Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Calheta Vacations

Pack those stellar shades. We have Calheta vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Calheta – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Calheta vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Calheta

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Calheta vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Calheta well.

Top Hotel Deals

See all 34 Hotels in Calheta
PJA - Sao Jorge Youth Hostel

PJA - Sao Jorge Youth Hostel

Canada da Vinha Nova, Calheta (Sao Jorge Island)
2.0 out of 5.0

Situated in Calheta, this hostel is 6.5 mi (10.5 km) from Pico da Esperanca and within 16 mi (25 km) of Velas Bullfighting Arena and Igreja de Sao Jorge. Velas ...

Aldeia das Adegas

Aldeia das Adegas

Rua das Adegas 3A, Sao Roque do Pico
4.5 out of 5.0

Situated near the beach, this apartment building is within 1 mi (2 km) of Convent of Sao Roque do Pico and Sao Roque Church. Caiado Lagoon and Museu do Vinho ...

A Casa do Ouvidor

A Casa do Ouvidor

Estrada Regional, 22, Sao Roque do Pico
4.5 out of 5.0

Situated near the beach, this villa is 0.4 mi (0.7 km) from Sao Roque Church and 1.5 mi (2.4 km) from Convent of Sao Roque do Pico. Caiado Lagoon is 8.8 mi (14.2 ...

Cantinho das Buganvillias

Cantinho das Buganvillias

Rua Padre Augusto Teixeira, Velas
4.5 out of 5.0

Situated in Velas, this aparthotel is 2.9 mi (4.6 km) from Velas Bullfighting Arena and within 6 mi (10 km) of Igreja de Sao Jorge and Velas Marina. Pico da ...

Casa do Comendador

Casa do Comendador

Rua de Baixo, No 17 S.Miguel Arcanjo, Sao Roque do Pico
4.0 out of 5.0

Situated by the ocean, this guesthouse is 1.2 mi (1.9 km) from Sao Roque Church and 2.4 mi (3.8 km) from Convent of Sao Roque do Pico. Caiado Lagoon and Lajes ...

Sara Village

Sara Village

Estrada Regional Nº1 Nº20, Sao Roque do Pico
3.5 out of 5.0

Situated in Sao Roque do Pico, this country house is close to Sao Roque Church and Convent of Sao Roque do Pico. Area attractions also include Caiado Lagoon ...

PJA - Pico Youth Hostel

PJA - Pico Youth Hostel

Rua João Bento Lima, Sao Roque do Pico
2.0 out of 5.0

Situated in Sao Roque do Pico, this hostel is within 1 mi (2 km) of Convent of Sao Roque do Pico and Sao Roque Church. Mount Pico and Caiado Lagoon are also ...

Adega do Lima

Adega do Lima

Rua do Porto, Sao Roque do Pico
3.0 out of 5.0

Located in Prainha, this country house is within 12 mi (20 km) of Sao Roque Church, Convent of Sao Roque do Pico, and Caiado Lagoon. Lajes Whaling Museum and ...

Houses In Pico

Houses In Pico

Caminho do Poço Diogo Vieira, Sao Roque do Pico
3.5 out of 5.0

Located in Prainha, this cottage is within 12 mi (20 km) of Sao Roque Church, Convent of Sao Roque do Pico, and Caiado Lagoon. Lajes Whaling Museum and Mount ...

São Jorge Garden

São Jorge Garden

Rua Machado Pires, Velas
3.5 out of 5.0

Situated in Velas, this hotel is within a 15-minute walk of Igreja de Sao Jorge and Velas Marina. Velas Bullfighting Arena is 1.7 mi (2.7 km) away.