Montegrossi Vacations from $1,134

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Your Montegrossi Vacation

The stress-free way to experience this city is with a tailor-made Montegrossi vacation package. Base yourself in the neighborhood of Badia Coltibuono, which is good for families, nature and walking or choose someplace else — our packages are all about you. Every trip to Montegrossi needs a well-designed itinerary. Fill yours with famous sights like Castle of Brolio, Meleto Castle and Badia a Coltibuono. Expedia will help you escape your daily routine. Tailor your vacation to Montegrossi to match your travel style, whatever that may look like.

The Latest Montegrossi vacation packages

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

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,657, price is now $1,134 per person
$1,134
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
Excelente servicio, las habitaciones las limpiaron todos los días, el desayuno muy completo, además muy cerca de plazas principales

Reviewed on May 27, 2026

Donati Luxury Tower Suites

Donati Luxury Tower Suites

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $3,230, price is now $2,204 per person
$2,204
per person
Jul 18 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (63 reviews)
Agradable estancia. Excelente servicio. La habitación la mantenían siempre limpia. Todo queda cerca del área. Muy recomendable

Reviewed on May 23, 2026

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $1,703, price is now $1,229 per person
$1,229
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,010 reviews)
The room smelled pretty bad even with the windows open. There's also a bunch of mosquitoes flying around, but everything else was ok!

Reviewed on May 27, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Price was $2,575, price is now $1,866 per person
$1,866
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (135 reviews)
Beautiful stay for our honeymoon. This is definitely a place to go and feel at peace in the Tuscan countryside. 15 min away from some wineries and 20 min away from Montepulciano. Great balance of feeling relaxed by the spa and pool with some quick getaways. Lastly, the restaurant was beyond excellent. Expensive but well worth it.

Reviewed on May 23, 2026

The James Suite Hotel Firenze 1564 - Small Luxury Hotels of the World

The James Suite Hotel Firenze 1564 - Small Luxury Hotels of the World

5 out of 5
Historic Centre of Florence
Price was $3,501, price is now $2,540 per person
$2,540
per person
Jul 18 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
10/10 Exceptional! (18 reviews)
Outstanding hotel and a remarkable experience staying there. The room was large and beautifully decorated as the rest of the hotel. Service was impeccable and friendly. Food was great. Lovely and intimate atmosphere. Attention to details and distinctive effort to attend to our needs. The hotel manager and Lavinia at the front desk stood out, but everybody else was extremely helpful. I hope to return!

Reviewed on Nov 14, 2025

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Discover the most popular places to visit in Montegrossi

Meleto Castle

Find out about the history of Gaiole in Chianti when you spend time at Meleto Castle. Discover the beautiful countryside in this walkable area, or enjoy its local tours.

Meleto Castle

Castle of Brolio

5/5(22 reviews)

You can find out about the history of Gaiole in Chianti with a stop at Castle of Brolio. Discover the beautiful countryside and wineries in this walkable area.

Castle of Brolio

Cantalici Winery

You can enjoy a tasting or tour at Cantalici Winery during your travels to Gaiole in Chianti. Discover the beautiful countryside in this walkable area, or enjoy its local tours.

Cantalici Winery

What to do in Montegrossi

Chianti Half Day Wine Tour from Florence

Chianti Half Day Wine Tour from Florence

$29
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

$54
per adult
86% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
Tuscany Hiking Tour from Siena Including Wine Tasting

Tuscany Hiking Tour from Siena Including Wine Tasting

$71
per adult
100% of travellers recommend
Tuscany Hiking Tour from Siena Including Wine Tasting
See all activities in Montegrossi

Montegrossi Hotel Deals

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
$227 nightly
The price is $256 total per night from Jun 26 to Jun 27
$256 total
Jun 26 - Jun 27
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
"Location is good. Large property with good parking. Staff is very helpful and friendly. The hotel aesthetic is bland and utilitarian. Breakfast is good. The rooftop deck is lovely but small."

Reviewed on May 26, 2026

Hotel Athena
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

5 out of 5
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
$550 nightly
The price is $617 total per night from Jun 22 to Jun 23
$617 total
Jun 22 - Jun 23
Total with taxes and fees
9.2/10 Wonderful! (605 reviews)
"Loved the location Restaurant was outstanding!!"

Reviewed on May 14, 2026

Grand Hotel Continental Siena – Starhotels Collezione
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34 Siena SI
Fully refundableReserve now, pay when you stay
$146 nightly
The price is $166 total per night from Jun 15 to Jun 16
$166 total
Jun 15 - Jun 16
Total with taxes and fees
9.4/10 Exceptional! (801 reviews)
"View of this hotel is amazing! It has a beautiful yard to sit and have a drink and watch the Tuscany hills. Short walk to major attractions and good breakfast. I would highly recommend this hotel."

Reviewed on May 19, 2026

Palazzo Ravizza
See all 5,890 properties in Montegrossi
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.

Find the Best Montegrossi Vacation Packages

Montegrossi Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Peretola Airport (FLR)
Top Sights
Castle of Brolio, Meleto Castle and Badia a Coltibuono

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Frequently asked questions

How much does a Montegrossi vacation package cost?
You'll find cheap prices from $1,134 on Expedia for your Montegrossi break. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Montegrossi costs.
What are the cheapest months to go to Montegrossi?
If you'd like to snag a cheap Montegrossi vacation package, consider planning a trip in August, October and November. You'll usually find better prices on flights and hotels during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Montegrossi?
Usually, a handful of days is enough to explore the main sights during your Montegrossi vacation. However, if you prefer to have more time to relax or take day tours, think about extending your trip.
How to find the best Montegrossi package deals?
Use Expedia's filter tool to help you find some tempting Montegrossi package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Montegrossi package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Montegrossi vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and accommodations separately. Better still, you can customize your Montegrossi trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Montegrossi?
If you're planning an impromptu Montegrossi getaway, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find incredible deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Montegrossi vacation packages?
Your Montegrossi trip should be a relaxing escape from your busy life, not a source of money-related stress. So to allow you that extra flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.