Title: Book the Best Wailuku WINERY Hotels in 2026 | Expedia.ca [Wailuku Travel Guide](https://expedia.ca/Wailuku.dx11585)[Hotels in Wailuku](https://expedia.ca/Wailuku-Hotels.d11585.Travel-Guide-Hotels)[Vacation Rentals in Wailuku](https://expedia.ca/Wailuku-Vacation-Rentals.d11585.Travel-Guide-VacationRentals)[Flights to Wailuku](https://expedia.ca/Cheap-Flights-To-Wailuku.d11585.Travel-Guide-Flights)[Things to do in Wailuku](https://expedia.ca/Things-To-Do-In-Wailuku.d11585.Travel-Guide-Activities)[Wailuku Car Rentals](https://expedia.ca/Car-Rentals-In-Wailuku.d11585.Car-Rental-Guide)[Wailuku Vacation Packages](https://expedia.ca/Wailuku.d11585.Destination-Travel-Guides) ![Wailuku featuring landscape views and mountains](https://images.trvl-media.com/place/11585/3e619ce6-9e8e-4de5-a654-c586d0081f02.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Hawaii Visitors and Convention Bureau # Find Winery Hotels in Wailuku, HI from CA $440 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Wailuku Winery Hotels Tonight [Dec 19 - Dec 20](https://www.expedia.ca/Hotel-Search?regionId=11585&startDate=2025-12-19&endDate=2025-12-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 20 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=11585&startDate=2025-12-20&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=11585&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=11585&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Wailuku hotels with winery ![Property grounds](https://images.trvl-media.com/lodging/31000000/30080000/30076000/30075955/efbb89ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/31000000/30080000/30076000/30075955/94ebe6cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/31000000/30080000/30076000/30075955/fc4e07c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, stereo](https://images.trvl-media.com/lodging/31000000/30080000/30076000/30075955/50f8ce41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront condo with WiFi & ground-floor lanai - see turtles right out front [](https://www.expedia.ca/Wailuku-Hotels-Oceanfront-Condo-With-WiFi-Ground-Floor-Lanai-See-Turtles-Right-Out-Front.h30075955.Hotel-Information) Wailuku 9.6/10 Exceptional (35) "We loved everything about this property!! The view, the location, the beach equipment, the amenities and decor were all very much appreciated. It was a great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darren H. CA $284 CA $711 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Wailuku-Hotels-Oceanfront-Condo-With-WiFi-Ground-Floor-Lanai-See-Turtles-Right-Out-Front.h30075955.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/34000000/33670000/33660100/33660091/9308d08a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/34000000/33670000/33660100/33660091/3372e14d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/34000000/33670000/33660100/33660091/73b3fd67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33670000/33660100/33660091/03be5cb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beachfront retreat with lanai, WiFi, pool, & hot tub - prime turtle spot [](https://www.expedia.ca/Wailuku-Hotels-Beachfront-Retreat-With-Lanai.h33660091.Hotel-Information) Wailuku 8.6/10 Excellent (68) "We had an excellent time! Everything was as advertised. Gorgeous location and very quiet and peaceful. Only downside is that while we were there the building was under construction for a new elevator so there was limited parking and quite a bit of space taken up by the construction " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dylan R. CA $271 CA $723 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Wailuku-Hotels-Beachfront-Retreat-With-Lanai.h33660091.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/35000000/34150000/34144200/34144170/132b813b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34150000/34144200/34144170/869f3035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34150000/34144200/34144170/6fdf6c67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34150000/34144200/34144170/dd9dd0c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Island Sands 401 Oceanfront Condo with Ocean View. Enjoy the saltwater oceanfront swimming pool. [](https://www.expedia.ca/Wailuku-Hotels-Island-Sands-401-Oceanfront-Condo-With-Ocean-And-Mountain-Views.h34144170.Hotel-Information) Wailuku 9.6/10 Exceptional (44) "Island sands is my favorite Condos" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michelle p. CA $200 CA $891 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Wailuku-Hotels-Island-Sands-401-Oceanfront-Condo-With-Ocean-And-Mountain-Views.h34144170.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/35000000/34150000/34144200/34144160/768f1269.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34150000/34144200/34144160/6654c4fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/35000000/34150000/34144200/34144160/w3598h2398x4y4-5006ed0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/35000000/34150000/34144200/34144160/78b37490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beachfront Resort Gorgeous 2Bd2Ba Oceanview [](https://www.expedia.ca/Wailuku-Hotels-Beachfront-Resort-Gorgeous-2Bd2Ba-Oceanview.h34144160.Hotel-Information) Wailuku 9.8/10 Exceptional (36) "Would stay here again! Great location. Not too many people and close to town. The condo was clean and had everything we needed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angie A. CA $357 CA $1,148 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Wailuku-Hotels-Beachfront-Resort-Gorgeous-2Bd2Ba-Oceanview.h34144160.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119920000/119914500/119914407/f9fb2682.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/120000000/119920000/119914500/119914407/963d081b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/120000000/119920000/119914500/119914407/cb814805.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/120000000/119920000/119914500/119914407/706df831.