A stone building with a clock tower, steps leading up to it, and people walking around.

Castellina in Chianti Vacation Rentals

Q: What are some of the best vacation home rentals in Castellina in Chianti?

Villa La Stella - Casa per Ferie : This vacation home rental outside Castellina in Chianti is located near the airport and has a garden, a library, and air-conditioning to put you at ease in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind. Some other top choices in Castellina in Chianti are Villa with large garden in the Chianti hills and Farmhouse in the heart of the real chiantishire .

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Dates

November 2026

December 2026

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Our top choices for Castellina in Chianti vacation rentals

A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

1. Casa Vacanze Squarcialupi

Castellina in Chianti

Jeffrey

￥21,070 total

includes taxes & fees

Nov 17 - Nov 18

A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

2. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

￥23,021 total

includes taxes & fees

Nov 29 - Nov 30

A dining area with a table set for two, featuring a view of greenery through a window.

3. La Locanda di Pietracupa

Tavarnelle Val di Pesa

Isabell

￥25,967 total

includes taxes & fees

Nov 22 - Nov 23

A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

4. Terre di Baccio

Greve in Chianti

Gage

￥45,962 total

includes taxes & fees

Nov 15 - Nov 16

A wine cellar with stone walls, wine racks, and tables with glasses and candles.

5. Il Battistero Siena - Residenza d'Epoca

Siena City Centre

Anthony

￥21,859 total

includes taxes & fees

Nov 13 - Nov 14

An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

6. Guild Living Siena Senior Resort & Residence

Scacciapensieri

"We booked this last - minute and were really impressed with the whole experience. The property and grounds are beautiful. Staff was so friendly and helpful. The rooms were well appointed and quiet. Beds were too firm for our liking, but it was easy to overlook as the entire stay was really great. Good options in the restaurant too. The block of hotel rooms is in a retirement resort, which I think is a wonderful idea! Very much enjoyed our stay. We had a car and parking was free."

Heidi

￥17,683 total

includes taxes & fees

Nov 25 - Nov 26

A bakery display with pastries and a coffee station.

7. B&B Il Corso

Siena City Centre

Heather

￥13,524 total

includes taxes & fees

Nov 15 - Nov 16

A table set with breakfast items on a balcony overlooking a historic town.

8. Residenza d'Epoca Palazzo Borghesi

Siena City Centre

Suelina

￥26,244 total

includes taxes & fees

Nov 26 - Nov 27

A table with two wine glasses, a bottle, and a book.

9. Domus il Palio B&B

Ravacciano

Leo

￥12,232 total

includes taxes & fees

Nov 18 - Nov 19

A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

10. PALAZZO DEL PAPA

Siena City Centre

Charles

￥27,546 total

includes taxes & fees

Nov 12 - Nov 13

A bathroom with a window view of a historic building and a tiled roof.

11. Siena Vip

Siena City Centre

John

￥15,876 total

includes taxes & fees

Nov 12 - Nov 13

A room with a white wardrobe, a glass-top table, a chair, and a large ornate mirror.

12. B&B Palazzo del Magnifico

Siena City Centre

Leslie

￥18,441 total

includes taxes & fees

Nov 15 - Nov 16

A terrace with outdoor seating, a view of the city, and a clock tower in the background.

13. Palazzo Alfieri Residenza d’epoca - Place of Charme

Historic Centre of Florence

robert

￥34,030 total

includes taxes & fees

Nov 26 - Nov 27

A spacious indoor area with arched windows, wooden furniture, and hanging plants.

14. Relais Villa Olmo - Place of Charme

Impruneta

Michael

￥16,233 total

includes taxes & fees

Nov 26 - Nov 27

An arched entrance with a lantern above, flanked by two potted plants.

15. Villa il Fedino

San Casciano in Val di Pesa

Justyna

￥28,529 total

includes taxes & fees

Nov 25 - Nov 26

A courtyard with a stone statue, a round table, and chairs.

