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Castellina in Chianti – 24 hotels and places to stay
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Hotel Palazzo Squarcialupi, hotel in Castellina in Chianti

Managed directly by the owner, Albergo Palazzo Squarcialupi is a 15th-century building in Castellina in Chianti. It offers a garden with outdoor swimming pool, and a spa.

Our room was on the first floor. Off the elevator there were still two small sets of steps to get to the room. Our room was large and overlooked the street below. Since traffic is only allowed on the street for an hour in the morning and afternoon, there was no noise. The room had a closet, safe and mini fridge. Bathroom had tub, shower and bidet. There was a spa in the basement with steam room, sauna and hot tub which I took advantage of every afternoon. The included breakfasts were fantastic. Everything you could possibly want. We ate dinner one night at the motel and it was very good. There were two restaurants across the street and multiple places to eat within easy walking distance. Also, lots of shops to explore. There is a pool which was not open when we were there.
9.1
Scored 9.1
Wonderful
Rated wonderful
652 reviews
Price from$210.44per night
Hotel Belvedere Di San Leonino, hotel in Castellina in Chianti

Surrounded by vineyards, Belvedere Di San Leonino is located in Castellina in Chianti, in the heart of the Chianti area.

Excellent location to explore Tuscany. Hotel is a very charming and updated building with spacious rooms. Staff was very friendly and the daily breakfast was plentiful providing both hot and cold food. I would book here again!
9.2
Scored 9.2
Wonderful
Rated wonderful
496 reviews
Price from$202.38per night
Hotel Colle Etrusco Salivolpi, hotel in Castellina in Chianti

Hotel Colle Etrusco Salivolpi is a recently converted farmhouse in the heart of Tuscany, near Castellina in Chianti. It is surrounded by a private garden with swimming pool and free Wi-Fi.

Beautiful place!! It’s like been inside a movie!!
9.0
Scored 9.0
Wonderful
Rated wonderful
666 reviews
Price from$141.59per night
Hotel Villa Casalecchi, hotel in Castellina in Chianti

With a pool, Villa Casalecchi is a 19th-century property 1.6 mi from Castellina in Chianti. It features free Wi-Fi and a sun terrace overlooking the vineyards and olive groves.

Our weekend retreat was so peaceful surrounded by lush greenery. Our room with a charming rustic style was cozy, clean, and had everything we needed for a comfy stay. Breakfast was good, with lots of tasty options to choose from. The gracious owner, a courteous lady who assisted us was really friendly and so nice. We'd recommend it for a relaxing getaway!
8.4
Scored 8.4
Very Good
Rated very good
226 reviews
Price from$184.13per night
Albergo Il Colombaio, hotel in Castellina in Chianti

Set in a tranquil location 328 feet from the village of Castellina in Chianti, Albergo Il Colombaio offers rustic-style rooms with free WiFi. It features an outdoor pool and a large garden.

Fantastic spot. Gorgeous old building with fantastic breakfast. In a great location - lots of restaurants and wineries very close by.
8.5
Scored 8.5
Very Good
Rated very good
127 reviews
Price from$162.37per night
Castello di Fonterutoli Wine Resort, hotel in Castellina in Chianti

Castello di Fonterutoli Wine Resort is a medieval country village in Tuscany's Chianti wine district 3.1 mi outside Castellina in Chianti. It offers a restaurant and wine cellar to visit.

Breakfast was lovely Staff are very friendly Location is beautiful Food at the bar was very good Great location to travel to San Gimignano, Siena and local vineyards
8.8
Scored 8.8
Excellent
Rated excellent
819 reviews
Price from$210per night
Villa Cristina, hotel in Castellina in Chianti

Villa Cristina is a 5-minute walk from Castellina in Chianti town center. It offers an outdoor pool and a garden. A continental breakfast is served buffet style every morning.

Beautiful, full of character old world but still completely clean, great breakfast, great staff. Beautiful location
7.9
Scored 7.9
Good
Rated good
391 reviews
Price from$106.08per night
AZ.AGR.POGGIO REGINI, hotel in Castellina in Chianti

Offering quiet street views, AZ.AGR.POGGIO REGINI in Castellina in Chianti offers accommodations, a garden, and barbecue facilities.

The property was beautiful! It was such a cool experience staying on a small family-owned farm. The family was absolutely outstanding! We highly recommend this to anyone considering a stay in Tuscany! Manuel was great with non-Italian speakers by using Google Translate. The free wine bottle from the vineyard was a great gift. The apartment was much bigger than expected, and it was very interesting to see how the family built this unit.
8.6
Scored 8.6
Excellent
Rated excellent
175 reviews
Price from$197.01per night
Castello La Leccia, hotel in Castellina in Chianti

Castello La Leccia is a restored medieval hamlet, featuring an 11th-century castle, an outdoor swimming pool, and free Wi-Fi.

