A narrow street with stone buildings, a 'Zona traffico limitato' sign, and people walking.

Radda in Chianti Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Radda in Chianti holiday rentals

A rural road leading to a stone building with a metal gate, surrounded by lush greenery and hills in the background.

1. Chianti dreaming in Radda-3 independent bedrooms with private bathroom and TV

Chianti dreaming in Radda-3 independent bedrooms with private bathroom and TV
Toscana
10.0 out of 10, Exceptional, (3 reviews)
"The apartment was perfect for what we needed. It was very clean and very comfortable. The beds were comfortable and the bathrooms were quite roomy and even had a place for your shampoo and soap in the shower. "
United States
Wendy T.
The price is HK$1,385
HK$2,631 total
includes taxes & fees
29 Oct - 30 Oct
Chianti dreaming in Radda-3 independent bedrooms with private bathroom and TV
A rustic interior with stone walls, wooden beams, a fireplace, and a dining area with tables and chairs.

2. Apartment 'Rifugio sulla via di Volpaia' with Private Terrace, Wi-Fi and Air Conditioning

Apartment 'Rifugio sulla via di Volpaia' with Private Terrace, Wi-Fi and Air Conditioning
Radda in Chianti
The price is HK$4,317
HK$4,352 total
includes taxes & fees
21 Oct - 22 Oct
Apartment 'Rifugio sulla via di Volpaia' with Private Terrace, Wi-Fi and Air Conditioning
A stone building with a swimming pool, wooden deck, and a tall tree.

3. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"A dream property come true. Breathtaking views, most accommodating hosts, Perfect Tuscan location."
United States
Amber M.
The price is HK$8,854
HK$13,071 total
includes taxes & fees
4 Nov - 5 Nov
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A stone building with a garden in front.

4. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (28 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is HK$1,482
HK$1,700 total
includes taxes & fees
25 Oct - 26 Oct
Borgo Argenina
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

5. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (80 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 HK$2,124
HK$2,371 total
includes taxes & fees
14 Nov - 15 Nov
Terre di Baccio
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

6. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is HK$1,316
HK$1,447 total
includes taxes & fees
21 Oct - 22 Oct
Villa di Sotto
A villa with a swimming pool, outdoor seating, and a tennis court.

7. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is HK$1,035
HK$1,174 total
includes taxes & fees
19 Oct - 20 Oct
Villa Curina Resort
A bakery display with pastries and a coffee station.

8. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (215 reviews)
"We enjoyed our stay very much. Staff was very friendly and offered great advise on places to eat. The rooms had great charm to them. We were delighted with our selection of where to stay."
United States
Enrique
The price is HK$578
HK$671 total
includes taxes & fees
2 Nov - 3 Nov
B&B Il Corso
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

9. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (90 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
The price is HK$909
HK$1,035 total
includes taxes & fees
25 Oct - 26 Oct
B&B La Fonte del Machiavelli
A bathroom with a window view of a historic building and a tiled roof.

10. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (490 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 HK$872
HK$994 total
includes taxes & fees
14 Nov - 15 Nov
Siena Vip
A spacious hotel room with a large bed, a sitting area with chairs, and a view through an arched doorway to another room.

11. La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (254 reviews)
"Great stay. Thanks for the hospitality and kindness."
United Kingdom
Agnieszka
The price is HK$1,009
HK$1,145 total
includes taxes & fees
2 Nov - 3 Nov
La Terrazza Sul Campo Rooming House
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

12. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (56 reviews)
"Amazing! Thank you!"
United Kingdom
Lucy
The price is HK$1,090
HK$1,235 total
includes taxes & fees
1 Nov - 2 Nov
Guild Living Siena Senior Resort & Residence
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

13. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (271 reviews)
"Very friendly and clean."
United States
Mohamed
The price is HK$975
HK$1,099 total
includes taxes & fees
16 Nov - 17 Nov
Relais Villa Olmo - Place of Charme
A table with two wine glasses, a bottle, and a book.

14. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (99 reviews)
"Place was great, beautiful, modern, well maintained and staff was very helpful. I didn’t like that it is far from everything, far from train station, not too many options for food in the vicinity."
United States
Waleska
The price is HK$518
HK$605 total
includes taxes & fees
20 Oct - 21 Oct
Domus il Palio B&B
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

15. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (116 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 HK$1,319
HK$1,486 total
includes taxes & fees
10 Nov - 11 Nov
PALAZZO DEL PAPA
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

16. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (355 reviews)
"Humming noise in the room. Slow internet. Fine bed. Good location."
Netherlands
Lauro
The price is HK$490
HK$574 total
includes taxes & fees
3 Nov - 4 Nov
ApartHotel Anghel
An arched entrance with a lantern above, flanked by two potted plants.

17. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (106 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is HK$1,742
HK$1,951 total
includes taxes & fees
20 Oct - 21 Oct
Villa il Fedino
A courtyard with a stone statue, a round table, and chairs.

18. Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (84 reviews)
"Location"
Canada
Sean
The price is HK$864
HK$986 total
includes taxes & fees
21 Oct - 22 Oct
Regis Condo
An open wooden door leading to an outdoor patio with a table and chairs.

19. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (114 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is HK$718
HK$1,054 total
includes taxes & fees
7 Nov - 8 Nov
Palazzo al Torrione 2
Reception

20. Teatro Luxury Apartments Firenze - Starhotels Collezione

Teatro Luxury Apartments Firenze - Starhotels Collezione
Historic Centre of Florence
9.8 out of 10, Exceptional, (140 reviews)
"Book this for our honeymoon and will definitely come back"
Canada
Kerby
The price is HK$1,355
HK$1,596 total
includes taxes & fees
8 Nov - 9 Nov
Teatro Luxury Apartments Firenze - Starhotels Collezione
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 Radda in Chianti Hotel Reviews

The Market Urban Hotel

The Market Urban Hotel

10/10 Excellent
"The hotel is excellent, breakfast was delicious, staff were very friendly and helpful and the amenities were nice. Very close to the train station which is convenient."
Anthony 4-night trip
Posted 4 hours ago
The Market Urban Hotel

Find out more about Radda in Chianti

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

  • View our selection of featured holiday rentals in Radda in Chianti
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  • Enter your travel dates to view the best deals on holiday rentals in Radda in Chianti while they last

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

Frequently asked questions

Can I find holiday rentals in Radda in Chianti?

Yes, there are holiday rentals in Radda in Chianti close to Borgo di Vescine - Tenute di Castelvecchi, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Radda in Chianti is known for its spas and countryside. While you're here, grab a bite or have a drink at the wineries.

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

Villa La Stella - Casa per Ferie: This holiday home rental outside of Radda 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 are there in Radda in Chianti?

Expedia has 7 holiday rentals for your stay in Radda in Chianti.

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

Explore the area and family-friendly sights such as Borgo di Vescine - Tenute di Castelvecchi, or get out into nature at a spot like Terme Antica Querciolaia. While here, Castello di Radda Winery and Castello di Albola are other places worth a visit.

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

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Radda in Chianti. Holiday rentals offer extras like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a family getaway.