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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 ¥114,825
¥130,901 total
includes taxes & fees
Dec 9 - Dec 10
Villa on the Umbria-Tuscany border—for families and friends—with a private pool

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 ¥13,154
¥17,119 total
includes taxes & fees
Nov 21 - Nov 22
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

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

The Rose Cottage - Vacation Home with a Garden in Umbria
Tavernelle
The price is ¥22,151
¥32,473 total
includes taxes & fees
Dec 6 - Dec 7
The Rose Cottage - Vacation Home with a Garden in Umbria

4. 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 ¥28,307
¥36,926 total
includes taxes & fees
Nov 21 - Nov 22
Holiday Home 'Il Forcone' with Shared Pool, Wi-Fi and Air Conditioning

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 ¥14,204
¥15,624 total
includes taxes & fees
Nov 15 - Nov 16
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 ¥33,388
¥45,930 total
includes taxes & fees
Nov 15 - Nov 16
Eagle House

7. "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 ¥17,665
¥20,315 total
includes taxes & fees
Nov 19 - Nov 20
"Il Focolare" Superior Apartment in Monticchiello

8. Sant Angelo House

Sant Angelo House
Acquapendente
The price is ¥16,694
¥18,637 total
includes taxes & fees
Nov 14 - Nov 15
Sant Angelo House

9. Sant'Angelo House

Sant'Angelo House
Acquapendente
The price is ¥16,694
¥18,637 total
includes taxes & fees
Nov 14 - Nov 15
Sant'Angelo House

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 ¥12,719
¥15,369 total
includes taxes & fees
Nov 17 - Nov 18
Federico's Cantuccio, a cozy apartment in the heart of Radicofani

11. 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 ¥28,618
¥34,625 total
includes taxes & fees
Nov 14 - Nov 15
Holiday Home 'Colline' with Balcony and Wi-Fi

12. 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 ¥17,168
¥18,885 total
includes taxes & fees
Nov 20 - Nov 21
Country House Le Case Coloniche

13. 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 ¥17,489
¥23,672 total
includes taxes & fees
Nov 19 - Nov 20
Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza

14. 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 ¥18,284
¥23,654 total
includes taxes & fees
Nov 27 - Nov 28
Quaint 1-bedroom house in lovely Sugano perfect for relaxing stays

15. Eva's house is waiting for you!

Eva's house is waiting for 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 ¥20,315
¥24,025 total
includes taxes & fees
Nov 21 - Nov 22
Eva's house is waiting for you!

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 ¥21,199
¥22,082 total
includes taxes & fees
Nov 14 - Nov 15
A Casa di Viola, a tourist destination: 1-bedroom house

17. 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 ¥19,079
¥25,969 total
includes taxes & fees
Nov 14 - Nov 15
Double room with private bathroom in the countryside, 5 minutes from Montepulciano

18. 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 ¥39,234
¥48,803 total
includes taxes & fees
Nov 15 - Nov 16
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.