A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

Find Romantic Hotels in Chianti Region

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check availability on Chianti Region Romantic Hotels

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Chianti Region romantic hotels

1. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
Canada
James
¥14,316
¥28,144 total
includes taxes & fees
Oct 22 - Oct 23
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

2. CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS

CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS
Ruffoli
United States
Caleb M.
¥22,338
¥47,157 total
includes taxes & fees
Oct 28 - Oct 29
CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS

3. Deluxe Room Nero su Bianco with A/C and Private Bathroom in Villa le Facezie B&B

Deluxe Room Nero su Bianco with A/C and Private Bathroom in Villa le Facezie B&B
Terranuova Bracciolini
United States
Lynn P.
¥23,401
¥23,933 total
includes taxes & fees
Oct 24 - Oct 25
Deluxe Room Nero su Bianco with A/C and Private Bathroom in Villa le Facezie B&B

4. Old medieval apartment

Old medieval apartment
Tavarnelle Val di Pesa
United States
Kathleen F.
¥18,349
¥22,249 total
includes taxes & fees
Oct 29 - Oct 30
Old medieval apartment

5. Sorbeto Vacation Home

Sorbeto Vacation Home
impruneta
United States
Christine F.
¥13,852
¥52,744 total
includes taxes & fees
Oct 21 - Oct 22
Sorbeto Vacation Home

6. Glicini 1, holiday home with pool 30' from Florence

Glicini 1, holiday home with pool 30' from Florence
Tavarnelle Val di Pesa
United States
Joe M.
Glicini 1, holiday home with pool 30' from Florence

7. Appartment with swimming pool 30 min of Florence, private garden, parking, WiFi

Appartment with swimming pool 30 min of Florence, private garden, parking, WiFi
Reggello
France
Jean-marc L.
¥14,183
¥17,729 total
includes taxes & fees
Oct 18 - Oct 19
Appartment with swimming pool 30 min of Florence, private garden, parking, WiFi

8. Colle di Val d'Elsa - Siena - White Apartment - D

Colle di Val d'Elsa - Siena - White Apartment - D
Colle di Val d'Elsa
¥15,317
¥28,082 total
includes taxes & fees
Oct 19 - Oct 20
Colle di Val d'Elsa - Siena - White Apartment - D

9. Tuscany countryside appartment with pool

Tuscany countryside appartment with pool
Reggello FI
¥17,728
¥21,274 total
includes taxes & fees
Oct 20 - Oct 21
Tuscany countryside appartment with pool

10. APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM

APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM
Monteriggioni
Italy
giuseppe z.
¥31,789
¥46,351 total
includes taxes & fees
Nov 1 - Nov 2
APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM
View all properties

Find out more about Chianti Region

Chianti Region attractions for couples

In the picturesque Chianti Region of Italy, travelers can immerse themselves in a tapestry of experiences that blend adventure, culture, and culinary delights. Begin your journey by exploring the charming town of Greve in Chianti, known for its vibrant piazza and wine shops where you can sample some of the finest Chianti Classico. Don't miss a visit to the historic Castello di Brolio, where you can tour the castle and its vineyards, learning about the winemaking process while enjoying breathtaking views of the rolling hills. For those looking to connect with nature, the Chianti hills offer numerous hiking trails that wind through vineyards and olive groves, perfect for a family day out. Indulge in local cuisine at a traditional trattoria, where you can savor dishes prepared with farm-fresh ingredients and paired with local wines. For a luxurious stay, consider accommodations in the quaint village of Radda in Chianti, where boutique hotels offer personalized service and stunning views. Here, you can unwind at a spa after a day of exploration, making each moment of your stay feel special and tailored to your family's needs.

Top Chianti Region Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"Beautiful quaint 1000 year old monastery turned into a hotel! The staff was extremely accommodating and we really enjoyed our stay. Very easy to get around all of Tuscany from this hotel."
Michelle 3-night trip
Posted 6 days ago
Castello di Spaltenna- Small Luxury Hotels of the World
Borgo Vescine

Borgo Vescine

10/10 Excellent
"The staff was amazing and incredibly kind."
Natalie 2-night trip
Posted 2 weeks ago
Borgo Vescine
Villa Le Barone

Villa Le Barone

10/10 Excellent
"Charming place in Tuscany! Everything was absolutely perfect. We highly suggest to dine at the villa, it was exceptional. Breakfast was delicious as well."
Tereza 2-night trip
Posted 3 weeks ago
Villa Le Barone
COMO Castello Del Nero

COMO Castello Del Nero

10/10 Excellent
"The most beautiful hotel in the heart of Chianti. The service was above and beyond. Everything about this charming hotel was amazing. We cannot wait to go back."
Lauren 3-night trip
Posted 1 month ago
COMO Castello Del Nero

Explore a world of travel with Expedia