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)

# Find Winery Hotels in Cyclades Islands from CA $69

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## Check availability on Cyclades Islands Winery Hotels

Tonight

[Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6051353&startDate=2025-12-27&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 28 - Dec 29](https://www.expedia.ca/Hotel-Search?regionId=6051353&startDate=2025-12-28&endDate=2025-12-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6051353&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6051353&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Cyclades Islands hotels with winery

![Premier Suite, Hot Tub, Sea View](https://images.trvl-media.com/lodging/52000000/51270000/51260300/51260204/26426d15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premier Suite, Hot Tub, Sea View](https://images.trvl-media.com/lodging/52000000/51270000/51260300/51260204/d8c8f002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Grand Suite, Sea View (Split Level)](https://images.trvl-media.com/lodging/52000000/51270000/51260300/51260204/438cd1be.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/e0c63620.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

(217)

"Beautiful stay"

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

Maria

CA $60

CA $69 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![Suite (Polymneia) | Terrace/patio](https://images.trvl-media.com/lodging/19000000/18170000/18164500/18164486/c6f5bf08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite (Polymneia) | Terrace/patio](https://images.trvl-media.com/lodging/19000000/18170000/18164500/18164486/e50128da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/19000000/18170000/18164500/18164486/69c38432.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite (Polymneia) | View from room](https://images.trvl-media.com/lodging/19000000/18170000/18164500/18164486/539c0539.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

(94)

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

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

Osman

CA $148

CA $170 total

includes taxes & fees

Jan 12 - Jan 13, 2026

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

![Seasonal outdoor pool, open 10:00 AM to 6:00 PM, free cabanas](https://images.trvl-media.com/lodging/2000000/1750000/1746400/1746352/206dcb9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1750000/1746400/1746352/42c750c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Master Suite Caldera View](https://images.trvl-media.com/lodging/2000000/1750000/1746400/1746352/536a922e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Grand Maisonette Caldera View | View from room](https://images.trvl-media.com/lodging/2000000/1750000/1746400/1746352/a817d32b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Suites of the Gods Cave Spa

[](https://www.expedia.ca/Santorini-Hotels-Suites-Of-The-Gods-Cave-Spa.h1746352.Hotel-Information)

Santorini

8.6/10

Excellent

(293)

"From check-in to check-out, everything felt smooth and welcoming. We would happily stay here again and would recommend it to anyone looking for a comfortable and pleasant stay."

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

LADONNA

CA $213

CA $249 total

includes taxes & fees

Jan 17 - Jan 18, 2026

[](https://www.expedia.ca/Santorini-Hotels-Suites-Of-The-Gods-Cave-Spa.h1746352.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/84000000/83180000/83170300/83170213/d09fc2fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Suite, 2 Bedrooms, Terrace | Living area](https://images.trvl-media.com/lodging/84000000/83180000/83170300/83170213/5e30398a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/84000000/83180000/83170300/83170213/825f8138.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Junior Studio Suite, Terrace | Living area](https://images.trvl-media.com/lodging/84000000/83180000/83170300/83170213/908066c9.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)

"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 $100

CA $115 total

includes taxes & fees

Jan 18 - Jan 19, 2026

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

![Outdoor pool, open 9:30 AM to 7:30 PM, sun loungers](https://images.trvl-media.com/lodging/7000000/6840000/6839300/6839252/6cec4f19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/7000000/6840000/6839300/6839252/4299c5c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; Mediterranean cuisine, ocean views ](https://images.trvl-media.com/lodging/7000000/6840000/6839300/6839252/d152041a.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

(525)

"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)

![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)

![Minibar, in-room safe, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/890000/889500/889455/b1ad50b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/1000000/890000/889500/889455/513a4b5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room amenity](https://images.trvl-media.com/lodging/1000000/890000/889500/889455/4a581f06.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

(270)

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

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

Amirthalingadoss

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

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1850000/1841600/1841550/95fabce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Junior Suite, Jetted Tub (Caldera View)](https://images.trvl-media.com/lodging/2000000/1850000/1841600/1841550/1ab51373.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Junior Suite, Jetted Tub (Caldera View) | Spa](https://images.trvl-media.com/lodging/2000000/1850000/1841600/1841550/04abb690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/2000000/1850000/1841600/1841550/72c411f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Nefeles Luxury Suites

[](https://www.expedia.ca/Santorini-Hotels-Nefeles-Luxury-Suites.h1841550.Hotel-Information)

Santorini

9.6/10

Exceptional

(164)

