Title: Book the Best ROMANTIC Hotels in Pine Plains, NY from CA $161 - Pine Plains Romantic Getaways | Expedia.ca [Hotels in Pine Plains](https://expedia.ca/Pine-Plains-Hotels.d3000449418.Travel-Guide-Hotels)[Vacation Rentals in Pine Plains](https://expedia.ca/Pine-Plains-Vacation-Rentals.d3000449418.Travel-Guide-VacationRentals)[Pine Plains Car Rentals](https://expedia.ca/Car-Rentals-In-Pine-Plains.d3000449418.Car-Rental-Guide)[Pine Plains Vacation Packages](https://expedia.ca/Pine-Plains.d3000449418.Destination-Travel-Guides) ![Sharon Ct, USA Fall foliage and autumn colors.](https://images.trvl-media.com/place/3000449418/5a051a27-c468-4a8e-88be-3b2cc0c3e88f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Romantic Hotels in Pine Plains, NY from CA $161 - ![](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 Pine Plains Romantic Hotels Tonight [Dec 6 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=3000449418&startDate=2025-12-06&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Dec 7 - Dec 8](https://www.expedia.ca/Hotel-Search?regionId=3000449418&startDate=2025-12-07&endDate=2025-12-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=3000449418&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) In two weeks [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000449418&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Top Pine Plains Romantic Hotels ![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) ![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/13000000/12620000/12611900/12611810/700c0e5d.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 and Delamater Inn Rhinebeck 8.4/10 Very good (800) "Really enjoyed staying at this lovely property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kenneth CA $142 CA $161 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Poughkeepsie-Hotels-Beekman-Arms-Hotel.h12611810.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/34000000/33700000/33696800/33696708/3a11949f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33700000/33696800/33696708/febcf9d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Bedroom Suite](https://images.trvl-media.com/lodging/34000000/33700000/33696800/33696708/fb2da365.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shared fridge, microwave](https://images.trvl-media.com/lodging/34000000/33700000/33696800/33696708/90960292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Nest Hudson Hudson 9.6/10 Exceptional (209) "What a beautiful stay right in the heart of Hudson. Cute, cozy, super clean with everything you need! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kseniya [](https://www.expedia.ca/Hudson-Hotels-The-Nest-Hudson.h33696708.Hotel-Information) ![Library](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/50a90cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/6349c6d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/52bc8d96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/e7ac793d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blackberry River Inn Norfolk 9.4/10 Exceptional (163) "Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paulina CA $227 CA $261 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Norfolk-Hotels-Blackberry-River-Inn.h95991149.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/ecdcd2fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (6) | Bathroom](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/0da0f7f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (5)](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/6375a3f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; Mediterranean cuisine ](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/32649720.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Millerton Inn Millerton 8.0/10 Very good (9) "Beautiful property, only stayed one night for business but it was very nice. Great burger at the restaurant downstairs! Possibly one of the best burgers I’ve ever had!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason CA $223 CA $252 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Millerton-Hotels-The-Millerton-Inn.h109821051.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/dbbfdf3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Ground Floor (Main Building)](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/db6c98da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Woodside, Pet Friendly) | Terrace/patio](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/30d59e52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, Lakeside | Terrace/patio](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/6575d812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Interlaken Inn & Resort Lakeville 8.2/10 Very good (270) "The staff is courteous and accommodating especially the restaurant staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christian CA $291 CA $335 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Torrington-Hotels-Interlaken-Inn-Resort.h19679605.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) ![Building design](https://images.trvl-media.com/lodging/34000000/33550000/33543100/33543005/0c2214a3.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) ### Hotel Kinsley Stockade District 9.0/10 Wonderful (330) "Room was great and staff very friendly" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Byron CA $307 CA $400 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Kingston-Hotels-HOTEL-KINSLEY.h33543005.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) ![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) ![Front of property](https://images.trvl-media.com/lodging/5000000/4680000/4672800/4672738/73438520.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Diamond Mills Resort Saugerties 9.4/10 Exceptional (344) "Amazing view from the room. We had a great stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Adam CA $372 CA $451 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Kingston-Hotels-Diamond-Mills-Hotel-Tavern.h4672738.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/f7468df3.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 (307) "The inn was lovely with attentive staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen CA $627 CA $760 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Poughkeepsie-Hotels-Mirbeau-Inn-Spa.h37230930.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/40000000/40000000/39997000/39996972/10e984da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/40000000/40000000/39997000/39996972/4146f75f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/40000000/40000000/39997000/39996972/16ad15d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/40000000/40000000/39997000/39996972/7c8a09e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Church Des Artistes a Hudson Valley retreat Rondout 9.8/10 Exceptional (10) "Beautiful, unique stay! Julie was really kind walking us through the ins and outs of the property during check-in. So much care and attention put into every room. And the book collection is amazing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Molly M. CA $1,865 CA $3,270 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Kingston-Hotels-Church-Des-Artistes-A-Hudson-Valley-Retreat.h39996972.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/24000000/23280000/23274600/23274540/aaef5562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/24000000/23280000/23274600/23274540/e73723b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23280000/23274600/23274540/b8dea340.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/24000000/23280000/23274600/23274540/a9d8787c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson Hudson 9.8/10 Exceptional (27) "Met our son and his girls for a little getaway. Very cool house complete with lots to do! Thank you. Hope to get to experience it during the summer months sometime." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathy M. CA $847 CA $1,519 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Hudson-Hotels-Light-Filled-Hudson-Home-With-Designer-Sauna.h23274540.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=2025-12-20&endDate=2025-12-21®ionId=3000449418&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Pine Plains Hotel Reviews ![Courtyard by Marriott Kingston](https://images.trvl-media.com/lodging/2000000/1370000/1364000/1363973/a5bfb382_y.jpg) ### Courtyard by Marriott Kingston 10/10 Excellent "Staff is very nice. Clean rooms and clean pool. Love the fireplace in the lobby as well. Second time staying and will be back again. " [](https://expedia.ca/Kingston-Hotels-Courtyard-By-Marriott-Kingston.h1363973.Hotel-Information) ![ Diamond Mills Resort](https://images.trvl-media.com/lodging/5000000/4680000/4672800/4672738/64adc8c9_y.jpg) ### Diamond Mills Resort 10/10 Excellent "Staff was great. Clean room. Massages were great and the bar was great. If I can change anything it would be they need a pool there. The spa needs to be attached to the hotel and a bigger place to have breakfast." [](https://expedia.ca/Kingston-Hotels-Diamond-Mills-Hotel-Tavern.h4672738.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Pine Plains? ### When is the best time of year for a romantic getaway to Pine Plains? ### What is there to do in Pine Plains? ### What's the best way to get to Pine Plains and around town during my romantic getaway? ## 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) - 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