Photo by Karen Dean

Search Cottages in Gaiole in Chianti

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Cottages in Gaiole in Chianti and around

BRUNELLO - Cozy cottage located in a peaceful & panoramic position in Tuscany
Outdoor pool
BRUNELLO - Cozy cottage located in a peaceful & panoramic position in Tuscany
9.8 out of 10, Exceptional, (60)
"This is a great property with loveku views and a great welcome. Loved our stay and will be going back."
BRUNELLO - Cozy cottage located in a peaceful & panoramic position in Tuscany
Apartment/ flat - Barberino val d'ElsaHouse with character
Pool
Apartment/ flat - Barberino val d'ElsaHouse with character
9.8 out of 10, Exceptional, (39)
"We had a lovely 12 day stay in this charming little villa near Tuscany. Loretta was a wonderful host and the location was perfect for us. We enjoyed exploring Sienna, Florence and nearby Poggibonsi, but days in the pool at the villa were hard to beat (especially with the 40 degree heat)."
Apartment/ flat - Barberino val d'ElsaHouse with character
Le Mogli house, typical Tuscan structure with pool, surrounded by nature
Exterior
Le Mogli house, typical Tuscan structure with pool, surrounded by nature
9.6 out of 10, Exceptional, (15)
"Ein wunderbar ruhiger Ort in der Toskana. Die Kommunikation war immer hervorragend. Der Pool war das Highlight für die Kinder. Um vom Parkplatz bis zur Unterkunft zu kommen, muss ein bisschen Muskelkraft aufgrund des Höhenunterschieds mit eingerechnet werden."
Le Mogli house, typical Tuscan structure with pool, surrounded by nature
Holiday house Talla for 4 - 6 persons with 2 bedrooms - Holiday house
Fridge, stovetop, dishwasher, coffee/tea maker
Holiday house Talla for 4 - 6 persons with 2 bedrooms - Holiday house
Holiday house Talla for 4 - 6 persons with 2 bedrooms - Holiday house
Cottage. DEPENDANCE IL BORRACCIO con vista giardino sulla campagna del Chianti.
Exterior
Cottage. DEPENDANCE IL BORRACCIO con vista giardino sulla campagna del Chianti.
9.0 out of 10, Wonderful, (18)
"We thoroughly enjoyed our stay. Comfortable cottage in an amazingly beautiful location. Conveniently located near Pisa and Sienna. Our hosts were very helpful and gracious."
Cottage. DEPENDANCE IL BORRACCIO con vista giardino sulla campagna del Chianti.
Fullino Nero
Lobby sitting area
Fullino Nero
9.6 out of 10, Exceptional, (41)
"I enjoyed the peacefulness surrounding the property, the views were beautiful and it has a lovely patio area to be able to enjoy it all."
The price is €109
includes taxes & fees
29 Sept - 30 Sept
Fullino Nero
Charming Farmhouse with Private Pool among Vineyards
Property grounds
Charming Farmhouse with Private Pool among Vineyards
9.4 out of 10, Exceptional, (49)
"This property is fantastic if you want to enjoy the real Tuscan life. The Villa, pool is all that is advertised. Olivia is the property manager and makes your stay everything you could hope for. We spent an entire month with 6 guests per week. Morning day trips afternoons by the pool and evenings watching the sunset with the estates wines. It was a month to remember. Cheers Steve Enna"
Charming Farmhouse with Private Pool among Vineyards
Fattorie Santo Pietro
Front of property
Fattorie Santo Pietro
10.0 out of 10, Exceptional, (1)
"Un excellent service à la clientèle. Un gros merci à Chiara pour son accueil et sa rapidité de régler une petite problématique "
The price is €260
includes taxes & fees
29 Sept - 30 Sept
Fattorie Santo Pietro
Purgatorio house, a typical Tuscan structure with pool, surrounded by nature.
Property grounds
Purgatorio house, a typical Tuscan structure with pool, surrounded by nature.
10.0 out of 10, Exceptional, (9)
"All in all: Perfect."
Purgatorio house, a typical Tuscan structure with pool, surrounded by nature.
Exceptionally pretty cottage with pool, views, in walking distance from Panzano
Pool
Exceptionally pretty cottage with pool, views, in walking distance from Panzano
10.0 out of 10, Exceptional, (42)
"We could not have had a better stay here! The home itself was unbelievably beautiful and comfortable and luxurious all at the same time! We came from a week of hiking in the Dolomites and were so happy to have a washing machine and a big comfortable bed! The kitchen was amazing to cook in, the outdoor spaces were endlessly lovely for any kind of weather or activity. The indoor space was also so amazing on the one afternoon we had thunderstorms! Lucrezia was an incredible host that helped us with...
Exceptionally pretty cottage with pool, views, in walking distance from Panzano
Charming 4-Bed Cottage 15 minutes from Florence
Fridge, coffee/tea maker
Charming 4-Bed Cottage 15 minutes from Florence
Charming 4-Bed Cottage 15 minutes from Florence
Countryside, 10 min from Siena
Outdoor dining
Countryside, 10 min from Siena
