Castellina in Chianti Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Castellina in Chianti vacation rentals

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

1. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is NT$4,221
NT$4,791 total
includes taxes & fees
Nov 11 - Nov 12
Agriturismo La Ferrozzola
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

2. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.2 out of 10, Wonderful, (5 reviews)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is NT$3,785
NT$4,385 total
includes taxes & fees
Nov 16 - Nov 17
Casa Vacanze Squarcialupi
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

3. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
Residenzia del Sogno
A stone building with a wooden door, a grill outside, and a stone wall.

4. Teranga in Chianti - Parking & Garden 3 BR

Teranga in Chianti - Parking & Garden 3 BR
Tavarnelle Val di Pesa
Teranga in Chianti - Parking & Garden 3 BR
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.

5. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (82 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is NT$8,583
NT$9,589 total
includes taxes & fees
Nov 10 - Nov 11
Terre di Baccio
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

6. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (61 reviews)
"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."
United States
Heidi
The price is NT$3,211
NT$3,680 total
includes taxes & fees
Nov 8 - Nov 9
Guild Living Siena Senior Resort & Residence
A narrow street with buildings on either side, featuring arched windows and a pedestrian walkway.

7. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (218 reviews)
"Very clean and comfortable, great location and staff"
United States
Heather
The price is NT$2,424
NT$2,814 total
includes taxes & fees
Nov 30 - Dec 1
B&B Il Corso
A table with two wine glasses, a bottle, and a book.

8. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (102 reviews)
"Very nice place. Nice people, clean and just nice"
Denmark
Leo
The price is NT$2,154
NT$2,517 total
includes taxes & fees
Nov 18 - Nov 19
Domus il Palio B&B
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

9. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (356 reviews)
"The staff were very friendly and helpful. I would recommend this hotel to any traveler"
United States
clifford
The price is NT$1,917
NT$2,257 total
includes taxes & fees
Nov 15 - Nov 16
ApartHotel Anghel
A stone building with a patio area featuring a table and chairs under a large umbrella.

10. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (275 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is NT$2,990
NT$3,400 total
includes taxes & fees
Nov 23 - Nov 24
Relais Villa Olmo - Place of Charme
A bathroom with a window view of a historic building and a tiled roof.

11. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (496 reviews)
"Very friendly staff and great location close to the center of town. Breakfast was a nice touch and just what we needed to start the day. Would recommend!"
United States
Jacob
The price is NT$3,268
NT$3,743 total
includes taxes & fees
Nov 8 - Nov 9
Siena Vip
A historic building with a clock tower, arched windows, and a shop selling souvenirs.

12. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (117 reviews)
"Hamza is so helpful!! Finding the property is a little tricky, but he helped every step of the way! He also provided excellent dining suggestions and a great cooking class!"
United States
Charles
The price is NT$5,088
NT$5,745 total
includes taxes & fees
Nov 8 - Nov 9
PALAZZO DEL PAPA
A bottle of wine, two glasses, and a decorative tray on a table by a window with a view of buildings.

13. Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (86 reviews)
"Excellent place to stay!"
United States
Jessica
The price is NT$2,552
NT$2,955 total
includes taxes & fees
Nov 29 - Nov 30
Regis Condo
An arched entrance with a lantern above, flanked by two potted plants.

14. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (109 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is NT$5,263
NT$5,937 total
includes taxes & fees
Dec 5 - Dec 6
Villa il Fedino
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.
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Top Castellina in Chianti Hotel Reviews

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

Castello La Leccia

Castello La Leccia
Castellina in Chianti

10/10 Excellent

We loved this place and it was by far the best place we stayed during our time in Italy. The property is breathtaking and the service/staff is amazing. All the food we had was phenomenal and fresh. The wine is to die for. This is the type of place that is so good that you almost don’t want to tell people about it to keep it secret. Hope to be back again someday.
United States
Sarah
Reviewed June 22, 2024
Castello La Leccia

Find out more about Castellina in Chianti

Search for holiday rentals in Castellina in Chianti on Expedia! You can easily find your home rentals, villas, holiday apartments in Castellina in Chianti using one of the methods below:

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Look no further and take a look at our great range of rental properties in Castellina in Chianti!

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.

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.