Tiny house vacation rentals in City of Winchester

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Popular amenities for City of Winchester tiny house rentals

Family-friendly tiny house rentals

Guest favorite
Place to stay in Hindhead
4.92 out of 5 average rating, 394 reviews

Tree Space~ a retreat bordering the South Downs

RosieRating, 5 stars1 week ago
Endless moment of magic! Tree Space has such a peaceful energy with the sound of birds and trees swaying a constant in the background. So comfy and cosy, would definitely suggest getting the fire pit although not sure why this is an additional charge. The surrounding area is stunning with endless walks and things to discover.
Guest favorite
Tiny home in Cowes
4.94 out of 5 average rating, 160 reviews

Seaside style cabin in central Cowes

JennyRating, 5 stars2 months ago
Melanie’s cabin was tucked away behind the main shopping strip in Cowes, only a few steps from the Red Jet ferry terminal. We had everything we needed and enjoyed our stay, we were only sorry it was the wrong time of year to enjoy the sun deck.
Top guest favorite
Home in Aldbourne
4.96 out of 5 average rating, 262 reviews

The Barn at Myrtle Cottage

EmmaRating, 5 stars2 weeks ago
Really great value for money; big and spacious enough for four, with 2 comfortable double beds, and Lynn even supplied us with breakfast things! The little courtyard was so lovely to sit outside.
Guest favorite
Guesthouse in Funtington
4.94 out of 5 average rating, 342 reviews

Funtington village B and B - Cartbarn Sleeps 5

SarahRating, 5 stars1 month ago
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!
Top guest favorite
Chalet in Cowes
4.99 out of 5 average rating, 184 reviews

Car Ferry 25% discount book before 7th July

NicolaRating, 5 stars5 days ago
Right before I booked, I sent Fiona a query. She was very responsive and reached out many times before my stay. Fiona offers to pick you up from the Red Jet terminal and you honestly feel like you have met before. I got the earlier ferry than planned and Fiona happily picked me up. Fiona gave me all the information I needed in the drive to the cabin, about buses and the island. If you are coming without the car, the buses are so easy to use and this is from a non bus user at home. The app is easy to use and the journey planner is fantastic. You can get anywhere you need to go from Newport. The cabin itself was spotless with fantastic views of the Solent. The waves can be heard from the beach as you sit on the decking. Fiona and Derek are both very friendly. Fiona provides many extras that I didn't expect. She really has thought of everything. Cheese scones, breakfast items, tea and coffee. It's an easy 20 minute stroll to Cowes along the seafront, 5 minutes to Gurnard.
Top guest favorite
Guesthouse in Kirdford
4.92 out of 5 average rating, 290 reviews

Private Annex with Hot Tub

ChloeRating, 5 stars1 week ago
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
Superhost
Guesthouse in Midhurst
4.87 out of 5 average rating, 195 reviews

Private Lodge in beautiful rural setting

RonanRating, 5 stars3 weeks ago
We were looking for something peaceful and quiet and full of countryside atmosphere and found it here. The Lodge is just beautiful, with everything you would need for a peaceful getaway. Tanya was very friendly and helpful, recommended a few places like The Unicorn pub, which was a delight. The English countryside is second to none
Guest favorite
Barn in Bramshott
4.95 out of 5 average rating, 150 reviews

Self-contained studio hideaway, with home cinema

LeonaRating, 5 stars1 month ago
Myself, my partner and dog had a lovely 2 night stay at the Bothy. The location is very secluded but we managed to find it with no issues when we followed the instructions provided. There was an issue with electricity on arrival but Cathy was very responsive and managed to sort this promptly. She offered really great recommendations of things to do/places to eat whilst we were there. There are some lovely walks nearby which our dog absolutely loved! The huge garden was also perfect for her. Highly recommend and hope to come back again one day.

