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Our top choices for Montegrossi hotels with a pool
9.6 out of 10, Exceptional, (133)
"Wonderful stay. 5-stars across the board if you’re looking for disconnecting and relaxing in the rolling hills of the Tuscan countryside. Easy day/dinner trips to Florence or Siena (rental car). "
Matthew
The price is 19.691.430 ₫
21.907.084 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Castel Monastero - The Leading Hotels of the World
Castel Monastero - The Leading Hotels of the WorldCastelnuovo Berardenga
8.8 out of 10, Excellent, (144)
"Had two wonderful nights at the Castel Monastero (wish we had more). Will definitely go back"
John
The price is 16.628.256 ₫
18.599.219 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Casa di Palaia
Casa di PalaiaGreve in Chianti
10.0 out of 10, Exceptional, (22)
"Very well located in the heart if the Tuscany region."
Eli
The price is 2.269.017 ₫
2.619.173 ₫ total
includes taxes & fees
23 Dec - 24 Dec
La Rocca della Magione
La Rocca della MagioneMonteriggioni
9.4 out of 10, Exceptional, (6)
"Lovely property in a 13th century convent. Situated on a hill overlooking a valley. Family owned, very sweet staff. Visitors (esp Americans) should know the owners speak little to no English, so come with your google translate or try and learn a little Italian prior. One major thing I learned in Italy is the importance of communicating your arrival plan with your host prior to arrival as many establishments are family owned and operated. Owner was very accommodating even though we were...
Jennifer
Agriturismo Crocino in Chianti
Agriturismo Crocino in ChiantiGaiole in Chianti
9.0 out of 10, Wonderful, (2)
"Eines der herzlichsten Hotels, welches wir auf unserer Reise besucht haben."
Cornelia
The price is 4.201.884 ₫
4.745.327 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Agritourism Tenuta Armaiolo
Agritourism Tenuta ArmaioloRapolano Terme
8.6 out of 10, Excellent, (38)
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LUIGI
The price is 3.361.479 ₫
3.820.913 ₫ total
includes taxes & fees
26 Dec - 27 Dec
9.8 out of 10, Exceptional, (186)
"The best in Siena."
David
The price is 5.657.417 ₫
6.315.600 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Agriturismo Montemagni di Sopra
Agriturismo Montemagni di SopraGreve in Chianti
9.0 out of 10, Wonderful, (8)
"The hostess is very accommodating and sweet. The beds were incredibly comfy and shower was spacious. A very lovely and peaceful stay! "
Rachel
The price is 2.521.130 ₫
2.896.498 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.