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Check availability on Cortona Old Town Romantic Hotels

Our top choices for Cortona Old Town romantic hotels

Outdoor pool, pool loungers
Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze
Montepulciano
9.8 out of 10, Exceptional, (278)
"Great room and service"
United States
ALFREDO
The price is 3.881.278 ₫
4.392.942 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Relais Villa Grazianella - UNA Esperienze
Indoor pool, open 9:00 AM to midnight, pool loungers
Albergo San Biagio

Albergo San Biagio

Albergo San Biagio
3.0 star property
Montepulciano
8.6 out of 10, Excellent, (200)
"Great place to stay"
Canada
Robert
The price is 16.777.037 ₫
18.578.277 ₫ total
includes taxes & fees
31 Dec - 1 Jan 2026
Albergo San Biagio
Outdoor wedding area
La Cantina Relais - Fattoria Il Cipresso

La Cantina Relais - Fattoria Il Cipresso

La Cantina Relais - Fattoria Il Cipresso
Arezzo
10.0 out of 10, Exceptional, (110)
"Stay was exceptional."
United States
Suzanne
La Cantina Relais - Fattoria Il Cipresso
Exterior
Locanda Poggioleone

Locanda Poggioleone

Locanda Poggioleone
3.0 star property
Castiglione del Lago
9.2 out of 10, Wonderful, (53)
"Not only is the location absolutely gorgeous, I have never in felt more welcome. The staff is phenomenal and reads every wish off your lips, rooms are very spacious, spotless clean and just great. Make sure to try their food. Its incredible. 10/10 recommend and will be back for sure "
United Kingdom
Stefanie
The price is 3.138.377 ₫
3.501.629 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Locanda Poggioleone
Lobby
Residenza Fabroni

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is 2.357.275 ₫
2.716.539 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Residenza Fabroni
Free daily cooked-to-order breakfast
San Michele al Borgo

San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is 3.397.241 ₫
3.860.501 ₫ total
includes taxes & fees
15 Dec - 16 Dec
San Michele al Borgo
Restaurant
Palazzo Nobile di San Donato

Palazzo Nobile di San Donato

Palazzo Nobile di San Donato
Montepulciano
9.4 out of 10, Exceptional, (68)
"Unique experience in a central location "
United States
Neil T
The price is 6.367.721 ₫
7.128.029 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Palazzo Nobile di San Donato
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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Frequently asked questions

Searching for romantic hotels in Cortona Old Town?
If you and your partner need a romantic escape, we've got just the thing. Couples enjoy Cortona Old Town for its historic landmarks. If you want to explore the sights and attractions with your partner, you might consider stopping by Giuseppe Garibaldi Memorial, Piazza della Repubblica or Casali Palace. Whether you're a couple that picks a place to stay to be close to top sights or you're looking for certain amenities for your stay, you might consider checking out these 2 romantic accommodation choices in Cortona Old Town.
What is there to do in Cortona Old Town?
There's nothing better than seeing a new place with your sweetheart, so consider checking out all there is to see and do in Cortona Old Town. If you're hoping to see some of the area's cultural attractions, you'll enjoy Cortona Old Town for its historic landmarks. A visit to Giuseppe Garibaldi Memorial, Piazza della Repubblica or Casali Palace might be just the ticket when you're checking out the sights.