A stone building with a tower, arched windows, and a red-tiled roof.

Search Holiday Rentals in Radda in Chianti

Q: 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.

Dates

November 2026

December 2026

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Our top choices for Radda in Chianti holiday rentals

A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

1. Terre di Baccio

Greve in Chianti

Gage

Rp5.226.630 total

includes taxes & fees

10 Nov - 11 Nov

A dining area with a table set for two, featuring a view of greenery through a window.

2. La Locanda di Pietracupa

Tavarnelle Val di Pesa

Isabell

Rp2.952.817 total

includes taxes & fees

10 Nov - 11 Nov

An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

3. Guild Living Siena Senior Resort & Residence

Scacciapensieri

"We booked this last - minute and were really impressed with the whole experience. The property and grounds are beautiful. Staff was so friendly and helpful. The rooms were well appointed and quiet. Beds were too firm for our liking, but it was easy to overlook as the entire stay was really great. Good options in the restaurant too. The block of hotel rooms is in a retirement resort, which I think is a wonderful idea! Very much enjoyed our stay. We had a car and parking was free."

Heidi

Rp2.010.818 total

includes taxes & fees

12 Nov - 13 Nov

A spacious indoor area with arched windows, wooden furniture, and hanging plants.

4. Relais Villa Olmo - Place of Charme

Impruneta

Michael

Rp1.845.227 total

includes taxes & fees

26 Nov - 27 Nov

A bakery display with pastries and a coffee station.

5. B&B Il Corso

Siena City Centre

Heather

Rp1.537.868 total

includes taxes & fees

9 Nov - 10 Nov

A bathroom with a window view of a historic building and a tiled roof.

6. Siena Vip

Siena City Centre

Jacob

Rp1.843.973 total

includes taxes & fees

9 Nov - 10 Nov

A table with two wine glasses, a bottle, and a book.

7. Domus il Palio B&B

Ravacciano

Leo

Rp1.371.817 total

includes taxes & fees

18 Nov - 19 Nov

An arched entrance with a lantern above, flanked by two potted plants.

8. Villa il Fedino

San Casciano in Val di Pesa

Justyna

Rp3.244.126 total

includes taxes & fees

23 Nov - 24 Nov

A modern lobby with white leather sofas, a glass coffee table, and potted plants.

9. ApartHotel Anghel

Siena

clifford

Rp1.158.228 total

includes taxes & fees

15 Nov - 16 Nov

A room with a white wardrobe, a glass-top table, a chair, and a large ornate mirror.

10. B&B Palazzo del Magnifico

Siena City Centre

Khaled

Rp2.097.045 total

includes taxes & fees

9 Nov - 10 Nov

A courtyard with a stone statue, a round table, and chairs.

11. Regis Condo

Siena City Centre

Jessica

Rp1.597.846 total

includes taxes & fees

29 Nov - 30 Nov

A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

12. PALAZZO DEL PAPA

Siena City Centre

Charles

Rp3.131.340 total

includes taxes & fees

12 Nov - 13 Nov

An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

13. B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

Stella

Rp2.378.540 total

includes taxes & fees

9 Nov - 10 Nov

A water park with a pool, slides, and a wooden deck area.

14. hu Firenze Certosa camping in town

Impruneta

Ana María

Rp1.012.895 total

includes taxes & fees

9 Nov - 10 Nov

A room with a bed, a leather sofa, and a window with a view of a building outside.

15. Al Mercato B&B

Siena City Centre

Sandra

Rp1.464.412 total

includes taxes & fees

17 Nov - 18 Nov

An outdoor dining area with multiple tables and chairs, surrounded by plants and hanging lights.

16. Hu Firenze Camping In Town

Florence

Debra

Rp1.161.555 total

includes taxes & fees

22 Nov - 23 Nov

A hot tub with two people, surrounded by trees and a wooden deck.

17. 2 Cuori e 1 Yurta Glamping in Toscana

Asciano

Rp4.823.269 total

includes taxes & fees

12 Nov - 13 Nov

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Find holiday rentals that suit your style

Top Radda in Chianti Hotel Reviews

An outdoor patio with tables and chairs, a pergola structure, and a stone building in the background.

Tenuta CorteDomina

Radda in Chianti

10/10 Excellent

Ambra

A rustic stone interior with a dining area, two armchairs, a table with a lamp, and a view through an arched doorway.

Castello di Volpaia

Radda in Chianti

10/10 Excellent

Tomi

A covered outdoor seating area with a wooden door, wicker chairs, and potted plants.

Borgo Vescine

Radda in Chianti

10/10 Excellent

I'd never heard of Radda before but this place is a gem, just outside of this little Tuscan town. Situated near In Greve, Castellina, and the Chianti road, the service, sights, and grounds are unbelievable. I travelled to this hotel with my parents and we each staying in rooms that felt like separate villas. Theirs had an amazing view and mine had a private porch that was tucked away, perfect for sitting with friends or family to have a late night glassw of wine or cigar. The grounds feel very...

