Title: Ashland Vacation Packages & Trips 2026 from CA $2,186 | Expedia.ca [Hotels in Ashland](https://expedia.ca/Ashland-Hotels.d3000422181.Travel-Guide-Hotels)[Vacation Rentals in Ashland](https://expedia.ca/Ashland-Vacation-Rentals.d3000422181.Travel-Guide-VacationRentals)[Ashland Car Rentals](https://expedia.ca/Car-Rentals-In-Ashland.d3000422181.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Ashland Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Top Ashland Vacation Deals Price found within the past 48 hours. Click for updated prices. ![The Haüs Windham](https://images.trvl-media.com/lodging/92000000/91140000/91133200/91133132/6cb986d8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Haüs Windham CA $2,186 per person Jun 23 - Jun 29 found 5 hours ago Roundtrip flight included Eureka (ACV) to Hudson (HCC) 7.6/10 Good! (25 reviews) Can’t complain one bit Reviewed on Apr 2, 2026 ![Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort](https://images.trvl-media.com/lodging/109000000/108750000/108748900/108748808/2bb9bc85_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort CA $5,107 per person Jun 23 - Jun 29 found 5 hours ago Roundtrip flight included Eureka (ACV) to Hudson (HCC) No reviews ![Perfect Family Vacation Home in the Mountains](https://images.trvl-media.com/lodging/112000000/111840000/111838100/111838029/3b795c89_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Perfect Family Vacation Home in the Mountains CA $3,586 per person Jun 23 - Jun 29 found 5 hours ago Roundtrip flight included Eureka (ACV) to Hudson (HCC) No reviews ![Wylder Hotel Windham](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/6a98f43b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wylder Hotel Windham CA $2,591 per person Jun 23 - Jun 29 found 5 hours ago Roundtrip flight included Eureka (ACV) to Hudson (HCC) 8.6/10 Excellent! (93 reviews) Beautiful scenery and great staff Reviewed on Mar 22, 2026 ![Discounted Winter Rates! Ski Retreat, Hot Tub, Fire Pit Windham Mountain House](https://images.trvl-media.com/lodging/123000000/122400000/122393500/122393412/355cb32d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Discounted Winter Rates! Ski Retreat, Hot Tub, Fire Pit Windham Mountain House CA $4,892 per person Jun 23 - Jun 29 found 5 hours ago Roundtrip flight included Eureka (ACV) to Hudson (HCC) No reviews ## Ready to book your vacation to Ashland? Choose your dates ## Ashland Hotel Deals ![Firepit, Cozy Farmhouse & Adventure Nearby | Catskill Park Farm by AvantStay](https://images.trvl-media.com/lodging/111000000/111000000/110993000/110992952/547a91de_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Firepit, Cozy Farmhouse & Adventure Nearby | Catskill Park Farm by AvantStay Prattsville NY 10/10 Exceptional! (3 reviews) Beautiful house and setting, friendly to pets and great location vis a vis skiing. Reviewed on Mar 9, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=19%2F04%2F2026&endDate=20%2F04%2F2026&selected=110992952&PinnedHotelID=110992952&HadPinnedHotel=true®ionId=3000422181) [](https://expedia.ca/Hotel-Search?startDate=19%2F04%2F2026&endDate=20%2F04%2F2026&selected=110992952&PinnedHotelID=110992952&HadPinnedHotel=true®ionId=3000422181) ![Hunter Lodge, a Bluebird by Lark](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/39016ef1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hunter Lodge, a Bluebird by Lark 7433 Main St Hunter NY Fully refundableReserve now, pay when you stay CA $188 CA $234 total Apr 16 - Apr 17 includes taxes & fees 9.2/10 Wonderful! (902 reviews) Really nice lodge. Breakfast was a little skimpy but everything else was good. Reviewed on Apr 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F04%2F2026&endDate=17%2F04%2F2026&selected=64238678&PinnedHotelID=64238678&HadPinnedHotel=true®ionId=3000422181) ![Hotel Vienna](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/f91cd0d7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Vienna 107 State Route 296 Windham NY 9.4/10 Exceptional! (790 reviews) Breakfast was awesome! Rooms were clean. Loved the pool. Reviewed on Apr 1, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=19%2F04%2F2026&endDate=20%2F04%2F2026&selected=893228&PinnedHotelID=893228&HadPinnedHotel=true®ionId=3000422181) [](https://expedia.ca/Hotel-Search?startDate=19%2F04%2F2026&endDate=20%2F04%2F2026&selected=893228&PinnedHotelID=893228&HadPinnedHotel=true®ionId=3000422181) [See all 1,637 properties in Ashland](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=06%2F04%2F2026&endDate=07%2F04%2F2026®ionId=3000422181) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app