A historic town with a prominent castle on a hill, surrounded by lush green fields and rolling hills in the background.

Holiday Homes in Chianciano Terme

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Chianciano Terme holiday homes

A swimming pool with lounge chairs, a stone building, and a garden with various plants and a large terracotta pot.

1. Eagle House

Eagle House
CHIANCIANO
10.0 out of 10, Exceptional, (3 reviews)
"Paolo and Monica were such gracious and enthusiastic hosts. The property is beautiful, and the hospitality was great. Paolo and Monica helped plan our itinerary each day which made for a stress-free week. The highlight was the interaction with owls, eagles, and other animals, as well as the wine cave and the history behind it. Thanks again, Paolo and Monica! "
United States
Rob C.
The price is €265
includes taxes & fees
2 Nov - 3 Nov
Eagle House
A rustic brick building with a mural, a clock, and various potted plants.

2. Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
Casamaggiore
10.0 out of 10, Exceptional, (1 review)
"Stayed 2 nights in June 2026. Beautiful place with garden and private parking and outdoor terrace - all you can need in quite spacious studio condo. Comfy big bed, aircon and a ceiling fan, dining table with 4 chairs and a kitchenette if you want to cook your own dinners (full with cutlery and crockery, fridge and coffee machine). Clean private bathroom with shower, toilet and bidet. Host was very lovely too, we need an iron and we could borrow it with no fuss alongside ironing board. Very...
United Kingdom
Anna
The price is €97
includes taxes & fees
2 Nov - 3 Nov
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

3. Double room with private bathroom in the countryside, 5 minutes from Montepulciano

Double room with private bathroom in the countryside, 5 minutes from Montepulciano
Toscana
The price is €157
includes taxes & fees
2 Nov - 3 Nov
Double room with private bathroom in the countryside, 5 minutes from Montepulciano
A covered patio with a brick wall, a round table with chairs, and a view of greenery.

4. Holiday Home in Villa Pandolfina near Montepulciano

Holiday Home in Villa Pandolfina near Montepulciano
Acquaviva
10.0 out of 10, Exceptional, (1 review)
"Pros: L'appartamento è molto spazioso e comodo con una vista panoramica sulla campagna di Montepulciano Cons: Nulla da rilevare"
Italy
Anonymous traveller
The price is €286
includes taxes & fees
2 Nov - 3 Nov
Holiday Home in Villa Pandolfina near Montepulciano
A park with picnic tables, a playground, and a gravel path.

5. Vacation home with a panoramic terrace, ideal for families and couples

Vacation home with a panoramic terrace, ideal for families and couples
Cortona
The price is €84
includes taxes & fees
26 Nov - 27 Nov
Vacation home with a panoramic terrace, ideal for families and couples
A stone house with a tiled roof, surrounded by dense greenery and a clear sky.

6. Le Roghete

Le Roghete
Acquapendente
9.4 out of 10, Exceptional, (3 reviews)
"The address of the hotel was wrong on the Hotels.com web site. After an anxious hour or so our host was kind enough to come and get us, we were on foot walking the Via Francigena and the additional 4 miles back would have been a killer. Our host arranged for a cab the next morning so we were back on schedule. Worth the cab expense to keep on schedule. Wonderful evening meal and a great hotel. I would visit it again."
United States
Mark
The price is €88
includes taxes & fees
4 Nov - 5 Nov
Le Roghete
A modern bedroom with a wooden headboard, a large bed with a textured blanket, bedside tables with lamps, and a mirror.

7. Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza

Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza
Bagni San Filippo
10.0 out of 10, Exceptional, (1 review)
"Terme House is just as described. It had all of the amenities mentioned and was clean. We wanted a place just off ss2 - perfect location and quiet town. 5 stars!!!"
United States
Lori
The price is €137
includes taxes & fees
3 Nov - 4 Nov
Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza
A stone building with a stone wall and a small bridge, surrounded by trees and grass.

8. Holiday Home 'Colline' with Balcony and Wi-Fi

Holiday Home 'Colline' with Balcony and Wi-Fi
Radicofani
8.0 out of 10, Very good, (1 review)
The price is €196
includes taxes & fees
2 Nov - 3 Nov
Holiday Home 'Colline' with Balcony and Wi-Fi
A brick building with a large sliding glass door, a brown door, and a small potted plant.

9. Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Foiano della Chiana
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
A swimming pool with a wooden deck and lounge chairs, surrounded by a scenic landscape with hills and a clear sky.

10. Agritourism in Val d'Orcia

Agritourism in Val d'Orcia
montalcino
Agritourism in Val d'Orcia
A narrow stone staircase leading to a building with balconies adorned with flower pots.