"Panos the manager was amazing & very attentive. The view was amazing & breakfast was delicious. "

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

Sydney

[](https://www.expedia.ca/Santorini-Hotels-Nefeles-Luxury-Suites.h1841550.Hotel-Information)

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

![Executive Suite, Hot Tub | Massage in accommodation](https://images.trvl-media.com/lodging/96000000/95960000/95952500/95952496/a2a6883e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, memory foam beds, in-room safe, blackout drapes](https://images.trvl-media.com/lodging/96000000/95960000/95952500/95952496/735c0ab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/96000000/95960000/95952500/95952496/2368976a.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)

"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 $298

CA $339 total

includes taxes & fees

Jan 19 - Jan 20, 2026

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

![Reception](https://images.trvl-media.com/lodging/77000000/76230000/76224500/76224483/a1fd0d5e.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)

"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)

![Luxury Suite, Patio, Sea View | Terrace/patio](https://images.trvl-media.com/lodging/107000000/106910000/106901000/106900963/db5c3d33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, Patio, Sea View | Terrace/patio](https://images.trvl-media.com/lodging/107000000/106910000/106901000/106900963/bab82b0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Basic Suite, Patio, Sea View | Terrace/patio](https://images.trvl-media.com/lodging/107000000/106910000/106901000/106900963/e9bb17bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Suite, Patio, Sea View | Living area](https://images.trvl-media.com/lodging/107000000/106910000/106901000/106900963/56b77440.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)

"Nice little town, way to navigate. "

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

Amanda

CA $163

CA $189 total

includes taxes & fees

Dec 29 - Dec 30

[](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=2026-01-10&endDate=2026-01-11&regionId=6051353&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true)

## Top Cyclades Islands Hotel Reviews

![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)

![Athina Luxury Suites](https://images.trvl-media.com/lodging/2000000/1850000/1841600/1841546/d25e88d8_y.jpg)

### Athina Luxury Suites

10/10 Excellent

"Food, specially the daily breakfast "

[](https://expedia.ca/Santorini-Hotels-Athina-Luxury-Suites.h1841546.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

"Cleaning service provided daily, all hotel staff was very kind and professional. "

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

![Merovigliosso Apartments](https://images.trvl-media.com/lodging/3000000/2810000/2806300/2806230/8c4dfa70_y.jpg)

### Merovigliosso Apartments

10/10 Excellent

"The only bus stop at Imerovigli was confusing and not label that caused us missing the bus for Fira. As infrequent as the bus schedule was in November, we were thankful being picked up by a wandering taxi to give us ride to Oia (30 Euro) and then Oia to Fira (30 Euro) which in my opinion much preferred in a tight schedule. The hotel offered me courtesy drop-off at the airport which was super nice of Kostas."

[](https://expedia.ca/Santorini-Hotels-Merovigliosso-Apartments.h2806230.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)

![Nefeli Homes - Adults Only](https://images.trvl-media.com/lodging/3000000/2910000/2909000/2908974/c271ee0e_y.jpg)

### Nefeli Homes - Adults Only

10/10 Excellent

"Nefeli homes was the best stay we had in Santorini. Our room had the best view and the views from the hotel pool is also amazing! It was super comfortable, spacious, had the friendliest staff who helped us with our every need. I highly recommend this place and would love to stay here again in the future"

[](https://expedia.ca/Santorini-Hotels-Nefeli-Homes.h2908974.Hotel-Information)

![Astro Palace Hotel & Spa](https://images.trvl-media.com/lodging/4000000/3630000/3625800/3625705/9bed4f63_y.jpg)

### Astro Palace Hotel & Spa

10/10 Excellent

"My husband and I stayed at this hotel with our 3-month-old baby for 2 nights — and immediately wished we had booked a longer stay. From the moment we arrived, the staff went above and beyond to make us feel welcome. We've travelled a lot around the world, but the reception team here truly stood out as the most friendly, helpful, and accommodating we've ever encountered. They made travelling with a young baby remarkably easy and we were so grateful. We booked a Senior Suite with an outdoor terrace and private jacuzzi — and it was absolutely perfect. The space was beautiful, and we loved having the jacuzzi to relax in. The pool area was peaceful with comfortable sun loungers, and breakfast each morning was a lovely experience, made even better by the attentive and kind staff. We also really appreciated the location — just an 8-minute uphill walk to the centre of Fira. Overall, we had a fantastic stay and would highly recommend this hotel to anyone visiting Fira."

[](https://expedia.ca/Santorini-Hotels-Astro-Palace-Hotel-Spa.h3625705.Hotel-Information)

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