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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Browse Select Gaiole in Chianti Apartments

ApartHotel Anghel
Lobby lounge

ApartHotel Anghel

8.2 out of 10, Very good, (322)
"Hotel is close to Siena and the check-in person (Gabriela) was very friendly and helpful. Room is spacious, functional with easy parking in front of the building and just a 3 minute drive to garage in Siena old-town so very convenient to visit this beautiful city. Excellent value for the money."
ApartHotel Anghel
Regis Condo
Grand Apartment with Garden | Private kitchen | Full-sized fridge, microwave, oven, stovetop

Regis Condo

9.4 out of 10, Exceptional, (63)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
Regis Condo
Villa Il Palagio
Front of property – evening/night

Villa Il Palagio

8.6 out of 10, Excellent, (56)
"We stayed 2 nights and loved it! We have a 2 bedroom , 2 bath apartment and it was so spacious. We enjoyed the kind staff and the breakfast had a lot of choices. It was great"
Villa Il Palagio
PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION
Outdoor dining

PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

9.8 out of 10, Exceptional, (50)
"Quaint, authentic and comfy. "
PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION
Gite Montemirello, with garden and swimming pool
Exterior detail

Gite Montemirello, with garden and swimming pool

9.8 out of 10, Exceptional, (54)
"Great property,only 30 mins from Siena, very peaceful large garden and large private pool. Just what we needed after doing 9 days touring Tuscan cities, highly recommend this property."
Gite Montemirello, with garden and swimming pool
Montalcino Villa - Breathtaking Views of the Val d'Orcia
Outdoor dining

Montalcino Villa - Breathtaking Views of the Val d'Orcia

9.8 out of 10, Exceptional, (43)
"We had a wonder stay at the villa. Gave a true Tuscan countryside experience in a luxurious, comfortable and convenient location."
Montalcino Villa - Breathtaking Views of the Val d'Orcia
Chic Tuscan apartment pool spectacular view modern comfort wifi air conditioning
Outdoor pool

Chic Tuscan apartment pool spectacular view modern comfort wifi air conditioning

9.8 out of 10, Exceptional, (59)
"We didn't spend too much time at the property but it was perfect. The a/c units worked great wand was able to accommodate our party of 7. The owner and his mother live in adjoining properties so they're very responsive if anything is needed. His mother was AMAZING with our daughter with special needs!"
The price is £404
includes taxes & fees
26 Aug - 27 Aug
Chic Tuscan apartment pool spectacular view modern comfort wifi air conditioning
Ancient App. Immersed in History
Outdoor dining

Ancient App. Immersed in History

8.6 out of 10, Excellent, (7)
"Il proprietario è stato gentilissimo, abbiamo perso l'autobus per colle val delsa e si è proposto di venirci a prendere a Siena. Si vede la sua passione per la sua città e la storia di colle val delsa."
Ancient App. Immersed in History
Palazzo Piccolomini
Flat-screen TV

Palazzo Piccolomini

The price is £276
includes taxes & fees
25 Aug - 26 Aug
Palazzo Piccolomini
Charming 2 Br Flat In City Center Siena Close To Piazza Del Campo
Dining

Charming 2 Br Flat In City Center Siena Close To Piazza Del Campo

9.4 out of 10, Exceptional, (57)
"This apartment is right in the medieval part of Siena and not far from the attractions. So it's got loads of charm and antiquity appeal, and we enjoyed that very much. We are in our 80s, but probably better shape than many at our age, so we can't really recommend it to older folks because there are quite a few steps up, pretty as they are. It is a comfortable place, though as usual the bathroom is adapted in a place that was not intended way back when it was built, and is thus pretty small. ...
Charming 2 Br Flat In City Center Siena Close To Piazza Del Campo
Rinidia Siena Centro
Luxury Duplex, Ensuite, City View (Roof Top Altana)

