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Calimera Vacations from $391

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The Latest Calimera Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Sep 15 - Sep 20

    Leone De Castris Wine Hotel + Flight

    Salice Salentino
    5 nights
    4.0 star property
    8.4/10 - Very Good (46 reviews)
    "Not what I was expected. I know we came during off season but in May. The winery seem to be well known in the area but it wasn't open. They don't really have staff in attendance, but you can always reach them by email or phone if you have local cell phone. They use an app to access the gate into the venue unfortunately that our connection wasn't always the greatest and we needed to ask our friend to open the gate for us. We only saw one or two other guests in the hotel so it is really too..."
    Reviewed July 16, 2025
    Roundtrip • London (LON) - Brindisi (BDS)
    STN - BDS • Nonstop BDS - STN • Nonstop
    $453
    $391
    per traveler
    found 1 day ago
    Leone De Castris Wine Hotel
  • Free daily buffet breakfast
    Sep 2 - Sep 8

    Bianco Riccio Suite Hotel + Flight

    Fasano
    5 nights
    5.0 star property
    9.4/10 - Exceptional (72 reviews)
    Roundtrip • New York (NYC) - Brindisi (BDS)
    JFK - BDS • 1 stop BDS - JFK • 1 stop
    $3,742
    $2,845
    per traveler
    found 1 day ago
    Bianco Riccio Suite Hotel
  • Presidential Suite (Paradiso) | Terrace/patio
    Sep 15 - Sep 20

    Palazzo Sant'Anna Lecce + Flight

    Lecce Historic Center
    5 nights
    5.0 star property
    10/10 - Exceptional (272 reviews)
    "This was the most magnificent property during our vacation. Outstanding customer service, phenomenal property, gorgeous decor and landscaping, incredible breakfast. Absolutely à gem of a hotel. Top notch luxury. Thank you to all the fabulous staff that took care of us. Andrew and Jim. Grazie!"
    Reviewed July 25, 2026
    Roundtrip • London (LON) - Brindisi (BDS)
    STN - BDS • Nonstop BDS - STN • Nonstop
    Save 100% on your flight
    $2,593
    $2,202
    per traveler
    found 15 hours ago
    Palazzo Sant'Anna Lecce
  • Superior Suite | Bathroom | Free toiletries, hair dryer, bathrobes, slippers
    Sep 18 - Sep 21

    Paragon 700 Boutique Hotel & SPA + Flight

    Ostuni
    2 nights
    5.0 star property
    9.6/10 - Exceptional (39 reviews)
    "Beautiful Hotel with amazing service and standards. It’s an experience itself just to stay in the iconic property. "
    Reviewed May 10, 2026
    Roundtrip • New York (JFK) - Brindisi (BDS)
    JFK - BDS • 1 stop BDS - JFK • 1 stop
    $2,365
    $2,071
    per traveler
    found 1 day ago
    Paragon 700 Boutique Hotel & SPA
  • View from property
    Sep 5 - Sep 9

    Casale del Murgese + Flight

    Fasano
    3 nights
    4.0 star property
    9.0/10 - Wonderful (12 reviews)
    "Wonderful resort, lush landscaping with olives and fruit trees, magnificent pool, very good breakfast. "
    Reviewed October 14, 2025
    Roundtrip • New York (NYC) - Brindisi (BDS)
    JFK - BDS • 1 stop BDS - JFK • 1 stop
    $1,670
    $1,465
    per traveler
    found 1 day ago
    Casale del Murgese

Calimera Hotel Deals

Exterior

B&B Il Geranio

B&B Il Geranio
< 0.1 mi from Calimera
9.4 out of 10, Exceptional, (14 reviews)
"This is an excellent place to stay in Calimera. The property is perfectly located in the center, steps away from the old town square where you’ll find great cafes, pastry shops and restaurants. Necessities like the supermarket, bank, pharmacy are all a short walk away as well. The property itself is very clean, quiet and well-managed. It’s the perfect place to rest in between day trips. The hosts are excellent: gracious, responsive and accomodating. 10 out of 10, highly recommended!"
$75 nightly
The price is $83
Jul 31 - Aug 1
Total with taxes and fees
B&B Il Geranio
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.
See all properties in Calimera

Frequently Asked Questions

How much does a Calimera vacation package cost?

You'll find cheap prices from $391 on Expedia for your Calimera escape. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Calimera costs.

What are the cheapest months to go to Calimera?

You can usually find lower rates and greater availability in October, November and December. Check out our cheap Calimera vacation packages and you could score some great off-season deals.

How many days is enough for Calimera?

Typically, a handful of days is enough to see the major attractions during your Calimera vacation. However, if you want to have some time to relax or take day tours, think about extending your trip.

How to find the best Calimera package deals?

Begin your search for a Calimera package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Calimera 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 Calimera escape off to a flying start.

Is it cheaper to book a Calimera vacation as a package?

Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Calimera vacation by choosing your favorite type of stay, airline and car class.

When to book a vacation package to Calimera?

If you're planning a spontaneous Calimera getaway, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find sensational deals on your flights and hotels by booking well in advance.

Does Expedia offer Book Now, Pay Later Calimera vacation packages?

Your Calimera trip is meant to be an escape from your daily routine, not a source of money-related stress. So to give you more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no hidden costs 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.