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Our top choices for Citta della Pieve vacation homes

1. 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 ¥114,789
¥131,213 total
includes taxes & fees
Nov 10 - Nov 11
Villa on the Umbria-Tuscany border—for families and friends—with a private pool

2. Holiday Home 'Il Forcone' with Shared Pool, Wi-Fi and Air Conditioning

Holiday Home 'Il Forcone' with Shared Pool, Wi-Fi and Air Conditioning
Panicale
The price is ¥27,525
¥36,141 total
includes taxes & fees
Nov 10 - Nov 11
Holiday Home 'Il Forcone' with Shared Pool, Wi-Fi and Air Conditioning

3. 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 ¥13,149
¥17,113 total
includes taxes & fees
Nov 10 - Nov 11
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

4. The Rose Cottage - Vacation Home with a Garden in Umbria

The Rose Cottage - Vacation Home with a Garden in Umbria
Tavernelle
The price is ¥22,075
¥32,185 total
includes taxes & fees
Dec 6 - Dec 7
The Rose Cottage - Vacation Home with a Garden in Umbria

5. 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 ¥14,200
¥15,620 total
includes taxes & fees
Nov 10 - Nov 11
Le Roghete

6. 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 ¥33,377
¥45,562 total
includes taxes & fees
Nov 10 - Nov 11
Eagle House

7. 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 ¥14,128
¥14,834 total
includes taxes & fees
Nov 11 - Nov 12
Double bedroom with private bathroom, private access, garden and swimming pool

8. "Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (12 reviews)
"An wonderfully presented apartment in a beautiful town away from the tourist areas but close enough with a short drive. It’s a beautiful town and the apartment is a welcome retreat when you have enjoyed enough of the Tuscan sun. It’s clear the owner has attention to detail and that made our stay even better! "
Australia
Dan
The price is ¥17,660
¥20,309 total
includes taxes & fees
Nov 10 - Nov 11
"Il Focolare" Superior Apartment in Monticchiello

9. Large apartment with garden in an old farmhouse with swimming pool

Large apartment with garden in an old farmhouse with swimming pool
Radicofani
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful location in the heart of Tuscany."
United States
Catherine J.
The price is ¥31,788
¥32,494 total
includes taxes & fees
Nov 10 - Nov 11
Large apartment with garden in an old farmhouse with swimming pool

10. 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 ¥12,715
¥15,364 total
includes taxes & fees
Nov 11 - Nov 12
Federico's Cantuccio, a cozy apartment in the heart of Radicofani

11. Sant'Angelo House

Sant'Angelo House
Acquapendente
The price is ¥16,689
¥18,632 total
includes taxes & fees
Nov 10 - Nov 11
Sant'Angelo House

12. Sant Angelo House

Sant Angelo House
Acquapendente
The price is ¥16,689
¥18,632 total
includes taxes & fees
Nov 10 - Nov 11
Sant Angelo House

13. Eva's house awaits you!

Eva's house awaits you!
Monterubiaglio
10.0 out of 10, Exceptional, (2 reviews)
"L'appartement est très grand (rez-de-chaussée d'une maison) et aménagé avec bcp de goût. Tout etait fournis à l'arrivée : linges de lit, serviettes de toilette, liquide vaisselle, éponge et torchons. L'accueil des propriétaires etaient chaleureux et leurs conseils bienvenus. Chien, chat, tortues nous ont réservés un acceuil amical. Le jardin est très grand, idéal lorsqu'on a des enfants. La piscine est un avantage non négligeable au vu des températures très élevées. Les villages villes...
France
Stéphanie D.
The price is ¥20,309
¥24,018 total
includes taxes & fees
Nov 10 - Nov 11
Eva's house awaits you!

14. 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 ¥28,609
¥34,613 total
includes taxes & fees
Nov 10 - Nov 11
Holiday Home 'Colline' with Balcony and Wi-Fi

15. 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 ¥17,483
¥23,664 total
includes taxes & fees
Nov 10 - Nov 11
Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza

16. A Casa di Viola, a tourist destination: 1-bedroom house

A Casa di Viola, a tourist destination: 1-bedroom house
Orvieto
The price is ¥21,192
¥23,135 total
includes taxes & fees
Nov 10 - Nov 11
A Casa di Viola, a tourist destination: 1-bedroom house

17. Quaint 1-bedroom house in lovely Sugano perfect for relaxing stays

Quaint 1-bedroom house in lovely Sugano perfect for relaxing stays
Sugano
The price is ¥15,894
¥21,263 total
includes taxes & fees
Nov 10 - Nov 11
Quaint 1-bedroom house in lovely Sugano perfect for relaxing stays

18. 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 ¥19,073
¥27,196 total
includes taxes & fees
Nov 10 - Nov 11
Double room with private bathroom in the countryside, 5 minutes from Montepulciano

19. Country House Le Case Coloniche

Country House Le Case Coloniche
Deruta
9.4 out of 10, Exceptional, (47 reviews)
"Fabulous stay. "
Australia
Anita
The price is ¥17,108
¥18,819 total
includes taxes & fees
Nov 20 - Nov 21
Country House Le Case Coloniche

20. 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 traveler
The price is ¥41,006
¥50,542 total
includes taxes & fees
Nov 10 - Nov 11
Holiday Home in Villa Pandolfina near Montepulciano
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 Citta della Pieve

Terracotta-hued buildings line medieval streets where you can explore the Renaissance painter Perugino's masterpieces in local churches. Climb the ancient bell tower for panoramic views, then join locals at Piazza Matteotti's cafes for aperitivo hour.

A hillside town with historic buildings and a prominent church.