Matt

A narrow street with buildings on either side, a flag, and a bench.

Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

10/10 Excellent

Anonymous traveller

Relais Santa Cristina

Radda in Chianti

10/10 Excellent

Our host Francesco was wonderful. Showed us our room in a restored 1840s building in their vineyard, and explained local things to see and do. The spacious rooom had log ceilings and a four poster bed. Had a free breakfast at Francesco's mothers cafe just around the corner. Early in the season so the pool wasn't open yet. Fantastic place to stay. Make sure you contact Francesco by phone before you arrive so he can meet you at checkin. His # is in the check in instructions.

Nicholas

A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

10/10 Excellent

This place is surreal. We felt like we were on the set of the Name of the Rose. Sleeping in a real XIV century monastery, with its own church (with amazing frescoes), on a hill overlooking the grapes and olive trees dotted countryside...just unbelievable. We stay in one the celle, which is a 3 bedroom apartment on 2 floors, with your own private garden...yes, that's correct. Simply unheard of. The location is great too (Siena is a short drive away). The only setbacks were breakfast, very...

Ivo

A table with breakfast items and a wicker chair, overlooking a scenic landscape.

Palazzo Ravizza

Siena Historical Center

10/10 Excellent

Very enjoyable stay at this Hotel, everywhere was very clean. All the staff were helpful and friendly, the receptionist who checked us out took the time to show us a scenic route south to our next stay. The parking on site was great and secure. Breakfast lovely too.The location was very central. We would definitely book this hotel if we were to return to Siena, which is highly likely, thank you for a great stay.

Stuart

Hotel Italia

Camollia

10/10 Excellent

Anonymous traveller

A courtyard with outdoor seating, potted plants, and a statue.

Hotel David

Oltrarno

10/10 Excellent

We stayed at the Hotel David for four nights. The staff are welcoming, pleasant and helpful. The cleaning staff did an invisible but excellent job, leaving our room immaculate every day. Our twin room was spacious, with ample storage space, and a large shower room off a small hallway. The bed was very comfortable. There a wide variety of food for breakfast, including fresh fruit and freshly made pastries and cakes. I would recommend this hotel to anyone who doesn't mind the 15-20-minute walk...

Anonymous traveller

An outdoor dining area with tables and chairs, surrounded by a brick wall and greenery.

Hotel Athena

Siena Historical Center

10/10 Excellent

Richard

A lobby with a marble floor, a chandelier, a reception desk, and large green plants.

Hotel Chiusarelli

Siena City Centre

10/10 Excellent

Fab hotel - staff were very helpful as we arrived before the room was ready. There are no lifts but the steps of the staircase were wide enough to not be a problem with luggage and the staff were available to help with dealing with that aspect. Hotel was a lovely boutique historical place and very close to everything in Siena. Small car park next door which was handy. Would absolutely recommend staying there - room was big and well appointed, a good shower and it was very relaxing.

VICTORIA

A formal garden with neatly trimmed hedges, a central fountain, and stone pathways.

Art Hotel Villa Agape - Place of Charme

Oltrarno

10/10 Excellent

Marie

A spacious living room with a large grey sofa, yellow armchairs, and a chandelier.

Hotel Horto Convento

Historic Centre of Florence

10/10 Excellent

Edna

A modern interior with a glass elevator, a seating area with orange cushions, and a bookshelf filled with books.

Hotel Milu Florence

Historic Centre of Florence

10/10 Excellent

Anonymous traveller

A pool area with lounge chairs and umbrellas, surrounded by greenery and a historic building in the background.

Castel Monastero - The Leading Hotels of the World

Castelnuovo Berardenga

10/10 Excellent

Find out more about Radda in Chianti

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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.

Search Holiday Rentals in Radda in Chianti

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Radda in Chianti holiday rentals

1. Terre di Baccio

2. La Locanda di Pietracupa

3. Guild Living Siena Senior Resort & Residence

4. Relais Villa Olmo - Place of Charme

5. B&B Il Corso

6. Siena Vip

7. Domus il Palio B&B

8. Villa il Fedino

9. ApartHotel Anghel

10. B&B Palazzo del Magnifico

11. Regis Condo

12. PALAZZO DEL PAPA

13. B&B La Fonte del Machiavelli

14. hu Firenze Certosa camping in town

15. Al Mercato B&B

16. Hu Firenze Camping In Town

17. 2 Cuori e 1 Yurta Glamping in Toscana

Find holiday rentals that suit your style

Top Radda in Chianti Hotel Reviews

Tenuta CorteDomina

10/10 Excellent

Find out more about Radda in Chianti

Frequently Asked Questions

Can I find holiday rentals in Radda in Chianti?

What are some of the best holiday rentals that Radda in Chianti has to offer?

How many holiday rentals are there in Radda in Chianti?

What’s there to see and do in Radda in Chianti?

What’s a holiday rental in Radda in Chianti like?