Montechiaro Vacations from $783

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Your Montechiaro Vacation

Say bye-bye to the hassle of planning and hello to a Montechiaro vacation package. With your travel details organized before you take off, you can focus on discovering every inch of this city, starting with Badia Coltibuono, which is great for families, nature and walking. If a sightseeing tour is on the agenda during your trip to Montechiaro, look around well-known attractions like Siena Cathedral, Torre del Mangia and Piazza del Campo. Whoever you're traveling with and whatever you want to spend, your ultimate Montechiaro vacation is just clicks away with Expedia.

The Latest Montechiaro vacation packages

Price found within the past 48 hours. Click for updated prices.
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,390, price is now $783 per person
$783
per person
Nov 12 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (470 reviews)
The hotel is located a 25 min walk away from the heart of Florence so very easy to access the main attractions within the city. The hotel itself is immaculate and the staff are extremely helpful with dealing with any questions you may have. Being able to access the spa everyday for 1 and 30 minutes is an excellent perk as the facilities are well worth a visit, you are also able to book massages for an extra fee. The breakfast also gives a variety of options to start each day and the room itself is spacious, with the shower particularly being very comfortable.

Reviewed on Aug 13, 2025

L'Andana

L'Andana

5 out of 5
Save 100% on your flight
Price was $2,626, price is now $1,752 per person
$1,752
per person
Oct 24 - Oct 31
found 12 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.4/10 Exceptional! (80 reviews)
What an amazing place I hope to get back here next year again everybody was super nice. Property was super nice. It is quite relaxing. Great food apparently a great wine as well but I don’t drink. I highly recommend anybody to go.

Reviewed on Jul 5, 2025

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Cortona Old Town
Save 100% on your flight
Price was $2,080, price is now $1,456 per person
$1,456
per person
Oct 24 - Oct 31
found 12 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
10/10 Exceptional! (230 reviews)
Beautiful property, magical, great friendly staff, fantastic breakfast. Everything was perfect

Reviewed on Aug 7, 2025

The Club House

The Club House

5 out of 5
Save 100% on your flight
Price was $2,450, price is now $1,717 per person
$1,717
per person
Oct 24 - Oct 31
found 12 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
10/10 Exceptional! (2 reviews)
Excellent overall. Amenities. Service. Food. Vibe. All top notch

Reviewed on Sep 2, 2025

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

5 out of 5
Save 100% on your flight
Price was $2,456, price is now $1,739 per person
$1,739
per person
Oct 24 - Oct 31
found 12 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.6/10 Exceptional! (247 reviews)
This was the most authentic place I have ever seen really takes back but all the amenities by far the best place to stay in Tuscany IT Fantastic staff 5star

Reviewed on Aug 31, 2025

Don't see what you're looking for?
See all available trips from Columbus to Montechiaro
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Discover the most popular places to visit in Montechiaro

Piazza del Campo which includes street scenes and a square or plaza

Piazza del Campo

Sit at a café and experience the atmosphere of Siena’s main square, known for its medieval architectural grandeur and famous horse races.

Piazza del Campo
Siena Cathedral which includes a church or cathedral, street scenes and heritage architecture

Siena Cathedral

Breathtaking masterpieces by some of the finest Italian artists of the Renaissance era decorate this grandiose 800-year-old religious complex.

Siena Cathedral
Palazzo Pubblico featuring a city, heritage architecture and night scenes

Palazzo Pubblico

Palazzo Pubblico is just one of the places to see in Siena, so why not enjoy the other things to explore during your travels? Discover the area's beautiful countryside, or seek out its local tours.

Palazzo Pubblico

What to do in Montechiaro

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

Siena & San Gimignano Day Trip from Florence with Chianti Views

$88
per adult
88% of travellers recommend
Siena & San Gimignano Day Trip from Florence with Chianti Views
Torre del Mangia

Siena and San Gimignano: Small-Group Tour with Lunch from Florence

$147
per adult
100% of travellers recommend
Siena and San Gimignano: Small-Group Tour with Lunch from Florence
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

$75
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
See all activities in Montechiaro

Montechiaro Hotel Deals

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundableReserve now, pay when you stay
$214 nightly
The price is $241 total per night from Sep 4 to Sep 5
$241 total
Sep 4 - Sep 5
Total with taxes and fees
Hotel Athena
Hotel Ristorante Alcide

Hotel Ristorante Alcide

4 out of 5
Viale Marconi, 67/A, Poggibonsi, SI
$50 nightly
The price is $63 total per night from Sep 7 to Sep 8
$63 total
Sep 7 - Sep 8
Total with taxes and fees
Hotel Ristorante Alcide
Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

5 out of 5
Strada Comunale 14 Siena - Vagliagli 18, Castelnuovo Berardenga, SI
Fully refundableReserve now, pay when you stay
$423 nightly
The price is $477 total per night from Sep 8 to Sep 9
$477 total
Sep 8 - Sep 9
Total with taxes and fees
Borgo Scopeto Wine & Country Relais
See all 5,288 properties in Montechiaro
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.

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Frequently asked questions

How much does a Montechiaro vacation package cost?
Offering excellent value package deals from $783 on Expedia, you'll be thrilled with how little a vacation to Montechiaro costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Montechiaro?
You can usually find reduced prices and greater availability in November, December and January. Take a look at our cheap Montechiaro vacation packages and you could score some great off-season deals.
How many days is enough for Montechiaro?
The ideal length for your Montechiaro vacation depends on what you'd like to do. Typically, a few days to a week will give you time to tick off all the top attractions and explore some hidden gems along the way.
How to find the best Montechiaro package deals?
Use Expedia's handy filters to help you find some fabulous Montechiaro package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Montechiaro package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Montechiaro vacation as a package?
You can enjoy significant savings on your next Montechiaro escape by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to view the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Montechiaro?
If you're considering a spur-of-the-moment Montechiaro trip, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can land sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Montechiaro?

  1. Choose when to go: Check your diary and get packing. Your preferred season and the type of activities on offer will also help you decide when to visit Montechiaro.
  2. Plan your budget wisely: Besides the cost of your accommodations, you should consider other expenses too. These include food, flights and transportation. Also, put aside some extra funds for unexpected expenses that could crop up during your trip to Montechiaro.
  3. Use Expedia's trip planning tool to explore Montechiaro: Research every aspect of your trip to Montechiaro with this comprehensive planner. Invite family or friends to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Decide how many days away: Start by listing all the sights and activities you'd like to experience in Montechiaro. Then, estimate how long you'll need at each, as well as any travel time.
  5. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a customized Montechiaro vacation package.
  6. Book experiences or activities in advance: Whether it's entrance to a major attraction or a walking tour, you won't have to worry about missing out on the best Montechiaro has to offer. Find all the exciting things to do in Montechiaro with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Montechiaro vacation packages?
Your Montechiaro break should be an escape from your daily routine, not a source of money-related stress. So to allow you a bit more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.