Title: Book the Best Cyclades Islands WINERY Hotels in 2026 | Expedia.ca

[Cyclades Islands Travel Guide](https://expedia.ca/Cyclades-Islands.dx6051353)[Hotels in Cyclades Islands](https://expedia.ca/Cyclades-Islands-Hotels.d6051353.Travel-Guide-Hotels)[Vacation Rentals in Cyclades Islands](https://expedia.ca/Cyclades-Islands-Vacation-Rentals.d6051353.Travel-Guide-VacationRentals)[Flights to Cyclades Islands](https://expedia.ca/Cheap-Flights-To-Cyclades-Islands.d6051353.Travel-Guide-Flights)[Cyclades Islands Car Rentals](https://expedia.ca/Car-Rentals-In-Cyclades-Islands.d6051353.Car-Rental-Guide)[Cyclades Islands Vacation Packages](https://expedia.ca/Cyclades-Islands.d6051353.Destination-Travel-Guides)

![Oia featuring a coastal town and a luxury hotel or resort](https://images.trvl-media.com/place/6051970/d6d7c83d-2485-4cdd-aedf-ad3614820b31.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6051970/d6d7c83d-2485-4cdd-aedf-ad3614820b31.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Cyclades Islands Winery Hotels

Tonight

[Jan 24 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6051353&startDate=2026-01-24&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 25 - Jan 26](https://www.expedia.ca/Hotel-Search?regionId=6051353&startDate=2026-01-25&endDate=2026-01-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6051353&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6051353&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Cyclades Islands hotels with winery

![Premium Room Caldera View with Outdoor Mini Plunge Pool Double | Balcony](https://images.trvl-media.com/lodging/2000000/1390000/1380900/1380881/dba784a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/2000000/1390000/1380900/1380881/e316b28b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Executive Room Caldera View with Outdoor Mini Plunge Pool Double](https://images.trvl-media.com/lodging/2000000/1390000/1380900/1380881/8f29bed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Rocabella Suite Caldera View with Outdoor Mini Plunge Pool for 6 Guests](https://images.trvl-media.com/lodging/2000000/1390000/1380900/1380881/4b2fd998.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rocabella Santorini Hotel & SPA 

[](https://www.expedia.ca/Santorini-Hotels-Rocabella-Santorini-Hotel-SPA.h1380881.Hotel-Information)

Santorini

9.4/10

Exceptional

(638 reviews)

"Balcony offered a nice view :)"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christopher Andrew

CA $131

CA $154 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Santorini-Hotels-Rocabella-Santorini-Hotel-SPA.h1380881.Hotel-Information)

![Superior Apartment, 3 Bedrooms, Terrace | Living area](https://images.trvl-media.com/lodging/84000000/83180000/83170300/83170213/8ab55ec9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Apartment, 3 Bedrooms, Terrace](https://images.trvl-media.com/lodging/84000000/83180000/83170300/83170213/df0b43b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Junior Studio Suite, Terrace](https://images.trvl-media.com/lodging/84000000/83180000/83170300/83170213/29d13d9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83180000/83170300/83170213/c1a40c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Elements Cave Suites

[](https://www.expedia.ca/Santorini-Hotels-Elements-Suites.h83170213.Hotel-Information)

Santorini

9.2/10

Wonderful

(16 reviews)

"Lovely place to stay in a quiet area that still has great restaurants and some shops around. "

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Kyle Schulz

CA $137

CA $156 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Santorini-Hotels-Elements-Suites.h83170213.Hotel-Information)

![Suite (Polymneia) | Beach/ocean view](https://images.trvl-media.com/lodging/19000000/18170000/18164500/18164486/d61fb9b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite (Melpomeni)](https://images.trvl-media.com/lodging/19000000/18170000/18164500/18164486/4113842e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite (Melpomeni)](https://images.trvl-media.com/lodging/19000000/18170000/18164500/18164486/51dbdca8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite (Polymneia) | Outdoor spa tub](https://images.trvl-media.com/lodging/19000000/18170000/18164500/18164486/4dffe149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mykonos Moussa Suites

[](https://www.expedia.ca/Mykonos-Hotels-Mykonos-Moussa-Suites.h18164486.Hotel-Information)

