Name: Hotel Borgo di Cortefreda Relais
Price range: $171 total
Rating: 9.2

Your Chianti Region Vacation

Lock in a vacation package to Chianti Region and enjoy what it means to travel on your own terms. You'll be charmed by its walking trails, cycling and views. Start your trip to Chianti Region with some time exploring San Gimignano visiting popular attractions like Medieval Criminal and Torture Museum and Piazza Duomo. Gaiole in Chianti is another city that draws travelers from near and far. Castello di Albola and Meleto Castle are two of the leading places to see in this destination. If you're ready to stop dreaming and start traveling, Expedia will help turn your Chianti Region vacation into reality.

The Latest Chianti Region vacation packages

Price found within the past 48 hours. Click for updated prices.

Aurum Uffizi

Historic Centre of Florence

Save 100% on your flight

$702

per person

Oct 31 - Nov 4

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

7.8/10 Good! (1,000 reviews)

Our stay was lovely, very comfortable, small but good choice of breakfast. Beds were comfy and room was clean when we arrived and cleaned everyday. I would only suggest maybe for a shower curtains as when we had a shower the bathroom floor would be all wet, but easily to clean. And just a note on how to use the phone if we need to call reception but overall the hotel facilities and the staff were brilliant if i could give more then 5 stars i would.

Reviewed on Aug 19, 2025

Palazzo Firenze by Baglioni Hotels & Resorts

Historic Centre of Florence

$9,312

per person

Oct 6 - Oct 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.4/10 Exceptional! (230 reviews)

I VERY MUCH ENJOYED THE STAY

Reviewed on Jul 18, 2025

The Moon Boutique Hotel & Spa

Historic Centre of Florence

Save 100% on your flight

$723

per person

Oct 30 - Nov 4

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.6/10 Exceptional! (462 reviews)

The hotel is located a 25 min walk away from the heart of Florence so very easy to access the main attractions within the city. The hotel itself is immaculate and the staff are extremely helpful with dealing with any questions you may have. Being able to access the spa everyday for 1 and 30 minutes is an excellent perk as the facilities are well worth a visit, you are also able to book massages for an extra fee. The breakfast also gives a variety of options to start each day and the room itself is spacious, with the shower particularly being very comfortable.

Reviewed on Aug 13, 2025

Aurum Firenze

Historic Centre of Florence

Save 100% on your flight

$1,008

per person

Sep 26 - Oct 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

7.6/10 Good! (1,007 reviews)

Great location. Few minutes away from train station. Not so quiet. You could hear people from outside even the windows closed. If you are staying for a few days, it’s a great location.

Reviewed on Aug 14, 2025

Collegio alla Querce - Auberge Resorts

Le Cure

Save 100% on your flight

$2,683

per person

Oct 14 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Florence (FLR)

10/10 Exceptional! (2 reviews)

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Discover the most popular places to visit in Chianti Region

Castello di Meleto, Gaiole in Chianti, Tuscany

Meleto Castle

Find out about the history of Gaiole in Chianti when you spend time at Meleto Castle. Discover the beautiful countryside in this walkable area, or enjoy its local tours.

Antinori nel Chianti Classico

You can enjoy a tasting or tour at Antinori nel Chianti Classico during your travels to Bargino. Check out the churches and wineries in this walkable area.

The Mall Luxury Outlet

During your visit to Reggello, you can search for that perfect souvenir at The Mall Luxury Outlet. Discover the acclaimed art scene and stunning cathedral in this walkable area.

What to do in Chianti Region

Tuscany Wine Tour : 2 Wineries & San Gimignano from Florence

$221

per adult

100% of travellers recommend

Chianti Wineries Tour with 7 Wine Tastings from Florence

$100

per adult

San Gimignano: Chianti wine tasting and lunch

$81

per adult

See all activities in Chianti Region

Chianti Region Hotel Deals

Hotel Ristorante Alcide

Viale Marconi, 67/A, Poggibonsi, SI

Fully refundableReserve now, pay when you stay

$51 nightly

$63 total

Aug 31 - Sep 1

Total includes taxes and fees

8/10 Very Good! (450 reviews)

Good Value for the cost !

"The hotel was good value for the price. The room was clean. The hotel is in a good, safe area. The A/C was able to keep up with the 98F temps outside. Check in was easy. The breakfast was very good. Parking is a little tricky but not to bad. The only issues we had with our room was the safe wouldnt ..."

Reviewed on Jul 7, 2025

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13, Gaiole in Chianti, SI

Fully refundableReserve now, pay when you stay

$430 nightly

$484 total

Aug 21 - Aug 22

Total includes taxes and fees

9.4/10 Exceptional! (244 reviews)

"Beautiful hotal located in such a paradise location amazing view very good food. The staff was very nice. The service was amazing. I definitely recommend the place. It’s a beautiful relaxing, gorgeous."

