A crowded beach with people swimming and sunbathing under umbrellas.

Calheta Vacations from $1,215

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The Latest Calheta Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Sep 11 - Sep 14

    Hotel da Graciosa + Flight

    Santa Cruz da Graciosa
    3 nights
    4.0 star property
    9.0/10 - Wonderful (51 reviews)
    "Hotel is nice, check-in was quick and easy. All was clean and stafg was extremely helpful. Location is close to the little marina with a beach, pretty much across the local road from the hotel. Unfortunately, we did not have time to check the sauna."
    Reviewed July 26, 2026
    Roundtrip Boston (BOS) - São Jorge Island (SJZ)
    BOS - PDLNonstop PDL - BOS1 stop
    $1,239
    $1,215
    per traveler
    found 1 day ago
    Hotel da Graciosa
  • Sep 18 - Sep 22

    Cabanas da Viscondessa + Flight

    Velas
    4 nights
    3.5 star property
    10/10 - Exceptional (10 reviews)
    "It was a perfect place to explore the island. Staff was super friendly and very helpful. A very peaceful place, would highly recommend. Would definitely come back and stay there again."
    Reviewed July 15, 2026
    Roundtrip Boston (BOS) - São Jorge Island (SJZ)
    BOS - PDLNonstop PDL - BOS1 stop
    $1,518
    $1,463
    per traveler
    found 1 day ago
    Cabanas da Viscondessa
  • Oct 1 - Oct 5

    Quinta da Magnólia + Flight

    Velas
    3 nights
    3.0 star property
    10/10 - Exceptional (31 reviews)
    "The property is situated in a beautiful location and very close to the airport. The staff was super helpful and kind. Breakfast was delicious. Room was big with great view. I would advise to bring your own toiletries. It only has shower cap and soap. I was prepared so it wasn't a big deal."
    Reviewed August 4, 2026
    Roundtrip Baltimore (BWI) - São Jorge Island (SJZ)
    BWI - PDL2 stops PDL - BWI2 stops
    $2,022
    $1,970
    per traveler
    found 2 hours ago
    Quinta da Magnólia
  • Sep 4 - Sep 9

    Casas dos Vimes + Flight

    Calheta
    4 nights
    3.0 star property
    10/10 - Exceptional (4 reviews)
    "Wonderful cozy house with a fully equipped kitchen. The food supplied on our arrival was unexpected and appreciated as we arrived later than expected. Quiet, friendly community right near the ocean with trails within walking distance of the home. "
    Reviewed April 14, 2024
    Roundtrip New York (EWR) - São Jorge Island (SJZ)
    EWR - PDLNonstop PDL - EWR1 stop
    $2,062
    $2,043
    per traveler
    found 20 hours ago
    Casas dos Vimes
  • Sep 4 - Sep 9

    Casa d'Avó Guesthouse + Flight

    Velas
    4 nights
    3.0 star property
    9.8/10 - Exceptional (58 reviews)
    "Our room had a patio with sliding doors overlooking the ocean! Gorgeous!!! There is a central kitchen that guests can use to make meals and lots of great places to sit. The staff are amazing. They help to call taxis, provide laundry service and any other help you may need. The owner came by regularly to check on how things were going and was easy to access."
    Reviewed July 11, 2026
    Roundtrip New York (EWR) - São Jorge Island (SJZ)
    EWR - PDLNonstop PDL - EWR1 stop
    $1,934
    $1,927
    per traveler
    found 20 hours ago
    Casa d'Avó Guesthouse

Where to stay in Calheta

Find the best Calheta areas and neighborhoods for the activities you enjoy most. Learn more about Calheta
Learn more about Calheta

Ribeira Seca

While there might not be top attractions in Ribeira Seca, you can explore the larger area and discover places like Fajãs das Lagoas de Santo Cristo e dos Cubres de São Jorge and Fajã dos Cubres.

Discover the most popular places to visit in Calheta

Calheta Hotel Deals

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.

Frequently Asked Questions

How much does a Calheta vacation package cost?

Offering excellent value package deals from $1,215 on Expedia, you'll be thrilled with how little a vacation to Calheta costs! Expedia's packages mean less travel planning for you and greater savings.

What are the cheapest months to go to Calheta?

You can generally find lower prices and greater availability in November, December and January. Check out our cheap Calheta vacation packages and you could land some great off-season deals.

How many days is enough for Calheta?

The ideal length for your Calheta vacation depends on what you'd like to do and see. Generally, a few days to a week will give you time to go to all the main sights and explore some hidden treasures along the way.

How to find the best Calheta package deals?

Use Expedia's handy filters to find some terrific Calheta package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Calheta 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 usually best to lock in your vacation package as soon as possible.

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

You can enjoy significant savings on your Calheta retreat by booking a personalized vacation package. Check the "Package" heading, then enter your destination and travel dates to view some great hotel and flight prices. 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 Calheta?

If you have your Calheta travel dates locked in, book as soon as you can to score some terrific deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are great for traveling on a whim.

How to plan a trip to Calheta?

  1. Pick your travel dates: The things you plan to do in Calheta and your favorite season can help you decide when to get away.
  2. Plan your budget wisely: Besides the price of your accommodations, you'll need to consider other expenses. These include transportation, food and flights. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Calheta.
  3. Organize your Calheta escape with Expedia's trip planning tool: Search for and book hotels and things to do all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Calheta together.
  4. Determine how many days away: Start by listing all the attractions you'd like to experience in Calheta. Then, estimate how long you'll need for each, including any travel time.
  5. Bundle your accommodations and airfare: After you've settled on your travel dates and duration, book the perfect Calheta vacation package for you.
  6. Book experiences or activities in advance: Whether it's entrance to a major attraction or a day trip, you won't have to worry about missing out on the highlights of Calheta. Find all the incredible things to do in Calheta with our dedicated travel guide.

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

If you're anything like us, you love traveling the world but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Calheta break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.