Montegrossi Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

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

Top hotels in Montegrossi

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundable
The price is S$243 per night from 28 Aug to 29 Aug
S$243
28 Aug - 29 Aug
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"I can’t say enough good things about this hotel. The property is not quite as rustic as some of the others in Siena - it looks like it was updated inside about 10-15 years ago but it’s still in wonderful shape - just not quite rustic or very modern. Coming from a hotel the night before that was also ..."

Reviewed on 22 Aug, 2025

Hotel Athena
Hotel Ristorante Alcide

Hotel Ristorante Alcide

4 out of 5
Viale Marconi, 67/A, Poggibonsi, SI
Fully refundableReserve now, pay when you stay
The price is S$90 per night from 28 Aug to 29 Aug
S$90
28 Aug - 29 Aug
includes taxes & fees
8/10 Very Good! (452 reviews)
Good Value for the cost !
"The hotel was good value for the price. The room was clean. The hotel is in a good, safe area. The A/C was able to keep up with the 98F temps outside. Check in was easy. The breakfast was very good. Parking is a little tricky but not to bad. The only issues we had with our room was the safe wouldnt ..."

Reviewed on 7 Jul, 2025

Hotel Ristorante Alcide
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

5 out of 5
Via Spaltenna 13, Gaiole in Chianti, SI
9.4/10 Exceptional! (246 reviews)
"Fabulous !! Not handicap friendly but everything else is perfect"

Reviewed on 19 Aug, 2025

Get rates
Castello di Spaltenna- Small Luxury Hotels of the World
See all 6,125 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.

Popular places to visit

Church of San Sigismondo

You can find out about the history of Gaiole in Chianti with a stop at Church of San Sigismondo. Discover the beautiful countryside and wineries in this quaint area.

Church of San Sigismondo

What to do in Montegrossi

Brolio Castle

Small-Group Chianti Trip with Wine Tasting from Siena

S$269
per adult
Small-Group Chianti Trip with Wine Tasting from Siena
Large cutting board, 6 wine tasting and Guided tour

Large cutting board, 6 wine tasting and Guided tour

S$90
per adult
Large cutting board, 6 wine tasting and Guided tour
Sunny day view of Monteriggioni, a Comune in Italy

Chianti Half Day Wine Tour from Florence

S$73
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
See all activities in Montegrossi

Frequently asked questions

How much does a Montegrossi holiday package cost?
You'll find cheap prices on Expedia for your Montegrossi break. However, factors like the season, choice of hotel and length of stay will influence how much your holiday to Montegrossi costs.
What are the cheapest months to go to Montegrossi?
January, February and November are the best times to search for cheap Montegrossi holiday packages. Choosing to travel in less busy periods means you can typically find lower prices on flights and hotels.
How many days is enough for Montegrossi?
Usually, a handful of days is enough to visit the main attractions during your Montegrossi holiday. But if you prefer to have time to relax or go on day tours, consider extending your trip.
How to find the best Montegrossi package deals?
Use Expedia's filter tool to help you find some tempting Montegrossi package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Montegrossi package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your holiday package well in advance.
Is it cheaper to book a Montegrossi holiday as a package?
An Expedia holiday package could land you considerable savings when compared to booking flights and accommodation separately. Better still, you can customise your Montegrossi trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a holiday package to Montegrossi?
If you're planning an impromptu Montegrossi getaway, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Montegrossi?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Montegrossi.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and food to flights and activities. Your hotel will probably be the biggest expense during your trip to Montegrossi.
  3. Determine how many days away: Start by compiling a list of the sights and activities you'd like to experience in Montegrossi. Then, estimate how long you'll need for each, including any travel time.
  4. Combine your accommodation and airfare: After you've settled on your trip dates and duration, lock in the right Montegrossi holiday package for you.

* 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.