The hotel exceeded all expectations! There are two buildings - main and annex, we stayed in the annex and could not wish for a better room. The room was spacious enough and had a beautiful view of the Chianti region. There is also a beautiful garden on the property with lots of seating areas to enjoy sunset with a glass of wine. The restaurant had a wonderful menu with daily specials and selection of wine produced at the property. There is also a wine tasting option available for hotel guests (highly recommended!) The staff were attentive enough and not bothersome, which we really appreciated. The location was perfect - between Florence and Siena - with about an hour drive in each direction, which allowed us to explore different regions. This is a truly romantic and tranquil place for a perfect getaway. If I could give this place 100/10, I would!
9.7
Scored 9.7
Exceptional
Rated exceptional
341 reviews
Price from$310.68per night
Villa Di Capovento, hotel in Castellina in Chianti

Set in the Chianti area, in the middle of the Tuscan countryside, Villa Di Capovento is an antique stone villa with outdoor pool. It is a 30-minute drive from Siena.

The hosts were very friendly and provide a great service to their customers. They cooked for us and were accommodating to any request you may have. The rooms were spacious and clean. The property itself is located on top of a hill overlooking the hills of Tuscany. In warmer weather the use of the pool would be a lot of fun. I would recommend Villa Di Capovento to anyone who is considering stay at an Agriturismo.
9.8
Scored 9.8
Exceptional
Rated exceptional
124 reviews
Price from$387.53per night
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What Guests Said About Castellina in Chianti:

  • 10
    Scored 10

    Quiet hill town with lots of amenities.

    Quiet hill town with lots of amenities. Well located to visit other towns if you are willing to drive. Pay VERY close attention to the information sent by the hotel about luggage drop off and pick up. Steep fines for driving into the old town if not done per instructions and timing.
    Tom Snyder
    United States of America
  • 10
    Scored 10

    I made a mistake with my comment about the car park.

    I made a mistake with my comment about the car park. There is good access and plenty of parking spaces. I muddled up my comments about another location. Castellina is a lovely town with some history and good places to eat.
    graham
    United Kingdom
  • 10
    Scored 10

    We loved the location, amazing scenery and ambience of the...

    We loved the location, amazing scenery and ambience of the property. It is an authentic rural family owned winery originally owned by Host’s grandparents. Excellent personal service is also a standout plus the split level room is very spacious and comfortable. Highly recommended.
    Mae
  • 10
    Scored 10

    Walking round the Tuscan vineyards is an amazing way to see...

    Walking round the Tuscan vineyards is an amazing way to see the local area. We walked around Castellina, Radda,. Giaole, Volpaie, San Gimignano, Volterra and Badia a Passignano. All fabulous walks - don’t forget to stop for coffee when you can, to sit and watch the world go by. Florence and Siena are a short distance away too and we’ll worth visiting - enjoy!
    Tina
    United Kingdom
  • 10
    Scored 10

    The location in the countryside was excellent.

    The location in the countryside was excellent. Plenty of room for parking, somebody always on duty at reception & beautiful large room with very spacious bathroom. Choice of either A La Carte or Set Menu & the food was excellent paired with local Chianti of course. Downtime can be spent at the pool & indulge in some wine tasting from their large stock on site. Had a free wine tasting in Castellina the following morning from a very informative host. The hotel is surrounded by local vines which just adds to the atmosphere of the area. Staff always available & always helpful. Sad to leave after a lovely breakfast with plenty of choices in the morning but must return for longer on our next trip now that we have found such a star offering.
    Donal Mc
    Ireland
  • 10
    Scored 10

    This was one of, if not, the best stay in recent memory.

    This was one of, if not, the best stay in recent memory. For anyone, or any couple, looking for a quiet getaway in one of the most beautiful villa’s in Tuscany, this is your place. Villa Di Capovento is even more beautiful in person than it is in pictures: the grounds are beautiful, the pool is amazing/incredibly relaxing and the rooms are spacious, air conditioned (!) and some even come with their own jacuzzi. The only thing that was more impressive than the Villa itself was the unmatched care that Stella, Ettore and Nerina (their cat) took of us on our entire stay. They were incredibly caring to all needs, flexible in setting up wine tastings/motor bikes for us to get around, and easily accessible for anything related to the room. Ettore even went the extra mile and drove to pick us up at a nearby winery when one of our bike tires went flat. On top of the beautiful grounds and the incredibly caring staff, we had the best food on our entire trip (Amalfi, Tuscany, Milan) at Villa Di Capovento. We will absolutely be back next year and hopefully for many years to come
    Gaelyn

