Search Castles in Chianti Region from CA $186

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Browse Select Chianti Region Castles

Castello Di Montemasso
Interior entrance

Castello Di Montemasso

10.0 out of 10, Exceptional, (4)
"This place was awesome. I travel a lot and this place was just a hidden gem. I am scared to give give it five stars because everyone will start discovering and I want to book for next fall or spring. The breakfast was excellent. Only 8 rooms. Overlooks Florence. The hosts were so nice. The host recommend a restaurant for in a small Villiage the first night. The steak Florentino in the village blew the steak in Florence away. We went for a quick weekend trip to watch MotoGP race. After...
The price is CA $186
CA $206 total
includes taxes & fees
Aug 6 - Aug 7
Castello Di Montemasso
Loft Castello e colline
Property grounds

Loft Castello e colline

10.0 out of 10, Exceptional, (1)
"We had a truly great time at this castle. It was everything we had hoped for during our stay. The castle is updated while keeping a lot of it's original charm. Driving to it was so scenic, with tons of green rolling hills to drive through and an olive tree lined path just before you get to the castle. It is not very far from Siena. And the church bells from the clock tower were very relaxing. Highly recommended."
Loft Castello e colline
Castle of Volognano
Outdoor dining

Castle of Volognano

10.0 out of 10, Exceptional, (35)
"Property is stunning and hosts and property manager are very kind. "
Castle of Volognano
Medieval Castle 15 km from Florence, in the heart of "Chianti Classico" region
Exterior

Medieval Castle 15 km from Florence, in the heart of "Chianti Classico" region

10.0 out of 10, Exceptional, (23)
"Giovanni and his crew were everything we could have wanted and more. This place was incredible. We stayed here and had our wedding here and it was one of the best trips. Everything was very clean and organized. We loved everything about this place. We will definitely be back."
Medieval Castle 15 km from Florence, in the heart of "Chianti Classico" region
Stunning private Castle 9 BR - 8 BA with pool just 7 miles from Florence!
Outdoor pool

Stunning private Castle 9 BR - 8 BA with pool just 7 miles from Florence!

10.0 out of 10, Exceptional, (6)
"We stayed here on a family vacation and had a fantastic time. The location is perfect. Only 30 minutes from Florence but feels nice and relaxing. The castle is charming with lots of interesting and beautiful features. The staff was superb in catering to our every need. We could not have asked for better. We definitely recommend staying here and would go back in a heartbeat (and will)!"
Stunning private Castle 9 BR - 8 BA with pool just 7 miles from Florence!
charming castle apartement with glorious views
Interior

charming castle apartement with glorious views

9.6 out of 10, Exceptional, (48)
"My boyfriend and I had the best time here. It’s such a perfect place in the best location. And the rooftop patio Is unbelievable.We’ll definitely stay there again."
charming castle apartement with glorious views
Panoramic castle with large pool on the walls. Ideal for weddings and events
Dining

Panoramic castle with large pool on the walls. Ideal for weddings and events

9.4 out of 10, Exceptional, (3)
"Wir hatten eine tolle Zeit und haben unseren Aufenthalt sehr genossen. Die Lage ist einzigartig und das Castello hat uns sehr gut gefallen."
Panoramic castle with large pool on the walls. Ideal for weddings and events
Montegufoni 23 - Apartment with swimming pool
Outdoor dining

Montegufoni 23 - Apartment with swimming pool

9.6 out of 10, Exceptional, (16)
"We loved our stay here. The castle is gorgeous, the rooms and the pool area is great, and the receptionists are very kind and helpful. We recommend this place to everyone, and will for sure come back👍 Thank you for wonderful days!"
Montegufoni 23 - Apartment with swimming pool
Beautiful apartment for 6 guests with WIFI, pool, panoramic view and parking
Outdoor dining

Beautiful apartment for 6 guests with WIFI, pool, panoramic view and parking

8.8 out of 10, Excellent, (23)
"It is a very beautiful castle with lovely scenic views. We were there in June. The rooms were very spacious and nice. It is very accessible to other towns in Tuscany. The staff was very helpful throughout our stay. The only problem we had was the mosquitoes. We had our windows shut throughout the nights although a few managed to come through..otherwise everything else was great!"
Beautiful apartment for 6 guests with WIFI, pool, panoramic view and parking
Montegufoni 34 - Apartment with swimming pool
Outdoor dining

