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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Radda in Chianti vacation rentals

A bakery display with pastries and a coffee station.

1. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (210 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 CA $163
CA $186 total
includes taxes & fees
Sep 30 - Oct 1
B&B Il Corso
A bathroom with a window view of a historic building and a tiled roof.

2. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (481 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
The price is CA $153
CA $175 total
includes taxes & fees
Oct 21 - Oct 22
Siena Vip
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 CA $212
CA $240 total
includes taxes & fees
Oct 4 - Oct 5
Villa Curina Resort
A table with two wine glasses, a bottle, and a book.

4. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (98 reviews)
"Everything was very clean and modern, working perfect. We didn’t meet anyone from the staff. And it would be nice if they leave some bottle of water for each room. We like the place a lot. People have to consider that it is outside Siena walls and it’s a pretty steep and long distance walk"
United States
María
The price is CA $95
CA $111 total
includes taxes & fees
Oct 20 - Oct 21
Domus il Palio B&B
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

5. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (39 reviews)
"Great spot"
Canada
Philippe
The price is CA $221
CA $307 total
includes taxes & fees
Oct 1 - Oct 2
Villa di Sotto
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

6. 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 CA $788
CA $873 total
includes taxes & fees
Sep 27 - Sep 28
Terre di Baccio
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

7. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (347 reviews)
"Humming noise in the room. Slow internet. Fine bed. Good location."
Netherlands
Lauro
The price is CA $122
CA $140 total
includes taxes & fees
Sep 27 - Sep 28
ApartHotel Anghel
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

8. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (111 reviews)
"We loved our stay The host made us feel appreciated and really went out of his way to show us the highlight spots to see and where to eat. Thanks you."
Canada
scott
The price is CA $274
CA $308 total
includes taxes & fees
Oct 12 - Oct 13
PALAZZO DEL PAPA
A stone building with a garden in front.

9. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (27 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is CA $245
CA $282 total
includes taxes & fees
Sep 28 - Sep 29
Borgo Argenina
A dining area with a table set for two, featuring a view of greenery through a window.

10. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (38 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is CA $226
CA $255 total
includes taxes & fees
Sep 27 - Sep 28
La Locanda di Pietracupa
A modern hotel room with a wooden door, a white sink, a bathtub, a bed with white bedding, and a bedside table with a lamp.

11. Piazza Paradiso Accomodation

Piazza Paradiso Accomodation
Siena City Centre
9.2 out of 10, Wonderful, (160 reviews)
"Great location and lovely staff!"
United States
Dawn
The price is CA $140
CA $161 total
includes taxes & fees
Oct 19 - Oct 20
Piazza Paradiso Accomodation
A view from a window overlooking a rural landscape with fields and a distant mountain range.

12. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (65 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
The price is CA $171
CA $196 total
includes taxes & fees
Oct 21 - Oct 22
B&B Palazzo Tortoli
A spacious hotel room with a large bed, a sitting area with chairs, and a view through an arched doorway to another room.

13. La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (250 reviews)
"Great stay. Thanks for the hospitality and kindness."
United Kingdom
Agnieszka
The price is CA $191
CA $217 total
includes taxes & fees
Oct 26 - Oct 27
La Terrazza Sul Campo Rooming House
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, (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 CA $324
CA $362 total
includes taxes & fees
Oct 25 - Oct 26
Villa il Fedino
A crowded square with a historic building featuring intricate architectural details.

15. Soggiorno Battistero

Soggiorno Battistero
Historic Centre of Florence
8.8 out of 10, Excellent, (431 reviews)
"The most central location you can stay in Florence! Good breakfast included. Staff gave us great recommendation for restaurants. They also let us store our bags after our check out time. Definitely recommend."
United States
Eugen
The price is CA $283
CA $334 total
includes taxes & fees
Oct 19 - Oct 20
Soggiorno Battistero
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, (113 reviews)
"They were very helpful to me when I arrived. I difficulty accessing there messages to me. They put me at ease"
United States
Angela
The price is CA $151
CA $214 total
includes taxes & fees
Sep 27 - Sep 28
Palazzo al Torrione 2
A garden with a stone pathway, wooden benches, and various potted plants.

17. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (85 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is CA $196
CA $223 total
includes taxes & fees
Oct 22 - Oct 23
Antico Borgo il Cardino
A terrace with outdoor seating, a view of the city, and a clock tower in the background.

18. Il Rivalta - Place of Charme

Il Rivalta - Place of Charme
4.0 star property
Historic Centre of Florence
9.4 out of 10, Exceptional, (626 reviews)
"Il Rivata was above and beyond my expectations. It was an incredible value in a wonderful location"
United States
Brian
The price is CA $467
CA $537 total
includes taxes & fees
Oct 27 - Oct 28
Il Rivalta - Place of Charme
A balcony with a table, wine glasses, and a bottle, overlooking a historic building with a clock tower and another tower.

19. Relais Piazza Signoria

Relais Piazza Signoria
Historic Centre of Florence
9.4 out of 10, Exceptional, (876 reviews)
"great staff. Very accessible and close to very good restaurants and gelaterias."
Canada
Melika
The price is CA $293
CA $341 total
includes taxes & fees
Oct 27 - Oct 28
Relais Piazza Signoria
A wooden door with a sign, a large potted plant, and a view of a historic building.

20. La Casa del Garbo - Luxury Rooms & Suite

La Casa del Garbo - Luxury Rooms & Suite
Historic Centre of Florence
9.6 out of 10, Exceptional, (306 reviews)
"Location was incredible. Staff was incredibly helpful and accommodating. We ended up missing check in due to a late train and they were very kind to set up late check in for us last minute. Rooms were so cute and spacious. Had read some reviews about the noise from the plaza being loud, but we couldn't hear a thing. Will be staying here again when visiting Florence."
United States
Kristin
The price is CA $221
CA $311 total
includes taxes & fees
Oct 27 - Oct 28
La Casa del Garbo - Luxury Rooms & Suite
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

c-hotels Ambasciatori

c-hotels Ambasciatori

8/10 Good
"The hotel Is nice and very centrally located rooms are small and the biggest problem is the shower is like a capsule of 3.5’x3.5’ i which you can hardly move without hitting yourselves everywhere Honestly I have never been a hotel with a shower that small Hotel breakfast was really good Thanks Jose"
Jose 5-night trip
Posted 6 hours ago
c-hotels Ambasciatori

Find out more about Radda in Chianti

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Radda in Chianti. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.