Explore guest reviews of hotels in Castellina in Chianti

  • 9.1
    Scored 9.1
    Wonderful
    Rated wonderful
     · 653 reviews
    What a wonderful hotel, right in the heart of Castellina in Chianti! The staff were extremely helpful and polite. Our rooms were large and comfortable. We had a view onto the main street in the village, but it was very quiet despite the activity right below us. The breakfast buffet was amazing, as was the terrace view while eating it! It was very near great restaurants and bars, and provided parking for our car. I would definitely stay here again when in Chianti!
    Tiffynyc
    United States of America
  • 9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 54 reviews
    Beautiful apartment with view from the terrace over vineyards and the countryside of the Chianti Classico region. There is a small pool where we relaxed after our excursions. The owners make their own excellent organic wine and offer wine tastings. The apartment is easily accessible via a well maintained unpaved road and a perfect location for trips to Siena, San Gimignano, Rada and of course Castellina in Chianti.
    Peter
    Germany
  • From $175.36 per night
    9.3
    Scored 9.3
    Wonderful
    Rated wonderful
     · 282 reviews
    The property is owned by a hotel down the street and also own a winery there. The apartment was absolutely adorable! We had a second floor with our balcony overlooking the beautiful hills of Vineyards! We enjoyed it so much that we cooked dinner there the 2out of 3 nights we stayed. We were able to enjoy the sunset while enjoying our dinner. A small coop store was within a 10 minute walk.
    Deborah
    United States of America
  • From $379.96 per night
    9.3
    Scored 9.3
    Wonderful
    Rated wonderful
     · 296 reviews
    A lovely hotel in the middle of luscious Tuscan hills with clean and comfortable rooms. The staff were always extremely kind and attentive to detail. As a bonus, the hotel has a top notch restaurant where we got to enjoy a 7-course degustation menu which was exquisite. There is also a spa and pool which we did not have time to enjoy so this will provide a nice excuse to return.
    Melanie
    Malta
  • From $107.17 per night
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 189 reviews
    Very quiet in the middle of Tuscanys nature, yet only 10min drive to Castellina in Chianti with wine bars, ristorante and small shops. La Fiaba is a lovely stonehouse with a garden where you can relax. The host Simone gave us a warm welcome and tipps to explore the Chianti region. The room was big and clean. We would definitely come again!
    Verena
    Germany
  • From $180.56 per night
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 666 reviews
    Location, location, location! Wonderful hotel and location for exploring Chianti. The town of Castellina is small, quaint, yet filled with restaurants. loved being able to walk to dinners in the evening Their staff is so welcoming, the grounds beautiful and a nice breakfast in the morning.
    Jamie
    United States of America
  • From $324.75 per night
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 819 reviews
    The location was exactly what we were looking for, a calm and vintage villa-style hotel in the heard of the Chianti region. Excellent breakfast and very friendly staff. We particularly enjoyed dinner at the Osteria, where we were able to taste local wine and meals.
    Cesar
    Colombia
  • 9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 385 reviews
    The owners are really nice, the breakfast was very good (especially the warm croissants), the rooms are really new and super comfortable. I also really liked the location close to Castellina in Chianti with some nice views of the wineyards. We loved our stay!
    Michael
    Austria
  • From $175.36 per night
    9.3
    Scored 9.3
    Wonderful
    Rated wonderful
     · 282 reviews
    Great Air conditioning, very welcoming and friendly staff throughout, wonderful restaurant at the hotel 5 minutes walk away and discount card supplied. Amazing view in a wonderful area. Everything we needed was within walking distance.
    Sue
    United Kingdom
  • From $187.27 per night
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 233 reviews
    Beautiful stay in the Colle Lungo vineyard and their Chianti, Campocerchi 2019, was the best Chianti we tasted throughout the Chianti region. The pool is an added bonus in the hot summer months! Fabiola was very helpful.
    Raymond
    United States of America
  • From $108.25 per night
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 227 reviews
    The location is amazing! It's a short walk to restaurants and wine bars allowing you to experience Castellina in Chianti. Host Serena is lovely and very accommodating. There was free parking also available .
    Nick
    Australia
  • From $324.75 per night
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 819 reviews
    Our stay was wonderful, the personnel both in the hotel, restaurant or in the winery was very friendly. I was supposed to spend one night and we ended up extending our stay as we loved the place.
    Roberta
    France
  • From $107.17 per night
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 189 reviews
    The host is the nicest host we met in Italy. He was informative, good English speaker, he helped us with restaurants names and wineries in the area. The room was clean and smelled good.
    Tahel
    Israel
  • 9.1
    Scored 9.1
    Wonderful
    Rated wonderful
     · 653 reviews
    Friendly staff (although not always responsive via Booking messaging before the stay). Nice location, large parking space for hotel guests, decent room, good restaurant.
    Lars Christian
    Sweden
  • From $333.41 per night
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 341 reviews
    A beautiful hotel in a lovely setting with incredible views. Very friendly and professional staff. Recently restored so in exceptional condition. Lovely wine your.
    James
    United Kingdom
  • From $244.21 per night
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 496 reviews
    The antica style of the hotel, cleanliness, surrounding breathtaking nature and vine yards. Breakfast was delicious with very good variety.
    Mai
    Saudi Arabia
  • From $206.76 per night
    8.4
    Scored 8.4
    Very Good
    Rated very good
     · 226 reviews
    The history, setting and charm. The staff were exceptionally friendly. This was my third stay at this hotel.
    David
    United States of America
  • From $244.21 per night
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 496 reviews
    beautiful little hotel in the heart of Chianti with lots of lovely wines to try and buy
    Peter
    United Kingdom
  • From $379.96 per night
    9.3
    Scored 9.3
    Wonderful
    Rated wonderful
     · 296 reviews
    Locanda Le Piazze is a beautiful property and a wonderful place to relax!
    Rhonda
    United States of America
  • 9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 385 reviews
    beautiful hotel in a beautiful location.
    Heather
    United States of America