Hotels in Castellina in Chianti

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Where to stay in Castellina in Chianti?

A stone-walled dining area with a table set for four, a bench, and a view through an open doorway to the outside.

1. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
9.4 out of 10, Exceptional, (193 reviews)
Escape to this charming farm stay in Castellina in Chianti with an outdoor pool and attached winery. After a massage, explore the garden or sip drinks at the bar. Nearby Casa Vinicola Luigi Cecchi and free WiFi enhance your Italian getaway.
The price is $98
$112 total
includes taxes & fees
Oct 28 - Oct 29
Borgo di Pietrafitta Relais
A spacious lobby with a stone archway, wooden ceiling beams, a bar area with a wine rack, and a reception desk.

2. Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (130 reviews)
The price is $105
$119 total
includes taxes & fees
Oct 28 - Oct 29
Hotel Colle Etrusco Salivolpi
A round table with a white tablecloth, two white chairs, and a vase of flowers on a terrace with a stone wall and a scenic view of green hills.

3. Palazzo Squarcialupi

Palazzo Squarcialupi
4.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (91 reviews)
The price is $199
$226 total
includes taxes & fees
Oct 28 - Oct 29
Palazzo Squarcialupi
A narrow stone pathway leading to a rustic building with a wooden door and a window.

4. Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
9.4 out of 10, Exceptional, (233 reviews)
Nestled in Castellina in Chianti, this B&B offers an attached winery and Italian cuisine at Osteria di Fonterutoli restaurant. Mazzei Winery sits nearby, with Walls of Monteriggioni just a short drive from this charming retreat.
The price is $168
$190 total
includes taxes & fees
Oct 28 - Oct 29
Castello di Fonterutoli Wine Resort
A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.

5. Castello La Leccia

Castello La Leccia
Castellina in Chianti
10.0 out of 10, Exceptional, (122 reviews)
The price is $166
$187 total
includes taxes & fees
Nov 3 - Nov 4
Castello La Leccia
A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.

6. Belvedere di San Leonino

Belvedere di San Leonino
4.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (211 reviews)
Surrounded by Chianti countryside, this serene hotel with winery charms visitors with Italian cuisine at Il Cortile restaurant. Cool off in the outdoor pool, unwind in the hot tub, or sample local vintages at the bar after exploring nearby attractions.
The price is $102
$119 total
includes taxes & fees
Oct 28 - Oct 29
Belvedere di San Leonino
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

7. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.2 out of 10, Wonderful, (5 reviews)
Set in historic Castellina in Chianti, this welcoming apartment provides a serene retreat with a garden terrace. Near the Archaeological Museum and Castellina Fortress, the cozy accommodations include convenient microwaves and refrigerators plus free WiFi and parking.
The price is $121
$139 total
includes taxes & fees
Nov 7 - Nov 8
Casa Vacanze Squarcialupi
A stately building with a grand entrance, multiple arches, and a well-lit facade.

8. Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti
10.0 out of 10, Exceptional, (43 reviews)
The price is $258
$290 total
includes taxes & fees
Oct 30 - Oct 31
Fattoria di Vegi
A stone building with an arched entrance, a wooden door, and a small balcony with a railing.

9. Albergo Il Colombaio

Albergo Il Colombaio
3.0 star property
Castellina in Chianti
8.4 out of 10, Very good, (66 reviews)
Immerse yourself in Chianti's charm at this tranquil retreat offering a refreshing outdoor pool and convenient bar. Located minutes from Casa Vinicola Luigi Cecchi and Castellina Fortress, enjoy daily housekeeping and free breakfast after exploring nearby vineyards.
The price is $152
$171 total
includes taxes & fees
Nov 1 - Nov 2
Albergo Il Colombaio
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

10. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (18 reviews)
Escape to this charming bed and breakfast with panoramic views of Chianti from the rooftop terrace. Just minutes from Archaeological Museum and Castellina Fortress, the hotel offers free WiFi and parking. Relax in the garden after exploring nearby attractions.
The price is $92
$105 total
includes taxes & fees
Oct 29 - Oct 30
Mariani Bed & Breakfast
A stone building with a staircase leading up to a window, surrounded by lush greenery and flowering plants.

