Find Romantic Hotels in Castellina in Chianti from $54

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Top Castellina in Chianti Romantic Hotels

Borgo di Pietrafitta Relais

Castellina in Chianti
9.4 out of 10, Exceptional, (169)
"Wonderful setting."
United Kingdom
Simon
$87 nightly
The price is $101
Jan 5 - Jan 6, 2026
Total with taxes and fees
Borgo di Pietrafitta Relais

PODERE 1384

Castellina in Chianti
$561 nightly
The price is $625
Dec 14 - Dec 15
Total with taxes and fees
PODERE 1384

Castello di Fonterutoli Wine Resort

Castellina in Chianti
9.4 out of 10, Exceptional, (198)
"Clean room, courteous staff, and good winery"
United States
Sangchun
$151 nightly
The price is $171
Dec 9 - Dec 10
Total with taxes and fees
Castello di Fonterutoli Wine Resort

Art Hotel Villa Agape

4.0 star property
Oltrarno
9.8 out of 10, Exceptional, (1006)
"A beautiful hotel, extremely clean and with stunning gardens."
United Kingdom
Elizabeth
$121 nightly
The price is $149
Jan 7 - Jan 8, 2026
Total with taxes and fees
Art Hotel Villa Agape

Orto De Medici Hotel

4.0 star property
Historic Centre of Florence
9.6 out of 10, Exceptional, (1003)
"We had a wonderful time staying and close to a lot of wonderful spots to visit. "
United States
JoAnn
$126 nightly
The price is $155
Dec 17 - Dec 18
Total with taxes and fees
Orto De Medici Hotel

Hotel Ginori al DUOMO

4.0 star property
Historic Centre of Florence
9.2 out of 10, Wonderful, (19)
"Highly recommend. Staff is friendly, everything was clean and the location was great. "
United States
Jenna
$65 nightly
The price is $88
Dec 11 - Dec 12
Total with taxes and fees
Hotel Ginori al DUOMO

Cellai Boutique Hotel

4.0 star property
Historic Centre of Florence
8.2 out of 10, Very Good, (676)
"Great location - good place to stay for price"
United States
Cynthia
$117 nightly
The price is $145
Dec 15 - Dec 16
Total with taxes and fees
Cellai Boutique Hotel

Villa Gelsomino Garden

Oltrarno
9.0 out of 10, Wonderful, (128)
"Great clean hotel not far from central Florence. "
United States
David
$37 nightly
The price is $54
Dec 16 - Dec 17
Total with taxes and fees
Villa Gelsomino Garden

Torre di Bellosguardo

4.0 star property
Oltrarno
9.0 out of 10, Wonderful, (103)
"Beautiful property and wonderful staff."
United States
Brad
$374 nightly
The price is $428
Dec 9 - Dec 10
Total with taxes and fees
Torre di Bellosguardo

Opera Boutique B&B

San Lorenzo
9.0 out of 10, Wonderful, (143)
"Beautiful quiet space. Lovely room. Easy walking to tourist attractions. Catch the tram just around the corner. Hostess wonderful. "
United States
leslie
Opera Boutique B&B
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.

Find out more about Castellina in Chianti

Castellina in Chianti attractions for couples

In the heart of Tuscany, Castellina in Chianti is a paradise for travelers eager to immerse themselves in the region's rich heritage and stunning landscapes. Start your journey at the historic Castello di Brolio, where you can explore the beautiful gardens and sample some of the finest Chianti wines produced on-site. For a taste of local culture, the annual Chianti Classico Wine Festival showcases the region's best vintages alongside artisanal food offerings, providing an unforgettable gastronomic experience for the whole family. Adventurous spirits can hike the scenic trails of the Chianti hills, where you'll encounter breathtaking views and charming vineyards. Don't miss a visit to the quaint village of Castellina itself, with its narrow streets lined with charming shops and cafes, perfect for a leisurely afternoon of exploration. For accommodations, consider staying at one of the beautifully restored villas or boutique hotels in the area, where attentive service and luxurious amenities create a pampering retreat after a day of adventure. Here, you can unwind in elegant surroundings while savoring local delicacies and enjoying the warm hospitality that Tuscany is known for.

Find the best romantic hotels in Castellina in Chianti

For couples seeking a romantic getaway in the enchanting Castellina in Chianti, Tuscany, these exquisite hotels offer intimate experiences and luxurious amenities perfect for lovers.

