Calheta Vacations from $895
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Your Calheta Vacation
The coastal scenery and spectacular views are just the beginning of the things Calheta has to offer. Enjoy the best parts of this interesting city your way with a customized Calheta vacation package. You'll want to do a little exploring during your trip to Calheta. Carve out some time for leading attractions such as Fajãs das Lagoas de Santo Cristo e dos Cubres de São Jorge, Pico da Esperanca and Santa Bárbara Church. Your ideal Calheta vacation is just a few clicks away. Browse flights, accommodations and more on Expedia for an adventure that's tailored to suit your style.
The Latest Calheta vacation packages
Price found within the past 48 hours. Click for updated prices.
Cabanas da Viscondessa
$1,140
per person
Dec 25 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sao Jorge Island (SJZ)
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 on Jul 15, 2026
Casa d'Avó Guesthouse
$1,083
per person
Dec 25 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sao Jorge Island (SJZ)
9.8/10 Exceptional! (61 reviews)
The location is fantastic, right on the oceanfront and a perfect base for exploring the island. The property is spotless, well-maintained, and has a wonderful atmosphere. There’s a shared kitchen with large, dedicated storage cabinets for each room, and it's fully equipped with everything you could possibly need. The service was impeccable—Paula and Diana were always accessible, welcoming, and spoke excellent English. They went above and beyond to provide everything we needed with genuine generosity. Highly recommended!
Reviewed on Oct 5, 2026
Stay near popular Calheta attractions
Fajãs das Lagoas de Santo Cristo e dos Cubres de São Jorge
9.6/10 (8 reviews)
Explore the great outdoors at Fajãs das Lagoas de Santo Cristo e dos Cubres de São Jorge, a lovely green space in Calheta.
Cascata do Cruzal
Commune with nature and explore the great outdoors at Cascata do Cruzal during your travels in Santo Antão.
Fajã dos Cubres
You can take time to visit Fajã dos Cubres during your travels to Calheta.
Calheta Hotel Deals
Azores Youth Hostels - São Jorge
Canada da Vinha Nova Calheta
7.6/10 Good! (26 reviews)
"Very nice staff, great parking, a/c worked great, and a reasonable price. Our shower did not drain and flooded the bathroom. We couldn't take showers."
Reviewed on Sep 9, 2026
Kuanza Nature Experience
Faja do Belo Calheta Azores
$116 nightly
$125 total
Nov 2 - Nov 3
Total with taxes and fees
9.6/10 Exceptional! (11 reviews)
"Kuanza is absolutely gorgeous. My only regret is that we didn't get their famous baked bread in the morning. I was looking forward to it!"
Reviewed on Aug 8, 2026
Casas dos Vimes
Fajã dos Vimes Calheta Azores
10/10 Exceptional! (5 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 on Apr 14, 2024
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 Calheta Vacation Packages
Calheta Essential Information
Language | Portuguese |
|---|---|
Currency | Euros |
Local Welcome | Olá |
Local Goodbye | Adeus |
Closest Airport | Pico Island Airport (PIX) |
Population | 3,800 |
Max Temp Winter | 60ºF |
Max Temp Summer | 70ºF |
Top Sights | Igreja de Sao Jorge, Fajãs das Lagoas de Santo Cristo e dos Cubres de São Jorge and Velas Marina |
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Frequently asked questions
How much does a Calheta vacation package cost?
Offering excellent value package deals from $895 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?
- Pick your travel dates: The things you plan to do in Calheta and your favorite season can help you decide when to get away.
- 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.
- 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.
- 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.
- Bundle your accommodations and airfare: After you've settled on your travel dates and duration, book the perfect Calheta vacation package for you.
- 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.
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- Flights from Dallas (DFW) to Sao Jorge Island (SJZ)
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
