Montemesola Vacations from $1,580

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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

The Latest Montemesola vacation packages

Price found within the past 48 hours. Click for updated prices.
Ostuni Palace Hotel Ristorante & SPA

Ostuni Palace Hotel Ristorante & SPA

4 out of 5
Price was $1,737, price is now $1,580 per person
$1,580
per person
Dec 26 - Dec 31
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Brindisi (BDS)
9.2/10 Wonderful! (181 reviews)
Beautiful hotel!

Reviewed on Nov 4, 2026

Borgo Egnazia

Borgo Egnazia

5 out of 5
Price was $3,704, price is now $3,137 per person
$3,137
per person
Dec 26 - Dec 31
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Brindisi (BDS)
9.6/10 Exceptional! (346 reviews)

Paragon 700 Boutique Hotel & SPA

Paragon 700 Boutique Hotel & SPA

5 out of 5
Price was $3,745, price is now $3,229 per person
$3,229
per person
Dec 27 - Jan 2
found 16 hours ago
Roundtrip non-stop flight included
New York (NYC) to Brindisi (BDS)
9.6/10 Exceptional! (46 reviews)

Vinilia Wine Resort

Vinilia Wine Resort

4 out of 5
Price was $3,168, price is now $2,801 per person
$2,801
per person
Dec 27 - Jan 2
found 16 hours ago
Roundtrip non-stop flight included
New York (NYC) to Brindisi (BDS)
9.4/10 Exceptional! (91 reviews)

Tenuta Moreno

Tenuta Moreno

4 out of 5
Price was $2,461, price is now $2,201 per person
$2,201
per person
Dec 28 - Jan 2
found 6 hours ago
Roundtrip non-stop flight included
New York (NYC) to Brindisi (BDS)
8.6/10 Excellent! (72 reviews)
My Sons Wedding. Perfect in all ways. Super helpful staff, lovely, clean rooms, Outstanding food, Young man on the bar was brilliant, well kept grounds and pool area, Thank you! A beautiful experience for all our family.

Reviewed on Sep 10, 2026

Don't see what you're looking for?
See all available trips from Columbus to Montemesola
View all trips

What to do in Montemesola

Valle d'Itria: Winery Tour and Classic Wine Tasting

Valle d'Itria: Tenute Girolamo Cellar Tour and Classic Wine Tasting

$22
per adult
Valle d'Itria: Tenute Girolamo Cellar Tour and Classic Wine Tasting
Taranto: Mar Piccolo Tour – history and nature

Taranto: Mar Piccolo Tour among history and nature

$56
per adult
Taranto: Mar Piccolo Tour among history and nature
Martina Franca: Taste Wine & Local Specialities

Martina Franca: Taste Wine & Local Specialities

$55
per adult
Martina Franca: Taste Wine & Local Specialities
See all activities in Montemesola

Montemesola Hotel Deals

Hotel Monte Sarago

Hotel Monte Sarago

4 out of 5
Corso Mazzini 233 Ostuni BR
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $95 total per night from Nov 14 to Nov 15
$95 total
Nov 14 - Nov 15
Total with taxes and fees
Hotel Monte Sarago
Trulli Holiday Albergo Diffuso

Trulli Holiday Albergo Diffuso

Piazza XXVII Maggio, 38 Alberobello BA
$105 nightly
The price is $122 total per night from Nov 9 to Nov 10
$122 total
Nov 9 - Nov 10
Total with taxes and fees
9.6/10 Exceptional! (753 reviews)
"Brilliant experience checked in early and left our bags with the admin office. Came back at 3pm and were shown to our Trulli house just a few minutes walk away. Beautifully decorated with underfloor heating and a gorgeous bathroom with all modern convenience. Close by I had pre booked La Cantina ..."

Reviewed on Nov 1, 2026

Trulli Holiday Albergo Diffuso
Ostuni Palace Hotel Ristorante & SPA

Ostuni Palace Hotel Ristorante & SPA

4 out of 5
Corso Vittorio Emanuele 218 Ostuni BR
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $110 total per night from Nov 12 to Nov 13
$110 total
Nov 12 - Nov 13
Total with taxes and fees
9.2/10 Wonderful! (184 reviews)
"Beautiful hotel!"

Reviewed on Nov 4, 2026

Ostuni Palace Hotel Ristorante & SPA
See all 5,435 properties in Montemesola
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.

Find the Best Montemesola Vacation Packages

Montemesola Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Population
4,000
Top Sights
Cathedral of San Cataldo, Aragonese Castle and Ducal Palace

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Montemesola vacation package cost?
You'll find cheap prices from $1,580 on Expedia for your Montemesola escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Montemesola costs.
What are the cheapest months to go to Montemesola?
If you'd like to snag a cheap Montemesola vacation package, consider traveling in January, March and November. You'll generally find lower prices on hotels and airfares during these quieter months — ideal for travelers wishing to save money.
How many days is enough for Montemesola?
Typically, a handful of days is enough to visit the major sights during your Montemesola vacation. However, if you prefer to have time to kick back or take day trips, consider extending your trip.
How to find the best Montemesola package deals?
Begin your search for a Montemesola package deal by entering your destination and travel dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Montemesola package deal straight away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Montemesola adventure underway.
Is it cheaper to book a Montemesola vacation as a package?
You can enjoy significant savings on your next Montemesola retreat by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Montemesola?
If you've got your Montemesola travel dates confirmed, book early to grab some terrific deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for setting off on a whim.
Does Expedia offer Book Now, Pay Later Montemesola vacation packages?
Set off on your ideal getaway to Montemesola with help from Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait for your next paycheck — we've teamed up with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans mean you can spread the cost over 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily budget for your trip and snap up bargains while they last.

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.