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kanai A Nalu 416 Oceanfront 2 bedroom Overlooking South Maui Ocean [](https://www.expedia.ca/Wailuku-Hotels-Kanai-A-Nalu-416-Oceanfront-2-Bedroom-Overlooking-South-Maui-Ocean.h119914407.Hotel-Information) Wailuku CA $405 CA $1,089 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Wailuku-Hotels-Kanai-A-Nalu-416-Oceanfront-2-Bedroom-Overlooking-South-Maui-Ocean.h119914407.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/28000000/27450000/27441600/27441539/w1675h1055x0y0-6392a616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27450000/27441600/27441539/2db77916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/28000000/27450000/27441600/27441539/44ed2965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/28000000/27450000/27441600/27441539/9285d001.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embark on a journey through Maui with Aloha Glamp [](https://www.expedia.ca/Haiku-Hotels-Embark-On-A-Journey-Through-Maui-With-Aloha-Glamp.h27441539.Hotel-Information) Haiku-Pauwela 9.6/10 Exceptional (38) "We booked this Jeep for our honeymoon stay on Maui. It was a wonderful drive, handled every road we were on beautiful, and provided a great place to sleep. Sebastian had all the necessities packed and it made for an easy trip. Couldn’t be happier. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sage B. CA $190 CA $435 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Haiku-Hotels-Embark-On-A-Journey-Through-Maui-With-Aloha-Glamp.h27441539.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/31000000/30370000/30366800/30366711/33364465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30370000/30366800/30366711/3a2415af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/31000000/30370000/30366800/30366711/620c8551.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/31000000/30370000/30366800/30366711/1d7fda21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Haleakala Sunrise Home, Kula, Maui, Hawaii [](https://www.expedia.ca/Kula-Hotels-Haleakala-Sunrise-Home.h30366711.Hotel-Information) Kula 9.8/10 Exceptional (89) "Great stay and hosts! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) svetha d. CA $344 CA $632 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Kula-Hotels-Haleakala-Sunrise-Home.h30366711.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/19000000/18990000/18980100/18980054/w1170h877x0y5-51fd63d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/19000000/18990000/18980100/18980054/291eb0e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18990000/18980100/18980054/96d0f8ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18990000/18980100/18980054/8b711bd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles! [](https://www.expedia.ca/Kihei-Hotels-Reviews-Say-Clean.h18980054.Hotel-Information) North Kihei 10/10 Exceptional (267) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Noah C. CA $123 CA $524 total includes taxes & fees Jan 9 - Jan 10, 2026 [](https://www.expedia.ca/Kihei-Hotels-Reviews-Say-Clean.h18980054.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/c4332c51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/3fdca3f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/93574a25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/972eccb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16 [](https://www.expedia.ca/Makawao-Hotels-Historic-Upcountry-Maui-Property-With-Pool.h29873066.Hotel-Information) Makawao 10/10 Exceptional (71) "We had an amazing vacation here. We had 4 generations ranging from 4 months to 81 years and everyone had a great time. There was room to spread out and room to all gather together. Having the private pool and spa was perfect. Host was available when we needed her and the B and B was well stocked. We also loved the Maui feel of the accommodations and being out of the busier parts of Maui. I highly recommend this venue for larger groups! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kari L. CA $2,197 CA $4,368 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Makawao-Hotels-Historic-Upcountry-Maui-Property-With-Pool.h29873066.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/19000000/18980000/18978200/18978176/89e2225f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/19000000/18980000/18978200/18978176/b355457a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18980000/18978200/18978176/265e1013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18980000/18978200/18978176/a9c993e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles! [](https://www.expedia.ca/Kihei-Hotels-Reviews-Say-Clean.h18978176.Hotel-Information) North Kihei 9.8/10 Exceptional (297) "Locally convenient, price was right for the location, property management was on top of things and made sure that we were well taken car of. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark CA $135 CA $540 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Kihei-Hotels-Reviews-Say-Clean.h18978176.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=2026-01-02&endDate=2026-01-03®ionId=11585&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Wailuku Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Hotels near Coral Beach ](https://www.expedia.ca/Coral-Beach-Hotels.0-l553248635977231273-0.Travel-Guide-Filter-Hotels) - [Hotels near Ho'aloha Park ](https://www.expedia.ca/Hoaloha-Park-Hotels.0-l553248635976197547-0.Travel-Guide-Filter-Hotels) - [Hotels near Kaʻahumanu Church ](https://www.expedia.ca/Kaahumanu-Church-Hotels.0-l553248621532639051-0.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Kaanapali ](https://www.expedia.ca/Kaanapali-Hotels-Couples-Resorts-Hotels.0-0-d800065-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Kaanapali ](https://www.expedia.ca/Kaanapali-Hotels-Hotel-With-Early-Check-In.0-0-d800065-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - 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