
Tiny house holiday rentals in City of Winchester
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Top-rated tiny house rentals in City of Winchester
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Popular amenities for City of Winchester tiny house rentals
Family-friendly tiny house rentals

Tree Space~ a retreat bordering the South Downs
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.

Seaside style cabin in central Cowes
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.

Shepherd's Hut with large hot tub near Stonehenge
An absolutely dreamy escape for two! complete with scenic views, and enough special touches to feel at home. Fiona made everything so comfortable and we look forward to coming back!

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!

Car Ferry 25% discount book before 7th July
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.

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

Private Lodge in beautiful rural setting
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

Self-contained studio hideaway, with home cinema
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

Eco Cabin near Frensham Great Pond
Frensham is a beautiful, idyllic mix of lovely countryside and village life. The accommodation put us in a perfect spot for amazing walks, river dip on the way back from the lovely HollyBush pub, and early morning lake swim (along side my dog). What an absolute treat. Saw greenfinches and nesting wrens while relaxing in the pretty garden. Thank you. We love where you live.

Charming Bosham Garden Lodge | Pass The Keys
Beautiful garden room, lovely furnishings, garden stunning you will not be disappointed this a 5star accommodation.

Hideaway in quintessential Wiltshire village
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.

Tiny home-garden cabin near Freshwater Bay
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.

Peaceful seaside stay in beautiful Bosham village
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 .

Holiday chalet in Selsey
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.

Unique stable conversion, log burner, rural view.
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.

Hut 1 - Luxury New Forest Shepherd Huts.
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

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

Ivy shepherds hut with hot tub
It was nice a cost inside the Ivey shepherd huts host was helpful and there was some lovely biscuits left on the side a pint of milk and bottle of wine in the fridge the surrounding was nice and quite and u was left alone

Self contained getaway near coast & South Downs
The cabin is a perfect base for a short stay near Chichester. The garden is beautiful & we appreciated the option of sitting directly outside the cabin or elsewhere in the garden, depending on if we wanted sun or shade. With a bus stop at the end of the lane it makes it easy to get into Chichester without taking the car. We also made use of the pub a stones throw away for a nice meal, though we preferred the Berkeley Arms at Bosham. Elaine & Tony are very welcoming hosts, giving useful tips on the area. We would definitely recommend!

Private Lodge close to beaches and Goodwood
Angela was a great host. Clear instructions. Very helpful and communicative. The cabin was just what we needed. Somewhere local to Goodwood, well priced and somewhere to sleep. Would definitely stay again. Thankyou

The Piggery, Henley Hill
This was our second stay at The Piggery and it was just as lovely as I remember. Our two dogs loved it too! Highly recommend the walk to the pub through the woods and also The Georgian in Haslemere is lovely for a meal (and dog friendly). I am sure we will be back, thank you for having us!

Granary Grain Store with Oak Beams
Thank you, we had a lovely stay in the Granary which is very cosy and is well kitted out with everything you need to be self catering. I booked a few days away for my husband's birthday and it proved an ideal spot to cycle around on the quieter roads with plenty of pubs on route! We would highly recommend it Thank you, Alana and Roger

300m from South Downs Way Houghton, Stunning Views
The cabin is wonderful. It was comfortable, cosy, clean and exactly as described on the App. The outside area was perfect with excellent views, great garden furniture and a lovely place to relax into the evening. Added touches, like the curtains being closed and the fan being on when we arrived to keep the cabin cool, were really nice as it was an extremely hot couple of days/nights. The chicken eggs left and then topped up in the fridge were delicious. Anna’s communication was spot on from start to end of the booking process and our stay. We would thoroughly recommend this place. You will not be disappointed. It’s a real gem.

Remote Off-Grid Cabin. Views Over South Downs
We had a wonderful stay at Tom’s cabin. The setting couldn’t be more beautiful and we thoroughly enjoyed using the fire-pit accompanied by champagne looking the view of the South Downs. The cabin was spotlessly clean and had all the amenities we needed for a very comfortable stay. We appreciated Tom providing a trolley to carry all of our stuff to the cabin. Wish we could have stayed longer!
Quick stats about tiny house rentals in City of Winchester
Total rentals
10 properties
Nightly prices starting at
$50 NZD before taxes and fees
Total number of reviews
2.3K reviews
Wi-Fi availability
10 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
Local attractions
Marwell Zoo, Southampton Common and Mayflower Theatre
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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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- Stonehenge
- Windsor Castle
- Hampton Court Palace
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- RHS Garden Wisley
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- Worthing Pier
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