Rinidia Siena Centro

8.0 out of 10, Very good, (1)
"The property is in a FANTASTIC location."
The price is £155
includes taxes & fees
12 Sept - 13 Sept
Rinidia Siena Centro
Enchanting Tuscany Vacation Rental in Medieval Fortress Town Panoramic Views
Interior

Enchanting Tuscany Vacation Rental in Medieval Fortress Town Panoramic Views

10.0 out of 10, Exceptional, (112)
"Barberino Val D’Elsa is a charming town, perfect for a slow paced vacation. The rental apartment had everything we needed, including laundry facilities. The views from the bedroom were amazing. Cindy’s directions to the apartment and to check in were detailed so we had no problem. Parking was a 3 minute walk away and free. This rental was a hidden Tuscan gem, definitely recommend. "
Enchanting Tuscany Vacation Rental in Medieval Fortress Town Panoramic Views
Borgo Antico Residence
Front of property

Borgo Antico Residence

10.0 out of 10, Exceptional, (3)
"Great place to relax take in the local culture and enjoy Tuscany."
The price is £83
includes taxes & fees
13 Sept - 14 Sept
Borgo Antico Residence
Nice apartment in Castel San Gimignano
Fridge, microwave, stovetop, dishwasher

Nice apartment in Castel San Gimignano

10.0 out of 10, Exceptional, (1)
"Top top "
Nice apartment in Castel San Gimignano
Cozy Nest for 2 with Garden and Parking over Piazzale Michelangelo
Property grounds

Cozy Nest for 2 with Garden and Parking over Piazzale Michelangelo

9.0 out of 10, Wonderful, (57)
"The Cozy Nest is a gem of a place nestled in a small village just minutes outside of Florence. My wife and I chose this location so we could have the first couple days of our holiday to adjust to the time change and detox from our busy lives. The Cozy Nest was exactly what we needed. The host went above any beyond and was kind enough to allow us an early check in on Easter Sunday. Their property was absolutely beautify and a perfect spot to watch the sunsets. My only regret is that we didn't...
Cozy Nest for 2 with Garden and Parking over Piazzale Michelangelo
Beautiful apartment in San Gimignano - RoccaiaCasa'70
Outdoor pool, an infinity pool

Beautiful apartment in San Gimignano - RoccaiaCasa'70

9.8 out of 10, Exceptional, (41)
"Quiet place to stay"
Beautiful apartment in San Gimignano - RoccaiaCasa'70
Castello di Modanella
Property entrance

Castello di Modanella

7.6 out of 10, Good, (14)
"Property is closing and looks like it. Very unfortunate, I was there 30 years ago with fond memories! Obviously I should have done more homework!! Very sad."
Castello di Modanella
Villa Norcenni Aparthotel
Indoor pool, 3 outdoor pools, open 10 AM to 6 PM, pool umbrellas

Villa Norcenni Aparthotel

2.0 star property
7.4 out of 10, Good, (20)
"It was clean and safe."
The price is £158
includes taxes & fees
17 Aug - 18 Aug
Villa Norcenni Aparthotel
Tenuta Tegolato
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool umbrellas

Tenuta Tegolato

10.0 out of 10, Exceptional, (23)
"Its a beautiful place and a great price quality resort - highly recommended !"
Tenuta Tegolato
WHITE HOUSE STALLOREGGI-near the Cathedral.
Interior

WHITE HOUSE STALLOREGGI-near the Cathedral.

9.2 out of 10, Wonderful, (11)
"The communication manager and the check-in process was top-notch. Very friendly very quick with responses. Parking however, was an issue. It was pretty far away. There really wasn’t any place to hang our clothes. And no shelves anywhere in the bathrooms to speak of.Would I stay here again yes"
The price is £214
includes taxes & fees
20 Aug - 21 Aug
WHITE HOUSE STALLOREGGI-near the Cathedral.
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.
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Top Gaiole in Chianti Hotel Reviews

Hotel Athena

Hotel Athena

10/10 Excellent
"Amazing staff and phenomenal food and views "
Cassandra 1-night trip
Posted 1 day ago
Hotel Athena