Montemassi Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €350 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Montemassi

Price found within the past 48 hours. Click for updated prices.
Hotel Miceli - Civico 50
Hotel L'Orologio Firenze
Hotel La Scaletta Al Ponte Vecchio
Hotel Alessandra
Maxim Axial

Top hotels in Montemassi

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

5 out of 5
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
The price is €2,166 per night from 3 May to 4 May
€2,166
3 May - 4 May
includes taxes & fees
10/10 Exceptional! (75 reviews)
If you don’t like th it s place, then there will never be a place on earth that you like.. it’s actually above a 5 star!! Over the top service.. food seasons breakfast fantastic…fell very lucky to have stayed here.. thank you

Reviewed on 8 Apr 2026

Castiglion del Bosco, A Rosewood Hotel
Hotel La Pineta

Hotel La Pineta

3 out of 5
Via Delle Collacchie, 67 Follonica GR
The price is €73 per night from 26 Apr to 27 Apr
€73
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (295 reviews)
Nicely renovated room. Staff was very friendly and helpful.

Reviewed on 25 Sept 2025

Hotel La Pineta
Borgo Santo Pietro

Borgo Santo Pietro

5 out of 5
Loc. Palazzetto Chiusdino SI
The price is €2,813 per night from 15 May to 16 May
€2,813
15 May - 16 May
includes taxes & fees
Borgo Santo Pietro
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.

Popular places to visit

What to do in Montemassi

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.