
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
If you’re looking for a quiet, peaceful, calm and relaxing stay, look no further.

Superb cottage edge of new forest near paultons
The house was absolutely lovely, very clean and comfortable, everything you needed. Hot tub was a bonus. I will definitely be going back when I’m back in the area working. Gaby and Joel responded very quickly and even brought us a fan in short notice as the weather was getting hot. 5 stars

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!

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.

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

A beautiful country cottage, near to the beach
Stayed here with my partner for a long weekend getaway and had an excellent time. The cottage was spotless, well maintained and beautiful. We also spoke with Phil who was extremely welcoming and friendly, and gave us many good recommendations for the area. Overall we had an amazing time and would love to stay again!

Farthings - genuine Austen charm cottage & garden
This beautiful old cottage was an absolute treat to stay in for the weekend. Louise has thought of every detail, so we felt at home and had all we needed for our stay. Chawton is a gorgeous village and we did several of the activities that are local to it (Jane Austen's House, Chawton House, the Watercress Line steam train). The Greyfriars pub is a few doors down and we had a super evening meal in there (it was a busy Saturday night, so it was lucky that we'd booked in advance). Louise was very communicative and helpful and she very kindly allowed us to stay a little later on our day of departure. We loved our stay, thank you!

Luxury Cottage near Stonehenge & Salisbury
Very relaxing, welcoming and comfortable accommodation in a beautiful setting. The pub over the road was a huge bonus. Would highly recommend.

Self contained, rural cottage, 2 double bedrooms
We stayed at The Twig whilst visiting family in the area and it was absolutely perfect for our needs. The cottage was spacious, clean and the animals were an added bonus especially for our 3 year old daughter. We will definitely be back when next visiting the area, thank you!

Modern Cottage with Rural Views - Remote Location
Such a lovely home, we didn't want to leave! Hosts were excellent communicators and also very warm and kind people. Loved our walks along the canal and peaceful surroundings. We will be back!

Luxury Spa-Like Retreat on Millstream near Sea
Beautiful location and the host added very thoughtful amenities like a choice of bubble baths to choose from, a massager machine, fans in every bedroom which was very much needed during this heatwave. The choice of teas and coffees were amazing too.

Beautiful Cottage in New Forest, Romantic Getaway
My wife and I had a lovely weekend away at this property. It's perfect for a couples getaway and had plenty a lovely walks nearby for the dogs. I'd highly recommend a stay here and we will be looking forward to returning.

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

Beautiful barn conversion by lovely bluebell woods
We had a lovely stay and Sumaiya & Richard were great hosts. Lovely little touches for the Christmas period & lovely treats for us when we arrived. The barn was really comfortable & cosy, with everything we needed for a relaxing break. It was very rainy when we were there but with all the books & games we had plenty to do. Thank you!

The Stone Barn - Luxury Barn in Rural Wiltshire
We had a wonderful time at the Stone Barn! Nicky and Mark provided a beautiful home away from home that couldn’t have been better. It’s so peaceful and the views are amazing. The place was clean (beware if you’re not a fan of spiders though as there are a decent amount in corners, bathroom, etc due to the countryside location I’m sure) and they even gave us a lovely welcome package with local food items. They were responsive and made sure we had everything we need. Highly recommend to anyone looking for a place to call home in the Cotswolds area. We were within 1-1.5 hrs drive of all the major sightseeing places which was perfect.

The Nestle House City Centre Luxury
Julia is an amazing host, extremely friendly in her messages and so helpful - she went above and beyond in enabling us to have the best stay. She was flexible on check-in and check-out, her instructions were clear and helpful and she was quick to respond. She had gone out of her way to ensure the cottage was one of the best equipped places in which we have stayed and it was spotlessly clean. Great to have a parking space in Winchester, so close to the house. Thank you so much, Julia and for the extras like toiletries, tea, coffee, milk and prosecco - all much appreciated! We wish you well for the future.

The Cottage at Lupton House, Froxfield Petersfield
Had an amazing stay in Anna’s cottage - the rooms and bathrooms are all very nice and the living room was a great space for our group to hang out. The surrounding area has great hikes and lovely countryside pubs m. Although this cottage is on Anna’s own property, there is still lots of privacy and this was never an issue. Anna is also very welcoming, friendly and thoughtful, ensuring we had a great time during our stay. Would definitely come back here! :)

Lower Mews - Beautiful setting near Salisbury
Our stay was great. Jade and Mark helped us resolve any issues we had and were very friendly. The place itself is well equipped and in a lovely countryside area with beautiful walks all around. It was also a good base for trips to Salisbury and surrounding areas, easy to access and far from any road noise etc.

Edge of South Downs Nat Park, private Annexe
We enjoyed our stay so much the first time, we returned a 2nd time and stayed a bit longer. The Annexe is really spacious and clean.. Sarah has thought of everything, from toys for children of varying ages to books and games for adults. Clean, crisp white linen and comfy beds and pillows. Lovely fluffy white towels and premium toiletries. We had a lovely welcome supply of food items upon arrival too! The weather was very warm during our stay and Sarah had put up a paddling pool and slide for our children which was so thoughtful. The location is very peaceful and the extensive gardens are great for the children to play in or to just have an evening stroll. We can’t wait to return. Thank you again Sarah & Neil!

2 Bedroom Luxury Cottage (Secure & Quiet)
We stayed at Rachel’s lovely cottage for two nights over Ascot race weekend, and it was an absolute delight. From the beautiful decor to the spotless cleanliness, every detail was perfect. We were especially touched by the thoughtful breakfast items left for us — such a personal and generous gesture that we’ve rarely experienced elsewhere. The beds were incredibly comfortable, with high-quality mattresses, pillows, and duvets that made for a great night’s sleep. I thoroughly enjoyed our stay and wouldn’t hesitate to return if we’re ever in the area again. Highly recommended!

The Coachman's Cottage
This was our second stay in this charming cottage which really says it all. It is perfectly located for us to visit friends and family. The property offers safe off-street parking which is great when you have a rented car. Sandra is welcoming, friendly and unobtrusive. We just relaxed and thoroughly enjoyed our week here.
Quick stats about cottage rentals in City of Winchester
Total rentals
100 properties
Nightly prices starting at
$30 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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