Photo by Davide Taviani

Radda in Chianti Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Tonight
23 Dec - 24 Dec
Tomorrow
24 Dec - 25 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Radda in Chianti holiday rentals

Interior
Chianti dreaming in Radda-3 independent bedrooms with private bathroom and TV

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 HK$1,304
HK$2,513 total
includes taxes & fees
24 Dec - 25 Dec
Chianti dreaming in Radda-3 independent bedrooms with private bathroom and TV
Pool
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

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 HK$14,734
HK$20,580 total
includes taxes & fees
26 Dec - 27 Dec
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Food and drink
San Giuliano Inn - Adults Only

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
Birthday party area
Siena Vip

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (422)
"A great location!"
Canada
Cheryl
The price is HK$1,087
HK$1,232 total
includes taxes & fees
4 Jan - 5 Jan 2026
Siena Vip
32-inch Smart TV with digital channels, TV, streaming services
B&B Il Corso

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
Lobby lounge
ApartHotel Anghel

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 HK$486
HK$572 total
includes taxes & fees
24 Dec - 25 Dec
ApartHotel Anghel
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

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
Premium bedding, Select Comfort beds, minibar, in-room safe
La Terrazza Sul Campo Rooming House

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
View from room
B&B Palazzo del Magnifico

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
Exterior
PALAZZO DEL PAPA

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 HK$1,476
HK$1,661 total
includes taxes & fees
28 Dec - 29 Dec
PALAZZO DEL PAPA
View from room
Residenza d'Epoca Palazzo Borghesi

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 HK$1,424
HK$1,602 total
includes taxes & fees
6 Jan - 7 Jan 2026
Residenza d'Epoca Palazzo Borghesi
Private kitchen
Regis Condo

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

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.
The price is HK$1,549
HK$2,214 total
includes taxes & fees
29 Dec - 30 Dec
La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !
Daily buffet breakfast (EUR 10 per person)
DormiVeglia B&B

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
Seasonal outdoor pool, open 8 AM to 8 PM, pool umbrellas, pool loungers
Tenuta Sant'Ilario

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
Outdoor pool, pool umbrellas, pool loungers
Chianti Village Morrocco

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
Premium bedding, down duvets, in-room safe, blackout curtains
Terre di Baccio

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
Exterior detail
Villa il Fedino

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 HK$1,023
HK$1,162 total
includes taxes & fees
22 Jan - 23 Jan 2026
Villa il Fedino
Terrace/patio
Numa Palazzo San Niccolò

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 HK$714
HK$895 total
includes taxes & fees
7 Jan - 8 Jan 2026
Numa Palazzo San Niccolò
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas
Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo
4.0 star property
Florence
8.2 out of 10, Very good, (228)
"We stayed two days with kids. Perfect resort feeling, enjoyed sun rising, perfect ample amount of healthy and fresh breakfast, very welcoming and friendly helpful staff, room are spacious and clean, and cozy remote control heating options, washrooms are very clean and water is always hot. "
Canada
Manjeet
The price is HK$532
HK$714 total
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.
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

Hotel Delle Nazioni

Hotel Delle Nazioni

10/10 Excellent
"Good loca"
Peter 1-night trip
Posted 1 day ago
Hotel Delle Nazioni

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 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.