Tiny house rentals with a patio

Guest favorite
Cabin in Frensham
4.94 out of 5 average rating, 102 reviews

Eco Cabin near Frensham Great Pond

DarrellRating, 5 stars1 month ago
we were lucky to stumble across this gem due to a last minute cancellation. it was exactly what we were hoping for and more. the location, the cabin, the surroundings were magical and the break from reality we so needed. thank you so much Clare for all your help and for allowing us to see your part of the world in such a perfect way. I'm sure we will be back one day xxx
Guest favorite
Guesthouse in Bosham
4.9 out of 5 average rating, 111 reviews

Charming Bosham Garden Lodge | Pass The Keys

SamRating, 5 stars6 days ago
Beautiful garden room, lovely furnishings, garden stunning you will not be disappointed this a 5star accommodation.
Top guest favorite
Shepherd’s hut in Wiltshire
4.96 out of 5 average rating, 161 reviews

Hideaway in quintessential Wiltshire village

FrannyRating, 5 stars2 weeks ago
The most wonderful stay in the most beautiful little hut. From the moment I arrived I felt instantly relaxed. Emily has created the most perfectly peaceful space, inside and out. She is also a wonderful host & was able to help me with my forgotten item. Waking up to the sound of the birds, with the greenery outside the window was my favourite part. Emily’s hut is a delightfully comfortable space and the log burner keeps you very cosy in the evening. The village itself is also delightful to walk around, there is plenty to explore in the area and a great pub on the doorstep. The only downside was checking out.
Top guest favorite
Tiny home in Downsway, Blackbridge Road
4.96 out of 5 average rating, 167 reviews

Tiny home-garden cabin near Freshwater Bay

JulieRating, 5 stars3 days ago
Well laid out tiny home in it’s own garden at the rear of the house. Good location for walking and exploring the coastal path. Great cafe around the corner with a local shop for supplies. Will definitely be back.
Guest favorite
Guesthouse in Bosham
4.95 out of 5 average rating, 156 reviews

Peaceful seaside stay in beautiful Bosham village

AnitaRating, 5 stars3 weeks ago
We had a wonderful stay in Emily's air BnB in Bosham .It was furnished to a very high standard ,spotless and very pretty with fresh flowers .The location was beautiful and quiet yet walking distance to two great pubs and harbour walks .Highly recommended .We will go again .
Top guest favorite
Tiny home in Selsey
4.99 out of 5 average rating, 160 reviews

Holiday chalet in Selsey

RobertaRating, 5 stars1 week ago
Spotlessly clean and in general a lovely little chalet, we felt right at home and really cozy. It was easy to find and access. I will definitely book again.
Top guest favorite
Tiny home in Hampshire
5 out of 5 average rating, 142 reviews

Unique stable conversion, log burner, rural view.

KarenRating, 5 stars1 week ago
We loved every minute of our stay at Foxtrot. Shelagh is such a lovely lady who has a fantastic eye for detail and really looks after her guests. We were expecting a small space and just needed a bed for a couple of nights, but it was so gorgeous that we didn’t want to leave. It was all so beautifully designed and tastefully done with absolutely everything we could possibly need. We woke up to see the sheep and birds through the patio doors and could sit outside or inside to watch them. We then discovered a pair of binoculars and ID guide and a book with bird calls to help us identify everything. Highly recommended in every aspect - not enough characters available to tell you everything - just stay and be delighted! Shelagh has a small pottery studio next door and makes the most beautiful mugs and jugs which are very reasonably priced and are for sale as well as for use in the cottage.
Top guest favorite
Shepherd’s hut in Lymington
4.98 out of 5 average rating, 105 reviews

Hut 1 - Luxury New Forest Shepherd Huts.

NickRating, 5 stars4 days ago
A lovely hut in the New Forest, beside the local pub (which we didn’t actually try). A peaceful location! Really well appointed, luxurious hut, with v comfy bed and a lovely bathroom! What more could you want!

Tiny house rentals with outdoor seating

Top guest favorite
Shepherd’s hut in West Tytherley
4.97 out of 5 average rating, 158 reviews

The Burrow, off-grid Shepherd’s Hut on family farm

EmilyRating, 5 stars1 week ago
We had a really wonderful stay at The Burrow. The hut is beautiful, very well thought out with everything you need, all with its own place. The hut is in a peaceful location, with a calming view and felt very private. The weather was bad for most of our stay, but we felt very cosy in the hut, reading and painting, and enjoyed exploring the local villages. Rob and Jess were excellent hosts, very responsive over messages and arranged everything for us, including the delicious local produce boxes (would highly recommend!) despite our last minute booking. They’d thought through every detail, including providing towels to dry the buggy. We really appreciated their recommendations in the local area, which made our break even more relaxing as we didn’t have to put much thought into where we went. We enjoyed the Silver Plough, Pumphouse Bakes, Salt and Kimbridge Barn. Thank you very much for a very peaceful and relaxing stay.
Guest favorite
Shepherd’s hut in Hampshire
4.95 out of 5 average rating, 443 reviews

