Cottage vacation rentals in Province of Siena

We stayed at this lovely cottage in late November and we were delighted with every aspect of the stay. The cottage was clean and comfortable, and was well equipped. The hot-tub was wonderful and sitting there on a chilly night with a view of SG was amazing. Annalisa and Davide were really nice and friendly and very helpful- great hosts. It was about 35 minutes to walk to the town, so quite walkable, and wonderfully quiet and rural (one morning there were 3 deer walking past the window). We had a very nice day out in Sienna which was easy to drive to. I would definitely recommend this place as somewhere really special.

Lovely, peaceful, spacious place with a kind and generous host in Simone. He met us as we arrived and used his wagon to help move our luggage into the cottage. Big rooms, lots of space, many handy supplies in the kitchen. Good shower, comfortable bed. Enough bench space in the bathroom to put your things. Simone was really helpful with local recommendations for restaurants and where to park the car. One day he made a delicious tart and bought us in half. Would recommend staying at his place.

2 Nights of Dreams! We were greeted by Niccolò, perfect in everything, he gave us many tips on both places to see and where to go to eat, we followed them all and we stayed with God! The very nice cottage, has everything you need even for longer stays, the view is wonderful ,and the hot tub is a treat , both day and night . They welcomed us with a bottle of sparkling wine and red petals, which was not at all obvious, everything was perfect , thank you very much Natasha and Niccolò 😊

Beautiful spot in a peaceful setting. Gloria was a fantastic host. We had a wonderful stay.

Very good, it was perfect The host were so friendly Thank you very much

Charming home with amazing pool and a great location Massimo was so helpful and always quick to respond offering restaurant reccos as well The ac was great and the bedrooms stay completely dark if you close the shutters which was nice to sleep a little later despite the morning light There were paper towels, salt oil even some coffee and filters, many basics provided We did not hear cars or highway sounds, just owls, roosters and quiet, it truly is a special place

Beautifull quite and lovely place. Good location to visit surroundings by car on day trips.

We had a wonderful stay at Orto Cottage. The cottage is very comfortable, the views are divine and the surrounding area is beautiful. We were in our own private world. Frank and Phil are great hosts, very friendly, responsive to any requests and helpful with suggestions. We loved their Private Guidebook. It was packed with great suggestions of places to visit, great restaurants and activities. Orto Cottage is highly recommended if you would like a lovely place to stay in the Tuscan hills that is private and an easy drive to all that the area has to offer.

Our stay at Gabriele's place was great and we enjoyed the week we have with him. The house has a cinematic sweeping view of the Tuscan countryside and the pool just like that. The pool is perfect for cooling off on the hot summer days. The house is beautiful, rustic, clean and cool. Air conditioning also helps. We have been a family of 4, with children of 4 and 7 years. We have enjoyed it every day! Gabriele and his wife were very friendly, welcoming and always easy to reach if needed. They helped make our stay just perfect. Thanks to them! We can only recommend a stay with Gabriele and his “Le Capannacce”.

Beautiful accommodation, well maintained and very clean. The only flaw was the very small hair dryer and there was no paper towels in the kitchen. Everything else is well-stocked and very quiet.

We had a pleasant stay at Vito's. The house is very well arranged and offers many amenities. The place is idyllic surrounded by olive groves and high up allowing exceptional views of Tuscany. The pool is simply fantastic, spacious and extremely well maintained thanks to Vito's right-hand man who takes great care of the entire property. This is a property to remember that we highly recommend.

The Di Maggio farm is a unique place where you can regenerate, immersed in a beautiful natural setting where you can fully experience contact with Nature. The apartment is well cared for and furnished in a rustic style with ethnic touches. The outdoor veranda is priceless where you can see the farm animals and also the peacocks. The owners are very kind and helpful people with whom it is pleasant to converse and learn local news and curiosities. We fell in love.

We stayed at Leonardo's cottage for almost two weeks and we enjoyed it very much. The pool was a real highlight for us. You will have the pool all to yourselves and are privately located. The area is very quiet and the view from the cottage fantastic. However, you will have to sit in the car to visit a larger supermarket (~20 minutes) or go to a town (Sienna, Perugia for example). We enjoyed the peace and weather and privacy. There is a restaurant within walking distance, which is definitely recommended! The cottage itself was very well cleaned when we arrived and Leonardo also offered new bedding after a week if we wanted, very neat. Furthermore, the cottage is simple and it is not big, but everything you need is in it (fridge with freezer, dishwasher, good TV, good internet, etc) and if you are there on vacation, of course you are not going to sit inside... Maybe we'll come back!

