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

Search Holiday Rentals in Castellina in Chianti

Q: What are some of the best holiday rentals that Castellina in Chianti has to offer?

Villa La Stella - Casa per Ferie : This holiday 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 holiday rental also comes with free parking to give you added peace of mind.

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Dates

November 2026

December 2026

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Our top choices for Castellina in Chianti holiday 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

฿4,446 total

includes taxes & fees

11 Nov - 12 Nov

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

2. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

฿4,857 total

includes taxes & fees

11 Nov - 12 Nov

A two-story house with a patio area, potted plants, and outdoor furniture.

3. La Locanda di Pietracupa

Tavarnelle Val di Pesa

Isabell

฿5,479 total

includes taxes & fees

1 Dec - 2 Dec

A bedroom with a stone wall, a large mirror, a bed with white linens, a potted plant, and a view through a window with curtains.

4. Terre di Baccio

Greve in Chianti

Gage

฿9,719 total

includes taxes & fees

13 Nov - 14 Nov

A narrow hallway with a wooden bench, a radiator, and a wooden cabinet.

5. Il Battistero Siena - Residenza d'Epoca

Siena City Centre

Anthony

฿4,881 total

includes taxes & fees

2 Dec - 3 Dec

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

฿3,731 total

includes taxes & fees

12 Nov - 13 Nov

A narrow street with buildings on either side, featuring arched windows and a pedestrian walkway.

7. B&B Il Corso

Siena City Centre

Heather

฿2,854 total

includes taxes & fees

15 Nov - 16 Nov

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

8. Residenza d'Epoca Palazzo Borghesi

Siena City Centre

Suelina

฿5,772 total

includes taxes & fees

26 Nov - 27 Nov

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

9. Domus il Palio B&B

Ravacciano

Leo

฿2,545 total

includes taxes & fees

18 Nov - 19 Nov

A historic building with a clock tower, arched windows, and a shop selling souvenirs.

10. PALAZZO DEL PAPA

Siena City Centre

Charles

฿5,810 total

includes taxes & fees

12 Nov - 13 Nov

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

11. Siena Vip

Siena City Centre

John

฿3,422 total

includes taxes & fees

11 Nov - 12 Nov

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

฿3,891 total

includes taxes & fees

12 Nov - 13 Nov

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

฿6,913 total

includes taxes & fees

23 Nov - 24 Nov

A stone building with a patio area featuring a table and chairs under a large umbrella.

14. Relais Villa Olmo - Place of Charme

Impruneta

Michael

฿3,424 total

includes taxes & fees

26 Nov - 27 Nov

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

15. Villa il Fedino

San Casciano in Val di Pesa

Justyna

฿6,020 total

includes taxes & fees

23 Nov - 24 Nov

A bottle of wine, two glasses, and a decorative tray on a table by a window with a view of buildings.

16. Regis Condo

Siena City Centre

Jessica

฿3,104 total

includes taxes & fees

11 Nov - 12 Nov

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

17. ApartHotel Anghel

Siena

clifford

฿2,449 total

includes taxes & fees

30 Nov - 1 Dec

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

฿2,884 total

includes taxes & fees

13 Nov - 14 Nov

A courtyard with a large building featuring arched windows and a tower. There is a parking lot with several cars.

19. Al Mercato B&B

Siena City Centre

Sandra

฿2,930 total

includes taxes & fees

17 Nov - 18 Nov

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

฿3,856 total

includes taxes & fees

30 Nov - 1 Dec

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Find holiday 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

Iain

A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

Belvedere di San Leonino

Castellina in Chianti

10/10 Excellent

Jess

A stone building with a tiled roof, green shutters, and a small staircase leading to a door.

Castello di Fonterutoli Wine Resort

Castellina in Chianti

10/10 Excellent

Claire

Casa Vacanze Squarcialupi

Castellina in Chianti

10/10 Excellent

Paul

A stone building with an arched entrance, a wooden door, and a small balcony with a railing.

Albergo Il Colombaio

Castellina in Chianti

10/10 Excellent

Anonymous traveller

An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.

