Title: Book the Best Castellina in Chianti LUXURY Hotels - Upscale Hotels in Castellina in Chianti | Expedia.ca [Castellina in Chianti Travel Guide](https://expedia.ca/Castellina-In-Chianti.dx55534)[Hotels in Castellina in Chianti](https://expedia.ca/Castellina-In-Chianti-Hotels.d55534.Travel-Guide-Hotels)[Vacation Rentals in Castellina in Chianti](https://expedia.ca/Castellina-In-Chianti-Vacation-Rentals.d55534.Travel-Guide-VacationRentals)[Flights to Castellina in Chianti](https://expedia.ca/Cheap-Flights-To-Castellina-In-Chianti.d55534.Travel-Guide-Flights)[Castellina in Chianti Car Rentals](https://expedia.ca/Car-Rentals-In-Castellina-In-Chianti.d55534.Car-Rental-Guide)[Castellina in Chianti Vacation Packages](https://expedia.ca/Castellina-In-Chianti.d55534.Destination-Travel-Guides) ![Castellina in Chianti showing heritage architecture, religious elements and a church or cathedral](https://images.trvl-media.com/place/55534/68deebc9-9310-492d-8f83-85d906ba54aa.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/55534/68deebc9-9310-492d-8f83-85d906ba54aa.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Castellina in Chianti Luxury Hotels Tonight [Jan 31 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=55534&startDate=2026-01-31&endDate=2026-02-01&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Feb 1 - Feb 2](https://www.expedia.ca/Hotel-Search?regionId=55534&startDate=2026-02-01&endDate=2026-02-02&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=55534&startDate=2026-02-06&endDate=2026-02-08&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=55534&startDate=2026-02-13&endDate=2026-02-15&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for Castellina in Chianti luxury hotels ![Exterior](https://images.trvl-media.com/lodging/4000000/3560000/3556600/3556560/bc613474.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/4000000/3560000/3556600/3556560/78e0602e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3560000/3556600/3556560/w2048h1317x0y48-09a38abb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/4000000/3560000/3556600/3556560/58e19d9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Locanda le Piazze [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Locanda-Le-Piazze.h3556560.Hotel-Information) Castellina in Chianti 9.8/10 Exceptional (183 reviews) "Great place to stay!! Plenty of vineyards and towns close by! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Conor [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Locanda-Le-Piazze.h3556560.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-14&endDate=2026-02-15®ionId=55534&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Top Castellina in Chianti Hotel Reviews ![Grand Hotel Baglioni](https://images.trvl-media.com/lodging/1000000/10000/6400/6371/849fb031_y.jpg) ### Grand Hotel Baglioni 10/10 Excellent "Amazing hotel! Centrally located, very nice room and staff is great! Breakfast is the perfect place to begin your day with the incredible views and a good pizza place right across the street. " [](https://expedia.ca/Florence-Hotels-Grand-Hotel-Baglioni.h6371.Hotel-Information) ![Hotel Albani Firenze](https://images.trvl-media.com/lodging/1000000/30000/26000/25903/a7e1bd67_y.jpg) ### Hotel Albani Firenze 10/10 Excellent "Spotless staff great breakfast super" [](https://expedia.ca/Florence-Hotels-Hotel-Albani-Firenze.h25903.Hotel-Information) ![Bernini Palace](https://images.trvl-media.com/lodging/1000000/20000/14000/13999/84743cc7_y.jpg) ### Bernini Palace 10/10 Excellent "spotlessly clean room amazing staff fantastic breakfast " [](https://expedia.ca/Florence-Hotels-Bernini-Palace.h13999.Hotel-Information) ![The Market Urban Hotel](https://images.trvl-media.com/lodging/1000000/110000/108100/108028/7e915af7_y.jpg) ### The Market Urban Hotel 10/10 Excellent "Super clean room, great location, friendly staff and lots of toiletries in the vanity kit that came in handy. Would recommend!" [](https://expedia.ca/Florence-Hotels-The-Market-Urban-Hotel.h108028.Hotel-Information) ![Hotel