Visit Montemassi: 2026 Travel Guide for Montemassi, Roccastrada

The Sense Experience Resort - Preferred Hotels & Resorts

Viale Italia 315 Follonica GR

$205 nightly

$232 total

Oct 11 - Oct 12

Total with taxes and fees

Book a stay at this luxury hotel in Follonica. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...

9.2/10 Wonderful! (235 reviews)

"Le site est très bien entretenu. Belle plage et bon cocktail."

Reviewed on Sep 14, 2026

Grand Hotel Bastiani

Piazza Gioberti 64 Grosseto GR

$72 nightly

$84 total

Oct 5 - Oct 6

Total with taxes and fees

Book a stay at this luxury hotel in Grosseto. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Our guests praise the property condition in our reviews. ...

8.6/10 Excellent! (253 reviews)

"The breakfast buffet was absolutely delicious, the barista made the best cappuccinos! The rooms are clean and beautiful. The bathrooms are glorious, glorious. The bathtubs are deep and long, for a luxurious soak after a long day of walking in the old town. This is close to cafés and Gelateria’s. ..."

Reviewed on Sep 16, 2026

Castiglion del Bosco, A Rosewood Hotel

Localita Castiglion del Bosco Montalcino SI

Fully refundableReserve now, pay when you stay

$2,349 nightly

$2,596 total

Oct 8 - Oct 9

Total with taxes and fees

Book a stay at this luxury hotel in Montalcino. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Castiglion del Bosco Winery and Corte ...

10/10 Exceptional! (81 reviews)

"Very warm and friendly service."

Reviewed on Sep 13, 2026

See all 2,202 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.

PuntAla Camp & Resort

Punta Ala Castiglione della Pescaia GR

Book a stay at this beach campground in Castiglione della Pescaia. Enjoy free WiFi, free parking, and 2 restaurants. Popular attractions Cala Violina and Cala ...

8.6/10 Excellent! (63 reviews)

"Lovely camping, very safe and clean! Calm if you choose to be, or active if you choose to be…. Activities organized for young and old… nice beach, sun beds for rent, or your own towel…. Easy to rent water equipment, reasonable prices in restaurants, good choice of cuisine, delicious and satisfying ..."

Reviewed on Jul 17, 2026

Gitavillage Le Marze

Strada Provinciale n.158 km 30,200 Grosseto GR

Book a stay at this beach campground in Grosseto. Enjoy free parking, an outdoor pool, and a beach locale. Popular attractions Cantina Sociale i Vini di Maremma ...

8.8/10 Excellent! (54 reviews)

"I had a wonderful experience staying at this rental apartment. It was clean, comfortable, and had everything I needed. The location was perfect—close to shops, restaurants, and public transportation, but still quiet and relaxing. The host was very friendly and helpful, and check-in was easy. The ..."

Reviewed on Jul 24, 2025

Camping Maremma Sans Souci

Località Casa Mora Castiglione della Pescaia GR

Book a stay at this beach campground in Castiglione della Pescaia. Enjoy free WiFi, free parking, and a private beach. Popular attractions Natural Reserve Diaccia ...

8/10 Very Good! (29 reviews)

"The place is a very organized camping ground. With that being said, it’s not close to anything, it’s like a 25-30 min walk to the marina and downtown restaurants. They have access to to the beach and a small store that is necessary if you bring nothing. There’s a restaurant but we did not try it, ..."

Reviewed on May 22, 2026

See all 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.

Things to do

La Maliosa Farm Experience & Wine Tasting

La Maliosa Summer Farm Experience & Wine Tasting

$53

per adult

100% of travellers recommend

Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal

$128

per adult

See all activities in Montemassi

Frequently asked questions

When is the best time to visit Montemassi?

The best time to visit Montemassi is from May through September, when the climate is most favorable. For fewer crowds and better value, the quieter months of December through February are a good option, offering a cooler experience for exploring the area.

Can I book a refundable hotel in Montemassi?

Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Montemassi by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.

Why book a trip to Montemassi with Expedia?

Expedia makes it easier to plan your Montemassi trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.

Should I stay in a hotel or vacation rental in Montemassi?

The best choice depends on your travel style. Hotels in Montemassi can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.

How can I manage my Montemassi trip on Expedia?

Once you've booked your Montemassi trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.

What if I need help during my Montemassi trip?

Expedia offers customer support before, during, and after your Montemassi trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.

How can Expedia help me plan my first trip to Montemassi?

If it's your first trip to Montemassi, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.

How can I save on my Montemassi hotel booking with Expedia?

Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Montemassi hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Montemassi

Travel Guide