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Città di Castello Vacation Packages

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A historic town with medieval architecture, a prominent tower, and a river in the background.

Città di Castello
Umbria
Italy
Europe
Hotwire.com

Città di Castello Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Albergo Torre Sangiovanni

3 out of 5

Price was $1,484, price is now $1,428 per person

$1,428

per person

Dec 26 - Dec 31

found 16 hours ago

Roundtrip flight included

Chicago (ORD) to Ancona (AOI)

Book a stay at this family-friendly hotel in Todi. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Santuario dell'Amore Misericordioso di Madre Speranza and Cantina Todini are located nearby.

Borgo Tre Vaselle

5 out of 5

Price was $1,931, price is now $1,762 per person

$1,762

per person

Dec 26 - Dec 31

found 16 hours ago

Roundtrip flight included

Chicago (ORD) to Ancona (AOI)

Book a stay at this luxury hotel in Torgiano. Enjoy free breakfast, free parking, and 2 restaurants. Popular attractions Wine Museum and Olive Oil Museum are located nearby.

Amazing spot! Much better than the pictures. Amazing food, quiet and relaxing place.

Reviewed on Oct 9, 2026

Posta Donini 1579 UNA Esperienze

5 out of 5

Price was $1,813, price is now $1,667 per person

$1,667

per person

Dec 26 - Dec 31

found 16 hours ago

Roundtrip flight included

Chicago (ORD) to Ancona (AOI)

Book a stay at this luxury hotel in Perugia. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Wine Museum and Olive Oil Museum are located nearby.

great hotel , nice breakfast, helpful staff.

Reviewed on Oct 17, 2026

Sina Brufani

5 out of 5

Price was $2,055, price is now $1,904 per person

$1,904

per person

Dec 30 - Jan 6

found 1 day ago

Roundtrip flight included

Spokane (GEG) to Ancona (AOI)

Book a stay at this luxury hotel in Perugia. Enjoy free WiFi, a full-service spa, and a rooftop terrace. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Rocca Paolina and Museo delle Porte e delle Mura Urbiche are located nearby.

Agriturismo Agrileisuretime

5 out of 5

Price was $1,704, price is now $1,620 per person

$1,620

per person

Dec 26 - Dec 31

found 16 hours ago

Roundtrip flight included

Chicago (ORD) to Ancona (AOI)

Book a stay at this luxury farm stay in Spoleto. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions Cattedrale di Spoleto and Palazzo Racani Anoni are located nearby.

Prenotata per ferragosto il giorno stesso. Bella piscina, camere nuove e accoglienti, in cima a una collina con temperature serali piacevoli. Campi da Beach volley, padel, tennis. Cibo molto buono. Ci ritorneremo.

Reviewed on Aug 24, 2026

Hotel Vannucci

4 out of 5

Price was $2,445, price is now $2,327 per person

$2,327

per person

Dec 24 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Seattle (SEA) to Ancona (AOI)

Book a stay at this business-friendly hotel in Citta della Pieve. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Centro Servizi Turistici Citta della Pieve and Santa Maria dei Bianchi Oratory are located nearby.

Great!!

Reviewed on Nov 13, 2026

Abbazia Collemedio Resort & Spa

4 out of 5

Price was $2,090, price is now $2,042 per person

$2,042

per person

Dec 24 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Seattle (SEA) to Ancona (AOI)

Book a stay at this business-friendly hotel in Collazzone. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Antica Fornace Deruta and Sambuco Ceramics Store are located nearby.