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

RM705 total

includes taxes & fees

1 Jul - 2 Jul

Villa Cassia di Baccano

Loro Ciuffenna

Ralphvincent

RM666 total

includes taxes & fees

2 Jul - 3 Jul

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

Villa di Sotto

Castelnuovo Berardenga

Jeremy

RM766 total

includes taxes & fees

5 Jul - 6 Jul

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

San Casciano in Val di Pesa

Raymundo

RM528 total

includes taxes & fees

12 Jul - 13 Jul

Ca' Bianca Tuscany Relais

Siena

Talha

RM1,429 total

includes taxes & fees

30 Jun - 1 Jul

Villa Curina Resort

Castelnuovo Berardenga

Dr Anne

RM753 total

includes taxes & fees

30 Jun - 1 Jul

Il Pozzo di Sant'Andrea

Siena

Prem

RM556 total

includes taxes & fees

27 Jul - 28 Jul

Villa il Fedino

San Casciano in Val di Pesa

rose

RM1,189 total

includes taxes & fees

30 Jun - 1 Jul

Casa di Campagna in Toscana

Sovicille

Sally

RM705 total

includes taxes & fees

30 Jun - 1 Jul

I Parigi Corbinelli

Florence

Stefano

RM484 total

includes taxes & fees

5 Jul - 6 Jul

Palazzo al Torrione 2

San Gimignano City Centre

Sophie

RM620 total

includes taxes & fees

5 Jul - 6 Jul

B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

Ruben

RM616 total

includes taxes & fees

30 Jun - 1 Jul

Mariani Bed & Breakfast

Castellina in Chianti

Chie

RM439 total

includes taxes & fees

30 Jun - 1 Jul

Villa La Ginestra

Subbiano

Philippe

Sportland

Colle di Val d'Elsa

Giorgio

RM236 total

includes taxes & fees

5 Jul - 6 Jul

Fontelunga Hotel & Villas

Foiano della Chiana

Shelby

RM1,666 total

includes taxes & fees

5 Jul - 6 Jul

Siena Vip

Siena City Centre

David

RM604 total

includes taxes & fees

13 Jul - 14 Jul

Piazza Paradiso Accomodation

Siena City Centre

Mauricio

RM524 total

includes taxes & fees

16 Jul - 17 Jul

Minibar, desk, blackout curtains, free WiFi

PALAZZO DEL PAPA

Siena City Centre

Diane

RM804 total

includes taxes & fees

6 Jul - 7 Jul

DormiVeglia B&B

Monte San Savino

Melissa Hyun Joo

RM438 total

includes taxes & fees

5 Jul - 6 Jul

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Top Gaiole in Chianti Hotel Reviews

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."

Hu Firenze Camping In Town

10/10 Excellent

"I absolutely loved staying here and would stay here again! Very clean and vibrant facility. The glamping tent was such a fun place to stay. Some of the best sleep I've ever had while traveling. The staff was friendly, and the convenience of having a market and restaurant on-site was wonderful. Excellent food and service! The bus line runs right out front so it's super easy to get into the touristy section of Florence. The Ridemovi bike share bikes were nearby as well, which made transportation so easy. This place far exceeded my expectations. Highly recommended!"

Ultimo Mulino Wellness Country Hotel

10/10 Excellent

"Loved this boutique property. Stayed five nights in the newer section, Le Noci, and would love to go back. The staff were all excellent, friendly and helpful. The pool was stunning. The room was large, comfy, and quiet. Breakfast was delicious and eating on the outside terrace was wonderful as the view was incredible. The only downside was the restaurant over at the older section. Would not recommend as the waitress was rude/pushy (made the evening uncomfortable) and the food was just okay. Would recommend going to nearby Radda or Gaiole instead. Highly recommend Il Papavero in Barbischio, a few minutes east of Gaiole. The dinner we had there was the best and a highlight of the trip."

Find out more about Gaiole in Chianti