Montemassi Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Montemassi

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 S$1,785 per night from 6 Dec to 7 Dec
S$1,785
includes taxes & fees
6 Dec - 7 Dec
9.8/10 Exceptional! (54 reviews)
"Everything was to PERFECTION."

Reviewed on 20 Sep,2024

Rosewood Castiglion del Bosco
Hotel Airone
Hotel Airone
4 out of 5
Via Senese, 35, Grosseto
Fully refundableReserve now, pay when you stay
The price is S$135 per night from 22 Dec to 23 Dec
S$135
includes taxes & fees
22 Dec - 23 Dec
8.4/10 Very Good! (83 reviews)
"The staff were kind, positive, pleasant and will to help. A person in my travel party arrived in the breakfast hall only a few minutes before closing time. Rather than just start closing up a staff member was kind enough to ask us if we needed more time. Consequently, the breakfast was presented ..."

Reviewed on 7 Nov,2024

Hotel Airone
Borgo Santo Pietro
Borgo Santo Pietro
5 out of 5
Loc. Palazzetto, Chiusdino, SI
9.4/10 Exceptional! (44 reviews)
"The property is gorgeous. We had plans to visit other places nearby but ended up spending more of our time within the property itself because we enjoyed it so much."

Reviewed on 7 Oct,2024

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Borgo Santo Pietro
See all 2,006 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.

Frequently asked questions

How much does a Montemassi holiday package cost?
Starting from as little as , 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 holiday 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 holiday 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 holiday?
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 holiday package?
With a holiday 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 holiday package?
Yes you can, and we’re here to help. You may be able to cancel and rebook your Montemassi holiday 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.

What to do in Montemassi

The Maremma in its splendor

The Maremma

S$1,072
Per adult
The Maremma
Fly Brunello - Heli Wine Tour

Fly Brunello - Heli Wine Tour

S$12,272
Per adult
Fly Brunello - Heli Wine Tour
Detail of the Tarot Garden

Tarot Garden and Maremma Park

S$623
Per adult
Tarot Garden and Maremma Park
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.