Montalcino Vacation Packages 2026 from $1,242

Montalcino flight + hotel vacation packages

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

Hotel Meridiana

Santissima Annunziata

$1,242

per person

Aug 11 - Aug 15

found 23 hours ago

Roundtrip flight included

Chicago (ORD) to Florence (FLR)

This hotel features a bar/lounge, a coffee shop, and free WiFi in public areas. A garden, luggage storage, and concierge services are also on offer.

Hotel San Luca

Cortona Old Town

$1,291

per person

Aug 11 - Aug 15

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Florence (FLR)

This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. Self parking, a hair salon, and dry cleaning are also offered.

Best Western Hotel San Marco

$1,316

per person

Aug 11 - Aug 15

found 22 hours ago

Roundtrip flight included

Chicago (ORD) to Florence (FLR)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the business center, conference center, and conference space. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.

Hotel Europa

$1,278

per person

Aug 11 - Aug 15

found 23 hours ago

Roundtrip flight included

Chicago (ORD) to Florence (FLR)

A restaurant and a bar/lounge are featured at this hotel. Traveling for business? Take advantage of the free WiFi in public areas, express check-in, and conference space. Enjoy the free buffet breakfast each morning.

Hotel Villa Il Castagno

Santissima Annunziata

$1,280

per person

Aug 11 - Aug 15

found 22 hours ago

Roundtrip flight included

Chicago (ORD) to Florence (FLR)

A bar/lounge and a terrace are featured at this hotel, along with free self parking. WiFi in public areas is free. A garden, a snack bar/deli, and a hair salon are also on offer.

Top Montalcino hotels deals

Castello di Velona Resort Thermal SPA & Winery

Località Velona Montalcino SI

Free Cancellation

Reserve now, pay when you stay

$752 nightly

$839 total

Jul 16 - Jul 17

Total with taxes and fees

This luxury hotel features an attached winery, a full-service spa, and hot springs. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and free valet parking. Enjoy the 2 outdoor pools and free perks like cooked-to-order breakfast and free self parking.

Pool

Hot Tub

Castiglion del Bosco, A Rosewood Hotel

Localita Castiglion del Bosco Montalcino SI

Free Cancellation

Reserve now, pay when you stay

$2,310 nightly

$2,553 total

Jul 20 - Jul 21

Total with taxes and fees

This luxury hotel features a golf course, an attached winery, and a full-service spa. There's fun for all ages with a children's club and an arcade/game room, and in-room childcare is an added bonus. Enjoy a meal in one of the 2 restaurants and free perks like valet parking and WiFi in public areas.

Pool

Spa

SI Montalcino Hotel

Via Osticcio 21 Montalcino SI

Free Cancellation

Reserve now, pay when you stay

$115 nightly

$136 total

Jun 28 - Jun 29

Total with taxes and fees

This hotel features a seasonal outdoor pool and a bar/lounge. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Free parking, a terrace, and a garden are also offered.

Pool

Breakfast included

Mastrojanni Relais - Small Luxury Hotels of the World

Localita Loreto e San Pio Montalcino SI

Free Cancellation

Reserve now, pay when you stay

$503 nightly

$565 total

Jul 5 - Jul 6

Total with taxes and fees

An attached winery and a restaurant are featured at this smoke-free farm stay. Business travelers can take advantage of the free WiFi in public areas. Enjoy the gym and free perks like buffet breakfast and free self parking.

Pool

Breakfast included

Hotel Dei Capitani

Via Lapini 6 Montalcino SI

Free Cancellation

Reserve now, pay when you stay

$162 nightly

$187 total

Jun 30 - Jul 1

Total with taxes and fees

An outdoor pool, free self parking, and concierge services are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a library are also on offer.

Pool

Breakfast included

Drogheria & Locanda Franci

Piazzale Fortezza 5 Montalcino SI

Free Cancellation

Reserve now, pay when you stay

$202 nightly

$233 total

Jul 11 - Jul 12

Total with taxes and fees

This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast and free WiFi. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls and litter boxes. Dry cleaning, luggage storage, and concierge services are also on offer.

Breakfast included

Pet friendly

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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.

Popular places to visit

Castello Banfi

4/5(6 reviews)

You can enjoy a tasting or tour at Castello Banfi during your travels to Poggio alle Mura. Visit the area's spas, or simply enjoy its wineries.

Fortress of Montalcino

5/5(5 reviews)

Find out about the history of Montalcino with a stop at Fortress of Montalcino. Visit the area's spas, or simply enjoy its wineries.

Tenuta Greppo Franco Biondi Santi

You can enjoy a tasting or tour at Tenuta Greppo Franco Biondi Santi during your travels to Montalcino. Discover the area's countryside and spas.

Frequently asked questions

How much are vacation packages to Montalcino?

Packages, which include flights and hotels in Montalcino, start from $1,242. Make your travel dreams a reality and book your dream trip with Travelocity today.

How long should my Montalcino vacation be?

Around 3 nights is the average time frame visitors vacation in Montalcino. But the perfect trip length all depends on how many cherished memories you want to create. Why not stay a few extra days and explore some of the lesser-known spots?

Where can I get the best vacation package deals for Montalcino?

Look no further than Travelocity. With as many as 400 partner airlines and 1,000,000 properties around the world, it's a breeze to put together a Montalcino package deal that fits your budget.

Why should I purchase my Montalcino vacation bundle via Travelocity?

From amazing destinations to fun experiences, we have everything you need to satisfy your love for travel. Our 24/7 support will also make sure you're being taken care of before, during and after your vacation. And don't stress if you notice a better price on your reservation, we'll match it. That's our Price Match Guarantee.

Will I save money on my Montalcino car rental if I book it with a hotel or flight?

With a Montalcino vacation package, you can bundle your hotel, car and flight bookings and save tons. If you want to uncover the best of this awesome city, why not make tracks to St. Peters Basilica? This renowned attraction is 95 mi from Montalcino. With a rental car, you'll be there in a flash.

What is the best time of year to go to Montalcino?

You'll be able to avoid the tourist crowds and save a nice sum in September, October and December, the quietest period for tourism. High season months of February, April and May are livelier (and pricier), but there'll be more happening around Montalcino. Lock in a hotel in and you'll get the best value for your dollar. Room rates are usually highest in .

Which airport is best for Montalcino?

The major airport for Montalcino is Peretola Airport (FLR). It's located 55 mi south of the downtown area.

What is there to do in Montalcino?

While veering off the tourist trail is rewarding, you shouldn't miss the big-name sights that make a place famous. Abbazia di SantAntimo and Castello Banfi are a couple of them in Montalcino.

Where should I stay when visiting Montalcino?

The Hotel Dei Capitani is recommended by many visitors. Book soon to avoid missing out.