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

Radda in Chianti Holiday Rentals

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Our top choices for Radda in Chianti holiday rentals

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 NZ$547
includes taxes & fees
23 Sept - 24 Sept
Chianti dreaming in Radda-3 independent bedrooms with private bathroom and TV

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 NZ$600
includes taxes & fees
13 Oct - 14 Oct
Apartment 'Rifugio sulla via di Volpaia' with Private Terrace, Wi-Fi and Air Conditioning

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 NZ$1,934
includes taxes & fees
23 Sept - 24 Sept
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

4. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (97 reviews)
"Rooms were clean and spacious ! Happy there was a good blow dryer in the room and a heated towel rack. Staff were very friendly and helpful . Would stay again !"
Canada
Alissia
The price is NZ$145
includes taxes & fees
12 Oct - 13 Oct
Domus il Palio B&B

5. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
The price is NZ$758
includes taxes & fees
21 Sept - 22 Sept
Terre di Baccio

6. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (119 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is NZ$146
includes taxes & fees
15 Oct - 16 Oct
Chianti Village Morrocco

7. 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 NZ$640
includes taxes & fees
5 Oct - 6 Oct
Borgo Argenina

8. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (39 reviews)
"Great spot"
Canada
Philippe
The price is NZ$306
includes taxes & fees
21 Sept - 22 Sept
Villa di Sotto

9. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (479 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
The price is NZ$218
includes taxes & fees
21 Oct - 22 Oct
Siena Vip

10. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (208 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 NZ$232
includes taxes & fees
27 Sept - 28 Sept
B&B Il Corso

11. 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 NZ$189
includes taxes & fees
27 Sept - 28 Sept
ApartHotel Anghel

12. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (79 reviews)
"Unique property good value staff was great. Nice location to other areas"
United States
Joe
The price is NZ$310
includes taxes & fees
27 Sept - 28 Sept
Villa Curina Resort

13. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (111 reviews)
"Fantastic location, walkable to everything, very clean & Hamza was a great host with lots of tips on what to see & where to eat"
United Kingdom
Diane
The price is NZ$438
includes taxes & fees
8 Oct - 9 Oct
PALAZZO DEL PAPA

14. Sapiti Modern by Mmega

Sapiti Modern by Mmega
Historic Centre of Florence
9.2 out of 10, Wonderful, (17 reviews)
"Affordable and walking distance to points of interest"
United States
Francisco J
The price is NZ$364
includes taxes & fees
9 Oct - 10 Oct
Sapiti Modern by Mmega

15. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (89 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveller
The price is NZ$99
includes taxes & fees
22 Sept - 23 Sept
Camping Boschetto Di Piemma

16. Villa Il Palagio

Villa Il Palagio
Rignano sull'Arno
8.8 out of 10, Excellent, (82 reviews)
"Great loved everything thank you!"
United States
Amber
The price is NZ$207
includes taxes & fees
21 Sept - 22 Sept
Villa Il Palagio

17. La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (249 reviews)
"Great stay. Thanks for the hospitality and kindness."
United Kingdom
Agnieszka
The price is NZ$350
includes taxes & fees
21 Oct - 22 Oct
La Terrazza Sul Campo Rooming House

18. 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 NZ$438
includes taxes & fees
19 Oct - 20 Oct
Villa il Fedino

19. Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1,736 reviews)
"Love this place, came back twice. Literally had all you need . The shuttle downtown is amazing, exploring with families can be chaotic this helped. The pool gets a bit crowded during peak season but still worth a visit."
United States
Ama
The price is NZ$131
includes taxes & fees
21 Oct - 22 Oct
Hu Firenze Camping In Town

20. 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 NZ$267
includes taxes & fees
23 Sept - 24 Sept
Palazzo al Torrione 2
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

Find out more about Radda in Chianti

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Radda in Chianti holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Radda in Chianti. 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 Radda in Chianti. 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 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 holiday 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 Radda in Chianti short-term rentals, that won’t be hard to do.

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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.