
Cottage vacation rentals in City of Winchester
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Top-rated cottage rentals in City of Winchester
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Popular amenities for City of Winchester cottage rentals
Cottage rentals with a hot tub

Cosy little country cottage with luxury hot tub
had such a lovely stay at the little cottage. great spot to just relax and be in a secluded little sun trap away from any hustle and bustle. hot tub was perfection, garden is just perfect to sit and read our books and have some drinks, kitchen was easy to use and got the job done for cooking, shower was nice and hot and good pressure (sounds silly but i think the shower is always worth a mention!) bed was so comfy, best we’ve slept in weeks! really appreciate the sky box being included, great value for money here. big thanks to Lorraine!

80 acre Wood, Dutchtub, Lake, Treehouse & Zip-line
What a wonderful and truly beautiful home. Was a pleasure to stay in this serene countryside hotspot with a tree house, playground, incredible private lake and surrounding natural beauty. Very special. Can’t recommend enough!

The Old Piggery, East Boldre, New Forest
This was our second stay at The Old Piggery, and again we absolutely loved it. It’s such a beautiful location. Grant is really helpful.

Superb cottage edge of new forest near paultons
This was a really lovely house and we thoroughly enjoyed our stay. The kitchen area - the size, brightness, appliances and crockery etc - was the highlight. It was particularly well stocked with some generous goodies left for us. The garden was also lovely - great to eat outside at the large wooden table, as well as enjoying the last of the day’s sun in the corner seating area. The table tennis table was very well used by the 4 of us and great fun. Thanks for a great stay

Luxury New Forest Cottage, with hot tub & log fire
Wonderful little cottage, where get to see horses and donkeys everyday. We loved staying here and are already looking to book again in the autumn. Joyce & David are lovely and we’re happy to show us around the farm and tell us all about the animal, thank you so much.

Wisteria Lodge, a self-contained unit with spa
This was our second time staying and we loved it as much as the first time. The place is so peaceful and cosy. Jane was very responsive and helpful. Looking forward to booking another stay in the future!

Cottage in beautiful Hampshire village
We just had a wonderful long weekend in Wherwell in Rob & Sue’s beautiful cottage. Such a stunning village, the cottage exceeded our expectations, Rob & Sue were fantastic hosts & the breakfast pack was great. We finished the weekend with a lovely soak in the hot tub. Thank you Rob for the lift on the Saturday & your kindness.

Detached and romantic cottage with hot tub.
Had a wonderful two days at The Bothy. Such a beautiful spot and the cottage I think looks even better in real life - and it looks pretty wonderful in the photos! We felt right at home straight away- Chrissy had left some welcome staples which was appreciated and there is everything you need for a truly lovely stay. We made use of the hot tub which was fab and it’s in a very peaceful but convenient location to explore the New Forest. Come - we hope to go back soon.
Pet-friendly cottage rentals

Converted barn perfect for families and couples
What a fantastic host! Stayed here prior to getting married at new barn farm and every last detail was just perfect. The property was spacious, clean and beautifully presented. The host did so much to make us feel welcome and added lots of little touches which made the experience so memorable. I have never stayed anywhere that has been this attentive before and would absolutely return in a heart beat. Thank you so much for all you did for us on such a special occasion, we will never forget it.

Thatched cottage, Wherwell, Test Valley Hampshire
We had a wonderful relaxing time, lovely local walks and some great pubs nearby.

Manor Farm Cottage
Truely stunning stay. Such a beautiful home and location. Would recommend for a family stay as little ones loved the toys, charm and ample space.

Quintessential South Downs Cottage
Caroline was a very kind and accommodating host; we felt right at home in her beautiful slice of the South Downs. The house is small but cosy and well-equipped with everything you might need. The garden is a particular attraction for families in the summer months - look out for the tortoise!

Gardeners cottage-pet friendly,New forest bolthole
We loved our relaxing few nights away at the cosy cottage & would highly recommend it to anyone. Paul was friendly & helpful when approached/messaged. The cottage is so pretty & ideal for a short stay. We loved the fact you can walk straight from the front door into the beautiful countryside, which we did 2 / 3 times a day with our dog. We only used our van a couple of times to go to Lyndhurst & Bartley, otherwise we just enjoyed the cottage & the local surroundings. The dog shower outside was fab to clean off mucky paws. The garden was great too - large, lots of seating & ideal for our dog - very friendly gardener, too! The pub right next door was handy, we ate & drunk there a couple of times. Follow Paul's instructions to get to the cottage & don't follow sat nav when you're near, otherwise it sends you across the fast A31.