11. La Casa del Viandante – Holiday Apartment in Radicofani, Val d’Orcia

La Casa del Viandante – Holiday Apartment in Radicofani, Val d’Orcia
Radicofani
10.0 out of 10, Exceptional, (1 review)
"This is a lovely place to stay. Quiet and quaint with everything you need to enjoy a stay in Radicofani."
Canada
Chantale M.
La Casa del Viandante – Holiday Apartment in Radicofani, Val d’Orcia
A pathway leading to a building with stone walls and a tree.

12. A typical Tuscan country house

A typical Tuscan country house
Montalcino
The price is €147
includes taxes & fees
3 Nov - 4 Nov
A typical Tuscan country house
A stone building with a tiled roof, a staircase leading to a lower level, and a garden with various plants.

13. Double bedroom with private bathroom, private access, garden and swimming pool

Double bedroom with private bathroom, private access, garden and swimming pool
Radicofani
The price is €84
includes taxes & fees
2 Nov - 3 Nov
Double bedroom with private bathroom, private access, garden and swimming pool
A stone building with a wooden door and shutters, a small outdoor seating area with a table and chairs, and potted plants.

14. Federico's Cantuccio, a cozy apartment in the heart of Radicofani

Federico's Cantuccio, a cozy apartment in the heart of Radicofani
Radicofani
The price is €90
includes taxes & fees
3 Nov - 4 Nov
Federico's Cantuccio, a cozy apartment in the heart of Radicofani
A stone patio with a round table and chairs, surrounded by lush greenery and potted plants.

15. Romantic farm in the Sienese hills

Romantic farm in the Sienese hills
Trequanda, Siena
7.0 out of 10, Good, (2 reviews)
"Zum positiven: Kommunikation mit dem Gastgeber war sehr gut und informativ. Check in war gut, Antonio der die Übergabe der Schlüssel und die Erläuterung zum Appartement machte sprach leider nur italienisch, aber er war sehr freundlich und mit Händen und Füßen funktionierte es gut. Das Apartment war wirklich sehr schön und mit Liebe zum Detail eingerichtet. Die Location war wirklich sehr schön.Nun zum negativen: An allen Fenstern der Unterkunft waren keine Fliegengitter angebracht was es...
United States
Harald B.
The price is €200
includes taxes & fees
2 Nov - 3 Nov
Romantic farm in the Sienese hills
A neatly made bed with white bedding and two rolled towels.

16. Sant'Angelo House

Sant'Angelo House
Acquapendente
The price is €117
includes taxes & fees
2 Nov - 3 Nov
Sant'Angelo House
A small, cozy room with a bed, a chair, and a desk.

17. Sant Angelo House

Sant Angelo House
Acquapendente
The price is €117
includes taxes & fees
2 Nov - 3 Nov
Sant Angelo House
A terrace with a table and chairs, surrounded by greenery, overlooking a landscape with hills.

18. Villa on the Umbria-Tuscany border—for families and friends—with a private pool

Villa on the Umbria-Tuscany border—for families and friends—with a private pool
Città della Pieve
10.0 out of 10, Exceptional, (57 reviews)
"Beautiful place, where we had a wonderful week. The host was responsive and gave excellent introduction both to the house and the local area. Highly recommended."
United States
Jens Kristian T.
The price is €537
includes taxes & fees
2 Nov - 3 Nov
Villa on the Umbria-Tuscany border—for families and friends—with a private pool
A rectangular swimming pool with stone steps leading into it, surrounded by a grassy area with trees and umbrellas.

19. Nice apartment with A/C, pool, WIFI, TV, patio, pets allowed, panoramic view, close to Montepulciano

Nice apartment with A/C, pool, WIFI, TV, patio, pets allowed, panoramic view, close to Montepulciano
Torrita Di Siena
Nice apartment with A/C, pool, WIFI, TV, patio, pets allowed, panoramic view, close to Montepulciano
A terrace with a table set for breakfast, overlooking a mountainous landscape.

20. Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views

Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views
Castelnuovo dell'Abate
10.0 out of 10, Exceptional, (1 review)
"Il Borghetto is a renovated house in the little village of Castelnuovo dell'Abate, one of the medieval hilltop villages in the UNESCO world heritage-listed Val D'Orcia. It is charming and the beds are very comfortable, but be prepared to take luggage up a steep street to the front door and then steep stairs to both bedrooms. Each bedroom is on a different floor so there is considerable privacy. The piece de la resistance is the rooftop terrace, with 180 degree panoramic views over the valley and...
Australia
Judith F.
The price is €159
includes taxes & fees
2 Nov - 3 Nov
Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views
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 Chianciano Terme Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Relaxing property!"
Natalie 5-night trip
Posted 18 hours ago
Monastero di Cortona Hotel & Spa

Find out more about Chianciano Terme

Chianciano Terme Holiday Homes information

Number of reviews
70
Accommodation
998 Holiday Homes
Lowest Price
€84
Highest Price
€537