11. Collelungo

Collelungo
Castellina in Chianti
9.2 out of 10, Wonderful, (50 reviews)
Escape to this rustic farm stay in Castellina where you can sip local wines at the attached winery. Relax by the outdoor pool, explore the garden, and discover nearby Archaeological Museum and Castellina Fortress. Monteriggioni Station is just a short drive away.
The price is $126
$143 total
includes taxes & fees
Oct 30 - Oct 31
Collelungo
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

12. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.8 out of 10, Exceptional, (16 reviews)
Immerse in Castellina in Chianti's charm at this intimate lodging with a refreshing outdoor pool and welcoming bar/lounge. Free WiFi and parking complement garden and terrace spaces, with renowned wineries just minutes away.
The price is $132
$150 total
includes taxes & fees
Oct 30 - Oct 31
Residenzia del Sogno
A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

13. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
The price is $128
$145 total
includes taxes & fees
Nov 11 - Nov 12
Agriturismo La Ferrozzola
A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.

14. Locanda le Piazze

Locanda le Piazze
4.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (207 reviews)
Escape to this charming hotel in Castellina in Chianti featuring a winery and restaurant. Unwind at the spa with hot stone massages or lounge by the outdoor pool with cocktails from the poolside bar. Near Lilliano Estate Winery with free breakfast and parking.
The price is $406
$454 total
includes taxes & fees
Oct 28 - Oct 29
Locanda le Piazze
Infinity pool

15. PODERE 1384

PODERE 1384
Castellina in Chianti
10.0 out of 10, Exceptional, (3 reviews)
The price is $594
$660 total
includes taxes & fees
Nov 1 - Nov 2
PODERE 1384
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.

16. Hotel Casafrassi

Hotel Casafrassi
4.0 star property
Castellina in Chianti
8.2 out of 10, Very good, (247 reviews)
Surrounded by beautiful countryside scenery, this Castellina in Chianti hotel offers Italian dining at Osteria di Casafrassi and a winery on-site. Enjoy free breakfast near Mazzei Winery, just 9 minutes from Monteriggioni Badesse Station.
The price is $60
$73 total
includes taxes & fees
Oct 28 - Oct 29
Hotel Casafrassi
A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

17. La Certosa di Pontignano - Place of Charme

La Certosa di Pontignano - Place of Charme
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (578 reviews)
The price is $90
$108 total
includes taxes & fees
Nov 26 - Nov 27
La Certosa di Pontignano - Place of Charme
A large building with multiple rooms, surrounded by a field of lavender.

18. Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
5.0 star property
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (233 reviews)
The price is $363
$410 total
includes taxes & fees
Nov 4 - Nov 5
Borgo Scopeto Wine & Country Relais
The entrance to a hotel with a sign reading "HOTEL ITALIA". There are two receptionists standing at the reception desk.

19. Hotel Italia

Hotel Italia
3.0 star property
Camollia
9.2 out of 10, Wonderful, (1,004 reviews)
Atmospheric hotel near Siena Station offers hiking and mountain biking trails nearby. Enjoy the terrace, bar, and attentive service praised by fellow travelers. Porta Camollia and Siena Stadium are just minutes away from this convenient retreat.
The price is $69
$79 total
includes taxes & fees
Nov 22 - Nov 23
Hotel Italia
A lobby with a marble floor, a chandelier, a reception desk, and large green plants.

