Castellina in Chianti Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Castellina in Chianti holiday rentals

A stone building with a tiled roof, surrounded by greenery and a large terracotta pot.

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 S$185
includes taxes & fees
14 Nov - 15 Nov
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 S$169
includes taxes & fees
16 Nov - 17 Nov
Casa Vacanze Squarcialupi
A stone building with a covered patio, a table with chairs, and a hanging plant.

3. 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 S$385
includes taxes & fees
14 Nov - 15 Nov
Terre di Baccio
A historic building with ornate iron gates, potted plants, and a visible staircase leading to an upper floor.

4. Signoria Collection

Signoria Collection
Historic Centre of Florence
9.8 out of 10, Exceptional, (24 reviews)
"The property location was ideal for visiting the landmarks, churches and museums."
United States
SCOTT
The price is S$166
includes taxes & fees
1 Dec - 2 Dec
Signoria Collection
A villa with multiple bedrooms, a swimming pool, and a garden.

5. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (277 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is S$130
includes taxes & fees
29 Nov - 30 Nov
Relais Villa Olmo - Place of Charme
A bakery display with pastries and a coffee station.

6. 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 S$108
includes taxes & fees
22 Nov - 23 Nov
B&B Il Corso
A bedroom with a bed, bedside tables, a wardrobe, and a hanging light fixture.

7. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (498 reviews)
"The room was modern and clean. Enjoyed the breakfast."
Australia
John
The price is S$130
includes taxes & fees
15 Nov - 16 Nov
Siena Vip
A hotel room with a large bed, a bedside table, a lamp, and a view of a dome through a window.

8. San Giuliano Inn - Adults Only

San Giuliano Inn - Adults Only
Historic Centre of Florence
9.8 out of 10, Exceptional, (462 reviews)
"Great place to stay!!"
United States
Neil
The price is S$150
includes taxes & fees
14 Dec - 15 Dec
San Giuliano Inn - Adults Only
A building with multiple windows, a balcony with balustrade, and storefronts with awnings.

9. Anchor Santa Croce

Anchor Santa Croce
Historic Centre of Florence
9.8 out of 10, Exceptional, (9 reviews)
"Amazing place to stay. Clean, close to main touristic attractions in Florence."
Canada
Adina
The price is S$150
includes taxes & fees
16 Nov - 17 Nov
Anchor Santa Croce
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

10. 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 S$87
includes taxes & fees
1 Dec - 2 Dec
ApartHotel Anghel
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

11. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (62 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 S$142
includes taxes & fees
15 Nov - 16 Nov
Guild Living Siena Senior Resort & Residence
A pool area with a view of rolling hills and a clear sky.

12. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (94 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
The price is S$168
includes taxes & fees
7 Dec - 8 Dec
B&B La Fonte del Machiavelli
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

13. 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 S$243
includes taxes & fees
15 Nov - 16 Nov
PALAZZO DEL PAPA
A balcony with a table, wine glasses, and a bottle, overlooking a historic building with a clock tower and another tower.

14. Relais Piazza Signoria

Relais Piazza Signoria
Historic Centre of Florence
9.6 out of 10, Exceptional, (898 reviews)
"The staff is very nice and helpful. Best location, close to everything. I would recommend staying here."
United States
Marjorie
The price is S$161
includes taxes & fees
3 Dec - 4 Dec
Relais Piazza Signoria
A room with a bed, a leather sofa, and a window with a view of a building outside.

15. Al Mercato B&B

Al Mercato B&B
Siena City Centre
9.0 out of 10, Wonderful, (107 reviews)
"This B and B is great. In the centre of everything."
Canada
Sandra
The price is S$111
includes taxes & fees
14 Dec - 15 Dec
Al Mercato B&B
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.
View all properties

Find holiday rentals that suit your style

Apartment image
Apartments
Apartments
apart-hotel image
Aparthotels
Aparthotels

Top Castellina in Chianti Hotel Reviews

A four-poster bed with a floral canopy, a wooden floor, a bedside table with a book and a cup, and a television on a shelf.
Hotel David

Hotel David

Hotel David
Oltrarno

10/10 Excellent

Excellent staff, great room with amenities. Thoughtful facilities, security.
Singapore
Timothy
Reviewed September 29, 2023
Hotel David

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.