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

[Greek Islands Travel Guide](https://expedia.ca/Greek-Islands.dx6271742)[Hotels in Greek Islands](https://expedia.ca/Greek-Islands-Hotels.d6271742.Travel-Guide-Hotels)[Vacation Rentals in Greek Islands](https://expedia.ca/Greek-Islands-Vacation-Rentals.d6271742.Travel-Guide-VacationRentals)[Flights to Greek Islands](https://expedia.ca/Cheap-Flights-To-Greek-Islands.d6271742.Travel-Guide-Flights)[Things to do in Greek Islands](https://expedia.ca/Things-To-Do-In-Greek-Islands.d6271742.Travel-Guide-Activities)[Greek Islands Car Rentals](https://expedia.ca/Car-Rentals-In-Greek-Islands.d6271742.Car-Rental-Guide)[Greek Islands Vacation Packages](https://expedia.ca/Greek-Islands.d6271742.Destination-Travel-Guides)

![Paleokastritsa Beach showing general coastal views](https://images.trvl-media.com/place/6105704/ed59c85e-33c3-4f6e-88d7-af5b4373672d.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6105704/ed59c85e-33c3-4f6e-88d7-af5b4373672d.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Greek Islands Winery Hotels

Tonight

[Jan 23 - Jan 24](https://www.expedia.ca/Hotel-Search?regionId=6271742&startDate=2026-01-23&endDate=2026-01-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 24 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6271742&startDate=2026-01-24&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6271742&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6271742&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Greek 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)

![Executive Room Caldera View with Outdoor Mini Plunge Pool Quadruple | View from room](https://images.trvl-media.com/lodging/2000000/1390000/1380900/1380881/7d7ccc40.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)

![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)

### 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 $111

CA $131 total

includes taxes & fees

Jan 24 - Jan 25

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

![Exterior](https://images.trvl-media.com/lodging/90000000/89770000/89767000/89766945/9c033abb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Grand Suite](https://images.trvl-media.com/lodging/90000000/89770000/89767000/89766945/246cdada.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89770000/89767000/89766945/f5778c8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/90000000/89770000/89767000/89766945/a863e526.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mythical Coast Wellness Retreat

[](https://www.expedia.ca/Lesvos-Hotels-Mythical-Coast-Wellness-Retreat.h89766945.Hotel-Information)

Lesvos

8.6/10

Excellent

(46 reviews)

"Brand new hotel, lovely staff. "

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

Timothy

[](https://www.expedia.ca/Lesvos-Hotels-Mythical-Coast-Wellness-Retreat.h89766945.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)

![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)

![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)

![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)

### 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 $147

CA $168 total

includes taxes & fees

Feb 16 - Feb 17

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

![2 outdoor pools](https://images.trvl-media.com/lodging/75000000/74680000/74674700/74674614/w5755h3835x5y5-688d33e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/75000000/74680000/74674700/74674614/25c01526.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Minibar, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/75000000/74680000/74674700/74674614/f827bb7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Minibar, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/75000000/74680000/74674700/74674614/a280b6a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Manili Boutique Suites & Villas

[](https://www.expedia.ca/Archanes-Asterousia-Hotels-Manili-Boutique-Suites-Villas.h74674614.Hotel-Information)

Archanes-Asterousia

9.6/10

Exceptional

(27 reviews)

"Exceptional accommodations in a truly destination village. Great staff, pools everywhere and architecturally a treat! "

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

David

CA $146

CA $170 total

includes taxes & fees

Feb 7 - Feb 8

[](https://www.expedia.ca/Archanes-Asterousia-Hotels-Manili-Boutique-Suites-Villas.h74674614.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 (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)

![Villa (Thaleia) | View from room](https://images.trvl-media.com/lodging/19000000/18170000/18164500/18164486/b0590b52.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 $157

CA $180 total

includes taxes & fees

Feb 9 - Feb 10

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

![Superior Suite, Hot Tub, Oceanfront](https://images.trvl-media.com/lodging/108000000/107220000/107215400/107215367/82052c59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Suite, Hot Tub, Oceanfront](https://images.trvl-media.com/lodging/108000000/107220000/107215400/107215367/611204e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Suite, Hot Tub, Oceanfront | Beach/ocean view](https://images.trvl-media.com/lodging/108000000/107220000/107215400/107215367/05c96ae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach/ocean view](https://images.trvl-media.com/lodging/108000000/107220000/107215400/107215367/638dc0c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Elia Sea Suites

[](https://www.expedia.ca/Chania-Hotels-Elia-Sea-Suites.h107215367.Hotel-Information)

Chania Town

9.8/10

Exceptional

(39 reviews)

"Amazing hotel"

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

Richard

CA $184

CA $214 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Chania-Hotels-Elia-Sea-Suites.h107215367.Hotel-Information)

![Breakfast area](https://images.trvl-media.com/lodging/32000000/31080000/31070800/31070774/39798d7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast buffet](https://images.trvl-media.com/lodging/32000000/31080000/31070800/31070774/61c9d9f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Junior Suite, Balcony | Living area](https://images.trvl-media.com/lodging/32000000/31080000/31070800/31070774/41f64b71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/32000000/31080000/31070800/31070774/a20ba758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Menta City Boutique Hotel

[](https://www.expedia.ca/Rethymno-Hotels-Menta-City-Boutique-Hotel.h31070774.Hotel-Information)

Rethymno

9.8/10

Exceptional

(112 reviews)

"Super clean hotel, and the staff was beyond friendly! Especially the guy who helped us at the front desk - super patient and eager to make sure we enjoyed our visit. Would definitely stay again!"

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

Kaitlyn

CA $73

CA $86 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Rethymno-Hotels-Menta-City-Boutique-Hotel.h31070774.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/3000000/2520000/2511100/2511078/fbaf780f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/3000000/2520000/2511100/2511078/cd3e01da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/3000000/2520000/2511100/2511078/354256eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/3000000/2520000/2511100/2511078/42d198a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Strada Marina

[](https://www.expedia.ca/Zakynthos-Hotels-Hotel-Strada-Marina.h2511078.Hotel-Information)

Zakynthos

8.2/10

Very good

(305 reviews)

"Nice hotel in great location with lovely roof top bar and dining "

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

Barry

[](https://www.expedia.ca/Zakynthos-Hotels-Hotel-Strada-Marina.h2511078.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1260000/1259500/1259477/5241c8c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1260000/1259500/1259477/b3cbfa5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Courtyard](https://images.trvl-media.com/lodging/2000000/1260000/1259500/1259477/fa0e4112.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/2000000/1260000/1259500/1259477/f49059dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Halepa Hotel

[](https://www.expedia.ca/Chania-Hotels-Halepa-Hotel.h1259477.Hotel-Information)

Halepa

9.0/10

Wonderful

(362 reviews)

"Friendly staff, great location, good breakfast buffet. Would recommend."

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

stacey

[](https://www.expedia.ca/Chania-Hotels-Halepa-Hotel.h1259477.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)

![Breakfast, lunch, dinner served; Mediterranean cuisine, ocean views ](https://images.trvl-media.com/lodging/7000000/6840000/6839300/6839252/29bd552a.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)

![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)

### 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)

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=2026-02-06&endDate=2026-02-07&regionId=6271742&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true)

## Top Greek 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)