Guesthouse holiday rentals in City of Winchester

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Popular amenities for City of Winchester guesthouses

Family-Friendly guesthouses

Guest favourite
Guesthouse in Petersfield
4.97 out of 5 average rating, 250 reviews

Converted Granary, South Downs nr Goodwood

RuthRating, 5 stars1 week ago
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
Guest favourite
Guesthouse in Alderbury
4.91 out of 5 average rating, 256 reviews

Garden Room

AmberRating, 5 stars1 month ago
The most lovely host, and perfect stay. Forever grateful and would recommend 100x over.
Superhost
Guesthouse in Langton Matravers, Swanage
4.67 out of 5 average rating, 167 reviews

The Chalet at Primrose Hill BH19 3EE

Sean And ClaireRating, 5 stars3 weeks ago
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.
Guest favourite
Guesthouse in Chippenham
4.97 out of 5 average rating, 440 reviews

The Loft - Exceptional views, hot tub & balcony

LucasRating, 5 stars2 months ago
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 !!!
Guest favourite
Guesthouse in Christchurch
4.88 out of 5 average rating, 377 reviews

The Studio B&B Luxury Garden Room

FlorinaRating, 5 stars1 day ago
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 *****
Top Guest favourite
Guesthouse in Hampshire
4.99 out of 5 average rating, 413 reviews

Caister Cottage Barn

ArletteRating, 5 stars3 weeks ago
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.
Top Guest favourite
Guesthouse in Isle of Wight
4.98 out of 5 average rating, 273 reviews

Perfect cycling, walking and star gazing base

CarlaRating, 5 stars2 weeks ago
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
Top Guest favourite
Guesthouse in Shalford
4.91 out of 5 average rating, 139 reviews

Charming cottage in Shalford, in the Surrey Hills

LouiseRating, 5 stars1 week ago
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

Guest favourite
Guesthouse in Isle of Wight
4.92 out of 5 average rating, 166 reviews

Studio 114- 1 bedroom guest house.

AnnaRating, 5 stars1 day ago
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. ❤️
Guest favourite
Guesthouse in Bosham
4.95 out of 5 average rating, 152 reviews

Peaceful seaside stay in beautiful Bosham village

LaviniaRating, 5 stars2 days ago
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!
Guest favourite
Guesthouse in Burley
4.9 out of 5 average rating, 228 reviews

Castle Hill Cottage

SamRating, 5 stars1 day ago
Lovely stay, location was perfect and private, especially with the resident animals we were able to see. Perfect getaway
Top Guest favourite
Guesthouse in West Sussex
4.98 out of 5 average rating, 155 reviews

Comfortable Cabin

RuthRating, 5 stars1 week ago
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.
Top Guest favourite
Guesthouse in Lower Bourne
4.95 out of 5 average rating, 219 reviews

Self contained studio in Lower Bourne, Farnham

RichardRating, 5 stars3 days ago
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!
Top Guest favourite
Guesthouse in Midhurst
5 out of 5 average rating, 224 reviews

Peaceful one bedroom hideaway with hot tub

KeithRating, 5 stars1 week ago
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!
Top Guest favourite
Guesthouse in Cliddesden
4.91 out of 5 average rating, 141 reviews

Large self-contained detached studio

SarahRating, 5 stars1 week ago
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!
Guest favourite
Guesthouse in Middle Wallop
4.94 out of 5 average rating, 211 reviews

‘The Den’ Self contained one bedroom annexe.

RalphRating, 5 stars1 month ago
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

Top Guest favourite
Guesthouse in Hawkley
4.97 out of 5 average rating, 202 reviews

Daily Red Kite Feed & Pool - Countryside Apartment

KateRating, 5 stars3 weeks ago
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.
Top Guest favourite
Guesthouse in Dorset
5 out of 5 average rating, 108 reviews

Beautiful rural retreat, outskirts of Swanage

MichaelRating, 5 stars2 days ago
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.
Guest favourite
Guesthouse in West Wittering
4.86 out of 5 average rating, 195 reviews

Walk to West Wittering Beach | Pass The Keys

JulietRating, 5 stars2 weeks ago
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!
Top Guest favourite
Guesthouse in East Southbourne
4.95 out of 5 average rating, 205 reviews

Modern Garden Room under 5 min walk to beach

MarkRating, 5 stars3 days ago
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.
Guest favourite
Guesthouse in Surrey
4.94 out of 5 average rating, 232 reviews

14th Century Dairy

AnnabelRating, 5 stars1 day ago
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!
Top Guest favourite
Guesthouse in Hampshire
4.95 out of 5 average rating, 147 reviews

The Old Cart Shed

KatherineRating, 5 stars1 month ago
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.
Guest favourite
Guesthouse in Dorset
4.88 out of 5 average rating, 321 reviews

The Lazy Lodge

ClaireRating, 5 stars3 weeks ago
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!
Guest favourite
Guesthouse in Hampshire
4.94 out of 5 average rating, 317 reviews

Beautiful studio with direct access to New Forest

RaynorRating, 5 stars4 days ago
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

Destinations to explore