Top Cottages in Province of Siena in 2026

A historic town with a prominent tower and a rainbow arching over it.

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Top Cities in Province of Siena

A historic town with tightly packed buildings, a prominent tower, and a church.

Our top choices for Province of Siena cottages

A stone building with a rustic entrance, a small patio area with outdoor furniture, and a wooden fence in the foreground.

1. Fullino Nero

Siena

AED 446 total

includes taxes & fees

20 Oct - 21 Oct

A balcony with a table set for two, featuring a floral tablecloth, a vase with flowers, a teapot, a cup, and a pair of glasses on an open book.

2. FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops

Poggibonsi

Wendy M.

A stone building with a pathway leading to it, surrounded by trees and greenery.

3. Casa il Cipresso, in the heart of Chianti with swimming pool

Castellina in Chianti

A stone building with a large arched window and a door, outdoor seating, and a view of the countryside.

4. COTTAGE WITH 2 BEDROOMS AND 2 ENSUITE BATHROOMS.PANORAMIC POOL.1 KM TO THE TOWN

La Corsina

Theresa V.

A stone villa with a swimming pool, surrounded by lush greenery and mountains in the background.

5. Charming farmhouse with private pool among Brunello vineyards_A real Escape!

Camigliano

Craig C.

A stone building with green shutters, a staircase, and potted plants.

6. agriturismo la roggiola

Monticiano

Tabea S.

A large swimming pool with a red deck, surrounded by a well-maintained lawn and several lounge chairs.

7. Suite indipendent apartment located in Historic Estate from 1600

murlo - siena, tuscany

A patio with two lounge chairs and a large umbrella, overlooking a scenic landscape.

8. Lovely cottage with outdoor patio and small terrace. Panoramic pool and bbq.

La Corsina

A stone building with two arched windows, a covered patio with outdoor furniture, and a small garden area.

9. Countryside, 10 min from Siena

MONTERIGGIONI

Francesca M.

A stone building with two windows, a staircase leading up to it, and white flowers growing around it.

10. Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property

Gaiole in Chianti, Prov. Siena, Toscana

"It’s a nice place with a nice pool, the road to go there is a bit bumpy but can be done easy. Next supermarket is 20 min away. The apartment was in a ok cleaned condition. As soon as it got dark it started that centipede went out of there places and being everywhere at the walls. You could not see them on daytime. We left after 3 nights from 6 booked ones, after we got bites from bed bugs everywhere on our feets. Afterwards we discussed with the owner about cash back due to that we could/would...

Max M.

A covered outdoor seating area with a bed, a table, and chairs.

11. Cottage nel Chianti con Piscina. Vista Sulle Colline e sui Vigneti Toscani

Toscana

"This a a great property for a home base in Tuscany. It seems most all of Tuscany is within 30 min. We were able to day trip all the important places we wanted to see with ease. Eva is a great host and took great care of us. Eva made a wonderful four course dinner for us. She definitely supplies the real Italian culinary experience. She made biscotti and Eva cake to finish a phenomenal dinner. The property has great views with beautiful sunsets. There is a great winery that abuts her property...

daniel w.

A stone building with a view of rolling hills.

12. Casa Belvedere cottage with swimming pool in the heart of Chianti

Castellina in Chianti

A rustic building with a tiled roof, surrounded by a well-maintained lawn and potted plants.

13. A typical Tuscan country house with a pool and grounds, five minutes from San Galgano

Monticiano

"A great place for a family vacation. An intimate cottage on a hill with a very large garden and a private swimming pool allows for a great rest. A small town with a delicious pizza (Bar L'Incontro) and a great wine bar (Benedetto Vino) A great starting point to Florence, Siena, San Gimignano, Volterre and the seaside (Follonica, Cecina). Very friendly and cordial owner Michele always helpful and providing support in times of need (eg where is the best food, where to go on a trip). I heartily...

Paweł R.

A stone house with a tiled roof, a wooden door, and a small porch.

14. In Chianti along the Francigena - La Voliera Country House

Colle di Val d'Elsa

Anibal C.

An outdoor patio with a table and chairs, surrounded by greenery and a view of the countryside.

15. Panorama Nest - Countryside charm with private pool

Colle Val D'elsa

Tino B.

A stone building with a small entrance, a chimney, and a view of green hills.

16. CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL

Castellina in Chianti

lyndon s.

A vineyard with rows of grapevines, a stone house with a swimming pool, and surrounding greenery.

17. Traumblick in die Toskana vom Landhaus mit Pool auf Hügel zw. Siena u. Florenz

Toscana

A stone building with a gravel driveway, a large flower pot, and a lamp post.

18. Glicine, romantic cottage with outdoor patio, on the hills of San Gimignano

San Gimignano

David T.

A stone building with a staircase leading to a door, surrounded by potted plants and a cobblestone path.

19. Charming and Cozy Cottage in Tuscany! Visit Montepulciano Pienza, Cortona, Siena

Chianciano Terme

Jen and Brent F.

An outdoor dining area with a table set for two, surrounded by olive trees and a view of a cityscape in the distance.

20. Il Casale della Gazza Ladra is a completely independent cottage located in the heart of the Tuscan countryside, right in front of the famous towers of San Gimignano.

San Gimignano

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Top Province of Siena Hotel Reviews

Hotel Athena

10/10 Excellent

"Lovely hotel in Siena. Well located for exploring on foot with the main Palazzo and the Duomo no more than 15 minutes away. Really enjoyed the rooftop patio!"