Holiday Homes in Sinalunga

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Our top choices for Sinalunga holiday homes

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

Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Foiano della Chiana
The price is €81
includes taxes & fees
15 Nov - 16 Nov
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

2. 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
9 Nov - 10 Nov
Romantic farm in the Sienese hills

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
9 Nov - 10 Nov
Double room with private bathroom in the countryside, 5 minutes from Montepulciano

4. 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 €77
includes taxes & fees
9 Nov - 10 Nov
Vacation home with a panoramic terrace, ideal for families and couples

5. Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi

Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi
Monte San Savino
6.0 out of 10, (2 reviews)
"My husband and I booked this place and were unable to stay due to lack of communication regarding check-in procedure. The listing states the host will make contact 3 days before which didn’t happen. We sent several messages the day of check-in and didn’t hear from the host until well after the check-in time (4pm). Given the remote location and time of day, we were worried we wouldn’t have anywhere to stay for the night so we booked a hotel in Arezzo which we were lucky to get on a holiday...
Canada
Anonymous traveller
The price is €203
includes taxes & fees
16 Nov - 17 Nov
Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi

6. Montecchio di Cortona

Montecchio di Cortona
Montecchio
9.0 out of 10, Wonderful, (2 reviews)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is €93
includes taxes & fees
11 Nov - 12 Nov
Montecchio di Cortona

7. Apartment with WIFI, A/C, pool, TV, patio, pets allowed, panoramic view, close to Montepulciano

Apartment with WIFI, A/C, pool, TV, patio, pets allowed, panoramic view, close to Montepulciano
Torrita Di Siena
The price is €246
includes taxes & fees
15 Nov - 16 Nov
Apartment with WIFI, A/C, pool, TV, patio, pets allowed, panoramic view, close to Montepulciano

8. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
The price is €97
includes taxes & fees
9 Nov - 10 Nov
Dolce Casa 2 by Tiny Away

9. 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 €98
includes taxes & fees
9 Nov - 10 Nov
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

10. Arc two-bedroom apartment

Arc two-bedroom apartment
Cortona
The price is €274
includes taxes & fees
15 Nov - 16 Nov
Arc two-bedroom apartment

11. Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
The price is €103
includes taxes & fees
9 Nov - 10 Nov
Dolce Casa 1 by Tiny Away

12. Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi

Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi
foiano
The price is €1,098
includes taxes & fees
15 Nov - 16 Nov
Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi

13. Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
Cortona
8.8 out of 10, Excellent, (3 reviews)
"Angelo was so friendly. He met us at the property and showed us around. The house is beautiful and peaceful. Thank you for a lovely stay."
United States
Bonnie B.
The price is €119
includes taxes & fees
9 Nov - 10 Nov
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

14. Holiday Home 'Casa Corniolo' with Mountain View, Private Terrace and Balcony

Holiday Home 'Casa Corniolo' with Mountain View, Private Terrace and Balcony
Monte San Savino
Holiday Home 'Casa Corniolo' with Mountain View, Private Terrace and Balcony

15. Apartment with A/C, pool, WIFI, TV, terrace, pets allowed, panoramic view, close to Montepulciano

Apartment with A/C, pool, WIFI, TV, terrace, pets allowed, panoramic view, close to Montepulciano
Torrita Di Siena
The price is €246
includes taxes & fees
16 Nov - 17 Nov
Apartment with A/C, pool, WIFI, TV, terrace, pets allowed, panoramic view, close to Montepulciano

16. Chalet "Azzurro" with Mountain View, Shared Pool & Wi-Fi

Chalet "Azzurro" with Mountain View, Shared Pool & Wi-Fi
Trequanda
The price is €471
includes taxes & fees
9 Nov - 10 Nov
Chalet "Azzurro" with Mountain View, Shared Pool & Wi-Fi

17. 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
15 Nov - 16 Nov
Holiday Home in Villa Pandolfina near Montepulciano

18. Apartment with A/C, pool, WIFI, TV, patio, pets allowed, panoramic view, close to Montepulciano

Apartment with A/C, pool, WIFI, TV, patio, pets allowed, panoramic view, close to Montepulciano
Torrita Di Siena
The price is €314
includes taxes & fees
15 Nov - 16 Nov
Apartment with A/C, pool, WIFI, TV, patio, pets allowed, panoramic view, close to Montepulciano

19. Vacation Home 'Il Granaio' with Pool, Private Terrace & Wi-Fi

Vacation Home 'Il Granaio' with Pool, Private Terrace & Wi-Fi
Monte San Savino
The price is €324
includes taxes & fees
16 Nov - 17 Nov
Vacation Home 'Il Granaio' with Pool, Private Terrace & Wi-Fi

20. Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is €353
includes taxes & fees
10 Nov - 11 Nov
Charming Siena Countryside Stay
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.

Learn more about Sinalunga

This medieval hilltop town offers authentic Tuscan charm with its historic piazza and Renaissance-era Collegiate Church of San Martino. Enjoy local wines at family-run vineyards, then explore nearby Val d'Orcia's rolling landscapes or visit the thermal baths in Chianciano Terme.

A historic town with a prominent church tower on a hill, surrounded by lush greenery and traditional buildings.