Skip to main content

The best cottages in Siena Area

Check out our pick of great cottages in Siena Area

Filter by:


Review score

Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest price first Star rating and price Top reviewed

See the latest prices and deals by choosing your dates.

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. views, location, amazing restaurant on site

Show more Show less
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. Very nice hotel and staff. Diner in the restaurant was excellent!

Show more Show less
9.4
Superb
1,153 reviews
Price from
US$103
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. Good food , good prices and amazing wine for the label Nottolo

Show more Show less
9
Superb
2,103 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. It was a lovely village in the vineyards. A great family who looked after us. Nice pool, very peaceful location, very pleasant manners and infomrative hosts.

Show more Show less
9.3
Superb
1,264 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. Amazing place ,very welcoming people!!! The breakfast and the dinner was so tasty. We recommend it 100% .

Show more Show less
9
Superb
1,065 reviews
Price from
US$141
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. Wauw, where to begin?! A real gem in the Val d'Orcia region! Beautiful peaceful property, very spacious rooms, totally renovated while keeping the authentic elements, cool appartments with built in fans (no need for airco), all windows have built-in mosquito screens, mirrors with integrated lights/heating ...?! Veryyy large pool, enough lounge corners with nice furniture Good breakfast! Very friendly staff!!!! Thank you!

Show more Show less
9.5
Exceptional
109 reviews
Price from
US$319
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. We had a superb and unforgettable stay during the whole week. Sonia and Alessio (and Kevin!) treated us in a perfect way. They made great recommendations for visits, served delicious homemade local food (breakfast and dinner), and most importantly: they made our family feel welcome from the first minute, and were incredibly attentive and helpful. The location is stunning, staying in a charming and super clean guesthouse, with perfect views on the Tuscan hills. The location is also ideal for trips to medieval towns. Options for charging EV are available on site and nearby. Our stay exceeded our expectations, and we left with gratitude and sweet memories. Warmly recommended!

Show more Show less
9.8
Exceptional
113 reviews
Price from
US$113
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.

Show more Show less
9.5
Exceptional
253 reviews
Price from
US$199
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.

Show more Show less
9.5
Exceptional
123 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. The place is very clean, julia and the stuff were kind and friendly. Amazing breakfast.

Show more Show less
9.4
Superb
363 reviews
Price from
US$126
per night

Most booked cottages in Siena Area this month

FAQs about cottages in Siena Area

Cottages that guests love in Siena Area