Mykonos

9.8/10

Exceptional

(97 reviews)

"Great hospitality. Great sea view. Close to nice beaches. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Osman

CA $156

CA $179 total

includes taxes & fees

Feb 7 - Feb 8

[](https://www.expedia.ca/Mykonos-Hotels-Mykonos-Moussa-Suites.h18164486.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/52000000/51270000/51260300/51260204/b2d922b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down comforters, minibar, in-room safe](https://images.trvl-media.com/lodging/52000000/51270000/51260300/51260204/7aa64699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premier Suite, Sea View](https://images.trvl-media.com/lodging/52000000/51270000/51260300/51260204/7e188c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Suite, Sea View](https://images.trvl-media.com/lodging/52000000/51270000/51260300/51260204/b4c27391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Phaos Santorini Suites

[](https://www.expedia.ca/Santorini-Hotels-Rhapsody-Apartments.h51260204.Hotel-Information)

Santorini

9.2/10

Wonderful

(221 reviews)

"Beautiful stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Maria

CA $55

CA $63 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Santorini-Hotels-Rhapsody-Apartments.h51260204.Hotel-Information)

![Outdoor pool, open 9:30 AM to 7:30 PM, sun loungers](https://images.trvl-media.com/lodging/7000000/6840000/6839300/6839252/cca15556.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, Hot Tub, Resort View (Elegant - Private Pool) | Living area](https://images.trvl-media.com/lodging/7000000/6840000/6839300/6839252/1f10251a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/7000000/6840000/6839300/6839252/e2793b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Villa, 2 Bedrooms, Private Pool, Vineyard View](https://images.trvl-media.com/lodging/7000000/6840000/6839300/6839252/eb6419c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### De Sol Spa Hotel

[](https://www.expedia.ca/Santorini-Hotels-De-Sol-Spa-Hotel.h6839252.Hotel-Information)

Santorini

9.4/10

Exceptional

(529 reviews)

"The rooms were clean and the service outstanding. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Teresa

[](https://www.expedia.ca/Santorini-Hotels-De-Sol-Spa-Hotel.h6839252.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/77000000/76230000/76224500/76224483/ed0c3fd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Suite, Sea View & Outdoor Hot Tub | View from room](https://images.trvl-media.com/lodging/77000000/76230000/76224500/76224483/87c95800.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aelia Suite, Sea View & Outdoor Hot Tub | Terrace/patio](https://images.trvl-media.com/lodging/77000000/76230000/76224500/76224483/b11620ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![V.I.P. Suite Sea View | Living area](https://images.trvl-media.com/lodging/77000000/76230000/76224500/76224483/ebc8a3c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aelia Luxury Suites

[](https://www.expedia.ca/Santorini-Hotels-Aelia-Luxury-Suites.h76224483.Hotel-Information)

Santorini

8.8/10

Excellent

(16 reviews)

"We really had nice stay during our trip to beautiful Santorini! "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Lobsang

[](https://www.expedia.ca/Santorini-Hotels-Aelia-Luxury-Suites.h76224483.Hotel-Information)

![Villa (Balance) | View from room](https://images.trvl-media.com/lodging/19000000/18250000/18243500/18243419/c7d1e91f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/19000000/18250000/18243500/18243419/d300519c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Villa (Virtue) | Terrace/patio](https://images.trvl-media.com/lodging/19000000/18250000/18243500/18243419/172c5b1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/19000000/18250000/18243500/18243419/915f43a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Good Life Greece Eco Villas

[](https://www.expedia.ca/Syros-Hotels-Good-Life-Greece-Eco-Villas.h18243419.Hotel-Information)

Syros

9.0/10

Wonderful

(2 reviews)

"Great place for a relaxing holiday. Beautiful villas transporting you to serene, peaceful village life. Apartment has all the modern facilities so we have the best of both worlds..modern amenities surrounded by village tranquility."