The Barn - Delightful Wiltshire Holiday Home
Absolutely stunning and peaceful . We booked with family for my 40th and we had such a lovely time. Its an amazing Airbnb really clean and very well catered. beautiful surroundings

Dapple Cottage - Brook Farmhouse
A wonderful little cottage in a great location. My husband and I took two friends away as a retirement gift and the layout couldn’t have been better. Having the two bedrooms with en-suites either end of the property worked brilliantly as it gave us ample of space and privacy. Mike our host was there to great us and was extremely friendly and helpful. I would definitely recommend this to our friends, family and anyone who wants to explore the beautiful Isle of Wight.

The Old Stables
Gorgeous place to come and stay and fully relax..The property was a fantastic find, extremely peaceful and beautiful views, we enjoyed looking at the horses and having a wander around grounds. The property was close to the town centre, where we went to the escape rooms great fun. we will definitely be back again..Ruth was a brilliant host thank you x
Private cottage rentals

Little Lantern
A lovely self-contained annexe attached to Deb and her husbands cottage, with private access and parking off road. Really clear instructions provided by Deb prior to arrival. Very friendly when we met and came out to greet us and say goodbye. Otherwise left to our own devices but was welcomed to just knock on her door if we needed anything. Very comfortable including the bed zzzz

The Stone Barn - Luxury Barn in Rural Wiltshire
My wife and I stayed here for a portion of an overall longer trip. This was by far our favorite stay. A beautiful place just as described, with easy access to the surrounding community. We will be back if we get the chance.

The Old School House, Ascot, Berkshire
Sean & Caroline were the perfect hosts and the cottage is perfect. It’s larger enough to spread out, cosy enough to feel relaxed and super quiet to rest. I’m so glad I booked it and would love to return.

Cosy cottage in nature reserve with heated pool.
Stayed for 4 nights at The Bothy- it’s a lovely home, very comfortable beds, plenty of towels, including beach towels, nice bedding and had basics like oil, vinegar, tea and coffee. The pool was a real bonus as we had good weather and used it every day- it’s lovely and warm. The area is quiet and very peaceful, lovely walks and costal views. You can walk to The Haven, great food- fish finger sandwich is epic, and into Lymington along the sea wall or down country lanes in the daytime, takes 20 minutes or so. A car is fairly essential here due to the quiet location. Sarah was an excellent host and was always on hand for any queries. I can highly recommend this place and we hope to stay again.

The Cot, Characterful 400-year-old Cottage.
The Cot is an absolute gem — cosy, charming, and beautifully put together. We especially loved reading through the welcome pack and learning about the cottage’s history, which added such a personal touch to our stay. The decor is tasteful and inviting, but what truly stood out for us were the little luxuries — the high-quality linen and wonderfully comfortable pillows made all the difference. Thank you again, Joanna, for creating such a lovely space! – Rhianna & Jamie

Beautifully renovated cottage - Prince's Forge
We enjoyed our stay very much. Kitchen and living are very comfortable and the beds offered a refreshing sleep. It may take a while for the shower to be warm, but the bathroom was clean and complete. Great place to stay. Great atmosphere and a beautiful area to walk. Vanessa was very hospitable and helpful when needed.

Lower Mews - Beautiful setting near Salisbury
This was the most perfect Airbnb we have ever stayed in. The location is beautiful and extremely peaceful. The house was absolutely spotless and so many little details had been thought about and provided, where they are so often missed in many other places. Could not have been more perfect And we hope to come back another day soon.

Idyllic cottage in the New Forest
We had a lovely stay at Ana’s house. It had everything we needed to stay in and relax, and some great pubs nearby to eat out too. It was more spacious than the pictures suggest, with a great living area which looked out over a grassy field, trees and river. We managed some very British wildlife sightings too from the comfort of the living room with visits from red kites, deer and a young hare! Ana went above and beyond as a host welcoming us on arrival with a fresh loaf of home baked sourdough bread. It was a perfect stay!
Quick stats about cottage rentals in City of Winchester
Total rentals
100 properties
Nightly prices starting at
G$6,277 GYD before taxes and fees
Total number of reviews
5.5K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
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- New Forest national park
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