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Holiday Rentals in Radda in Chianti

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Our top choices for Radda in Chianti holiday rentals

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, (1)
"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 €284
includes taxes & fees
23 Dec - 24 Dec
Chianti dreaming in Radda-3 independent bedrooms with private bathroom and TV

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, (1)
"Pros: Świetna lokalizacja i przyjemne otoczenie domu. Dom położony na wzniesieniu z którego roztaczał się piękny widok. Cons: Osoba opiekująca się domem nie mówiła po angielsku co utrudniało komunikację. Nie byliśmy świadomi że dom podzielony jest na 2 części góra i piwnica w której były dodatkowe 3 pokoje. Uszkodzona pralka która nie dopierała pranych ubrań - brudna woda z zanieczyszczeniami które dodatkowo brudziły ubrania."
Poland
Anonymous traveller
The price is €2,248
includes taxes & fees
25 Dec - 26 Dec
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

San Giuliano Inn - Adults Only

San Giuliano Inn - Adults Only
Historic Centre of Florence
10.0 out of 10, Exceptional, (406)
"Great inn. "
United States
Carol
San Giuliano Inn - Adults Only

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (422)
"A great location!"
Canada
Cheryl
The price is €135
includes taxes & fees
4 Jan - 5 Jan 2026
Siena Vip

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (192)
"Safe, clean, close to all attractions"
Canada
Carlo
B&B Il Corso

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (335)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is €62
includes taxes & fees
24 Dec - 25 Dec
ApartHotel Anghel

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (193)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House

B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (63)
"Great location. Room spacious and clean. Personnel friendly and great service walkable to best historic places. Could find something better "
United States
Rodolfo
B&B Palazzo del Magnifico

PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (96)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
The price is €184
includes taxes & fees
27 Dec - 28 Dec
PALAZZO DEL PAPA

Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (116)
"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."
United States
Linda
The price is €184
includes taxes & fees
6 Jan - 7 Jan 2026
Residenza d'Epoca Palazzo Borghesi

Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
Regis Condo

La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !

La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !
Siena
10.0 out of 10, Exceptional, (66)
"Great Place and super nice Host. Location is very nice, top equiped and located only a couple of minutes away from Siena. Host is a really nice Person that has super good ideas where to go, in turism and wine/food matters. Really loved our stay (me and my Kids 14years), definitely come back. Highly recommended"
Germany
Michael G.
La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (27)
"This was our favourite B&B. The owner Simona was absolutely wonderful. The hot tub in our room was out of this world. If you have the chance to visite this gem…DO IT!!"
Canada
Claude
DormiVeglia B&B

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (33)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
Tenuta Sant'Ilario

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (108)
"Front desk was very helpful and very comfortable room. "
United States
Chris
Chianti Village Morrocco

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (71)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
Terre di Baccio

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
The price is €141
includes taxes & fees
7 Jan - 8 Jan 2026
Villa il Fedino

Numa Palazzo San Niccolò

Numa Palazzo San Niccolò
Historic Centre of Florence
9.4 out of 10, Exceptional, (174)
"Clean, amenities, breakfast! "
United States
Laury
The price is €104
includes taxes & fees
5 Jan - 6 Jan 2026
Numa Palazzo San Niccolò

Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo
4.0 star property
Florence
8.2 out of 10, Very good, (228)
"The property is perfect if you’re looking for a place to relax and have the most wonderful views of Tuscany area, the staff, Andrea was really helpful and kind. It’s better if you rent a car to get there, by bus you’ll have to walk a lot. But the place is totally worth it,"
United States
Jorge
The price is €78
includes taxes & fees
10 Jan - 11 Jan 2026
Fattoria il Milione Agriturismo
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

Everything you need to know about Radda in Chianti holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Radda in Chianti holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Radda in Chianti holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Radda in Chianti holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Radda in Chianti. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Radda in Chianti holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Radda in Chianti holiday rentals we have selected for you start as low as €78 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Radda in Chianti rentals

At Expedia, we put the best Radda in Chianti holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Radda in Chianti rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Radda in Chianti holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Radda in Chianti. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

QK Costa58 Home Tower: This holiday home rental outside of Radda in Chianti is located in the historical district, and offers a terrace, air conditioning and daily housekeeping to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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 Chianti Sculpture Park. 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.