
Cottage holiday 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
A beautiful cottage, small but perfectly formed! Private, everything you need, great hot-tub, cosy, tastefully decorated, lovely area!

Blashford Manor Farm - The New Forest Cottage
Martin’s cottages are beautiful converted stables on a lovely farm. Everything is very high quality and we had a great weekend.

80 acre Wood, Dutchtub, Lake, Treehouse & Zip-line
Amazing property for the family - so calm and beautiful. Kids loved the zip line and we felt right at home

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.

Luxury New Forest Cottage, with hot tub & log fire
Fantastic stay at a beautiful location in the New Forest. The hosts were really welcoming and couldn’t have been more helpful with local recommendations, the property is lovely, and all the animals were a big bonus for the kids. Highly recommended and we’d love to return.

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 with Covered Hot Tub Godshill New Forest
We had a lovely few days, lots of room in the house, hot tub and games room a bonus, along with the deer in the garden yesterday morning! Many thanks for the welcome pack and milk.

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.
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.

The Forge
We had a wonderful stay at The Forge. This was our first time staying in an Airbnb and we really enjoyed the experience. The cottage was very clean with good sized rooms and the kitchen had everything we needed for meal times. Particularly great for our young children with the books and toys available and a lovely outdoor space with a seesaw. Maxine answered all our questions and was a great host.

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
A gorgeous little spot to enjoy the peace and calm and incredible countryside views. Very cosy with everything we could possibly need, and the lovely Caroline couldn’t have been more welcoming and helpful!

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.

Forest’s Edge - Ashurst
Place was exactly as described. Perfect location for exploring the New Forest for a couple of days, whilst the very large garden allowed us to chill in the evenings. Very detailed instructions made finding the place and check in easy.

Quaint Coach House Cottage in the heart of the IOW
Great location for dog walking. Comfortable and quiet, yet close to Newport.
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

Bear Cottage, Beaulieu
We really enjoyed our stay at Bear Cottage. It was warm and cosy, and had everything we needed for our long weekend. A short walk to Beaulieu and ideally situated for visiting the Motor Museum. We especially enjoyed using the tennis courts (agreed by prior arrangement). Thank you Angy - a wonderful host!

Watch the deer from your cosy barn near Goodwood
This is a truly lovely spot. The barn is spotless and comfortable and had everything we needed. Sophie's care package of breakfast items - milk, eggs, bread, cereal, juice - was most welcome. The barn is within a secure gated plot, and delightfully peaceful: ducks on the lake, deer, alpacas, all as stated, yet only 10 minutes drive on easy roads from central Chichester. Other destinations within easy reach include the Weald and Downland (Repair Shop) museum, Goodwood, and Bosham village. If returning to the area we'd hope to stay here again.

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.

Luxury cottage in the heart of The New Forest
Absolute Perfection. We have been fortunate to stay at some great Airbnb’s over the past 10 years but this has to be the best! Maria was a fantastic host. She was always friendly and quick to reply to queries, she gave a us loads of helpful information as well as tips of places to visit and go for food. She greeted us at the cottage and gave us the warmest welcome and even baked us a cake! There were other welcoming gifts too including an activity pack and chocolate buttons for our daughter, a bottle of wine, milk, sourdough & local jam. All were lovely. The cottage itself is beautiful, full of character and charm, it felt cosy whilst spacious enough at the same time. It was spotlessly clean and contained everything we could need for our stay. Beds were large and very comfortable. The outdoor space is incredible! There is off road parking for atleast 2 cars, a large fully enclosed front garden, decking with lovely seating area over looking the rear wonderful rear garden.

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.

Highcliff Cottage - Clifftop Paradise
Such a lovely place to stay and everything is very well kept in the home. My one and only comment would have to be that whilst trees are beautiful things its such a shame you can't see the views at this time of year very well. It's such a stunning home and location that the glorious views would be wonderful with a few less trees surrounding the building.
Quick stats about cottage rentals in City of Winchester
Total rentals
100 properties
Nightly prices starting at
$50 NZD 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
- Bournemouth Beach
- Kimmeridge Bay
- Paultons Park Home of Peppa Pig World
- Oxford University
- Boscombe Beach
- Goodwood Motor Circuit
- Stonehenge
- Windsor Castle
- Hampton Court Palace
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- Highclere Castle
- RHS Garden Wisley
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- Winchester Cathedral
- The Tank Museum
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