
Montepulciano Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Montepulciano Vacation
Get to know the hilltop city of Montepulciano with a Montepulciano vacation package and immerse yourself in the best it can offer. From its rich history and cultural experiences to its spectacular views, prepare to fall for the charms of this vibrant destination. A trip to Montepulciano is a superb opportunity to do some sightseeing. Make sure you visit big-name attractions such as Pienza Cathedral, Palazzo Piccolomini and Tenuta Valdipiatta. Whoever you're heading away with and whatever your bank balance, your ultimate Montepulciano vacation is only clicks away with Expedia.
Top Montepulciano Vacation Deals
Price found within the past 48 hours. Click for updated prices.


Hotel Duomo Firenze
Historic Centre of Florence
Price was CA $2,419, price is now CA $1,481 per person
CA $1,481
per person
Jan 25 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Amazing location. So cool to be literally across from the Duomo. Easy walk to so many places to shop and eat. Free sparkling and still water was great. Snacks and free gelato! Staff was the most friendly and helpful. Highly recommend this place!
Reviewed on Nov 3, 2026

The Hoxton, Florence
Historic Centre of Florence
Price was CA $1,919, price is now CA $1,423 per person
CA $1,423
per person
Jan 25 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Florence (FLR)
9.4/10 Exceptional! (370 reviews)
The Hoxton was so nice. There was only one or two things that were not optimal, but totally did not outweigh the other positives. We stayed on the ground floor and had a small courtyard area which was lovely, but the door to our room was pretty difficult to open. And, lastly the bathroom had a musty, odd smell to it. I think there might be some venetalation issues, but again neither outweighed all of the positives of our stay. Everything else in the room was perfect however. The bed was comfortable, the temperature controls, and we absolutely loved the courtyard area of our room.
The staff was also so fabulous - from the front desk, the cocktail bar, to breakfast. Along with that the property was absolutely gorgeous. During our stay we took advantage of the buffet breakfast during one day and it was so worth it. It was delicious and exceeded our expecations. The cocktail lounge area was amazing as well. The drinks and apps were delicious. So, overall I would highly reccomend staying here!
Reviewed on Nov 10, 2026


Villa Tolomei Hotel & Resort
Oltrarno
Price was CA $2,980, price is now CA $2,557 per person
CA $2,557
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
8.8/10 Excellent! (445 reviews)
The property was lovely. A former 15th(?) century monastery located on a hilltop overlooking parts of Florence. Surrounded by olive and fruit trees, and gardens. It's past the Roman gate, about a 30 euro cab ride from the center of town. Though they didn't tell us until we asked, there's a shuttle that will take you down the hill to the Roman Gate where taxis and busses can be found.
We arrived just after the hotel restaurant had closed for the afternoon by a minute. They were kind/professional enough to serve us something from the cold selections; and it was delicious. The breakfast buffet the next day was outstanding with excellent selection and quality. The usual 3 or 4 hot items: scrambled eggs, breakfast meat, roasted tomatoes. Where it really excelled were the cold items. Fresh juices, local yogurts, fruits, meats, cured salmon. Perfectly executed pastry, and breads with honeycomb stood out. Dinner was a mixed bag.
The big downside was that we arrived in October. Apparently, the property has to commit each year to the local authorities when they will close the pool, and switch from A/C to heat in the rooms. We booked through Expedia and therefore information on things may be incomplete. No mention that the pool was closed. It was almost worse that it was too warm to sleep well at night. We had even contacted the front desk after the first night and they said they'd send someone to look at it. Which we learned later made no sense BC it was off for the season.
Reviewed on Nov 6, 2026
Montepulciano Hotel Deals

Precise Tale Poggio Alla Sala
Via Di Poggio Alla Sala, 10 Montepulciano SI

Nuovo Etruria Resort
Via di S. Martino snc Montepulciano SI
The price is CA $138 per night from Nov 20 to Nov 21
CA $138
CA $160 total
Nov 20 - Nov 21
includes taxes & fees

Hotel Panoramic Montepulciano
Via di Villa Bianca, 8 Montepulciano SI
8.8/10 Excellent! (265 reviews)
"Ok."
Reviewed on Oct 9, 2026
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.
Stay near popular Montepulciano attractions
What to do in Montepulciano

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
CA $189
per adult
98% of travellers recommend

Montepulciano Wine Tasting in the Tuscan Countryside
CA $40
per adult

Montepulciano: Artisan Heroic Wine Tasting at the Terrace
CA $64
per adult
Frequently asked questions
Explore a world of travel with Expedia
- Trequanda Hotels
- Hotels with Tennis Courts in Montepulciano
- Relais & Chateaux Hotels in Montepulciano
- Agriturismo Renello
- Villas in Val d'Orcia
- Luxury Hotels in Montepulciano
- Hotels with Kitchenettes in Montepulciano
- Apartments in Montepulciano
- Romantic Hotels in Montepulciano
- Pienza Hotels
- Hotels with a Pool in Val d'Orcia
- Family Hotels in Montepulciano
- Farmstay in Val d'Orcia
- Hotels with a Pool in Montepulciano
- Luxury Tuscan Villa in Val d'Orcia
- Monticchiello Hotels
- Podere Lamino with Swimming pool
- Winery Hotels in Montepulciano
- Winery Hotels in Val d'Orcia
- Montepulciano Hotels
- 5 Star Hotels in Val d'Orcia
- Abbadia Sicille Relais
- Casa M Vineyard View Room
- Sinalunga Hotels
- Lgbt Friendly Hotels in Chianciano Terme
- Pet-Friendly Hotels in Val d'Orcia
- Winery Hotels in Pienza
- Rv Parks in Montepulciano Stazione
- Agriturismo Cognanello
- B&B Camere La Vite
- Farmstay in Montepulciano
- Luxury Hotels in Val d'Orcia
- Amorosa Hotels
- Best Western Hotels in Montepulciano
- Resorts in Sinalunga
- B&B in Montepulciano
- La Foce Hotels
- Villas in Montepulciano
- Fonte Bertusi
- Hotel Mizar
- Chianciano Terme Hotels
- Agriturismo Ardene
- 4 Star Hotels in Montepulciano
- Hotels with Free Parking in Montepulciano
- Room in Guest Room
- Il Rondò Boutique Hotel
- Castles in Montepulciano
- Family Hotels in Val d'Orcia
- Vacation Homes in Val d'Orcia
- Relais La Saracina
- Piscine Termali Theia
- Cortona Vacations
- Visit Chianciano Terme
- Palazzo Ricci
- Pienza Vacations
- Visit Montepulciano Stazione
- Montalcino Vacations
- Tenuta Valdipiatta
- Bagni San Filippo Vacations
- Visit Pienza
- Tenuta Greppo Franco Biondi Santi
- Visit Petroio
- Visit Sinalunga
- Art Studio di Adelina Quadri
- Visit Montepulciano
- Terme di Montepulciano Spa
- Visit Val d'Orcia
- Ski Vacation Packages Val d'Orcia
- Pienza Cathedral
- Visit Montefollonico
- Avis Rental Cars in Montepulciano
- Car rental Sinalunga
- Car rental Torrita di Siena
- Car rental Montepulciano
- Car rental Montepulciano Stazione
- Car rental Pienza
- Car rental Trequanda
- Car rental Chiusi
- Auto Rent Rental Cars in Val d'Orcia
- Car rental Sarteano
- Europcar Rental Cars in Montepulciano
- Hertz Rental Cars in Montepulciano
- Drive-A-Matic Rental Cars in Val d'Orcia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







