Castellina in Chianti Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €185 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Castellina in Chianti

Price found within the past 48 hours. Click for updated prices.
Hotel Villani
Palazzo Firenze by Baglioni Hotels & Resorts
Hotel Franchi
Grand Hotel Cavour
Hotel Santa Maria Novella

Things to do near Castellina in Chianti

Castellina in Chianti is perfect for a romantic getaway, offering a blend of outdoor adventures and entertainment. Visitors can indulge in spa treatments, enjoy local theatre performances, and explore the stunning landscapes through cycling and hiking tours. Additionally, a trip through the picturesque Chianti region is a must for those seeking to experience the beauty and charm of Tuscany.

Shopping

In Castellina in Chianti, enjoy charming local boutiques filled with artisan crafts and wine. If you're up for a drive, The Mall Luxury Outlet, 29.0km away, and Conte of Florence Factory Outlet, 41.8km away, offer a broader shopping experience with various brands.

Recreation

Explore the Palasport Mens Sana for a vibrant sports atmosphere, located 16.1km from Castellina in Chianti. Alternatively, visit the Chianti Observatory, just 6.4km away, where you can enjoy family-friendly entertainment and marvel at the night sky.

Adventure

The Sentierelsa Trail, located 12.9km from Castellina in Chianti, offers stunning outdoor scenery for hiking enthusiasts. For a thrilling experience, visit Saltalbero Adventure Park, 32.2km away, where you can zipline through the trees. Finally, enjoy the natural beauty at Biolago Geotermico Acqua Harda, situated 48.3km from the town.

Nightlife

Experience the charming nightlife of Castellina in Chianti at Il Fiaschetto, a delightful drinking pub located 25.7km away. With its romantic ambiance and lively entertainment, it's the perfect spot to unwind and enjoy the local vibe after a day of exploration.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Castellina in Chianti

Castellina in Chianti offers a delightful blend of romance and outdoor activities, perfect for an entertaining getaway. Visitors can explore charming churches, picturesque piazzas, and historic castles while immersing themselves in the local culture. Notable attractions include stunning villas, renowned Chianti wineries, and the impressive Castellina fortress, making it an ideal destination for those seeking a rich city experience in the enchanting Chianti region.

  • Monteriggioni Castle: This enchanting historic castle, located 9.7km from Castellina in Chianti, offers a unique glimpse into the past with its well-preserved medieval walls and stunning views of the Chianti landscape. Explore its charming streets and immerse yourself in the rich culture that permeates this ancient site.
  • Castello di Radda Winery: Situated 8.0km away, this romantic winery is housed in a picturesque castle setting, perfect for wine enthusiasts. Enjoy guided tours and tastings while learning about the region's winemaking traditions amidst breathtaking vineyards.
  • Medieval Criminal and Torture Museum: Located 19.3km from Castellina in Chianti, this museum offers a fascinating yet unsettling exploration of medieval justice. Discover the chilling instruments of torture and delve into the darker aspects of history that shaped society.

Best time to go to Castellina in Chianti

The best time to visit Castellina in Chianti can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Castellina in Chianti falls in July, when visitor numbers are slightly high and weather is sunny with no rain. The coolest average temperature in Castellina in Chianti falls in January, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January40.8°F (4.9°C)Light RainMostly SunnyAverageSlightly Low
February42.8°F (6.0°C)Light RainMostly SunnyAverageSlightly Low
March47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
April54.0°F (12.2°C)Light RainMostly SunnySlightly HighAverage
May60.4°F (15.8°C)Light RainMostly SunnyAverageSlightly High
June69.8°F (21.0°C)Light RainSunnyAverageSlightly High
July75.9°F (24.4°C)No RainSunnySlightly HighAverage
August75.6°F (24.2°C)No RainSunnySlightly HighAverage
September67.1°F (19.5°C)Light RainMostly SunnyAverageSlightly High
October58.5°F (14.7°C)Light RainMostly SunnySlightly LowAverage
November50.0°F (10.0°C)Light RainMostly SunnySlightly LowSlightly Low
December43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage

Tips to save on your trip to Castellina in Chianti

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Castellina in Chianti during the low season (January to February and November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Top hotels in Castellina in Chianti

c-hotels Ambasciatori

c-hotels Ambasciatori

4 out of 5
Via Luigi Alamanni 3 Florence FI
Fully refundableReserve now, pay when you stay
The price is €126 per night from 22 Feb to 23 Feb
€126
22 Feb - 23 Feb
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
It was amazing and clean and really really perfect

Reviewed on 17 Feb 2026

c-hotels Ambasciatori
IQ Hotel Firenze

IQ Hotel Firenze

4 out of 5
Via Camillo Cavour, 88 Florence FI
Fully refundableReserve now, pay when you stay
The price is €103 per night from 22 Feb to 23 Feb
€103
22 Feb - 23 Feb
includes taxes & fees
9.6/10 Exceptional! (1,156 reviews)
The hotel was very nice. The staff was very nice, very clean, very cozy. Just a beautiful hotel.

Reviewed on 15 Feb 2026

IQ Hotel Firenze
Bernini Palace

Bernini Palace

5 out of 5
Piazza San Firenze 29 Florence FI
Fully refundableReserve now, pay when you stay
The price is €257 per night from 26 Feb to 27 Feb
€257
26 Feb - 27 Feb
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
Hotel was AMAZING! Staff is welcoming and extremely helpful! Located right in the city center, walkable to all sights and museums! Room was spotless and comfortable!! Breakfast was delicious with so many options!! Highly recommend!!

Reviewed on 16 Feb 2026

Bernini Palace
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.

What to do in Castellina in Chianti

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.