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

Radda in Chianti Vacation 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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Radda in Chianti vacation rentals

A stone building with a garden in front.

1. 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 NT$6,120
NT$7,022 total
includes taxes & fees
Oct 25 - Oct 26
Borgo Argenina
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

2. 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 NT$8,705
NT$9,719 total
includes taxes & fees
Nov 14 - Nov 15
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.

3. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is NT$5,948
NT$6,543 total
includes taxes & fees
Oct 28 - Oct 29
Villa di Sotto
A villa with a swimming pool, outdoor seating, and a tennis court.

4. 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 NT$4,459
NT$5,051 total
includes taxes & fees
Oct 26 - Oct 27
Villa Curina Resort
A bakery display with pastries and a coffee station.

5. 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 NT$2,388
NT$2,772 total
includes taxes & fees
Nov 2 - Nov 3
B&B Il Corso
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

6. 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 NT$3,725
NT$4,241 total
includes taxes & fees
Oct 25 - Oct 26
B&B La Fonte del Machiavelli
A bathroom with a window view of a historic building and a tiled roof.

7. 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 NT$3,573
NT$4,074 total
includes taxes & fees
Nov 14 - Nov 15
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.

8. 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 NT$4,166
NT$4,728 total
includes taxes & fees
Nov 2 - Nov 3
La Terrazza Sul Campo Rooming House
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

9. 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 NT$4,470
NT$5,061 total
includes taxes & fees
Nov 4 - Nov 5
Guild Living Siena Senior Resort & Residence
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

10. 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 NT$4,028
NT$4,540 total
includes taxes & fees
Nov 16 - Nov 17
Relais Villa Olmo - Place of Charme
A table with two wine glasses, a bottle, and a book.

11. 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 NT$2,124
NT$2,480 total
includes taxes & fees
Oct 25 - Oct 26
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.

12. 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 NT$5,445
NT$6,135 total
includes taxes & fees
Nov 10 - Nov 11
PALAZZO DEL PAPA
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

13. 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 NT$2,031
NT$2,379 total
includes taxes & fees
Nov 3 - Nov 4
ApartHotel Anghel
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, (106 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is NT$7,140
NT$7,997 total
includes taxes & fees
Oct 20 - Oct 21
Villa il Fedino
A courtyard with a stone statue, a round table, and chairs.

15. Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (84 reviews)
"Location"
Canada
Sean
The price is NT$4,278
NT$4,852 total
includes taxes & fees
Nov 11 - Nov 12
Regis Condo
An open wooden door leading to an outdoor patio with a table and chairs.

16. 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 NT$2,965
NT$4,351 total
includes taxes & fees
Nov 7 - Nov 8
Palazzo al Torrione 2
Reception

17. 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 NT$5,555
NT$6,542 total
includes taxes & fees
Nov 15 - Nov 16
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Radda in Chianti Hotel Reviews

aparto Florence Manifattura

aparto Florence Manifattura

8/10 Good
"The facilities and property was relatively new and it was decently located."
Kane 2-night trip
Posted 3 hours ago
aparto Florence Manifattura

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
  • Use the map to find apartments and other holiday homes in the Radda in Chianti neighbourhood you prefer
  • 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 vacation rentals in Radda in Chianti?

Yes, we offer vacation rentals in Radda in Chianti close to Borgo di Vescine - Tenute di Castelvecchi, or you can select a secluded option if you're looking for extra privacy while you relax. 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 vacation rentals that Radda in Chianti has to offer?

Villa La Stella - Casa per Ferie: This vacation 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 vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Radda in Chianti?

Expedia has 7 vacation 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 vacation rental in Radda in Chianti like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Radda in Chianti. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.