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Montespertoli – 59 hotels and places to stay
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Villa La Cappella

Hotel in Montespertoli

Set on Aliano Hill in a 7000-m² park filled with ancient cypress trees, Villa La Cappella dates back to the 12th century. It features 1 outdoor heated pool with views of the Chianti countryside. Breakfast was amazing, with a wide choice of cooked and continental foods. Staff paid meticulous regard to Covid restrictions, as guests were given their own table and had to be served for the buffet breakfast. The room was lovely and decorated in a traditional Tuscan way. The rooms are very clean and the grounds are extensive. Parking was also good. I really enjoyed my stay.

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9.1
Awesome
204 reviews
Price from
$182
per night

Villa Le Calvane

Hotel in Montespertoli

Offering a seasonal infinity pool and hot tub, Villa Le Calvane is set in Montespertoli, on the hills overlooking the Chianti region. Olive oil and wine are produced on site. Hotel is beautiful and very cozy. Amazing view over the Tuscan hills. You can relax by the pool while enjoying the view. Delicious food and outstanding service.

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9.5
Exceptional
163 reviews
Price from
$519
per night

Il Molino Del Ponte

Hotel in Montespertoli

Il Molino Del Ponte is located along the Via Volterrana, one of Chianti's oldest wine roads. Everything was great! Great hosts, great location. Great beautifully landscaped surroundings. A very suitable starting point for exploring Tuscany by motorbike. Upon arrival from the tour, a pool awaits you. :) Just a few steps from the accommodation is nice restaurant.

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9.1
Awesome
153 reviews
Price from
$68
per night

Le Mandrie di Ripalta

Montespertoli

Surrounded by a 33-hectare garden on the peaceful Tuscan hills, among olive trees and vineyards, Le Mandrie di Ripalta is just 1.9 mi from Montespertoli. The food , the staff, the room, location, the view, everything

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9.2
Awesome
784 reviews
Price from
$143
per night

Podere Dell'Anselmo

Montespertoli

The Podere dell'Anselmo is a small farmhouse offering independent apartments, an on-site swimming pool, horseback riding facilities, wine tasting and a cooking school. We had such a wonderful time, the staff were so friendly and the place and views were amazing! They offer a dinner for €25 a person every night, it is a true Italian meal where the food just keeps on coming and you get to try out the wine the produce onsite. The owner also shows guests his wine cellar and gives a tour which was pretty cool. The facilities are perfect, this was our 3rd stop in our travels around Italy and it was the first time we actually had a comfortable bed and a full sized shower. Our room also had a view of the grounds that over looked the pool. The pool is a great place to relax and looks out on to the Tuscan hills. It wasn't very busy when we were there but there are so many different areas to sit and relax I think even at it's busiest it wouldn't feel crowded. We were only 45 minutes outside of Florence which wasn't an issue for us to drive but if you are looking to do more trips into Siena, Pisa etc it might be a little out of the way. Would definitely go back!!

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8.7
Excellent
118 reviews
Price from
$129
per night

Fattoria Poggio Capponi

Montespertoli

Fattoria Poggio Capponi dates back to the 16th century. Standing on a hill in Montespertoili, surrounded by woods, vineyards and olive groves, the property includes a villa, farmhouse and wine cellar,... - great location, 30 minutes from Firenze (Florence), 60 minutes from Pisa or Siena - beautiful scenic view, and feel of local life (next to a still-functioning rooster farm) - host is wonderful, and met all our needs - we have a disabled member in our party and the facilities provided her were above and beyond we are in love with this place!

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8.8
Excellent
125 reviews
Price from
$84
per night

Podere Casanova

Montespertoli

Located in Montespertoli, 21 mi from San Gimignano, Podere Casanova features a seasonal outdoor swimming pool and free WiFi. Perfect location, very comfortable and clean apartment. The owner Lisa is very friendly and welcoming host. Thank you so much for your hospitality Lisa !

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9.4
Awesome
195 reviews
Price from
$126
per night

Il Gufo del Chianti

Montespertoli

Offering an outdoor pool and views of the garden, Il Gufo del Chianti is set in Montespertoli. Florence is 15 mi away. Free private parking and free WiFi are available. Awesom stay, amazing place in middle of vineyards and olive trees. Driving distance to Florence, San Gimignano or Spiaggie Bianche at Vada. Excellent personnel, especialy Valentina😀Had problems with my car, Valentina fixed me a repair shop and drove me there. She is a gem😀

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9.3
Awesome
62 reviews
Price from
$113
per night

Borgo Divino

Montespertoli

Located 2.2 mi from the center of Montespertoli, Borgo Divino offers a seasonal outdoor swimming pool, restaurant and garden. Free WiFi is available throughout. Borgo Divino is truly exceptional!This place is among the best that I have ever stayed in. For the first time in my life I got a free upgrade from a double room to the junior suit. It was such a nice gesture, I greatly appreciated it. The view, the nature, the staff - everything is 10/10!

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9.2
Awesome
195 reviews
Price from
$89
per night

Le Fonti A San Giorgio

Montespertoli

Le Fonti a San Giorgio is set in a farmhouse on the very top of San Lorenzo hill, right in the heart of Chianti area, between Florence and San Gimignano. The quiet, peaceful, remote position. Sabrina was extremely helpfully. Breakfast and diñer were excellent and table setting outside was just superb. Pool was wonderfully refreshing.

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8.9
Excellent
39 reviews

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