20. Hotel Chiusarelli

Hotel Chiusarelli
3.0 star property
Siena City Centre
9.0 out of 10, Wonderful, (1,004 reviews)
Wake up to a celebrated breakfast at this Tuscan treasure, just a 10-minute walk from Piazza del Campo and near Stadio Artemio Franchi. The garden, terrace, and attentive staff create a refreshing retreat after exploring Siena's medieval marvels.
The price is $93
$106 total
includes taxes & fees
Nov 17 - Nov 18
Hotel Chiusarelli
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.
View all properties

Check out pet-friendly hotels in Castellina in Chianti

A stone-walled dining area with a table set for four, a bench, and a view through an open doorway to the outside.
Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
9.4 out of 10, Exceptional, (193)
The price is $98
$112 total
includes taxes & fees
Oct 28 - Oct 29
Borgo di Pietrafitta Relais
View all properties

You may also like hotels with pools in Castellina in Chianti

A round table with a white tablecloth, two white chairs, and a vase of flowers on a terrace with a stone wall and a scenic view of green hills.
Palazzo Squarcialupi

Palazzo Squarcialupi

Palazzo Squarcialupi
4.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (91)
The price is $199
$226 total
includes taxes & fees
Oct 28 - Oct 29
Palazzo Squarcialupi
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.
View all properties

When is the best time to visit Castellina in Chianti?

Our prices for hotels in Castellina in Chianti are cheapest in February
Price trends for hotels in Castellina in Chianti
Pricing is based on two traveler single night rates
View properties in October
Currently viewing crowd sizes and weather for October.
Typical weather for Castellina in Chianti
October
High 20°C / low 11°C. Sunny most days.
View properties in October
20°
weather_sun
October, no crowd data, average high temperature 20 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
11°
14°
weather_sun
November, no crowd data, average high temperature 14 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
7°
10°
weather_sun
December, no crowd data, average high temperature 10 degrees Celsius, average low temperature 3 degrees Celsius. Sunny most days.
3°
9°
weather_partly_sunny
January, no crowd data, average high temperature 9 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
2°
11°
weather_partly_sunny
February, no crowd data, average high temperature 11 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
2°
14°
weather_sun
March, no crowd data, average high temperature 14 degrees Celsius, average low temperature 4 degrees Celsius. Sunny most days.
4°
18°
weather_sun
April, no crowd data, average high temperature 18 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
7°
21°
weather_sun
May, no crowd data, average high temperature 21 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
10°
27°
weather_sun
June, no crowd data, average high temperature 27 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
31°
weather_sun
July, no crowd data, average high temperature 31 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
31°
weather_sun
August, no crowd data, average high temperature 31 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
26°
weather_sun
September, no crowd data, average high temperature 26 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
Monthly weather averages (˚C)

Top landmarks in Castellina in Chianti

Buondonno Winery

9.6/10 (4 reviews)
Travelers might want a tour of Buondonno Winery, just one of the places to visit, and located 3.9 mi (6.3 km) from central Castellina in Chianti.
See properties

Learn more about Castellina in Chianti

Notable for its wineries, Castellina in Chianti features attractions such as City Hall Castellina In Chianti and Castellina Fortress. This relaxing city has something for everyone including sights like Archaeological Museum of Chianti and Walls of Monteriggioni within a rural setting.

See all hotels in Castellina in Chianti
A stone building with a clock tower, steps leading up to it, and people walking around.

Check out reviews of Castellina in Chianti hotels guests love

Hotel Paris

Hotel Paris

10/10 Excellent
"Perfect location"
Lambros 2-night trip
Posted 17 hours ago
Hotel Paris

Frequently asked questions

What accommodations do travelers like in Castellina in Chianti?
Guests like Borgo Vescine.
Where can I find free parking with my stay in Castellina in Chianti?
Park your car for free at Castello di Fonterutoli Wine Resort.
Can I book a refundable hotel in Castellina in Chianti?
If you need the flexibility to change your plans to Castellina in Chianti, most properties provide refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Castellina in Chianti if I want a vacation home instead of a traditional hotel?
If you're looking for a good alternative to a hotel, browse our selection of 31 vacation homes. You can also book one of 16 apartments or 27 villas.
What will the weather in Castellina in Chianti be like during my visit?
August and July are typically the warmest months in Castellina in Chianti when the average temp is 72°F. January and February are the coldest months when the average temperature is 44°F. November and October are the months with the most rain.
Why should I book my Castellina in Chianti accommodation with Hotels.com?
There are lots of reasons to book your Castellina in Chianti trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.