Title: Book the Best ROMANTIC Hotels in Shady, Woodstock from CA $174 - Shady Romantic Getaways | Expedia.ca [Vacation Rentals in Woodstock](https://expedia.ca/Woodstock-Vacation-Rentals.d176573.Travel-Guide-VacationRentals)[Flights to Woodstock](https://expedia.ca/Cheap-Flights-To-Woodstock.d176573.Travel-Guide-Flights)[Things to do in Woodstock](https://expedia.ca/Things-To-Do-In-Woodstock.d176573.Travel-Guide-Activities)[Shady Car Rentals](https://expedia.ca/Car-Rentals-In-Shady.d553248635976471788.Car-Rental-Guide)[Shady Vacations](https://expedia.ca/Shady.d553248635976471788.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Romantic Hotels in Shady, Woodstock from CA $174 ![](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 Shady Romantic Hotels Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976471788&startDate=2025-10-13&endDate=2025-10-14&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976471788&startDate=2025-10-14&endDate=2025-10-15&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976471788&startDate=2025-10-17&endDate=2025-10-19&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976471788&startDate=2025-10-24&endDate=2025-10-26&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Shady Romantic Hotels ![Lobby sitting area](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/c80f19a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/1ee74f16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Chalet | Private kitchen](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/59b3ee8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/2fc1a4e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hunter Lodge, a Bluebird by Lark Hunter 9.2/10 Wonderful (781) "Amazing place for a quality weekend." CA $160 CA $203 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Kingston-Hotels-The-Hunter-Inn.h64238678.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/ab673905.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Motel Style Room with 2 Queen Beds - Pet Friendly](https://images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/af6d3144.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/da41475a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/8bf1ed7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beekman Arms Hotel Rhinebeck 8.2/10 Very good (749) "Fantastic stay, clean, hugh room with fireplace, can walk throughout the town. Great breakfast!!" CA $153 CA $174 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Poughkeepsie-Hotels-Beekman-Arms-Hotel.h12611810.Hotel-Information) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/38000000/37830000/37829500/37829454/50a36232.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/38000000/37830000/37829500/37829454/71708036.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/38000000/37830000/37829500/37829454/85b9c523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room No. 2 | View from room](https://images.trvl-media.com/lodging/38000000/37830000/37829500/37829454/52feac0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stonehill's Farmhouse Accord 9.8/10 Exceptional (38) "Kelsey gave us a warm welcome, and our room was lovely. The location is so peaceful. We hope to be back soon!" CA $210 CA $306 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Poughkeepsie-Hotels-Stonehills-Farmhouse.h37829454.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/34000000/33550000/33543100/33543005/367b2752.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/34000000/33550000/33543100/33543005/5e48b31d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, Frette Italian sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/34000000/33550000/33543100/33543005/69c42c71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Building design](https://images.trvl-media.com/lodging/34000000/33550000/33543100/33543005/0c2214a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Kinsley Kingston Stockade District 9.0/10 Wonderful (316) "Really clean, quaint, pleasant hotel!" CA $308 CA $401 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Kingston-Hotels-HOTEL-KINSLEY.h33543005.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/9a683bd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, blackout drapes, free WiFi, bed sheets](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/ce5990b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Japanese Futon](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/97246a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/5e7a20ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winwood Condominiums by Windham Mountain Club Windham 8.8/10 Excellent (340) "Clean rooms" CA $251 CA $271 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Kingston-Hotels-Winwood-Inn-Condominiums.h15409739.Hotel-Information) ![Deluxe Room, 1 King Bed, Balcony](https://images.trvl-media.com/lodging/5000000/4680000/4672800/4672738/64adc8c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/5000000/4680000/4672800/4672738/1923ad8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, hot tub, body treatments, aromatherapy](https://images.trvl-media.com/lodging/5000000/4680000/4672800/4672738/7da9e2bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/5000000/4680000/4672800/4672738/4c471df7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Diamond Mills Resort Saugerties 9.4/10 Exceptional (328) "Wonderful place for calm and relaxation!" CA $368 CA $447 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Kingston-Hotels-Diamond-Mills-Hotel-Tavern.h4672738.