Vacations in Cortona

From $189.16 per night

Attraction

Montepulciano: Winery Tour & Tasting Experience

Guided 1.5-hour wine tasting in a 16th-century Montepulciano cellar with Etruscan tunnels, tomb, and sommelier led four-wine tasting

From $40.26

Best places to stay in Cortona

Find the perfect stay for your trip

Villa Borgo San Pietro

Scored out of 10, guest rating 9.3

Wonderful - What previous guests thought, 672 reviews

From $165.29 per night

Sign in to save 10% or more

Unlock members-only discounts with a free Booking.com account and start saving with Genius.

Hotel San Michele

Scored out of 10, guest rating 9.0

Wonderful - What previous guests thought, 658 reviews

Villa di Piazzano - Small Luxury Hotels of the World

Scored out of 10, guest rating 9.6

Exceptional - What previous guests thought, 333 reviews

From $840.45 per night

Monastero di Cortona Hotel & Spa

Scored out of 10, guest rating 9.4

Wonderful - What previous guests thought, 594 reviews

Hotel San Luca

Scored out of 10, guest rating 8.5

Very Good - What previous guests thought, 987 reviews

From $138.94 per night

Il Falconiere Relais & Spa

Scored out of 10, guest rating 9.1

Wonderful - What previous guests thought, 193 reviews

From $571.77 per night

Relais Villa Baldelli

Scored out of 10, guest rating 9.0

Wonderful - What previous guests thought, 213 reviews

Locanda Del Molino

Scored out of 10, guest rating 9.0

Wonderful - What previous guests thought, 365 reviews

From $214.16 per night

Locanda agli Amici

Scored out of 10, guest rating 9.3

Wonderful - What previous guests thought, 309 reviews

From $178.42 per night

Reasons to book vacations with Booking.com

Build your perfect trip
Book the best flights, stays, and more – all in one place
Stay flexible
Keep your travel plans flexible with free cancellation options
Get 24/7 support
Contact us anytime and get support in multiple languages

Vacations in Cortona: Things to know

Most booked car type	Small car
Avg. daily price for Small car	$38 per day
Avg. cost of stay	$208 per night
Best time to visit	May and June

Best places to visit in Cortona

Make the most of your vacation with tours, activities, and more

Classic Wine Tasting with Traditional Tuscan Products

A family-run cellar wine tasting with producers on a panoramic terrace under an ancient white mulberry tree

From $32.30

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

A wine tasting paired with a typical Tuscan lunch in a medieval castle in Montalcino

From $67.94

Arezzo Walking Tour with Audio and Written Guide by a Local

Arezzo, Italy

Self-guided digital guide to Arezzo covering key monuments, local food specialties and Italian aperitivo spots

From $7.50

Perugia Walking Tour with Audio and Written Guide by a local

Perugia, Italy

Self-guided digital guide of Perugia with local support, detailing major monuments, local foods and aperitivo in authentic restaurants

From $8.08

Montepulciano: Wine Tasting & Lunch in a typical winery

A wine tasting and typical Tuscan lunch in an ancient wine cellar in central Montepulciano

From $63.44

Panoramic Electric Minibus Tour

A comfortable way to see Montepulciano with discounted admission to the Temple of San Biagio

From $11.54

Horseback riding through the vineyards in Montepulciano Tuscany

Guided horseback tour from farm stables through Montepulciano vineyards and hills, returns with wine or coffee

From $92.28

Siena: Chianti Sunset Tour with Dinner & Wine Tasting

Guided family-run winery near Siena with vineyard and cellar tour wine tasting and sunset terrace dinner

From $109.58

Horseback Riding in the Tuscan Vineyards