment
We stayed for four nights with our two teenage city kids to give them a taste of countryside life!! They loved the spacious apartment, all of the nature, birds, badger, deer and of course the kites, the warm pool, and freedom to explore the extensive grounds! A fabulous Airbnb with very generous and kind hosts.

Beautiful rural retreat, outskirts of Swanage
Just back from a beautiful stay near Swanage. Loved the comfortable and cosy cottage provided by our warm and welcoming hosts Charlotte and Will. Such a peaceful and tranquil location. Stylishly furnished too and equipped with everything you need for your holiday. Some lovely touches as well, including fresh bread, goodies, a chilled bottle of rose and lovely Beauty Pie shower products. The location is just perfect. A 10 minute stroll to the Southwest Coast Path and Durleston Country Park just a 20 minute walk away. An easy 20 minute walk in to Swanage but allow an extra 10 mins for the uphill walk back. We would definitely come back again to enjoy the delights of the beautiful Isle of Purbeck and were better to stay. Thank you for sharing your cottage with us.

Walk to West Wittering Beach | Pass The Keys
A brilliant long weekend in this cosy annexe. Susan was really friendly, giving us space but also being there when we needed a little support. We would definitely recommend!

Modern Garden Room under 5 min walk to beach
We've just had a two night stay at the Garden Room. Location is excellant for the beach and local shops, we were extremely lucky with the weather so added bonus spending some time on the lovely sandy beach. Lovely coastal walks Hengistbury head etc..nearby. The Garden Room was clean and tidy, check in and communication from Suzy and Andrew was also excellent. Would highly recommend.

14th Century Dairy
Thank you so much Beth for having us to stay in your gorgeous Dairy. Your house is truly beautiful and the Dairy was wonderful and private. Great area to explore Surrey, with walkable pubs and a village shop. Kids loved all the local wildlife and didn’t want to leave!

The Old Cart Shed
A stunning home from home. Gorgeous countryside all around and a lovely enclosed private garden. The barn is beautifully decorated, with really personal touches. Breakfast and essentials provided. Comfortable and just a total delight. Anna was helpful, responsive and courteous at all times. Cannot recommend highly enough.

The Lazy Lodge
We had a great stay at Maria and Marks - thank you! The cabin was homely and comfortable and we all enjoyed the hot tub! The location is fantastic and we appreciated the recommendations Maria provided! Visiting Moors Valley and getting the ferry over the Mudeford Spit / Sandbank for the beautiful beaches were our highlights!

Beautiful studio with direct access to New Forest
Lovely peaceful location, studio as described, very good communication. Great recommendation of the local pub
Quick stats about guesthouse rentals in City of Winchester
Total rentals
150 properties
Nightly prices starting at
$46 AUD 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
- Boscombe Beach
- Oxford University
- Southbourne Beach
- Paultons Park Home of Peppa Pig World
- Goodwood Motor Circuit
- Twickenham Stadium
- Stonehenge
- Winchester Cathedral
- Hampton Court Palace
- Port Meadow
- West Wittering Beach
- Arundel Castle
- Chessington World of Adventures Resort
- Highclere Castle
- Goodwood Racecourse
- Tapnell Farm Park
- RHS Garden Wisley
- The Tank Museum
- Marwell Zoo
- Thorpe Park Resort
- Worthing Pier
- Things to do City of Winchester
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