We stayed 4 nights in Mario's place and would love to come back anytime. Mario is a super likeable and open host who welcomed us warmly. The location of the accommodation is super idyllic - great for excursions in the region or simply to relax on the terrace. We'd love to come back any time. Thanks so much!

Cottage Elena is nothing short of a dream and the pictures don’t do justice to how beautiful and serene the views are. We are already planning our next trip back! The hospitality was truly special.

Cozy idyllic house with a great view overlooking the Tuscany landscape. The road to the house is a bit widning and long so if you're looking to go out often maybe not the most convenient. However if you're looking for a quiet peaceful getaway, it's an amazing location.

The stay with Fausto and his wife (Anna's parents) was really great: a clean cottage in a great beautiful area. The kindness and helpfulness of the hosts was heartwarming. For example, we got a bunch of herbs from their own garden, they came to bring medicine when one of us was sick and they were always ready to answer our questions. After another place we booked canceled a few days before departure, Anna's place was still available and she was quick to respond. We couldn't have found a better place to stay than this one and will definitely go back.

Cute cottage overlooking vineyard on Ulisse's and his family's estate. Although its located on their property, there's enough privacy. Good communication, great environment. The space itself is well equipped. Recommended!

We spent a beautiful and relaxing week of vacation in the restored barn of Villa Parigini . The house is very quiet, cozy and comfortable and is well organized. It has a nice garden and pool to cool off and relax. Great location to visit Siena and the Chianti area. Giada and her mom are very kind and helpful Hosts. We look forward to coming back.

We had a very nice stay with the family (5 adults) in this beautiful part of Tuscany. This beautiful cottage is part of a series of cottages managed by a cooperative. We had a villa that would have used to be a barn with its own swimming pool on the edge of a large olive grove. A breathtaking view from the living room and garden over the region. Insane. There are two restaurants at walking distance. For the rest, everything can be reached within an hour or less. The COOP and Lidl are a 20-minute drive, Siena 50 minutes away and the discovery of this holiday Arezzo is less than half an hour away. What a beautiful city with rich history and fantastic restaurant. Our neighbors from Germany who had the big villa were really friendly. It was during the European Championship so it was nice to watch the matches together. 1 evening we watched football in the ice cream parlor in the village. Was also very cozy. Very friendly people.

We had a wonderful time at the cottage in Cennina. The setting was absolutely beautiful. We felt remote yet were just a few minutes from nearby Ambra and Bucine. We highly recommend this place and we hope to return soon.

The place was great with an excellent view of the valley and San Gimignano town, which was located at a 10 min drive. Great place to relax away from all the city noise. Marco addressed all concerns in a timely manner.

We loved our peaceful stay at Serena’s beautiful property. The house was cozy, rustic, and spacious. She was very accommodating with a high chair and baby crib. My 1 year old especially enjoyed the horse, donkeys, dogs, and cats on the farm. She recommended fantastic local wineries, and even cooked us a delicious Florentine “farm to table” meal. Would recommend to anyone looking for a farm stay away from the bustle of the busy and crowded cities. Thanks Serena!!!

Our stay at Pornanino was amazing. We were there the 2nd week in May, and the weather was a little cool and rainy the first 2 days (we were grateful to have heat in the house, even if gas is expensive!), but the weather was beautiful after that. The cottage is totally charming, the beds and the overstuffed chairs in the living room quite comfortable, the kitchen is very functional, and well-stocked. Francesca was very friendly, super responsive, and totally fluent in English. She was often around the grounds in the afternoons working on the gardens, so we could chat as much as we wanted, and ask whatever questions we had about the region, the house, or anything else. She was also very responsive if we had questions or problems via WhatsApp. It is a bonus that it is a working olive farm. Matteo (also fluent in English) gave us a demo of the olive mill the last day we were there, which was super interesting. Pornanino also worked well for our somewhat unique needs, as we were doing a mix of cycling and working remotely while we were there. The road up to Castellina was a bit too steep and rough for us to ride (we used the car when we wanted to go that direction!), but we were able to connect to a week’s worth of great cycling routes going the other direction, either up towards Radda or Lecchi or down towards Vagliagli. The internet connection was good enough for telecommuting—video calls were a bit iffy, but audio was pretty good. And the little desk with the big windows looking out was a pretty sweet place to sit. You could still get a connection with a computer sitting outside in the garden, but tablets lost the signal. We would unequivocally highly recommend this place!