Montemassi Vacation Packages

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Your Montemassi Vacation

When you organize a vacation package to Montemassi, you can relax and enjoy your break knowing that all your travel plans are in order. Uncover the many charms of this lively city while based in a neighborhood like Valpiana, which is good for views. Make your trip to Montemassi even more enjoyable by going sightseeing. Podere Ristella Vineyards and Winery, Church of San Nicola and Sassoforte Castle are among the major attractions worth exploring. Whatever your travel plans or the size of your budget, putting together the ultimate tailored Montemassi vacation is a cinch with Expedia.

Top Montemassi Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

3 out of 5
Oltrarno
Save 100% on your flight
per person
Aug. 31 - Sep. 7
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
8.6/10 Excellent! (622 reviews)
We loved everything at La Scaletta! The best thing is the Sky Bar and roof top restaurant! Wide variety of excellent food and drinks, super conveniently located at a few steps away from Ponte Vecchio.

Reviewed on Jun. 13, 2024

Aurum Uffizi

Aurum Uffizi

4 out of 5
Santa Croce
Save 100% on your flight
per person
Aug. 31 - Sep. 7
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
8/10 Very Good! (890 reviews)
Great location for attractions and dining options

Reviewed on Jun. 11, 2024

Hotel Balestri

Hotel Balestri

4 out of 5
Santa Croce
per person
Aug. 31 - Sep. 7
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
9.2/10 Wonderful! (824 reviews)
We thoroughly enjoyed our stay at Hotel Balestri. The room was even nicer than the pictures depicted. A balcony with the river view is a must, so peaceful and beautiful.

Reviewed on Jun. 13, 2024

Hotel L'Orologio

Hotel L'Orologio

4 out of 5
Santa Maria Novella
per person
Aug. 31 - Sep. 7
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (979 reviews)
Nice hotel But very overpriced Bad breakfast Not very nice customer service Will not stay there again Very good location though

Reviewed on Jun. 2, 2024

Glance Hotel In Florence

Glance Hotel In Florence

4 out of 5
San Lorenzo
per person
Aug. 31 - Sep. 7
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (1,000 reviews)
Great hotel in the heart of Florence. Friendly staff and enjoyed the rooftop bar.

Reviewed on Jun. 12, 2024

Montemassi Hotel Deals

The Sense Experience Resort
The Sense Experience Resort
4 out of 5
Viale Italia 315, Follonica, Grosseto
Fully refundableReserve now, pay when you stay
The price is CA $535 per night from Jun. 16 to Jun. 17
CA $535
CA $596 total
includes taxes & fees
Jun 16 - Jun 17
8.8/10 Excellent! (94 reviews)
"Very relaxing and good offering of food and drinks. But very pricey. The hotel is very near Follonica and so would suggest eating out. Watersports hire is a huge bonus."

Reviewed on Jun. 3, 2024

The Sense Experience Resort
Rosewood Castiglion del Bosco
Rosewood Castiglion del Bosco
5 out of 5
Localita Castiglion del Bosco, Montalcino, SI
Fully refundableReserve now, pay when you stay
The price is CA $2,695 per night from Jul. 2 to Jul. 3
CA $2,695
CA $2,980 total
includes taxes & fees
Jul 2 - Jul 3
9.8/10 Exceptional! (49 reviews)
"Nice view, quiet , very beautiful golf course."

Reviewed on Jun. 9, 2024

Rosewood Castiglion del Bosco
L'Andana
L'Andana
5 out of 5
Tenuta La Badiola, Castiglione della Pescaia, GR
The price is CA $604 per night from Jun. 16 to Jun. 17
CA $604
CA $679 total
includes taxes & fees
Jun 16 - Jun 17
9.4/10 Exceptional! (61 reviews)
"Excellent service and remembering dining experience"

Reviewed on Oct. 3, 2023

L'Andana
See all 2,169 properties in Montemassi
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Montemassi vacation package cost?
Starting from as little as CA $2,126, you can build your own Montemassi package the way you want. Simply bundle hotels, flights and rental cars and we’ll reward you with discounts.
How do I get a cheap travel package to Montemassi?
Combine your bookings with Expedia to save on your next adventure. With more than 550 partner airlines and 1,000,000 hotel options worldwide, your Montemassi vacation package can be customized exactly to suit your budget. With all that extra money, why not throw in one or more awesome tours and activities? It’s an easy way to unlock even more savings. Your dream vacation in Montemassi is much closer than you thought!
Where should I stay in Montemassi?
If you plan to check out Podere Ristella Vineyards and Winery, skip commuting and stay close by. It’s one of the best attractions in this area.
What are the top hotels in Montemassi?
Get your escape off to a fantastic start by reserving a room at Casolare San Giusto Maremma 1 Floor Apartment. It’s one of most sought-after hotels in Montemassi. Another comfortable option is Casolare San Giusto Maremma Ground Floor Apartment.
How far in advance should I book my Montemassi vacation?
While prices fluctuate, we generally advise booking your flight as early as possible. Many international fares are found on Expedia up to 12 months in advance. If you’re booking late, you may still get lucky. Discount prices to Montemassi sometimes emerge in the weeks prior to departure.
What does an Expedia Montemassi travel package include?
With Expedia, you can select any combination of hotels, car rentals and flights to build your ideal Montemassi package. Once you’ve made your booking, you can add on the fun things like day tours and activities. Don’t forget — the more you bundle, the more you stand to save!
What should I know before booking a Montemassi travel package?
We already have low prices. However, you’ll score an even better deal when you book your hotels, flights and car rentals together. With an Expedia travel package, you’ll always get transparent pricing and lots of choice.
Can I choose my airline with a Montemassi Expedia vacation package?
With a vacation package, you’re in charge. Whether you’d like to fly to Montemassi in coach or business class, simply pick from the available airline options. Expedia has access to more than 550 airline partners worldwide.
If I'm not able to travel, can I cancel my Montemassi vacation package?
Yes you can, and we’re here to help. You may be able to cancel and rebook your Montemassi vacation package for free within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company if your booking is older than that. If your circumstances suddenly change, have a look at our Customer Service Portal for further information.

Discover the most popular places to visit in Montemassi

Image for I Canaloni del Torrente Farma

I Canaloni del Torrente Farma

Commune with nature and explore the great outdoors at I Canaloni del Torrente Farma during your travels in Roccastrada. Discover the area's countryside and spas.

I Canaloni del Torrente Farma
Image for Podere Ristella Vineyards and Winery

Podere Ristella Vineyards and Winery

You can enjoy a tasting or tour at Podere Ristella Vineyards and Winery during your travels to Roccastrada. Wander the gardens or discover the area's countryside.

Podere Ristella Vineyards and Winery
Image for Castello del Belagaio

Castello del Belagaio

You can find out about the history of Roccastrada with a trip to Castello del Belagaio. Discover the area's countryside and wineries.

Castello del Belagaio

What to do in Montemassi

Image for Rocca di Frassinello Winery: Tour & Wine Tasting in Tuscany

Rocca di Frassinello Winery: Tour & Wine Tasting in Tuscany

CA $44
Per adult
Rocca di Frassinello Winery: Tour & Wine Tasting in Tuscany
See all activities in Montemassi
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.