Hotel Casafrassi

Castellina in Chianti

10/10 Excellent

Stuart

An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

10/10 Excellent

This place is surreal. We felt like we were on the set of the Name of the Rose. Sleeping in a real XIV century monastery, with its own church (with amazing frescoes), on a hill overlooking the grapes and olive trees dotted countryside...just unbelievable. We stay in one the celle, which is a 3 bedroom apartment on 2 floors, with your own private garden...yes, that's correct. Simply unheard of. The location is great too (Siena is a short drive away). The only setbacks were breakfast, very...

Ivo

A courtyard with wicker furniture, a building with multiple windows and arches, and well-maintained greenery.

Palazzo Ravizza

Siena Historical Center

10/10 Excellent

Very enjoyable stay at this Hotel, everywhere was very clean. All the staff were helpful and friendly, the receptionist who checked us out took the time to show us a scenic route south to our next stay. The parking on site was great and secure. Breakfast lovely too.The location was very central. We would definitely book this hotel if we were to return to Siena, which is highly likely, thank you for a great stay.

Stuart

A hotel room with a bed, a TV, a dining area with a table and chairs, and a view of the outside.

Hotel Italia

Camollia

10/10 Excellent

Anonymous traveller

A historic building complex with multiple structures, including a large central building with arches and smaller surrounding buildings.

Hotel Athena

Siena Historical Center

10/10 Excellent

Richard

A lobby with a marble floor, a chandelier, a reception desk, and large green plants.

Hotel Chiusarelli

Siena City Centre

10/10 Excellent

Fab hotel - staff were very helpful as we arrived before the room was ready. There are no lifts but the steps of the staircase were wide enough to not be a problem with luggage and the staff were available to help with dealing with that aspect. Hotel was a lovely boutique historical place and very close to everything in Siena. Small car park next door which was handy. Would absolutely recommend staying there - room was big and well appointed, a good shower and it was very relaxing.

VICTORIA

A courtyard with outdoor seating, potted plants, and a statue.

Hotel David

Oltrarno

10/10 Excellent

We stayed at the Hotel David for four nights. The staff are welcoming, pleasant and helpful. The cleaning staff did an invisible but excellent job, leaving our room immaculate every day. Our twin room was spacious, with ample storage space, and a large shower room off a small hallway. The bed was very comfortable. There a wide variety of food for breakfast, including fresh fruit and freshly made pastries and cakes. I would recommend this hotel to anyone who doesn't mind the 15-20-minute walk...

Anonymous traveller

A building with a staircase, potted plants, and a garden area.

Art Hotel Villa Agape - Place of Charme

Oltrarno

10/10 Excellent

Marie

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

Hotel Horto Convento

Historic Centre of Florence

10/10 Excellent

Edna

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

Anonymous traveller

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

One of the best hotels I have stayed - small, 'boutique' feel. Lovely, friendly and helpful staff - they seemed to want us to enjoy our stay ! Stayed 2 x one night, so had 2 different rooms - both quite different, but both excellent quality & space. Dinner in restaurant was superb; breakfast buffet excellent. c. 20 minute walk into the centre of Florence, maybe 30 mins to Ponte Vecchio, or use the shuttle bus or taxis. Highly recommended - can't wait to go back !

Ian

Find out more about Castellina in Chianti

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Frequently Asked Questions

Are there holiday rentals in Castellina in Chianti?

Yes, there are holiday rentals close to the most popular sights in Castellina in Chianti, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Castellina in Chianti has to offer?

Villa La Stella - Casa per Ferie: This holiday 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 holiday rental also comes with free parking to give you added peace of mind.

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

With 31 Expedia holiday rentals, you're guaranteed 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 holiday rental in Castellina in Chianti like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Castellina in Chianti. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for families.

Search Holiday Rentals in Castellina in Chianti

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Castellina in Chianti holiday 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 holiday 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 holiday rentals in Castellina in Chianti?

What are some of the best holiday rentals that Castellina in Chianti has to offer?

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

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

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