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

Castellina in Chianti Holiday Rentals

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. 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 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

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

includes taxes & fees

30 Nov - 1 Dec

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

3. La Locanda di Pietracupa

Tavarnelle Val di Pesa

Isabell

includes taxes & fees

13 Nov - 14 Nov

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

includes taxes & fees

14 Nov - 15 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

includes taxes & fees

29 Nov - 30 Nov

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

includes taxes & fees

24 Nov - 25 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

includes taxes & fees

18 Nov - 19 Nov

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

8. Residenza d'Epoca Palazzo Borghesi

Siena City Centre

Suelina

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

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

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

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

includes taxes & fees

30 Nov - 1 Dec

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

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

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

includes taxes & fees

24 Nov - 25 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

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

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

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

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

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

Belvedere di San Leonino

Castellina in Chianti

10/10 Excellent

Anthony

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

joe

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

Rebecca

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

Hotel Casafrassi

Castellina in Chianti

8/10 Good

Beautiful surroundings, lovely pool. The aircon was a bit ancient and noisy. A couple of little things we asked the staff to sort out were resolved in a very short space of time ( we asked for twin beds, and it was made up as one bed, the aircon stopped working, but was solved swiftly) The restaurant next door has good food for the most part, a car would certainly be a much better and would be a good place to explore the Chianti region

Sofia

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

Anonymous traveller

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

Palazzo Ravizza

Siena Historical Center

10/10 Excellent

Anna

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

Gary

A modern hotel room with a bed, a desk, a chair, and a TV.

Park Hotel Chianti

Tavarnelle Val di Pesa

10/10 Excellent

Andrew

A terrace with a table and chairs, overlooking a scenic landscape with rolling hills and a distant building.

La Cisterna

San Gimignano City Centre

10/10 Excellent

Jacquelyn

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

Hotel David

Oltrarno

10/10 Excellent

Allan

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

Art Hotel Villa Agape - Place of Charme

Oltrarno

10/10 Excellent

Amazing experience staying here! The villa is stunning you feel like you’re living as royalty. The gardens are beautiful despite the extreme heat of Italy. Don’t miss a sunset in the gardens. We had dinner twice, both nights had lovely food and service. The Buffett breakfast is definitely worth adding to your stay. The shuttle that takes you into town is such a good idea. Even though we had a car we didn’t have to worry about trying to park near the city to explore. Lovely Villa, thank...

Syvahna

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

Hotel Horto Convento

Historic Centre of Florence

10/10 Excellent

Kevin

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

Great hotel in fantastic location. Driving in and out is a nightmare. The parking arrangement let’s it down. You have to pay them separately and their payment machine was not working so you then have to go to their office. The hotel didn’t want to know, it would be a better arrangement for their clients if the hotel took the charge and passed it on to the parking garage so that customers are not inconvenienced.

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

kirsty

Find out more about Castellina in Chianti

Everything you need to know about Castellina in Chianti holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Castellina in Chianti holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Castellina in Chianti holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castellina in Chianti holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Castellina in Chianti. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Castellina in Chianti holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Castellina in Chianti holiday rentals we have selected for you start as low as NZ$131 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Castellina in Chianti rentals

At Expedia, we put the best Castellina in Chianti holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Castellina in Chianti rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Castellina in Chianti holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Castellina in Chianti. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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. 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 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.

Castellina in Chianti Holiday Rentals

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

Belvedere di San Leonino

10/10 Excellent

Find out more about Castellina in Chianti

Castellina in Chianti holiday rentals: An excellent choice for every season

How to find incredible deals on Castellina in Chianti rentals

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?

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