Chianti Region Guest Houses

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

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 prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Chianti Region guest houses

A building with a stone facade, a central arched doorway, and a window with a decorative frame.

1. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

HK$2,420 total

includes taxes & fees

9 Nov - 10 Nov

An outdoor seating area with tables and chairs, a wooden bar, and a view of the countryside.

2. Casa di Palaia

Greve in Chianti

Belisario

HK$890 total

includes taxes & fees

12 Oct - 13 Oct

A luxurious room with a chandelier, classical columns, and a dining area with wooden chairs and a table.

3. Dimora Casa Eugenia

Loro Ciuffenna

Hilde Stendal

HK$1,127 total

includes taxes & fees

12 Oct - 13 Oct

A two-story building with a patio area featuring outdoor seating and potted plants.

4. Homelink Poggibonsi

Barberino Val d'Elsa

Avinash

HK$391 total

includes taxes & fees

18 Oct - 19 Oct

A stone-walled room with a fireplace, a table with chairs, and a hanging light fixture.

5. Borgo Nuovo San Martino

Bucine

Josimar

HK$911 total

includes taxes & fees

12 Oct - 13 Oct

A living room with a sofa, a coffee table, and a television mounted on the wall.

6. Residenze Strozzi Firenze

Historic Centre of Florence

Marie Jo

HK$1,181 total

includes taxes & fees

20 Oct - 21 Oct

A pathway lined with trees and a large pot in the center.

7. Villa Montarioso

Montarioso

Michael

HK$748 total

includes taxes & fees

4 Nov - 5 Nov

A hotel room with a large bed, a desk with a chair, a dining area with chairs, and a view of a building through open windows.

8. Palazzina Fusi

Historic Centre of Florence

debbie

HK$928 total

includes taxes & fees

8 Nov - 9 Nov

9. AmiRooms Affittacamere

Siena City Centre

"We received great instructions from Amina on how to access the room which were easy to follow. If arriving in the day, the ground floor is where a lovely flower shop is, then up a lift. There are then 9 easy steps down to where the room is located. This was our 4th stop on our trip and by far the best room. Although in the centre of everything, the room is super quiet, modern, with a lovely-sized bathroom & powerful shower and great WiFi. We would highly recommend and will definitely return...

Michelle

HK$761 total

includes taxes & fees

4 Nov - 5 Nov

An outdoor courtyard with stone walls, arched doorways, and potted plants.

10. Residenza d'Epoca Palazzo Buonaccorsi

San Gimignano City Centre

Soni

HK$784 total

includes taxes & fees

4 Nov - 5 Nov

A dining area with a round table, wooden chairs, and hanging light fixtures.

11. podere la strega

Siena

Jenny

HK$1,617 total

includes taxes & fees

14 Oct - 15 Oct

A modern hotel room with a bed, two sofas, a table with a candle, glasses, and a champagne bottle.

12. Antico Centro Suites

Historic Centre of Florence

Juliet

HK$998 total

includes taxes & fees

10 Nov - 11 Nov

A courtyard with a domed building and a bell tower.

13. The Artists' Palace Florence

Historic Centre of Florence

Maryam

HK$1,249 total

includes taxes & fees

8 Nov - 9 Nov

A bedroom with a four-poster bed, a television on the wall, and a table with a lamp.

14. Uffizi Harmony

Historic Centre of Florence

zhi jin

HK$743 total

includes taxes & fees

9 Nov - 10 Nov

A building with a symmetrical facade, arched windows, and a central door.

15. Villa Gelsomino Garden

Oltrarno

Zaid

HK$475 total

includes taxes & fees

10 Nov - 11 Nov

A narrow courtyard with terracotta steps leading to a door, surrounded by potted plants and a small table with a chair.

16. Corte dell'albero

Historic Centre of Florence

Marjan

HK$882 total

includes taxes & fees

8 Nov - 9 Nov

A street view with a wooden door, a shop with a sign, and a red car parked on the sidewalk.

17. La Loggia del Porcellino

Historic Centre of Florence

Margarita

HK$866 total

includes taxes & fees

9 Nov - 10 Nov

A bedroom with a bed, a TV mounted on the wall, a window with a view of buildings, and a radiator.

18. Toscanelli Residenza D'epoca

Historic Centre of Florence

Emily

HK$930 total

includes taxes & fees

6 Nov - 7 Nov

A balcony with wicker furniture, a table with fruit, and a cityscape view.

19. Blossoms of Siena

Siena City Centre

Walter

HK$1,297 total

includes taxes & fees

11 Nov - 12 Nov

A historic building with intricate architectural details and a dome.

20. Guest House Bel Duomo

Historic Centre of Florence

Tracy

HK$651 total

includes taxes & fees

10 Nov - 11 Nov

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Chianti Region Hotel Reviews

Villa I Barronci Resort & Spa

10/10 Excellent

"Great spot and friendly staff."

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."

Hu Norcenni Girasole Village

10/10 Excellent

"My family and I had such a great time. Such a kid friendly place and at check in they even had a little playground while you waiting and gave the kids bubbles. So great to be in nature and all of the amenities were lovely. The waterparks that were padded on the ground were genius and we did a family wine tasting which was such a lovely memory. Our stay was so nice with the deck and the grocery store is so affordable for dinners in. Love love love! My toddler played all day and there were so many times we got to relax because they had everything that we wanted or needed right on property."

Find out more about Chianti Region