De La Ville](https://images.trvl-media.com/lodging/1000000/30000/21500/21408/85f0ef28_y.jpg) ### Hotel De La Ville 10/10 Excellent "The room was very clean and decorated in an elegant, classic palace style that I really liked. The staff were kind, attentive, and very helpful throughout my stay, making the whole experience comfortable and welcoming." [](https://expedia.ca/Florence-Hotels-Hotel-De-La-Ville.h21408.Hotel-Information) ![c-hotels Ambasciatori](https://images.trvl-media.com/lodging/1000000/10000/1900/1829/bddb8fbc_y.jpg) ### c-hotels Ambasciatori 10/10 Excellent "Very convenient " [](https://expedia.ca/Florence-Hotels-C-Hotels-Ambasciatori.h1829.Hotel-Information) ![Grand Hotel Cavour](https://images.trvl-media.com/lodging/1000000/20000/11000/10993/50470bbc_y.jpg) ### Grand Hotel Cavour 10/10 Excellent "great experience - highly recommend!" [](https://expedia.ca/Florence-Hotels-Grand-Hotel-Cavour.h10993.Hotel-Information) ![Solo Experience Hotel](https://images.trvl-media.com/lodging/3000000/2540000/2533900/2533892/2466c367_y.jpg) ### Solo Experience Hotel 10/10 Excellent "This is by far one of the best international stays I have had. I cannot state how AMAZING the staff was. Rooms were clean and spacious as well as a great location for walking and to the train station. I am already looking at going back just to visit the staff !!!" [](https://expedia.ca/Florence-Hotels-Solo-Experience-Hotel.h2533892.Hotel-Information) ![Hotel Spadai](https://images.trvl-media.com/lodging/11000000/10450000/10447300/10447242/14e556c2_y.jpg) ### Hotel Spadai 10/10 Excellent "Very clean, great size and well maintained room with staff attending to it promptly. " [](https://expedia.ca/Florence-Hotels-Hotel-Spadai.h10447242.Hotel-Information) ## Frequently asked questions ### What are the top-rated luxury hotels in Castellina In Chianti? > The 4-star Locanda le Piazze, with a 9.8 rating, is frequently praised by guests for its beautiful pool and spacious rooms. The on-site winery and garden-view restaurant are also great features, complemented by excellent food and service. > > > Belvedere di San Leonino, a 4-star hotel rated 9.6, offers a warm welcome with its friendly and wonderful staff. Guests often praise the cosy, clean rooms and the excellent food served at its garden-view restaurant. It also features an on-site winery and vineyard views. > > > The 4-star Palazzo Squarcialupi, also with a 9.8 rating, provides wellness experiences with a full-service spa, sauna, steam room, and hot tub. Its Beaux-Arts design and lovely garden and pool are frequently highlighted by guests, alongside the helpful staff and good breakfast. ### Which area of Castellina In Chianti is best to stay in for luxury hotels? > Guests seeking high-end accommodations will find many excellent options located in the rolling hills surrounding the main village. These hotels often feature their own vineyards, olive groves, and offer a peaceful escape with stunning vistas of the Tuscan countryside. You'll typically find them a short drive from the town's main road, Via Ferruccio, which is lined with small shops and eateries. > > > This setting is particularly well-suited for couples looking for a romantic and private getaway. The luxury hotels here often provide amenities like fine dining restaurants, spas, and infinity pools, making them ideal for unwinding after a day of exploring. ### How much does a luxury hotel in Castellina In Chianti cost? ### Which luxury hotels in Castellina In Chianti are good for families? > The 4-star Villa Casalecchi Country Hotel, with a 9.2 rating, offers an outdoor pool with sun loungers, making it suitable for families. Room service and air conditioning are also provided for guest comfort. > > > Belvedere di San Leonino, a 4-star hotel rated 9.6, features an onsite winery and a restaurant with garden views. Customers frequently praise the friendly and wonderful staff, the cosy and clean