Montegrossi Vacation Packages

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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.

Top Montegrossi Vacation Deals

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 CA $2,422, price is now CA $1,459 per person
CA $1,459
per person
Jun 3 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Great simple place.

Reviewed on Apr 9, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was CA $2,999, price is now CA $1,729 per person
CA $1,729
per person
Jun 3 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
7.6/10 Good! (1,000 reviews)
The room was clean and newly renovated. Having breakfast included was great for a quick bite so I could focus on exploring instead of searching and waiting in line. Would definitely recommend a stay here

Reviewed on Apr 9, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was CA $3,022, price is now CA $2,003 per person
CA $2,003
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
8.6/10 Excellent! (483 reviews)
The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.

Reviewed on Dec 13, 2025

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Price was CA $3,064, price is now CA $2,072 per person
CA $2,072
per person
May 26 - May 28
found 20 hours ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
9.4/10 Exceptional! (124 reviews)
Most gorgeous setting, lovely staff and delicious food. We will definitely be back!

Reviewed on Apr 5, 2026

Hotel Palazzo Ognissanti

Hotel Palazzo Ognissanti

4 out of 5
Historic Centre of Florence
Price was CA $2,622, price is now CA $1,833 per person
CA $1,833
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
7.8/10 Good! (490 reviews)
Very clean room. Helpful staff

Reviewed on Jan 24, 2026

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Montegrossi Hotel Deals

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
The price is CA $279 per night from Apr 23 to Apr 24
CA $279
CA $315 total
Apr 23 - Apr 24
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
Walkable to town center. Comfy beds and spotless rooms. Front desk is delightful and helpful. Excellent breakfasts that you will miss later :)

Reviewed on Apr 5, 2026

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
The price is CA $83 per night from Apr 26 to Apr 27
CA $83
CA $101 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (481 reviews)
I highly recommended

Reviewed on Oct 14, 2025

Hotel Ristorante Alcide
Hotel Chiusarelli

Hotel Chiusarelli

3 out of 5
Viale Curtatone 15 Siena SI
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Apr 20 to Apr 21
CA $193
CA $221 total
Apr 20 - Apr 21
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
Pretty basic stay, the bed was very hard and the pillows thin. Breakfast was generous in portions and okay given the accommodations. Staff was helpful and kind, including when we had a problem with the heating.

Reviewed on Apr 7, 2026

Hotel Chiusarelli
See all 5,798 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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Discover the most popular places to visit in Montegrossi

Medieval Tower of Barbischio

Find out about the history of Gaiole in Chianti when you take a trip to Medieval Tower of Barbischio. Discover the beautiful countryside in this quaint area, or enjoy its local tours.

Medieval Tower of Barbischio

Church of San Sigismondo

After visiting Church of San Sigismondo, make a plan to see the other sights and activities in Gaiole in Chianti. Discover the beautiful countryside in this walkable area, or enjoy its local tours.

Church of San Sigismondo

What to do in Montegrossi

Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

CA $72
per adult
86% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

CA $124
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
Chianti Half Day Wine Tour from Florence

Chianti Half Day Wine Tour from Florence

CA $39
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
See all activities in Montegrossi

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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.