Montegrossi Vacations from $1,001

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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.
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
Hands down the best place we have stayed. They accommodated to go breakfasts for our tours, arranged taxis, made cappuccino when we were heading out the door. Wonderful experience

Reviewed on Jun 6, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Great place to stay, so close to all attractions. Fantastic staff and service. A happy traveller.

Reviewed on Jun 25, 2025

Hotel Bencista

Hotel Bencista

3 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
7.2/10 Good! (11 reviews)
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
If one is not there for a fancy hotel room, but for sightseeing, this is a great, clean, bare bones room. It is close to the train station. We were on the 5th floor and had a great view! Breakfast was also on the 5th floor. Close proximity to all the museums and Duomo, 20 minute walk or less to everything. We walked everywhere!

Reviewed on Jun 21, 2025

Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Fantastic people and best view in Florence at night. Breakfast the best in Florence. Would go back in a heart beat

Reviewed on Jun 25, 2025

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Discover the most popular places to visit in Montegrossi

Castello di Meleto, Gaiole in Chianti, Tuscany

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(21 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

Brolio Castle

Small-Group Chianti Trip with Wine Tasting from Siena

$207
per adult
Small-Group Chianti Trip with Wine Tasting from Siena
Sunny day view of Monteriggioni, a Comune in Italy

Chianti Half Day Wine Tour from Florence

$56
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
From Florence: Siena & San Gimignano Day Trip with Lunch & Wine Tasting

From Florence: Siena & San Gimignano Day Trip with Lunch & Wine Tasting

$87
per adult
90% of travellers recommend
From Florence: Siena & San Gimignano Day Trip with Lunch & Wine Tasting
See all activities in Montegrossi

Montegrossi Hotel Deals

Hotel Athena
Hotel Athena
4 out of 5
P Mascagni 55, Siena, SI
Fully refundable
$145 nightly
The price is $166 total per night from Jul 25 to Jul 26
$166 total
Jul 25 - Jul 26
Total includes taxes and fees
9.2/10 Wonderful! (1,002 reviews)
"From the moment we arrived for our two night stay Matteo and Tomasso were kind helpful and informative - We wanted a bigger room and were immediately accommodated - room was clean and comfortable and the hotel was in walking distance to all activities"

Reviewed on Jun 21, 2025

Hotel Athena
Hotel Borgo di Cortefreda Relais
Hotel Borgo di Cortefreda Relais
4 out of 5
Via Roma 191, Barberino Tavarnelle, FI
Fully refundableReserve now, pay when you stay
$193 nightly
The price is $220 total per night from Jul 6 to Jul 7
$220 total
Jul 6 - Jul 7
Total includes taxes and fees
9.2/10 Wonderful! (420 reviews)
"Always our favorite stay!"

Reviewed on Jun 24, 2025

Hotel Borgo di Cortefreda Relais
Hotel Executive
Hotel Executive
4 out of 5
Via Nazareno Orlandi 32, Siena, SI
Fully refundableReserve now, pay when you stay
8.2/10 Very Good! (480 reviews)
"Really comfortable hotel , only stayed one night . A great nights sleep . All the staff without exception were friendly, helpful and could not do enough for us. Breakfast selection was in abundance but unfortunately the quality of the food was not great . Maybe less selection with better quality ..."

Reviewed on Oct 2, 2024

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Hotel Executive
See all 6,065 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 $1,001 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.