Ivy shepherds hut with hot tub

Sophia Pheonix AnaisRating, 5 stars1 month ago
We stayed at Anna and Chris's hut this weekend just gone, for our 6 year anniversary and it was nothing short of amazing. Shops are a minimum drive of 10 minutes. The area is beautiful with a small lake perfect for if you want to do some fishing. The hot tub was so relaxing and everything needed for the extras like BBQ, fire pit and hot tub was provided plus extras at small cost. Check in was quick and easy Anna was lovely the pack provided in the cabin was well detailed and included everything you would need. All around amazing and would definitely stay again well worth the money!!!
Top guest favorite
Guesthouse in Hampshire
4.97 out of 5 average rating, 176 reviews

The Studio; self contained guest house, Lymington

Maria Racquel ChristinaRating, 5 stars5 days ago
Had such a pleasant stay. Everything was as described. Location was also perfect as it is very near the train station and High Street. Will definitely be booking again this summer! 😊
Guest favorite
Cabin in Portchester
4.93 out of 5 average rating, 591 reviews

Salt Cabin - Luxury Romantic Hideaway Retreat by the Sea.

CarolineRating, 5 stars3 days ago
This place is truly one of a kind. The location is absolutely stunning . Even saw the resident fox .
Top guest favorite
Cabin in Chichester
4.89 out of 5 average rating, 200 reviews

Charming, self contained cabin near coast & Downs

MichaelRating, 5 stars5 days ago
Very easy to find, beautiful location, idyllic. Elaine and Tony are great hosts and the cabin was exactly as described. Lovely cabin set in a beautiful garden. They both enlightened us with the area, a very tranquil couple of days in a beautiful area. Lesley and I would thoroughly recommend the cabin
Top guest favorite
Barn in Kirdford
4.99 out of 5 average rating, 174 reviews

Delightful one bedroom Annexe in Rural location

FedericaRating, 5 stars3 weeks ago
Elaine was a great host she left some home made brownies for us and fresh laid eggs of her chicken . The annexe had everything we needed Aldo milk tea and coffee. Thank you Elaine
Top guest favorite
Barn in Isle of Wight
4.96 out of 5 average rating, 198 reviews

Little Wing peaceful barn with garden/parking

ChrisRating, 5 starstoday
Yvonne was a great host - very responsive and considerate. She left milk in the fridge, which was a lovely touch, and a folder of suggestions of things to do on the island which helped us quite a bit. The house was absolutely immaculate and beautifully presented - we felt right at home immediately. Location was very peaceful, the perfect place to come back to after a day of sightseeing. My only slight criticism is that the wifi was inconsistent. I’m not sure if it had a limit? It felt like it kept dropping out and then we had no internet at all, which was a shame. Overall though, absolutely fantastic place and we’d gladly come again.
Guest favorite
Cabin in Southampton
4.98 out of 5 average rating, 350 reviews

New Forest Luxury Couple Retreat Eling Tree Cabin

AlisonRating, 5 stars2 weeks ago
We loved this cabin so much! It's gorgeous and looks just like the photos. It feels very private when you're there which we liked. There's a little car park and then a path behind the other cabin (which we really never saw, they're so private from each other) and then the cabin. Stunning country views and scenery. There was a firepit with an honesty system for fire wood and a gas BBQ, both we used. The shower is a decent size, bring your own shampoo, conditioner and shower gel but they did have some bubble bath for the amazing bath. We made full use of the very local farm shop which also has a really nice cafe. Also walked to the Anchor Inn in Eling, about a 10 minute stroll, pleasant enough pub with really good food. There's a nice little nature reserve in Eling too with boardwalks around the reeds which we explored. The New Forest is on your doorstep but for us relaxation was king and staying near to the cabin was just what we needed.

Quick stats about tiny house rentals in City of Winchester

  • Total rentals

    10 properties

  • Nightly prices starting at

    ﺩ.ﺇ110 before taxes and fees

  • Total number of reviews

    2.3K reviews

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

  • Local attractions

    Marwell Zoo, Southampton Common, and Mayflower Theatre

Destinations to explore