Top Chalets in Province of Siena in 2026

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

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Our top choices for Province of Siena chalets

1. Wonderful family chalet, with swimming pool and panoramic terrace

Casole d'elsa siena

Karla H.

2. AGRITURISMO NOBILE CHALET IL FIENILE

Montepulciano Siena

3. Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,

Toscana

AED 1,596 total

includes taxes & fees

11 Aug - 12 Aug

4. Elegant chalet on the ground floor of approximately 80 m2 consisting of a large living room with fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.A double bedroom and a single bedroom,

Trequanda

AED 1,115 total

includes taxes & fees

27 Aug - 28 Aug

5. Villa Basilico - Cignella Resort Chalet in Tuscany

Trequanda

6. Apartment Azzurro- Cignella Resort Tuscany

Trequanda

7. Apartment Rosmarino- Cignella Resort Tuscany

Siena

8. Chalet Cigno - Apartment in Tuscany

Trequanda

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Top Province of Siena Hotel Reviews

Palazzo Ravizza

10/10 Excellent

"Two things that really made our stay at the Palazzo Ravizza exceptional were the charming terrace with a view of the Tuscan countryside, and the included continental breakfast offered in the morning, including plenty of drip coffee! ☕️ Our room was also undeniably European, with a painted ceiling and rustic furniture. The AC was sufficient, considering the daytime high on our visit was 100°. Service from the staff was very helpful, and they even called a taxi for us. The shower was hot with strong water pressure. The architecture of the hotel had some historic charm as well, with leaded glass doors, black and white marble floors, and vaulted ceilings in the public spaces. But that terrace... 😍"

Hotel Chiusarelli

8/10 Good

"Location was great - 5 mins to the bus station and town centre. Staff were friendly and helpful. Room was comfortable. Only issue we faced was with the hairdryer - attached to the wall in the bathroom - it kept cutting out. Luckily one of the team were able to bring a portable one - but was a bit of a pain. Would defo recommend if you are in Siena."

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while having breakfast - so it was easy to combine days by the pool with exploring one of Tuscany's most beautiful cities (and, inevitably, a bit of shopping to keep our teenage daughter happy). A fantastic place to stay, and one we'd happily recommend."

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San Giovanni A Cerreto Vacations

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Province of Siena chalets

1. Wonderful family chalet, with swimming pool and panoramic terrace

2. AGRITURISMO NOBILE CHALET IL FIENILE

3. Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,

4. Elegant chalet on the ground floor of approximately 80 m2 consisting of a large living room with fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.A double bedroom and a single bedroom,

5. Villa Basilico - Cignella Resort Chalet in Tuscany

6. Apartment Azzurro- Cignella Resort Tuscany

7. Apartment Rosmarino- Cignella Resort Tuscany

8. Chalet Cigno - Apartment in Tuscany

9. Apartment Rosmarino- Cignella Resort Tuscany

10. Chalet Cigno - Apartment in Tuscany

11. Apartment Azzurro- Cignella Resort Tuscany

12. Villa Basilico - Cignella Resort Chalet in Tuscany

Find vacation rentals that suit your style

Top Province of Siena Hotel Reviews

Palazzo Ravizza

Hotel Athena

Hotel Chiusarelli

Castello di Velona Resort Thermal SPA & Winery

Borgo Scopeto Wine & Country Relais

Castello di Spaltenna- Small Luxury Hotels of the World

La Certosa di Pontignano

Hotel Borgo San Luigi

Precise Tale Poggio Alla Sala

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