9.4 out of 10, Exceptional, (3)
"Thank you Letizia for a lovely two days. The flat is comfortable, tidy and well equipped. The location is peaceful. The road to get to the house is a little bumpy but worth it once you get there. Letizia is friendly and very kind and helpful. Our dog loved his time playing with the other dogs. Grazie mille Letizia"
Countryside, 10 min from Siena
Traumblick in die Toskana vom Landhaus mit Pool auf Hügel zw. Siena u. Florenz
Outdoor pool
Traumblick in die Toskana vom Landhaus mit Pool auf Hügel zw. Siena u. Florenz
9.8 out of 10, Exceptional, (27)
"This was truly a last minute-idea for us and the owners were extremely flexible and kind to let us come on such short notice. We had a nice stay, the wi-fi didn't work most of the time, but that was never a problem for us. A cozy house with a beautiful view!"
Traumblick in die Toskana vom Landhaus mit Pool auf Hügel zw. Siena u. Florenz
Paolina house, typical Tuscan structure with pool, surrounded by nature
Exterior
Paolina house, typical Tuscan structure with pool, surrounded by nature
10.0 out of 10, Exceptional, (2)
"Just perfect !"
Paolina house, typical Tuscan structure with pool, surrounded by nature
Podere le Fonti
Smart TV, fireplace
Podere le Fonti
Podere le Fonti
Casa Belvedere cottage with swimming pool in the heart of Chianti
Pool
Casa Belvedere cottage with swimming pool in the heart of Chianti
Casa Belvedere cottage with swimming pool in the heart of Chianti
Casa Antico Roseto - cottage with swimming pool
Dining
Casa Antico Roseto - cottage with swimming pool
8.0 out of 10, Very good, (1)
"The villa is lovely. The property is amazing. Check-in and out were easy and the owners are very kind. The only complaint we really had with our stay was that it is probably not the best place to stay during the summer months when it is 95+ outside. The villa has no air conditioning and even the fans they provided us did not prepare us for the heat inside even late at night. When we opened the windows we had a lot of mosquitoes and other bugs enter the house so we were forced to close up most of...
Casa Antico Roseto - cottage with swimming pool
Suite indipendent apartment located in Historic Estate from 1600
Outdoor pool
Suite indipendent apartment located in Historic Estate from 1600
10.0 out of 10, Exceptional, (25)
"Eloise is wonderful and the farm is a nice quiet get away!"
Suite indipendent apartment located in Historic Estate from 1600
Beautiful 1-bedroom cottage with garden and views over olive groves, pool
Exterior
Beautiful 1-bedroom cottage with garden and views over olive groves, pool
Beautiful 1-bedroom cottage with garden and views over olive groves, pool
Cottage "Podere in Volpaia" with Garden & Wi-Fi
Outdoor dining
Cottage "Podere in Volpaia" with Garden & Wi-Fi
10.0 out of 10, Exceptional, (3)
"Nous avons séjourné 10 jours dans cette charmante maison en Août 2023. Cristina nous a bien accueillie, la maison est très fonctionnelle, Il y a une belle terrasse couverte et un petit coin de verdure privé. La maison est entourée de vignes et d'oliviers, nous avons pu déguster l'huile et le chianti produits sur place. Cristina, la propriétaire, nous a organisé un repas et nous a fait déguster les vins de sa production. Le petit village de Radda est à 10 min en voiture, on y trouve tout ce...
Cottage "Podere in Volpaia" with Garden & Wi-Fi
Don't see what you're looking for?
See all available properties in Gaiole in Chianti
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Gaiole in Chianti

La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
Fridge, microwave, oven, stovetop
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
8.8 out of 10, Excellent, (3)
"Property is off the beaten track so very peaceful. La Luna was a little small in the kitchen lounge area for 4 people (needs another sofa). Unfortunately we had a few issues that we told the manager about at the end of our stay in the hope that they will be sorted for future visitors. We couldn’t get the tv to work (only wanted to watch Euro football finals!), dishwasher wouldn’t work and the plug sockets were a nightmare with a need for a lot more adapters or extension leads that would fit the...
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
Hu Firenze Camping In Town
Seasonal outdoor pool
Hu Firenze Camping In Town
8.8 out of 10, Excellent, (1199)
"The shuttle was extremely useful. "
The price is €88
includes taxes & fees
9 Oct - 10 Oct
Hu Firenze Camping In Town
Hu Norcenni Girasole Village
Exterior
Hu Norcenni Girasole Village
4.0 star property
8.6 out of 10, Excellent, (274)
"Great stay with the family. Not good for handicapped "
The price is €66
includes taxes & fees
1 Oct - 2 Oct
Hu Norcenni Girasole Village
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.