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

Radda in Chianti Vacation Rentals

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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$5,998
NT$6,883 total
includes taxes & fees
Oct 26 - Oct 27
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$8,626
NT$9,631 total
includes taxes & fees
Oct 16 - Oct 17
Terre di Baccio
A villa with a swimming pool, outdoor seating, and a tennis court.

3. 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$4,189
NT$4,750 total
includes taxes & fees
Oct 23 - Oct 24
Villa Curina Resort
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

4. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is NT$5,327
NT$5,859 total
includes taxes & fees
Oct 21 - Oct 22
Villa di Sotto
An arched entrance with a lantern above, flanked by two potted plants.

5. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (105 reviews)
"Tha parking was easy on the property. It was within walking distance to the villages with shops, restaurants and cafes. The best part was the staff. The owners were incredibly helpful, friendly and made you feel like family. Breakfast outside was lovely overlooking the hills of Tuscany. We met many people and had lovely conversations with other travelers during breakfast. A gem in Tuscany."
United States
Lori
The price is NT$7,075
NT$7,925 total
includes taxes & fees
Oct 21 - Oct 22
Villa il Fedino
A bathroom with a window view of a historic building and a tiled roof.

6. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (490 reviews)
"Great location right in the heart of everything and next to an escalator that takes you to the main plaza. Very comfortable bed, friendly staff. Convenient parking option very close by."
United States
Heather
The price is NT$3,541
NT$4,037 total
includes taxes & fees
Nov 2 - Nov 3
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.

7. 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$4,084
NT$4,635 total
includes taxes & fees
Nov 2 - Nov 3
La Terrazza Sul Campo Rooming House
A historic building with ornate iron gates, potted plants, and a visible staircase leading to an upper floor.

8. Signoria Collection

Signoria Collection
Historic Centre of Florence
9.8 out of 10, Exceptional, (17 reviews)
"Room was always clean. Location is amazing."
Canada
Doug
The price is NT$5,508
NT$6,486 total
includes taxes & fees
Nov 4 - Nov 5
Signoria Collection
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

9. 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$5,337
NT$6,014 total
includes taxes & fees
Nov 10 - Nov 11
PALAZZO DEL PAPA
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

10. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (55 reviews)
"Amazing! Thank you!"
United Kingdom
Lucy
The price is NT$4,429
NT$5,015 total
includes taxes & fees
Nov 1 - Nov 2
Guild Living Siena Senior Resort & Residence
A bakery display with pastries and a coffee station.

11. 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$2,341
NT$2,717 total
includes taxes & fees
Nov 9 - Nov 10
B&B Il Corso
A hotel room with a bed, pillows, a wall-mounted lamp, and a framed picture.

12. Anchor Santa Croce

Anchor Santa Croce
Historic Centre of Florence
9.8 out of 10, Exceptional, (7 reviews)
"Staff was very helpful and attentive. Location was perfect, within walking distance to many restaurants, piazza’s, shops."
United States
Franie
The price is NT$4,196
NT$5,043 total
includes taxes & fees
Nov 5 - Nov 6
Anchor Santa Croce
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
9.4 out of 10, Exceptional, (270 reviews)
"Very friendly and clean."
United States
Mohamed
The price is NT$4,392
NT$4,939 total
includes taxes & fees
Nov 13 - Nov 14
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 NT$2,105
NT$2,458 total
includes taxes & fees
Oct 20 - Oct 21
Domus il Palio B&B
A terrace with outdoor seating, a view of the city, and a clock tower in the background.

15. Palazzo Alfieri Residenza d’epoca - Place of Charme

Palazzo Alfieri Residenza d’epoca - Place of Charme
Historic Centre of Florence
9.2 out of 10, Wonderful, (854 reviews)
"Beautiful rooms and great location"
Canada
Taylor
The price is NT$8,156
NT$9,472 total
includes taxes & fees
Nov 12 - Nov 13
Palazzo Alfieri Residenza d’epoca - Place of Charme
A modern bedroom with a large bed, a desk with chairs, and a bathroom visible through an open door.

16. Palazzo Mannaioni Suites

Palazzo Mannaioni Suites
4.0 star property
Historic Centre of Florence
9.2 out of 10, Wonderful, (1,190 reviews)
"Great location"
United States
Diana
The price is NT$3,760
NT$4,635 total
includes taxes & fees
Nov 2 - Nov 3
Palazzo Mannaioni Suites
Room

17. La Torre Del Cestello

La Torre Del Cestello
Historic Centre of Florence
9.0 out of 10, Wonderful, (345 reviews)
"Great location easy to park car with car service they offer"
United States
Joanna
The price is NT$2,817
NT$3,597 total
includes taxes & fees
Nov 9 - Nov 10
La Torre Del Cestello
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

Bernini Palace

Bernini Palace

10/10 Excellent
"Absolutely amazing hotel. The room was incredible. The hotel staff were so beyond friendly. And the hotel is in a great location! Definitely recommend."
Kaylin 1-night trip
Posted 1 hour ago
Bernini Palace

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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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.