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The best cottages in Siena Area

Check out our pick of great cottages in Siena Area

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Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
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Offering an outdoor pool and a restaurant, Fattoria di Cinciano is located in Poggibonsi, a 10-minute drive from the centre. Free WiFi access is available in all areas.

Each apartment will provide you with a satellite flat-screen TV, air conditioning and a kitchenette with a microwave. Featuring a shower, the private bathroom also comes with a hairdryer and towels. Fattoria di Cinciano is a hidden gem in the Tuscan countryside. Perfectly positioned on a hilltop among olive groves and vineyards, it offers both peaceful seclusion and convenient access to nearby towns and attractions. Our apartment was spacious, comfortable, and well-equipped, making it feel like a home away from home. The estate features beautiful gardens and stunning views of the rolling Tuscan hills. The friendly staff provided excellent recommendations for local restaurants and activities, enhancing our experience of the region. What we appreciated most was the tranquil atmosphere - ideal for unwinding and experiencing the authentic charm of Tuscany. Highly recommended for anyone seeking a relaxing Italian countryside getaway with all the comforts.

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9.3
Superb
1,011 reviews

Set 9 km from Siena, this 19th-century country house features a restaurant and outdoor pool. It offers traditional Tuscan rooms with wood-beamed ceilings, surrounded by sunflower fields.

Air-conditioned rooms at Casa Di Campagna In Toscana come with terracotta floors and a memory foam mattress. Each room includes a private bathroom complete with hairdryer and toiletry set. The most authentic and beautiful place we’ve ever visited. We loved it. We had a great dinner at their restaurant and we wished we had more time to spend there. We loved Toscana and we definitely would come back again

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9.4
Superb
1,154 reviews
Price from
US$100
per night

Villa Nottola is a former noble residence in the countryside of Montepulciano, besides the namesake winery. It offers a sun terrace with swimming pool.

The elegant rooms of Villa Nottola feature ceilings with original wooden beams and brick vaults. The walls are painted in soft natural colours matching the Tuscan art furnishings. The wine tasting was excellent. The food in the restaurant was superior. The breakfast each morning was the best we had our entire Italian trip. The wait staff were wonderful and very comforting. Mony and Happi were lovely and very helpful

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9
Superb
2,111 reviews
Price from
US$111
per night

Set within 24 km of Piazza del Campo and 29 km of Piazza Matteotti, Agriturismo San Sano offers rooms with air conditioning and a private bathroom in Gaiole in Chianti. This farm stay has a pool with a view, a garden and free private parking. The farm stay features family rooms. This is an excellent guest house. The owners are wonderful. The room is wonderful. And the wine tasting is perfect. I hate Chianti. I love Chianti Classico. You can figure that out when you get there. The drive to the hotel is a bit of fun if you like hill driving and the village is unreal. You cannot miss in San Sano. We will be back with friends. You should, too.

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9.3
Superb
1,263 reviews

CastelBigozzi is surrounded by the Tuscan countryside, 12 km from San Gimignano. It offers an outdoor swimming pool with hydromassage, and rustic, air-conditioned rooms. You can book free guided excursions on the Via Francigena path. Location, charm, attention to details. The restaurant was the cherry on the cake

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9
Superb
1,061 reviews
Price from
US$165
per night

Boasting an infinity pool and views of mountain, Le Sorbelle D'Orcia is a recently renovated farm stay situated in Pienza, 39 km from Mount Amiata. The property has garden and inner courtyard views, and is 4.3 km from Parco dei Mulini. There is an outdoor fireplace and guests can make use of free WiFi, free private parking and an electric vehicle charging station. We had the most wonderful experience at Le Sorbelle D'Orcia. From the moment we arrived, Fabio and all the staff made us feel so welcome — their service was truly incredible and went far beyond our expectations. The atmosphere was warm and full of charm, and we really felt the magic and peace of the Tuscan countryside. The villa itself was spotless, comfortable, and beautiful, with views that were absolutely breathtaking — especially while relaxing by the pool. The food was simply outstanding: every meal was delicious, authentic, and prepared with so much love. Fabio and the team created such a special experience for us, and we are so grateful for their kindness and care. We left with full hearts and unforgettable memories, and we are already dreaming about coming back again soon.

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9.5
Exceptional
110 reviews
Price from
US$312
per night

At the farm stay, some units have a private entrance, dining area, fireplace and oven. Complete with a private bathroom equipped with a shower and a hair dryer, the units at the farm stay have a flat-screen TV and air conditioning, and certain rooms here will provide you with a terrace. At the farm stay, the units are equipped with bed linen and towels. Everything was smooth and amazing at Podere Grotta Antica — we absolutely loved the place. The room was beautiful, and the nature all around made the stay feel peaceful and special. The people were incredibly accommodating, kind, and helpful with us throughout our visit. We would definitely love to come back another time and truly recommend it!

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9.8
Exceptional
115 reviews
Price from
US$127
per night

Set within 49 km of Mount Amiata and 13 km of Terme di Montepulciano, Palazzo Massaini - Le Scuderie offers rooms with air conditioning and a private bathroom in Pienza. This property offers a pool with a view and free private parking. The farm stay features family rooms. The staff was great! Francesa, Camelia, Beatrice and Sole were very kind and helpful in all our experience at the Palazzo.

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9.5
Exceptional
258 reviews
Price from
US$294
per night

Set in Colle Val D'Elsa, Palazzo Galganetti Betti offers accommodation 26 km from Piazza del Campo and 41 km from Piazza Matteotti.

Featuring a private bathroom, units at the holiday home also have free WiFi. I was met by member of the property team and escorted to the residence. Super convenient.

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9.5
Exceptional
124 reviews
Price from
US$162
per night

Offering garden views, Agriturismo Casalino18 is an accommodation set in Tognazza, 10 km from Piazza del Campo and 43 km from Piazza Matteotti. Private parking is available on site at this recently renovated property. The farm stay has family rooms. Amazing breakfast. Beautiful picturesque property. Very peaceful.

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9.4
Superb
366 reviews
Price from
US$126
per night

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