16. Regis Condo

Siena City Centre

Jessica

￥14,716 total

includes taxes & fees

Nov 30 - Dec 1

A modern lobby with white leather sofas, a glass coffee table, and potted plants.

17. ApartHotel Anghel

Siena

clifford

￥11,611 total

includes taxes & fees

Nov 30 - Dec 1

A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

18. Tuscasì Aparthotel

Sovicille

Sergey

￥13,672 total

includes taxes & fees

Nov 20 - Nov 21

A room with a bed, a leather sofa, and a window with a view of a building outside.

19. Al Mercato B&B

Siena City Centre

Sandra

￥13,724 total

includes taxes & fees

Nov 17 - Nov 18

A modern bedroom with a large bed, a desk with chairs, and a bathroom visible through an open door.

20. Palazzo Mannaioni Suites

Historic Centre of Florence

Heather

￥18,281 total

includes taxes & fees

Nov 30 - Dec 1

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Find vacation rentals that suit your style

Top Castellina in Chianti Hotel Reviews

A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.

Castello La Leccia

Castellina in Chianti

10/10 Excellent

Sarah

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.

Belvedere di San Leonino

Castellina in Chianti

10/10 Excellent

Oh wow, perfect vacation and a real Tuscany atmosphere, the hotel is a magical old yet perfectly renovated property, the room was amazingly clean and equipped with everything we needed, the pool was open until 8pm and it’s never crowded, very peaceful area, almost like a fantasy movie, breakfast was great, especially the cheese , local pastries and coffee , the staff was lovely, very friendly and helpful, but the real deal was DINNER , I cannot say enough about the food and wine they make,...

Lior

A formal garden with neatly trimmed hedges, a central fountain, and stone pathways.

Art Hotel Villa Agape - Place of Charme

Oltrarno

10/10 Excellent

Amazing in every way. The beauty of waking around is unlike any other. When we got there after a long day of traveling we had just missed the lunchtime to eat, and when went to shower the handle broke off- this is not a complaint. First they extended lunch without being asked and fixed the shower within minutes. From there on everything was amazing. Take time to eat the incredible breakfast in the garden, watch the breathtaking sunset in the back it’s incredible. Alessio- does it all he was...

John

The entrance to Hotel Spadaï Firenze with a modern design, including a reception desk and a chandelier.

Hotel Spadai

Historic Centre of Florence

10/10 Excellent

Richard

A spacious living room with a large grey sofa, yellow armchairs, and a chandelier.

Hotel Horto Convento

Historic Centre of Florence

10/10 Excellent

Jassiel

A grand lobby with high ceilings, ornate columns, and a grand piano. Tables and chairs are arranged for guests.

Bernini Palace

Historic Centre of Florence

10/10 Excellent

Sarah

A modern interior with a glass elevator, a seating area with orange cushions, and a bookshelf filled with books.

Hotel Milu Florence

Historic Centre of Florence

10/10 Excellent

What a fantastic experience at Milu! To start, the staff was friendly and made us feel at home right away. Our room was clean and quiet, with the most amazing shower! We enjoyed the breakfast on the patio and found it to be a very satisfying way to start the day. The hotel maintained a relaxed feel while still being vibrant - colorful, modern art and design to enjoy while relaxing with a cup of tea from the open library. We would definitely stay again, thanks Milu for a great experience!

Kelly

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.

La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

10/10 Excellent

Jeffrey

A reception area with a check-in counter, a green door, potted plants, and a framed picture on the wall.

Il Malaspina - Place of Charme

Historic Centre of Florence

10/10 Excellent

Nadine

A rooftop terrace with a table set for dining, candles, and a vase of flowers, overlooking a historic cityscape with notable architecture.

Hotel Santa Maria Novella

Historic Centre of Florence

10/10 Excellent

Nick

A large, multi-story building with a courtyard, surrounded by greenery and trees.

Villa Neroli - Place of Charme

Coverciano

10/10 Excellent

Chainarong

A garden pathway with white flowers and a glass structure overhead.

