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 $72

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## Check availability on Cyclades Islands Winery Hotels

Tonight

[Dec 23 - Dec 24](https://www.expedia.ca/Hotel-Search?regionId=6051353&startDate=2025-12-23&endDate=2025-12-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 24 - Dec 25](https://www.expedia.ca/Hotel-Search?regionId=6051353&startDate=2025-12-24&endDate=2025-12-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6051353&startDate=2025-12-26&endDate=2025-12-28&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)

## 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)

![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)

![Exterior](https://images.trvl-media.com/lodging/52000000/51270000/51260300/51260204/88813a1a.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 $62

CA $72 total

includes taxes & fees

Jan 10 - Jan 11, 2026

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

![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)

![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)

![Presidential Suite outdoor private pool, Caldera View | Private pool](https://images.trvl-media.com/lodging/2000000/1750000/1746400/1746352/b73c6599.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 $214

CA $250 total

includes taxes & fees

Jan 21 - Jan 22, 2026

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

![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)

![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)

### 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 $156

CA $179 total

includes taxes & fees

Jan 23 - Jan 24, 2026

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

![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)

![Superior Apartment, 3 Bedrooms, Terrace | Living area](https://images.trvl-media.com/lodging/84000000/83180000/83170300/83170213/84afcb2a.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 $95

CA $109 total

includes taxes & fees

Jan 13 - Jan 14, 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)

![Exterior](https://images.trvl-media.com/lodging/7000000/6840000/6839300/6839252/e2793b08.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)

### 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)

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

![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)

![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

(267)

"The hotel staff were fantastic in helping us with luggage up the staircase. We had a comfortable stay in a great spot. "

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

Anthony

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

![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)

![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 Suite, Balcony | Living area](https://images.trvl-media.com/lodging/96000000/95960000/95952500/95952496/2e164eaa.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 $299

CA $340 total

includes taxes & fees

Jan 19 - Jan 20, 2026

[](https://www.expedia.ca/Naxos-Hotels-Naxos.h95952496.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) | 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/e319f3f7.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)

### 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)

![Elite Villa, 2 Bedrooms, Hot Tub, Sea View | Terrace/patio](https://images.trvl-media.com/lodging/118000000/117130000/117126700/117126687/79589fb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117130000/117126700/117126687/a28d18f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, Hot Tub, Sea View | Terrace/patio](https://images.trvl-media.com/lodging/118000000/117130000/117126700/117126687/0dacbe9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Suite, Hot Tub, Sea View](https://images.trvl-media.com/lodging/118000000/117130000/117126700/117126687/d9795ce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Three Domes Oia - an Iconic Collection

[](https://www.expedia.ca/Santorini-Hotels-Three-Domes-Oia-An-Iconic-Collection.h117126687.Hotel-Information)

Oía

9.4/10

Exceptional

(14)

"Beautiful views great pool and location "

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

Naisi

CA $249

CA $284 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Santorini-Hotels-Three-Domes-Oia-An-Iconic-Collection.h117126687.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/24000000/23570000/23567000/23566946/69c15898.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cozy Suite Outdoor Hot Tub Caldera View | View from room](https://images.trvl-media.com/lodging/24000000/23570000/23567000/23566946/90c09315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Honeymoon Suite Outdoor Hot Tub Caldera View | Jetted tub](https://images.trvl-media.com/lodging/24000000/23570000/23567000/23566946/1f511900.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cave Suite Indoor Hot Tub Shared Balcony](https://images.trvl-media.com/lodging/24000000/23570000/23567000/23566946/e24007e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aperto Suites - Adults Only

[](https://www.expedia.ca/Santorini-Hotels-Aperto-Suites-Adults-Only.h23566946.Hotel-Information)

Santorini

9.2/10

Wonderful

(75)

"Staff was very helpful, the room is so nice and the view is fantastic "

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

Ricardo

CA $230

CA $262 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Santorini-Hotels-Aperto-Suites-Adults-Only.h23566946.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=2026-01-06&endDate=2026-01-07&regionId=6051353&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true)

## Top Cyclades Islands Hotel Reviews

![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)

![Above Blue Suites](https://images.trvl-media.com/lodging/3000000/2490000/2482700/2482632/78716c47_y.jpg)

### Above Blue Suites

10/10 Excellent

"Our experience at Above Blue Suites was incredible. Everything was spotless, and the views were absolutely breathtaking. The breakfast was delicious and full of flavor we genuinely looked forward to it every morning. We loved being able to choose what we wanted and having it delivered right to our room. The staff was very kind, attentive, and professional. I have nothing but wonderful things to say and highly recommend booking your stay with them."

[](https://expedia.ca/Santorini-Hotels-Above-Blue-Suites.h2482632.Hotel-Information)

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

### Hotel Sunny Villas

10/10 Excellent

"The staff was incredible and the view was so beautiful. The people in Santorini were all so very kind. I would love to go back in the future"

[](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)

![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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