Locanda le Piazze

  • Why it's great for a couples retreat: Locanda le Piazze is an idyllic retreat for couples looking to bask in romance, a remarkable guest review rating of 9.8. This hotel features couples' treatment rooms and exclusive dining options designed for two, ensuring a serene and intimate atmosphere where guests can unwind and connect with each other amidst the beautiful Tuscan landscape.
  • Other amenities: In addition to its romantic offerings, guests can indulge in a full-service spa with a hot tub, outdoor pool, and various massage treatments including Swedish and Thai options. The hotel also provides complimentary breakfast, an electric car charging station, and a delightful garden view restaurant. Outdoor enthusiasts can take advantage of nearby hiking and mountain biking trails, making it easy to explore the stunning surroundings together.
  • Nearby attractions: Casa Vinicola Luigi Cecchi - 4.35 miles, City Hall Castellina In Chianti - 4.45 miles, Castellina Fortress - 4.57 miles

Belvedere di San Leonino

  • Why it's great for a couples retreat: With a stunning review rating of 9.6, Belvedere di San Leonino is a perfect choice for couples desiring a romantic escape. The enchanting terrace and vineyard views create a picturesque setting for guests, while the outdoor hot tub offers a relaxing spot for couples to unwind and enjoy each other’s company under the stars.
  • Other amenities: This hotel also features an outdoor pool, 24-hour airport shuttle service, and a delightful garden view restaurant. Guests will appreciate the concierge service, free self-parking, and daily housekeeping that ensures a comfortable and straightforward stay. The on-site winery adds an extra touch of romance, allowing couples to savor exquisite local wines together.
  • Nearby attractions: Mazzei Winery - 2.28 miles, Casina di Cornia Winery - 2.52 miles, Lilliano Estate Winery - 3.99 miles

Borgo di Pietrafitta Relais

  • Why it's great for a couples retreat: Borgo di Pietrafitta Relais is a romantic retreat that captures the essence of Tuscany, receiving an excellent review rating of 9.4. This hotel offers cozy outdoor spaces and a 24-hour pool, ideal for couples looking to relax together. The serene environment is enhanced by spa services that include massages, making it an ideal choice for those seeking relaxation and intimacy.
  • Other amenities: Guests can enjoy a variety of amenities, including a garden, a restaurant with garden views, and convenient self-parking. The hotel features an onsite winery, ensuring a delightful wine experience during their stay. Additional perks include a contactless check-in service, daily housekeeping, and a shared kitchenette, providing guests with flexibility and comfort during their romantic escape.
  • Nearby attractions: Casa Vinicola Luigi Cecchi - 2.4 miles, City Hall Castellina In Chianti - 2.5 miles, Castellina Fortress - 2.6 miles

Castello di Fonterutoli Wine Resort

  • Why it's great for a couples retreat: Castello di Fonterutoli Wine Resort is an enchanting haven for couples, earning a stellar review rating of 9.4. Nestled in a historical site, it boasts charming vineyard views and a cozy ambiance that sets the perfect backdrop for romance. The unique in-room amenities, including a fireplace and furnished balcony, create intimate spaces for guests to relax and connect.
  • Other amenities: In addition to its romantic atmosphere, the hotel features a delightful garden view restaurant and a shared kitchenette for those who prefer a more personal dining experience. Guests can explore the region's beauty through nearby biking and hiking trails, while the hotel’s daily housekeeping ensures a pristine environment throughout the stay. The winery on-site allows couples to indulge in wine tastings and tours, enhancing their romantic getaway.
  • Nearby attractions: Mazzei Winery - 0.48 miles, City Hall Castellina In Chianti - 3.12 miles, Casina di Cornia Winery - 2.43 miles

Top Castellina in Chianti Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Castellina in Chianti?
If you and your partner need a romantic vacation, we've got just the thing. Our guests also enjoy Castellina in Chianti for its wineries and countryside. You might consider checking out some of the nearby sights and attractions such as Buondonno Winery, Casa Vinicola Luigi Cecchi, or Castellina Fortress. If you're interested in staying near a particular destination, you can sort by neighborhood or distance to top sights, so you'll be able to see everything on your list.
How many romantic hotels will we find in Castellina in Chianti?
Expedia has 5 romantic Castellina in Chianti hotels for you both to enjoy.
When is the best time of year for a romantic getaway to Castellina in Chianti?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Castellina in Chianti: The hottest months are usually August and July with an average temp of 72°F, while the coldest months are January and February with an average of 44°F. Average annual precipitation for Castellina in Chianti is 37 inches.
What is there to do in Castellina in Chianti?
There's nothing better than experiencing a new destination with your sweetheart, so consider taking time to discover all there is to see and do in Castellina in Chianti. If you and your partner are interested in sampling the area's cuisine, you'll enjoy Castellina in Chianti for its wineries. Buondonno Winery, Casa Vinicola Luigi Cecchi, and Castellina Fortress are worth a stop when you're out and about.
What's the best way to get to Castellina in Chianti and around town during my romantic getaway?
These transportation options in Castellina in Chianti might help your romantic trip get off to a smooth start: Make your way to Castellina in Chianti with a flight to Florence Airport, Peretola (FLR), which is the closest major airport located 23.2 mi (37.4 km) from the city center. If you'd like to explore around the area, consider renting a car to take in more sights.

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