Visit Montegrossi: 2026 Travel Guide for Montegrossi, Gaiole in Chianti

La Certosa di Pontignano

loc. Pontignano, 5 Castelnuovo Berardenga SI

$91 nightly

$109 total

Oct 5 - Oct 6

Total with taxes and fees

Book a stay at this business-friendly B&B in Castelnuovo Berardenga. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the breakfast and ...

9.4/10 Exceptional! (564 reviews)

"Magical place! We loved jazz night and the amazing wine paired dinner. Fantastic place!"

Reviewed on Sep 16, 2026

Hotel Athena

P Mascagni 55 Siena SI

$235 nightly

$264 total

Oct 20 - Oct 21

Total with taxes and fees

Book a stay at this business-friendly hotel in Siena. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the breakfast and the helpful staff ...

9.4/10 Exceptional! (1,000 reviews)

"We had a wonderful stay at Hotel Athena in Siena. The service was exceptional, the staff were warm, welcoming and genuinely helpful throughout our visit. The location was fantastic for exploring Siena, with everything within walking distance, while the hotel itself provided a comfortable and relaxing ..."

Reviewed on Sep 11, 2026

Hotel Executive

Via Nazareno Orlandi 32 Siena SI

$75 nightly

$88 total

Oct 18 - Oct 19

Total with taxes and fees

Book a stay at this family-friendly hotel in Siena. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...

See all 6,006 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.

Villa Il Palagio

Via Il Palagio 59 Rignano sull'Arno FI

Book a stay at this family-friendly apartment in Rignano sull'Arno. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions The Mall Luxury Outlet ...

8.8/10 Excellent! (82 reviews)

"Great loved everything thank you!"

Reviewed on Sep 7, 2026

Hu Norcenni Girasole Village

Via Norcenni 7 Figline e Incisa Valdarno FI

Book a stay at this family-friendly campground in Figline e Incisa Valdarno. Enjoy free parking, 7 outdoor pools, and 3 restaurants. Popular attractions Fashion ...

8.6/10 Excellent! (331 reviews)

"Amazing venue , lots of kids entertainment. Lots of facilities- shops restaurants. Splash parks were brilliant. Highly recommended."

Reviewed on Sep 3, 2026

Chianti Village Morrocco

Strada Morrocco 36/A Barberino Tavarnelle FI

Book a stay at this family-friendly residence in Barberino Tavarnelle. Enjoy an outdoor pool, breakfast (surcharge), and room service. Popular attractions Poggio ...

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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.

Check Montegrossi hotel availability

Things to do

From Siena: Chianti and Castles Tour with Wine Tastings

$99

per adult

88% of travellers recommend

Siena, San Gimignano, Monteriggioni & Chianti from Florence

$61

per adult

88% of travellers recommend

Florence Day Trip: Medieval Villages & Cooking Class

$185

per adult

86% of travellers recommend

From Florence: Siena & San Gimignano Day Trip with Lunch & Wine Tasting

Tuscany Day Trip to Siena & San Gimignano with Optional Wine Tasting

$54

per adult

90% of travellers recommend

Tootbus Tuscany Intercity Multi-day Pass

Tootbus Tuscany Multi-Day Tours from Florence: Explore at Your Own Pace

$40

per adult

Siena: Taste Tuscany on a Full Meal Food Tour with a Local

Siena: Guided Walking Food Tour with Full Meal

$104

per adult

See all activities in Montegrossi

Frequently asked questions

When is the best time to visit Montegrossi?

The best time to visit Montegrossi is from May through September, when travelers can enjoy warm, pleasant weather. For fewer crowds and better value, the quieter months of November through February are a good bet, offering cooler temperatures and a more relaxed atmosphere.

Can I book a refundable hotel in Montegrossi?

Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Montegrossi 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 Montegrossi with Expedia?

Expedia makes it easier to plan your Montegrossi 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 Montegrossi?

The best choice depends on your travel style. Hotels in Montegrossi 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 Montegrossi trip on Expedia?

Once you've booked your Montegrossi 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 Montegrossi trip?

Expedia offers customer support before, during, and after your Montegrossi 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 Montegrossi?

If it's your first trip to Montegrossi, 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 Montegrossi 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 Montegrossi hotel.

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

Montegrossi

Travel Guide