Montegufoni 34 - Apartment with swimming pool

9.0 out of 10, Wonderful, (9)
"Majestic castle in the toscanian landscape with a very nice staff"
Montegufoni 34 - Apartment with swimming pool
Villa Osbert - Villa with shared pool
Outdoor dining

Villa Osbert - Villa with shared pool

9.2 out of 10, Wonderful, (30)
"Lugar muito agradável!"
Villa Osbert - Villa with shared pool
Lovely apartment for 6 people with pool, A/C, WIFI, panoramic view and parking
Outdoor dining

Lovely apartment for 6 people with pool, A/C, WIFI, panoramic view and parking

9.4 out of 10, Exceptional, (36)
"This was a real fantastic place to spend a couple weeks."
Lovely apartment for 6 people with pool, A/C, WIFI, panoramic view and parking
Castello di Mugnana
Porch

Castello di Mugnana

9.6 out of 10, Exceptional, (22)
"Stayed in third floor tower panorama room and views were STUNNING"
Castello di Mugnana
Cosy apartment for 5 people with pool, WIFI, A/C, terrace, panoramic view and parking
Outdoor dining

Cosy apartment for 5 people with pool, WIFI, A/C, terrace, panoramic view and parking

9.2 out of 10, Wonderful, (5)
"Very nice, large apartment in the castle with beatiful terrace."
Cosy apartment for 5 people with pool, WIFI, A/C, terrace, panoramic view and parking
Montegufoni 4 - Apartment with swimming pool
Outdoor dining

Montegufoni 4 - Apartment with swimming pool

9.6 out of 10, Exceptional, (28)
"Great location and a good restaurant with very helpful and friendly staff"
Montegufoni 4 - Apartment with swimming pool
Montegufoni 18 - Apartment with swimming pool
Outdoor dining

Montegufoni 18 - Apartment with swimming pool

9.6 out of 10, Exceptional, (8)
"Simply bellissimo and great Italian food at the restaurant."
Montegufoni 18 - Apartment with swimming pool
Beautiful apartment for 8 people with pool, WIFI, A/C, veranda, panoramic view and parking
Outdoor dining

Beautiful apartment for 8 people with pool, WIFI, A/C, veranda, panoramic view and parking

8.8 out of 10, Excellent, (15)
"Posto molto bello, appartamento confortevole. Unico appunto, la reception praticamente sempre chiusa. [English translation courtesy of Easy Reserve] Very nice place, comfortable apartment. Only note, the reception practically always closed."
Beautiful apartment for 8 people with pool, WIFI, A/C, veranda, panoramic view and parking
Beautiful apartment for 6 guests with pool, WIFI, A/C, panoramic view and parking
Outdoor dining

Beautiful apartment for 6 guests with pool, WIFI, A/C, panoramic view and parking

9.4 out of 10, Exceptional, (18)
"We stayed there for a week and and were quite fascinated: The castle is set in a wondeful landscape. The pool is nice, the restauarnt was great. Check - in and chek-out were without problems. The appartment was nice. You definetly need a car - but then Florence, Siena and Pisa are within easy reach."
Beautiful apartment for 6 guests with pool, WIFI, A/C, panoramic view and parking
Montegufoni - Montegufoni 19b
Outdoor dining

Montegufoni - Montegufoni 19b

Montegufoni - Montegufoni 19b
Montegufoni 8 - Apartment with swimming pool
Outdoor dining

Montegufoni 8 - Apartment with swimming pool

10.0 out of 10, Exceptional, (11)
"excellent stay. totally recommend it! will come back."
Montegufoni 8 - Apartment with swimming pool
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 Chianti Region Hotel Reviews

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

10/10 Excellent
"Great afternoon by the pool. Evening meal menu was odd. I think the chef was trying too hard to be different. The vegetarian chick pea dish was merely a bowl of cooked onions with some vegetable mush- my wife called it baby food. The chicken with truffles was tasty although came with flabby chicken skin. Breakfast was amazingly good in comparison. We had a room with a view of a 6 foot tall hedge, beyond the hedge was a fantastic view of Tuscany we couldn’t see, really strange. Staff were very good, the pool pleasingly cold and refreshing. Good but not a great stay."
Anonymous traveller 1-night trip
Posted 3 days ago
Hotel Borgo di Cortefreda Relais