Montegrossi Vacations from $730

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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 Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $928, price is now $730 per person
$730
per person
Mar 14 - Mar 16
found 1 hour ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.6/10 Good! (1,002 reviews)
9 day stay. The property hit my must-haves! Central location, clean, affordable, and safe. 5/5 in all these areas! There is nothing they can do about dirty streets but the filth did not cross the threshold. T2 tram from the airport is 2 blocks away. The central market is 2 blocks in the other direction. Key card swipe after dark. 24 hour desk service. Breakfast on the 5th floor with views. Very courteous staff. The only complaint is breakfast tables are cleared very quickly while I went for a americano refill. Will definitely return here.

Reviewed on Jan 3, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $937, price is now $734 per person
$734
per person
Mar 14 - Mar 16
found 1 hour ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Great Locations walkable to all the placese.

Reviewed on Dec 15, 2025

The St. Regis Florence

The St. Regis Florence

5 out of 5
Historic Centre of Florence
Price was $2,600, price is now $2,052 per person
$2,052
per person
Feb 15 - Feb 20
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.6/10 Exceptional! (261 reviews)
Nice property in a great location.

Reviewed on Jun 29, 2025

FH55 Hotel Villa Fiesole

FH55 Hotel Villa Fiesole

4 out of 5
Price was $1,017, price is now $823 per person
$823
per person
Mar 17 - Mar 23
just found
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
8.8/10 Excellent! (363 reviews)
We had a lovely stay… our room was spotless the bed very comfortable. The staff were si helpful and friendly. Bonus was on site parking and the bus stop ( bus #7) into Florence was a 2 minute walk down the road. I highly recommend this hotel.

Reviewed on Nov 21, 2025

Relais Uffizi, Tailor made Hotel

Relais Uffizi, Tailor made Hotel

4 out of 5
Historic Centre of Florence
Price was $1,416, price is now $1,146 per person
$1,146
per person
Feb 15 - Feb 20
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (120 reviews)
Phenomenal location!

Reviewed on Oct 18, 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

You can find out about the history of Gaiole in Chianti with a stop at Castle of Brolio. Discover the beautiful countryside and charming coffeehouses 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

Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

$61
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
Florence Day Trip: Medieval Villages & Cooking Class

Florence Day Trip: Medieval Villages & Cooking Class

$163
per adult
86% of travellers recommend
Florence Day Trip: Medieval Villages & Cooking Class
Chianti Half Day Wine Tour from Florence

Chianti Half Day Wine Tour from Florence

$51
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
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
$85 nightly
The price is $97 total per night from Jan 25 to Jan 26
$97 total
Jan 25 - Jan 26
Total with taxes and fees
9.2/10 Wonderful! (1,007 reviews)
Excellent stay!

Reviewed on Jan 2, 2026

Hotel Athena
Borgo Grondaie

Borgo Grondaie

3 out of 5
Strada delle Grondaie, 15 Siena SI
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $82 total per night from Feb 6 to Feb 7
$82 total
Feb 6 - Feb 7
Total with taxes and fees
9.6/10 Exceptional! (441 reviews)
Amazing place, super clean, great staff, beautiful and cozy.

Reviewed on Jan 3, 2026

Borgo Grondaie
Villa La Borghetta Resort

Villa La Borghetta Resort

4 out of 5
Via del Cesto Figline e Incisa Valdarno FI
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $102 total per night from Jan 7 to Jan 8
$102 total
Jan 7 - Jan 8
Total with taxes and fees
7.8/10 Good! (85 reviews)
Beautiful experience!

Reviewed on Jul 1, 2025

Villa La Borghetta Resort
See all 5,729 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 $730 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.