Reviewed on Aug 13, 2025

Hotel Borgo di Cortefreda Relais

Via Roma 191, Barberino Tavarnelle, FI

Fully refundableReserve now, pay when you stay

$149 nightly

$171 total

Aug 28 - Aug 29

Total includes taxes and fees

9.2/10 Wonderful! (446 reviews)

"The Borgo was exactly what we were looking for. A great pool, lounge chairs, view of the rolling hills, and wonderful outdoor pool side bar service. Easy access to Siena, Florence, and anywhere else in the area to explore. The decor is dated, but was we loved the unpretentious charm."

Reviewed on Aug 16, 2025

See all 5,176 properties in Chianti Region

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.

Things to do near Chianti Region

The Chianti Region in Tuscany is perfect for a romantic getaway or outdoor adventure. Visitors can indulge in relaxing spa treatments and explore charming local shops. Key activities include guided Chianti wine tours, tastings of exquisite wines, and luxury tours that showcase the region's stunning landscapes and rich culture. Don't miss the opportunity to immerse yourself in the enchanting world of Italian wines while enjoying the picturesque scenery.

Shopping

In the Chianti Region, visit The Mall Luxury Outlet, just 13 miles away, for luxury brands in a vibrant setting. Also, check out Fashion Groove, located 12 miles away, offering a fun shopping atmosphere. Ra-Ma snc, another store 12 miles away, is perfect for unique gifts and souvenirs.

Recreation

Experience luxury at Villa a Sesta Polo Club, where you can indulge in wellness treatments amidst serene countryside vibes. For a blend of culture and entertainment, visit Teatro dei Rinnovati, offering captivating performances perfect for families and couples alike.

Adventure

Explore the Sentierelsa Trail for a scenic hiking experience, located 14 miles from Chianti Region, where you can immerse yourself in stunning landscapes. For a thrilling ride, head to the Siena Circuit, situated 16 miles away, and enjoy an exhilarating karting adventure.

Nightlife

The Chianti Region offers a charming nightlife atmosphere, perfect for unwinding after a day of exploration. A great spot is Il Fiaschetto, a cozy drinking pub located 17 miles away. Enjoy its romantic vibes and lively entertainment, making it an ideal place to sip local wines and mingle.

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

Find the best attractions near Chianti Region

The Chianti Region in Tuscany, Italy, offers a romantic and entertaining outdoor vacation experience. Travelers can explore charming churches, castles, and picturesque piazzas while immersing themselves in the rich culture and romance of the area. Don't miss the chance to visit renowned Chianti vineyards, taste the region's finest wines, and discover its historic castles for an unforgettable experience in this beautiful wine region.

Castello di Albola: Nestled 2 miles from Chianti, this enchanting castle offers a romantic atmosphere steeped in history and culture. Explore its beautiful grounds and vineyards while enjoying stunning views of the Tuscan landscape, making it a perfect spot for couples and history enthusiasts alike.
Piazza Matteotti: Located 5 miles from Chianti, this vibrant square is a cultural hub surrounded by charming cafes and shops. Experience the lively city vibes as you mingle with locals, admire the architecture, and savor authentic Tuscan cuisine in the heart of the community.
Pieve di San Leolino: Situated 3 miles away, this historic church showcases remarkable architectural beauty and offers a serene atmosphere. Immerse yourself in its rich cultural heritage while appreciating the stunning artworks and peaceful surroundings that make it a spiritual oasis.

Best time to go to Chianti Region

The best time to visit Chianti Region is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is sunny with no rain. January is its coolest month on average. At this time, visitor numbers are moderately low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	40.6°F (4.800000000000001°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
February	42.8°F (6.0°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
March	47.5°F (8.6°C)	Light Rain	Mostly Sunny	Average	Average
April	54.0°F (12.2°C)	Light Rain	Mostly Sunny	Average	Average
May	60.4°F (15.8°C)	Light Rain	Mostly Sunny	Average	Slightly High
June	69.8°F (21.0°C)	Light Rain	Sunny	Average	Slightly High
July	75.9°F (24.4°C)	No Rain	Sunny	Moderately High	Average
August	75.6°F (24.200000000000003°C)	No Rain	Sunny	Moderately High	Average
September	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
October	58.5°F (14.7°C)	Light Rain	Mostly Sunny	Average	Average
November	50.0°F (10.0°C)	Light Rain	Mostly Sunny	Average	Slightly Low
December	43.2°F (6.2°C)	Light Rain	Mostly Sunny	Moderately Low	Average

Tips to save on your trip to Chianti Region

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chianti Region.
Consider traveling to Chianti Region 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.