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
19 Sep - 20 Sep
Tomorrow
20 Sep - 21 Sep
Next weekend
25 Sep - 27 Sep
In two weeks
2 Oct - 4 Oct

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
AED 340
AED 648 total
includes taxes & fees
22 Sep - 23 Sep
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
Lorna M.
AED 531
AED 1,121 total
includes taxes & fees
28 Sep - 29 Sep
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.
AED 557
AED 569 total
includes taxes & fees
5 Oct - 6 Oct
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.
AED 485
AED 578 total
includes taxes & fees
6 Oct - 7 Oct
Old medieval apartment

5. Tuscany countryside appartment with pool

Tuscany countryside appartment with pool
Reggello FI
AED 380
AED 464 total
includes taxes & fees
20 Sep - 21 Sep
Tuscany countryside appartment with pool

6. Superior Settimo Cielo with A/C and Private Bathroom in Villa le Facezie B&B

Superior Settimo Cielo with A/C and Private Bathroom in Villa le Facezie B&B
Terranuova Bracciolini
AED 569
AED 639 total
includes taxes & fees
5 Oct - 6 Oct
Superior Settimo Cielo with A/C and Private Bathroom in Villa le Facezie B&B

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.
AED 337
AED 422 total
includes taxes & fees
21 Sep - 22 Sep
Appartment with swimming pool 30 min of Florence, private garden, parking, WiFi

8. Wonderful Tuscan farmhouse with large spaces and panoramic views

Wonderful Tuscan farmhouse with large spaces and panoramic views
impruneta
United States
Christine F.
AED 401
AED 1,134 total
includes taxes & fees
6 Oct - 7 Oct
Wonderful Tuscan farmhouse with large spaces and panoramic views

10. Colle di Val d'Elsa - Siena - Apt Blue - C

Colle di Val d'Elsa - Siena - Apt Blue - C
Colle di Val d'Elsa
United States
ALLAN
AED 337
AED 632 total
includes taxes & fees
11 Oct - 12 Oct
Colle di Val d'Elsa - Siena - Apt Blue - C
View all properties

Top Chianti Region Hotel Reviews

Relais Vignale & Spa

Relais Vignale & Spa

10/10 Excellent
"Beautiful small medieval town with castle and narrow streets. Close to wineries but not much else to do….location is very beautiful on top of hill."
mark 1-night trip
Posted 2 hours ago
Relais Vignale & Spa
Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent
"very nice historic hotel with great views of the country side and great atmphere. Room size and ammenities were wonderful. The breakfeast was great. Restaurant was nice with historic dishes. Only down side was the gluten and nut free options were limited...mainly for gluten sufferers, since the only gluten free pasta is Penne, which is not great for all dishes and frustratingsince Italy produces a very large variety of great gluten free pasta shapes. Also, my travel partner and I did the same pasta, one gluten free (penne) and one not gluten free. The non-gluten-free pasta came beautifully presented, while the gluten-free pasta came like it was thrown together last minute… like as if you were sitting at your own kitchen table. Impression given with the dinner is that people with allergies, are more a bit of a bother, and the typical mission in Italy, to give visitors an excellent culinary experience, is more less abandoned for people with allergies. that said, accommodating allergies is very difficult these days and at least the menu was clear about which foods contain which allergens."
edward 2-night trip
Posted 1 day ago
Castello Vicchiomaggio
Palagina la Dimora

Palagina la Dimora

8/10 Good
"Nice property to relax. Pool is nice. Breakfast is meh but works. Room was spacious although felt outdated and lacking lighting. Some staff were very helpful while some could have been more friendly."
Rayvant 1-night trip
Posted 2 days ago
Palagina la Dimora
Borgo Vescine

Borgo Vescine

10/10 Excellent
"⭐️⭐️⭐️⭐️⭐️ We genuinely did not want to leave Borgo Vescine was everything we hoped a stay in Tuscany would be. The property is absolutely stunning, incredibly peaceful, and so beautifully cared for that once we arrived, we honestly didn’t want to leave. What made the experience even more special was the staff. Everyone we encountered was warm, welcoming and genuinely delightful. The hospitality never felt forced or overly formal. We simply felt very well taken care of throughout our stay. We had dinner at the property and the restaurant was excellent, which made staying in for the evening an easy decision. Breakfast was included with our stay and was such a delicious treat each morning. Being able to wake up somewhere this beautiful, have a wonderful breakfast and then simply enjoy the property was exactly the kind of Tuscan experience we were looking for. The grounds themselves are gorgeous and meticulously maintained, with beautiful views and so many quiet little areas to sit and take everything in. Despite everything the property offers, it still feels serene, intimate and wonderfully quiet. Borgo Vescine is the kind of place that makes you reconsider whatever plans you had for the day because you would rather just stay there. One of our favorite stays in Tuscany and a property I would happily return to. Highly recommend."
Nadege 1-night trip
Posted 9 days ago
Borgo Vescine
Villa Le Barone

Villa Le Barone

10/10 Excellent
"Excellent stay with wonderful , friendly staff!"
Kathleen 3-night trip
Posted 10 days ago
Villa Le Barone
Hotel Villa Campomaggio

Hotel Villa Campomaggio

10/10 Excellent
"This resort is one of the most beautiful properties I have ever stayed in. Free use of the spa just was icing on the cake! Great breakfast spread and our dinner in the restaurant was delicious! We will be back!!"
Jayni 2-night trip
Posted 10 days ago
Hotel Villa Campomaggio

Explore a world of travel with Expedia