Montegrossi Vacations from $684

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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
Save 100% on your flight
Price was $1,231, price is now $684 per person
$684
per person
Nov 20 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Good value for price and location.

Reviewed on Sep 8, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,435, price is now $865 per person
$865
per person
Nov 20 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (470 reviews)
We never had an opportunity to use the spa

Reviewed on Sep 8, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,137, price is now $701 per person
$701
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,000 reviews)
Right near the attractions. Easy to get around

Reviewed on Sep 4, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Save 100% on your flight
Price was $4,121, price is now $2,661 per person
$2,661
per person
Nov 10 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (458 reviews)
Villa Cora was delightful in every way. The only negative thing I have to say is that I am not currently still there. Alas, I would highly recommend Villa Cora as a jumping off point for your Tuscan or Firenze adventures.

Reviewed on Sep 6, 2025

Collegio alla Querce - Auberge Collection

Collegio alla Querce - Auberge Collection

5 out of 5
Le Cure
Save 100% on your flight
Price was $5,021, price is now $3,268 per person
$3,268
per person
Nov 2 - Nov 8
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
10/10 Exceptional! (3 reviews)
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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

Badia a Coltibuono

You can enjoy a tasting or tour at Badia a Coltibuono during your travels to Badia Coltibuono. Discover the beautiful countryside in this relaxing area, or enjoy its local tours.

Badia a Coltibuono

What to do in Montegrossi

Brolio Castle

Small-Group Chianti Trip with Wine Tasting from Siena

$210
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

$57
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
Torre del Mangia

Siena and San Gimignano: Small-Group Tour with Lunch from Florence

$148
per adult
100% of travellers recommend
Siena and San Gimignano: Small-Group Tour with Lunch 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
$217 nightly
The price is $245 total per night from Oct 6 to Oct 7
$245 total
Oct 6 - Oct 7
Total with taxes and fees
Hotel Athena
Hotel Ristorante Alcide

Hotel Ristorante Alcide

4 out of 5
Viale Marconi, 67/A, Poggibonsi, SI
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $76 total per night from Sep 28 to Sep 29
$76 total
Sep 28 - Sep 29
Total with taxes and fees
Hotel Ristorante Alcide
Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

5 out of 5
Strada Comunale 14 Siena - Vagliagli 18, Castelnuovo Berardenga, SI
Fully refundableReserve now, pay when you stay
$452 nightly
The price is $508 total per night from Sep 15 to Sep 16
$508 total
Sep 15 - Sep 16
Total with taxes and fees
Borgo Scopeto Wine & Country Relais
See all 6,076 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.

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Frequently asked questions

How much does a Montegrossi vacation package cost?
You'll find cheap prices from $684 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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