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The best cottages in Siena Area

Check out our selection of great cottages in Siena Area

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Wonderful: 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. The view from this accommodation was stunning! Looked right out over the whole of Tuscany. We spent many evenings sitting out with one of their wines watching the sunset. Very comfortable beds and traditional Tuscan style. Just beautiful. Lovely surprise having our beds made everyday. This place was one of our highlights from our whole trip!

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9.3
Wonderful
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. This location is amazing: well located, friendly staff, great restaurant. We recommend it to anyone who wants to visit Siena and the surrounding areas.

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9.4
Wonderful
1,151 reviews
Price from
$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. Everything! I could not ask for a better accommodation in Montepulciano. The room is big, charming and very clean. Breakfast is ample, and the view from this place is absolutely breathtaking! Plus points that they have their own wine tasting (their own brand of Nobile di Montepulciano is amazing) and restaurant. But the absolute best thing about Villa Nottola is their staff. Their sincere hospitality and friendliness are what I will most remember.

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9
Wonderful
2,128 reviews
Price from
$133
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. Everything, the place akd the people of Agriturismo San Sano

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9.3
Wonderful
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. Absolutely amazing breakfast, very friendly staff, beautiful views, quiet property just up the hill from town, for Via francigena walkers, a good stop before Monterriggioni, a little more pricey, but well worth it, you will not be disappointed!

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9
Wonderful
1,063 reviews
Price from
$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. Staff is exceptionally nice and were super helpful and welcoming. The place is in a great location in the middle of the valley. The place really beautiful and well maintained. Amazing fresh and locally produced breakfast. Pool looks great but was too cold for middle of Sep.

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9.5
Exceptional
111 reviews
Price from
$311
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. The owners, the view, the breakfast were all wonderful. Air conditioning also!

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9.8
Exceptional
117 reviews
Price from
$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. Staying at Palazzo Massaini - Le Scuderie was like stepping into a fairytale! Nestled in the heart of Tuscany, this magnificent castle, once home to Pope Pius II, offers a truly unique experience. The view from the property is simply breathtaking, with rolling hills and vineyards stretching as far as the eye can see, embodying everything you’d dream of in Tuscany. Our room was perfect—spacious, beautifully decorated, and filled with rustic charm that still delivered all the modern comforts. The ambiance was magical; waking up in a historic castle with such rich history is an experience I’ll never forget. The staff was gracious, attentive, and made us feel like royalty throughout our stay. If you’re looking for an extraordinary place to stay in Tuscany, Palazzo Massaini - Le Scuderie is a must. This is more than just accommodation; it’s an unforgettable journey through history with all the luxury and beauty you could ask for. Highly recommend for anyone seeking a dream getaway in a true Tuscan castle.

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9.5
Exceptional
263 reviews
Price from
$373
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
127 reviews
Price from
$162
per night

Agriturismo Casalino18 is set in Tognazza. With free private parking, the property is 10 km from Piazza del Campo and 43 km from Piazza Matteotti. The farm stay has family rooms.

At the farm stay, units come with a wardrobe. Featuring a private bathroom with a bidet and a hair dryer, units at the farm stay also feature free WiFi, while some rooms also feature a terrace. All units feature bed linen. Beautiful place, nice room, & tasty breakfast. Really enjoyed!

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9.4
Wonderful
370 reviews
Price from
$126
per night

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