Gaiole in Chianti Town Houses

A stone castle with battlements overlooking a lush valley with vineyards.

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Our top choices for Gaiole in Chianti town houses

L' Eroico

Gaiole in Chianti

Angela

P10,617 total

includes taxes & fees

Jul 4 - Jul 5

Villa Cassia di Baccano

Loro Ciuffenna

Ralphvincent

P9,327 total

includes taxes & fees

Jul 9 - Jul 10

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

San Casciano in Val di Pesa

Raymundo

P8,812 total

includes taxes & fees

Jul 13 - Jul 14

Ca' Bianca Tuscany Relais

Siena

Talha

Villa Curina Resort

Castelnuovo Berardenga

Dr Anne

P13,267 total

includes taxes & fees

Jul 5 - Jul 6

Il Pozzo di Sant'Andrea

Siena

Prem

P8,377 total

includes taxes & fees

Jul 6 - Jul 7

Casa di Campagna in Toscana

Sovicille

Sally

P10,104 total

includes taxes & fees

Jul 4 - Jul 5

Villa il Fedino

San Casciano in Val di Pesa

rose

P17,307 total

includes taxes & fees

Jul 4 - Jul 5

Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Villa di Sotto

Castelnuovo Berardenga

Jeremy

P11,537 total

includes taxes & fees

Jul 10 - Jul 11

Desk, iron/ironing board, free WiFi, bed sheets

Al Mercato B&B

Siena City Centre

Marie-Christine

P5,610 total

includes taxes & fees

Jul 14 - Jul 15

Terre di Baccio

Greve in Chianti

"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"

Julia

P21,299 total

includes taxes & fees

Jul 4 - Jul 5

DormiVeglia B&B

Monte San Savino

Melissa Hyun Joo

P6,604 total

includes taxes & fees

Jul 14 - Jul 15

I Parigi Corbinelli

Florence

Stefano

P6,649 total

includes taxes & fees

Jul 6 - Jul 7

Villa Fontis Rapolano

Rapolano Terme

Barbara

P6,656 total

includes taxes & fees

Jul 5 - Jul 6

B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

Ruben

P9,275 total

includes taxes & fees

Jul 5 - Jul 6

Minibar, desk, blackout drapes, free WiFi

PALAZZO DEL PAPA

Siena City Centre

Diane

P12,116 total

includes taxes & fees

Jul 16 - Jul 17

Mariani Bed & Breakfast

Castellina in Chianti

Chie

P6,810 total

includes taxes & fees

Jul 7 - Jul 8

Fontelunga Hotel & Villas

Foiano della Chiana

Shelby

P25,103 total

includes taxes & fees

Jul 7 - Jul 8

Siena Vip

Siena City Centre

David

P9,100 total

includes taxes & fees

Jul 26 - Jul 27

Palazzo al Torrione 2

San Gimignano City Centre

Sophie

P9,346 total

includes taxes & fees

Jul 5 - Jul 6

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Top Gaiole in Chianti Hotel Reviews

Hotel Chiusarelli

10/10 Excellent

"Perfect location in Siena, with soft, comfortable beds, cool air conditioning, and nice showers. Breakfast was yummy and provided a wonderful beginning to our day! No elevator, so I had to carry bags up several flights of stairs."

Hotel Athena

10/10 Excellent

"Great Siena spot just on outskirts of the historic city. Easy uphill walk to the main sites and dinning options. Room was excellent. Breakfast very good. On site parking was essential. Staff all pleasant and helpful. Enjoyed a wine on the terrace to watch an amazing thunder storm rolling around for over an hour."

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"This hotel is the definition of La Dolce Vita! Starting from the beginning, when first arrived to the hotel, they picked up our bags, showed us around the property and responded any questions that we had. Elisa was amazing! She showed us around the property, he gave us recommendations of where to go in Siena, and was super friendly and welcoming! The hotel has excellent amenities and everything that you need. The pool is wonderful, and the pool bar is amazing. Excellent service. Their breakfast area is beautiful, and they provide a very diverse breakfast. It was really good! In addition, their restaurant La Tinaia is phenomenal and Michelin star. They have a great wine selection and excellent food. They also have valet parking service, which is very convenient. All of the staff were very welcoming and nice! Thank you to the pool Bar bartender whose name I cannot recall, and also thanks to Elisa, Virginia, Davide, Asiz, Stefano, and everyone else! You all made our stay wonderful! The rooms were excellent and very comfortable. Shower was great too. My only comment would be that the A/C was not performing to my expectation for a 5 star hotel. However, I understand that there was a Heat Wave in Europe, and that it is out of their hands. Giancarlo helped us to lower the temp of the A/C, but it still did not work. They provided a fan though, and that helped a lot! Thank you! The location is excellent! You’re about an hour away from The Mall at Firenze, close to wineries, about a 20"

Villa Olmi Firenze

10/10 Excellent

"Wonderful property in every way! We accidentally left our passports in the room safe and the housekeeper immediately notified the front desk. The lady at the front desk, whose name was, Laura M., contacted us immediately. We were already in Venice, so she arranged a driver to drive our passports to us. She went over the top to ensure we had a wonderful vacation. The kindness was just amazing and the property was 10/10."

Hotel Italia

10/10 Excellent

"Hotel Italia was an absolute gem. The staff were incredibly friendly and helpful — they understood we were tired from traveling with teens and even nailed a salon recommendation that turned out to be the best hair wash of my life, just minutes from the hotel. Our room was spotless, quiet, and the A/C worked perfectly; we didn’t hear a sound from neighbors or stair traffic. The location is a sweet spot — only 5 to 10 minutes from the tourist sights, yet tucked in a local neighborhood with bakeries and grocery stores, giving us that refreshing, peaceful feeling of being disconnected from the tourist rush. Breakfast was amazing, and the little teen-approved Duomo and gelato challenges made exploring even more fun. Bottom line: we’d come back and stay here again in a heartbeat. For anyone visiting Siena, Hotel Italia at Porta Camollia gives you that perfect “live like a local” buffer before diving into the Duomo and Piazza del Campo — and if you need a salon, just ask reception; their pick is solid."

Find out more about Gaiole in Chianti