rooms, and the excellent food and great service provided, making it a pleasant stay for families. > > > The 4-star Hotel Casafrassi Wine Resort, with an 8.2 rating, offers a complimentary local breakfast and a restaurant with garden views. Its Beaux-Arts property design and onsite winery add to its unique character, alongside premium bedding and resort-inclusive housekeeping. > > > Palazzo Squarcialupi, a 4-star property with an outstanding 9.8 rating, boasts an onsite winery and a full-service spa with a sauna, steam room, and hot tub. Reviewers consistently highlight the friendly and helpful staff, the good breakfast, and the lovely garden and pool areas, which are beneficial for families. ### What are the best luxury hotels in Castellina In Chianti with a pool? > The 4-star Locanda le Piazze, with an exceptional 9.8 rating, features a beautiful pool complemented by a poolside bar and a garden view restaurant. Customers frequently praise the fantastic food and the spacious rooms. > > > The 4-star Belvedere di San Leonino, rated 9.6, offers both an outdoor and a seasonal outdoor pool. This hotel is praised for its friendly and wonderful staff, cosy and clean rooms, and excellent food, with an on-site winery. > > > Hotel Casafrassi Wine Resort, a 4-star property with an 8.2 rating, provides a seasonal outdoor pool and a resort-inclusive pool. Guests benefit from complimentary local breakfast and premium bedding within a Beaux-Arts property design. > > > The 4-star Palazzo Squarcialupi, also with a 9.8 rating, boasts a lovely seasonal outdoor pool. Reviewers often highlight the helpful staff, good breakfast, and the hotel's on-site winery, along with a full-service spa. > > > Villa Casalecchi Country Hotel, a 4-star establishment rated 9.2, offers both an outdoor pool and sun loungers, alongside a seasonal outdoor pool. ### Which luxury hotels in Castellina In Chianti are good for couples? > The 4-star Locanda le Piazze, with an exceptional 9.8 rating, offers an onsite winery and a poolside bar, ideal for romantic evenings. Many guests have praised the spacious rooms and the beautiful pool, alongside the fantastic food and great service provided by the staff. ### What luxury activities and experiences are there in Castellina In Chianti? > For couples, a private wine tour of a prestigious estate like Castello di Fonterutoli offers an intimate and educational experience. You'll often have a dedicated guide, access to exclusive cellars, and a tasting of their finest vintages, sometimes including rare library wines, paired with local cheeses and cured meats. Many estates also offer cooking classes focusing on traditional Tuscan cuisine, which can be a fun and romantic activity to do together. > > > Gourmet dining is another highlight. Restaurants such as Badia a Coltibuono or La Botte di Bacco provide exceptional culinary journeys, often featuring tasting menus that showcase seasonal, local ingredients paired with an extensive selection of Chianti Classico wines. These establishments frequently offer outdoor dining with stunning views of the rolling vineyards, great for a special occasion. > > > For those interested in local culture and history, arranging a private guided tour of Siena or Florence from Castellina In Chianti is highly recommended. ### How can I save on a luxury hotel in Castellina In Chianti with Expedia? ### Is it cheaper to book a luxury Castellina In Chianti hotel and flights as a package? ### Can I cancel my luxury hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [5 Star Hotels in Chianti Region ](https://www.expedia.ca/5Star-Chianti-Region-Hotels.s50-0-d603148.Travel-Guide-Filter-Hotels) - [Hotels near Castello di Monsanto ](https://www.expedia.ca/Castello-Di-Monsanto-Hotels.0-l6230523-0.Travel-Guide-Filter-Hotels) - [Hotels near Castello di Radda Winery ](https://www.expedia.ca/Castello-Di-Radda-Winery-Hotels.0-l553248621532501476-0.Travel-Guide-Filter-Hotels) - 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