Hotel Orto de’ Medici

Historic Centre of Florence

10/10 Excellent

Christopher

A dining area with a table set for two, a window with a view of historic buildings, and a chair with a cushion.

Hotel Pendini

Historic Centre of Florence

10/10 Excellent

William

A balcony with white cushions and a railing overlooking a river with a bridge.

Hotel degli Orafi

Historic Centre of Florence

10/10 Excellent

damian

A pool area with lounge chairs and umbrellas, surrounded by lush greenery and white flowers.

Hotel Ville sull'Arno - Preferred Hotels & Resorts

Campo di Marte

10/10 Excellent

If you are planning to visit Florence, this is the hotel you should book! It won't let you down. Your Florence stay will be brilliant and memorable. I booked this hotel after read someone's comment. As I learned, the location is a bit far from the center of city. Even so, it is still worth to stay at this hotel. If you take a taxi, it costs 10 euro from/to hotel approxilately. For money savers, taking a bus #14 just for 2 euro may be suitable. The bus stop for #14 is only 2 blocks walk...

Anonymous traveler

A modern hotel with a glass facade, a rooftop pool, and multiple balconies.

IQ Hotel Firenze

Historic Centre of Florence

10/10 Excellent

MUYUAN

Find out more about Castellina in Chianti

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Frequently Asked Questions

Are there vacation rentals in Castellina in Chianti?

Yes, you can find vacation rentals near the most popular attractions in Castellina in Chianti, or you can go with a more remote option if you're looking for relaxation. Visitors to Castellina in Chianti speak positively about the countryside and wineries in this destination. Make sure you have time to check out the forests while you're in the area.

What are some of the best vacation home rentals in Castellina in Chianti?

Villa La Stella - Casa per Ferie: This vacation home rental outside Castellina in Chianti is located near the airport and has a garden, a library, and air-conditioning to put you at ease in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind. Some other top choices in Castellina in Chianti are Villa with large garden in the Chianti hills and Farmhouse in the heart of the real chiantishire.

How many vacation rentals will I find in Castellina in Chianti?

With 31 Expedia vacation rentals, you're sure to find just the right place for your Castellina in Chianti stay.

What’s there to see and do in Castellina in Chianti?

While exploring the area, visit family-friendly sights like Chianti Observatory, or get outside and enjoy nature at Chianti Sculpture Park. While here, City Hall Castellina In Chianti and Castellina Fortress are other places worth a visit.

What’s a vacation rental in Castellina in Chianti like?

A vacation rental is a private property you can stay in for several days or longer in Castellina in Chianti. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great option for family gatherings.

Castellina in Chianti Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Castellina in Chianti vacation rentals

1. Casa Vacanze Squarcialupi

2. Agriturismo La Ferrozzola

3. La Locanda di Pietracupa

4. Terre di Baccio

5. Il Battistero Siena - Residenza d'Epoca

6. Guild Living Siena Senior Resort & Residence

7. B&B Il Corso

8. Residenza d'Epoca Palazzo Borghesi

9. Domus il Palio B&B

10. PALAZZO DEL PAPA

11. Siena Vip

12. B&B Palazzo del Magnifico

13. Palazzo Alfieri Residenza d’epoca - Place of Charme

14. Relais Villa Olmo - Place of Charme

15. Villa il Fedino

16. Regis Condo

17. ApartHotel Anghel

18. Tuscasì Aparthotel

19. Al Mercato B&B

20. Palazzo Mannaioni Suites

Find vacation rentals that suit your style

Top Castellina in Chianti Hotel Reviews

Castello La Leccia

10/10 Excellent

Find out more about Castellina in Chianti

Frequently Asked Questions

Are there vacation rentals in Castellina in Chianti?

What are some of the best vacation home rentals in Castellina in Chianti?

How many vacation rentals will I find in Castellina in Chianti?

What’s there to see and do in Castellina in Chianti?

What’s a vacation rental in Castellina in Chianti like?