Castellina in Chianti Holiday Rentals from €50: Search Short-Term 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 Beautiful house on Chianti hilltop with exceptional views. .

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Our top choices for Castellina in Chianti holiday rentals

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

1. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

includes taxes & fees

8 Nov - 9 Nov

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

2. Casa Vacanze Squarcialupi

Castellina in Chianti

Jeffrey

includes taxes & fees

6 Nov - 7 Nov

A stone-paved entrance with a grill, potted plants, and a door leading to an interior space.

3. Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi

Castellina in Chianti

A brick building with a garden, a metal fence, and a clear sky.

4. Casa Marisa in Castellina in Chianti

Castellina in Chianti

includes taxes & fees

8 Nov - 9 Nov

A rustic outdoor dining area with a stone wall, wooden furniture, and potted plants.

5. La Misura, cottage with garden and swimming pool on the hills of Chianti

Castellina in Chianti

Jami B.

A bedroom with a bed, bedside tables, a dresser, a window with curtains, and wall-mounted lights.

6. Apartment 'La Casa Della Gina' with Wi-Fi

Castellina in Chianti

"We loved our 13 night stay in Castellina in Chianti! The apartment was clean, spacious and well appointed! From the apartment you step out right onto the pedestrian street with shops, bars and restaurants. The grocery is a couple of minutes walking and everyone in town is so friendly! The host is very friendly and helpful and things could not have been better! I highly recommend the apartment for your stay in Tuscany and we were sad to leave!"

Diane W.

A stone building with a gravel path, outdoor seating, and greenery.

7. The Arch Among the Hills of Castellina

Topina

includes taxes & fees

8 Nov - 9 Nov

A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

8. Residenzia del Sogno

Castellina in Chianti

Katherine

A stone building with a wooden door, a grill outside, and a stone wall.

9. Teranga in Chianti - Parking & Garden 3 BR

Tavarnelle Val di Pesa

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.

10. Terre di Baccio

Greve in Chianti

Gage

includes taxes & fees

6 Nov - 7 Nov

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

11. 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

8 Nov - 9 Nov

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

12. B&B Il Corso

Siena City Centre

Heather

includes taxes & fees

8 Nov - 9 Nov

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

13. Domus il Palio B&B

Ravacciano

Leo

includes taxes & fees

18 Nov - 19 Nov

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

14. ApartHotel Anghel

Siena

clifford

includes taxes & fees

30 Nov - 1 Dec

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

15. Relais Villa Olmo - Place of Charme

Impruneta

Michael

includes taxes & fees

23 Nov - 24 Nov

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

16. Siena Vip

Siena City Centre

Jacob

includes taxes & fees

5 Nov - 6 Nov

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

17. PALAZZO DEL PAPA

Siena City Centre

Charles

includes taxes & fees

8 Nov - 9 Nov

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

18. Regis Condo

Siena City Centre

Jessica

includes taxes & fees

10 Nov - 11 Nov

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

19. Villa il Fedino

San Casciano in Val di Pesa

Justyna

includes taxes & fees

23 Nov - 24 Nov

A narrow alleyway with brick walls, wooden barrels, and potted plants.

20. San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

San Gimignano City Centre

Glenn

includes taxes & fees

5 Nov - 6 Nov

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Top Castellina in Chianti Hotel Reviews

Radisson Blu Hotel, Florence

10/10 Excellent

"Excelente hotel , desayuno muy completo , habitaciones muy cómodas."

Hotel Albani Firenze

8/10 Good

"A lovely old hotel. We were upgraded to a large suite. As the seasons were changing, the cooling system was no longer functioning and it was very stuffy. Its location close to the main train station meant that it was very noisy all night and our window was very close to the street with loud talking and loud cars all night long. Other than that, I would say that the accommodations were superior. The breakfast was very good with high quality offerings and a variety of items from which to choose."

Hu Firenze Camping In Town

10/10 Excellent

"Great convenient stay! We stayed with 3 kids. Perfect stay if you plan on spending most of your days sightseeing. Bus into town located directly across the road. Beds comfy enough..prob the easiest check in we have experienced so far.. definitely recommend. Super popular with many campers in vans and tents. The restaurant is super popular - American style fair - go into town for pasta - the pizzas and burgers were super popular. There are washing machines that work great. The dryers are hit and miss. The units are very clean. All in all woukd recommend for a family stay."

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, apart-hotels, 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 €50 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.

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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. Some other top choices in Castellina in Chianti are Villa with large garden in the Chianti hills and Beautiful house on Chianti hilltop with exceptional views. .

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.

Holiday Rentals in Castellina in Chianti

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Our top choices for Castellina in Chianti holiday rentals

1. Agriturismo La Ferrozzola

2. Casa Vacanze Squarcialupi

3. Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi

4. Casa Marisa in Castellina in Chianti

5. La Misura, cottage with garden and swimming pool on the hills of Chianti

6. Apartment 'La Casa Della Gina' with Wi-Fi

7. The Arch Among the Hills of Castellina

8. Residenzia del Sogno

9. Teranga in Chianti - Parking & Garden 3 BR

10. Terre di Baccio

11. Guild Living Siena Senior Resort & Residence

12. B&B Il Corso

13. Domus il Palio B&B

14. ApartHotel Anghel

15. Relais Villa Olmo - Place of Charme

16. Siena Vip

17. PALAZZO DEL PAPA

18. Regis Condo

19. Villa il Fedino

20. San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

Find holiday rentals that suit your style

Top Castellina in Chianti Hotel Reviews

Radisson Blu Hotel, Florence

Find out more about Castellina in Chianti

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