![Malaysia](https://a.travel-assets.com/egds/marks/flags/my.svg)

wing mow

[](https://www.expedia.ca/Syros-Hotels-Good-Life-Greece-Eco-Villas.h18243419.Hotel-Information)

![Superior Triple Room, Sea View | Living area](https://images.trvl-media.com/lodging/1000000/890000/889500/889455/d0cd358c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/1000000/890000/889500/889455/39a35fad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/1000000/890000/889500/889455/b5ca1be3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/890000/889500/889455/c7bbc750.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Theoxenia Caldera Hotel

[](https://www.expedia.ca/Santorini-Hotels-Theoxenia-Boutique-Hotel.h889455.Hotel-Information)

Santorini

9.2/10

Wonderful

(272 reviews)

"Room was very comfortable, staffs were great!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Amirthalingadoss

CA $163

CA $188 total

includes taxes & fees

Jan 30 - Jan 31

[](https://www.expedia.ca/Santorini-Hotels-Theoxenia-Boutique-Hotel.h889455.Hotel-Information)

![Premium Suite, Balcony | Room amenity](https://images.trvl-media.com/lodging/96000000/95960000/95952500/95952496/b0818739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/96000000/95960000/95952500/95952496/f65fd11b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Rooftop terrace](https://images.trvl-media.com/lodging/96000000/95960000/95952500/95952496/b79b6120.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Suite, Balcony | Room amenity](https://images.trvl-media.com/lodging/96000000/95960000/95952500/95952496/26506c42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Legato Spa Suites

[](https://www.expedia.ca/Naxos-Hotels-Naxos.h95952496.Hotel-Information)

Naxos

10/10

Exceptional

(24 reviews)

"First time in Greece and it was one of the best places i’ve stayed. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rosa

CA $278

CA $317 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Naxos-Hotels-Naxos.h95952496.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106910000/106901000/106900963/666b4dcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Basic Suite, Patio, Sea View | Living area](https://images.trvl-media.com/lodging/107000000/106910000/106901000/106900963/f61f001d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Suite, Patio, Sea View | Terrace/patio](https://images.trvl-media.com/lodging/107000000/106910000/106901000/106900963/931c9d0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Basic Suite, Patio, Sea View | Living area](https://images.trvl-media.com/lodging/107000000/106910000/106901000/106900963/29ff5d18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Yiota Collection 4 Suites & 4 Prive Jacuzzi

[](https://www.expedia.ca/Santorini-Hotels-Yiota-Collection-3Suites3Prive-Jacuzzi.h106900963.Hotel-Information)

Santorini

10/10

Exceptional

(8 reviews)

"Nice little town, way to navigate. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Amanda

CA $164

CA $191 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Santorini-Hotels-Yiota-Collection-3Suites3Prive-Jacuzzi.h106900963.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-07&endDate=2026-02-08&regionId=6051353&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true)

## Top Cyclades Islands Hotel Reviews

![Rocabella Santorini Hotel & SPA ](https://images.trvl-media.com/lodging/2000000/1390000/1380900/1380881/15e57ee3_y.jpg)

### Rocabella Santorini Hotel & SPA 

10/10 Excellent

"Balcony offered a nice view :)"

[](https://expedia.ca/Santorini-Hotels-Rocabella-Santorini-Hotel-SPA.h1380881.Hotel-Information)

![Ira Hotel & Spa - Adults Only](https://images.trvl-media.com/lodging/7000000/6120000/6116900/6116875/c1b6b3c6_y.jpg)

### Ira Hotel & Spa - Adults Only

10/10 Excellent

"The staffs are great . Clean is room and quiet . Amenities are great . The view in the hotel is stunning and amazing . Recommended ! Thank you Kostas for your great service . Maria and Tim "

[](https://expedia.ca/Santorini-Hotels-Ira-Hotel-Spa.h6116875.Hotel-Information)

![Hotel Sunny Villas](https://images.trvl-media.com/lodging/2000000/1100000/1095700/1095677/1e5cde74_y.jpg)

### Hotel Sunny Villas

10/10 Excellent

"Beautiful stay in Santorini!"

[](https://expedia.ca/Santorini-Hotels-Hotel-Sunny-Villas.h1095677.Hotel-Information)

![Volcano View Hotel Santorini](https://images.trvl-media.com/lodging/2000000/1080000/1071600/1071551/a63cc6f8_y.jpg)

### Volcano View Hotel Santorini

10/10 Excellent

"Excellent views and a good room with decent amenities. "

[](https://expedia.ca/Santorini-Hotels-Volcano-View-Hotel-Santorini.h1071551.Hotel-Information)

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