Holiday Rentals in Calheta

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Calheta

Herdade das Hortênsias

São Jorge
10.0 out of 10, Exceptional, (1)
"Ruhig gelegen mit genügend Platz."
Germany
Lukas R.
The price is €118
includes taxes & fees
2 Dec - 3 Dec
Herdade das Hortênsias

Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)

São Jorge
10.0 out of 10, Exceptional, (1)
"serviço competente e atencioso, arquitectura enquadrada no contexto, local ideal para passeios e descanso."
Portugal
Pedro E.
The price is €225
includes taxes & fees
30 Nov - 1 Dec
Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)

Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi

Topo Calheta São Jorge Açores
The price is €106
includes taxes & fees
2 Dec - 3 Dec
Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi

Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)

São Jorge
The price is €225
includes taxes & fees
30 Nov - 1 Dec
Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)

Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)

Calheta
The price is €170
includes taxes & fees
30 Nov - 1 Dec
Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)

Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)

São Jorge
The price is €150
includes taxes & fees
30 Nov - 1 Dec
Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)

Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)

São Jorge
10.0 out of 10, Exceptional, (4)
"location, location, location plus the thoughtful design, adaptive reuse of structures, and the evident and abundant care of ownership and staff all added up to bliss for our group perhaps not for everyone, but the adventure of getting there and provisioning one’s stay can make for an even more satisfying stay."
United States
David B.
The price is €246
includes taxes & fees
30 Nov - 1 Dec
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)

Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba

São Jorge
The price is €213
includes taxes & fees
30 Nov - 1 Dec
Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba

Aldeia das Adegas

4.0 star property
Sao Roque do Pico
9.4 out of 10, Exceptional, (63)
"Diana is friendly and responsive with our requests. We stayed at one bedroom apartment. It feels like staying at home but in the paradise. "
United States
Raechung
The price is €105
includes taxes & fees
30 Nov - 1 Dec
Aldeia das Adegas

Casa dos Felicias

São Roque do Pico
10.0 out of 10, Exceptional, (1)
"The house was clean, spacious, well-appointed, convenient to the port, swimming, the grocery, the church, the village center, shops, and had gorgeous views. "
United States
Maria N.
The price is €157
includes taxes & fees
30 Nov - 1 Dec
Casa dos Felicias

Vila Paim - Apart. Low

São Roque do Pico
10.0 out of 10, Exceptional, (1)
"Great getaway super quiet and very relaxing place."
United States
Joe F.
The price is €157
includes taxes & fees
30 Nov - 1 Dec
Vila Paim - Apart. Low

Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi

Lajes do Pico
The price is €49
includes taxes & fees
1 Dec - 2 Dec
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi

Silveira House

Lajes do Pico
The price is €92
includes taxes & fees
30 Nov - 1 Dec
Silveira House

Adega do Mirante

São Roque do Pico
8.0 out of 10, Very good, (1)
"The basic necessities are provided; beds are comfortable and the place is clean. Need to Whatsapp owner to get information to get onto the property because messaging in Portugese otherwise. Property said air conditioning but the air conditioning was broken. It was cool enough though so not a problem. Walkable to the ocean and natural pool and nice restaurant down the street. It is located in Sao Roque which is in the middle of the island so nothing is far away if you are driving. Parking ample...
United States
Sharon
The price is €157
includes taxes & fees
20 Dec - 21 Dec
Adega do Mirante

Holiday Home 'Adega Pérola' with Wi-Fi

Cais do Galego
The price is €143
includes taxes & fees
5 Dec - 6 Dec
Holiday Home 'Adega Pérola' with Wi-Fi

Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi

Engrade
10.0 out of 10, Exceptional, (1)
"Pros: The house was recently renovated, everything was nice and clean, very kind host, peaceful place with view of the ocean and vineyards"
United States
Anonymous traveller
The price is €220
includes taxes & fees
1 Dec - 2 Dec
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi

Amazing One Bedroom Apartment with Sea View

São Roque do Pico
The price is €80
includes taxes & fees
1 Dec - 2 Dec
Amazing One Bedroom Apartment with Sea View

Very well equipped apartment in the center of São Roque do Pico

São Roque do Pico
"I stayed in this apartment with my family of 4. The apartment itself was small but ok. Note that the management keeps the remote control for AC and if you need it, they charge a daily fee of 10EUR per day. The communication with the manager has been very difficult since the beginning. I’ve sent a message a month prior to arrival to confirm there was enough room for the 4 of us. I never got any answers. The day before our arrival, I sent another message that was again unanswered. Even VRBO...
Canada
Caroline P.
The price is €188
includes taxes & fees
23 Dec - 24 Dec
Very well equipped apartment in the center of São Roque do Pico

Panoramic Ocean Views from your Private Varand

São Roque do Pico
The price is €161
includes taxes & fees
30 Nov - 1 Dec
Panoramic Ocean Views from your Private Varand

Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi

Pontas negras
The price is €273
includes taxes & fees
30 Nov - 1 Dec
Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Calheta Hotel Reviews

Find out more about Calheta

Everything you need to know about Calheta holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Calheta holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Calheta holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Calheta holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Calheta. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Calheta holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Calheta holiday rentals we have selected for you start as low as €105 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Calheta rentals

At Expedia, we put the best Calheta holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Calheta rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Calheta holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Calheta. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Calheta?

Yes, there are holiday rentals close to the most popular sights in Calheta, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Calheta has to offer?

Matilde's House, in the paradise Fajã de São João: This highly rated holiday home rental in Calheta is located by the ocean, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals will I find in Calheta?

Choose from 12 Expedia holiday rentals in Calheta for a memorable holiday.

What can I see and do in Calheta?

Fajãs das Lagoas de Santo Cristo e dos Cubres de São Jorge and Cascata do Cruzal are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Fajã dos Cubres and Pico da Esperanca.

What are holiday rentals like in Calheta?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Calheta. Holiday rentals feature extras such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a family trip.