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/a8a403ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down comforters, memory foam beds](https://images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/7b46ec1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Penthouse, 1 King Bed, Bathtub, Mountain View](https://images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/a04d5bb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chalet, 1 Bedroom, Mountain View | Private kitchen](https://images.trvl-media.com/lodging/43000000/42570000/42566500/42566439/d2d6d133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Urban Cowboy Lodge Big Indian 9.2/10 Wonderful (168) "Just the whole experience was amazing. We enjoyed it so much (my daughter and I) that we want to return for Mother's Day. " CA $330 CA $370 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Big-Indian-Hotels-Urban-Cowboy-Lodge.h42566439.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/38000000/37240000/37231000/37230930/6536823f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, hot tub, steam room, body treatments](https://images.trvl-media.com/lodging/38000000/37240000/37231000/37230930/4a781955.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/38000000/37240000/37231000/37230930/8d56ff20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, hot tub, steam room, body treatments](https://images.trvl-media.com/lodging/38000000/37240000/37231000/37230930/64691c6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mirbeau Inn & Spa Rhinebeck 9.6/10 Exceptional (301) "Always an incredible time here. " CA $657 CA $795 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Poughkeepsie-Hotels-Mirbeau-Inn-Spa.h37230930.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/90000000/89670000/89666900/89666885/e87d8720.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/90000000/89670000/89666900/89666885/cc224003.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![STABLE HOUSE GARDEN SUITE - ROOM 15 | Terrace/patio](https://images.trvl-media.com/lodging/90000000/89670000/89666900/89666885/63f6b42c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89670000/89666900/89666885/0f40d11e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hasbrouck House Stone Ridge 9.0/10 Wonderful (49) "Great getaway property. We checked in for two nights, and stayed in a building with kitchen/2 bedrooms, which was great for our needs. We spent time in the property relaxing at the beautiful pool, sauna, and had a fabulous dinner at Butterfield. Played some shuffleboard, pool and video games in their clubhouse - very laid back vibe and perfect for a couples weekend. Great food options off property in the area, and my partner was able to get in a quick nine-hole game of golf at a nearby... CA $544 CA $610 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Stone-Ridge-Hotels-Hasbrouck-House.h89666885.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23600000/23593000/23592940/128d4637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/24000000/23600000/23593000/23592940/270-0079bb56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23600000/23593000/23592940/5f95c0a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23600000/23593000/23592940/c1109f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores Windham 9.0/10 Wonderful (51) "Great communication with host Nice spacious clean apartment. Good location " CA $154 CA $277 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Kingston-Hotels-Townhouse-Loft-30-Ft-Balcony-Mt-View6-Beds-Sleeps-6.h23592940.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=2025-10-27&endDate=2025-10-28®ionId=553248635976471788&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Shady Hotel Reviews ![Hotel Vienna](//images.trvl-media.com/lodging/1000000/900000/893300/893228/75609405_y.jpg) ### Hotel Vienna 10/10 Excellent "Great, clean hotel" [](https://expedia.ca/Kingston-Hotels-Hotel-Vienna.h893228.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Shady? > Are you looking for a romantic getaway? If you want to get out and explore the larger area, you might head to Hunter Mountain, Catskill Mountains, or Overlook Mountain Trailhead. If you're interested in staying close to a particular destination, you can sort by neighborhood or distance to top landmarks, so you'll be able to see everything on your list. ### What is there to do in Shady? > There's nothing better than seeing a new place with your sweetheart, so consider taking time to discover all there is to see and do in Shady. There's plenty to see in the greater Woodstock area, so you might plan to visit Hunter Mountain, Catskill Mountains, or Overlook Mountain Trailhead. ## Explore a world of travel with Expedia - Lodging - Flights - More ways to book - [Business Hotels in Albany](https://www.expedia.ca/Albany-Hotels-Business-Hotel.0-0-d603260-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Albany](https://www.expedia.ca/Albany-Hotels-Couples-Resorts-Hotels.0-0-d603260-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Albany](https://www.expedia.ca/Albany-Hotels-Hotel-With-Early-Check-In.0-0-d603260-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Albany](https://www.expedia.ca/Albany-Hotels-Hotels-With-Bar.0-0-d603260-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Hotels with Tennis Courts in Albany](https://www.expedia.ca/Albany-Hotels-Hotels-With-Tennis-Courts.0-0-d603260-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - 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