Title: Book the Best ROMANTIC Hotels in Hillsdale, NY from CA $117 - Hillsdale Romantic Getaways | Expedia.ca [Hillsdale Travel Guide](https://expedia.ca/Hillsdale.dx183683)[Hotels in Hillsdale](https://expedia.ca/Hillsdale-Hotels.d183683.Travel-Guide-Hotels)[Vacation Rentals in Hillsdale](https://expedia.ca/Hillsdale-Vacation-Rentals.d183683.Travel-Guide-VacationRentals)[Hillsdale Car Rentals](https://expedia.ca/Car-Rentals-In-Hillsdale.d183683.Car-Rental-Guide)[Hillsdale Vacation Packages](https://expedia.ca/Hillsdale.d183683.Destination-Travel-Guides) ![Red and Green Norway Maple Trees and Wood Fence](https://images.trvl-media.com/place/183683/4f99f7be-1e9f-40aa-ab8f-094fc6d499c2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Romantic Hotels in Hillsdale, NY from CA $117 - ![](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 Hillsdale Romantic Hotels Tonight [Nov 22 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-11-22&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Nov 23 - Nov 24](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-11-23&endDate=2025-11-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Top Hillsdale Romantic Hotels ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a25612d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/207845f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG Pittsfield 8.0/10 Very good (962) "Staff was very nice and helpful nice place restaurant was awesome great food and drinks" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frank CA $126 CA $141 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 King Bed, Jetted Tub | Jetted tub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f3c92221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3a8723ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/4ea5ab50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham Lenox 9.2/10 Wonderful (1006) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann CA $105 CA $117 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/9b4c64ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Untold Lenox 9.0/10 Wonderful (800) "We had a nice room and the food was delicious. Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vincent CA $131 CA $146 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Firehouse)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/71ef2331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d969459c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/9b7b4cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn Stockbridge 8.8/10 Excellent (1002) "I love the ambience - historic and comfortable and excellent food. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy CA $210 CA $298 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.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) ![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) ![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) ### 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 $241 CA $278 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Torrington-Hotels-Interlaken-Inn-Resort.h19679605.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/afbb4318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/9becd207.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/8c4366ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/614a1cdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Village Carriage House - Super Private!! Lanesborough 9.8/10 Exceptional (268) "The cottage was amazing. Hope to be visit again and again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark M. CA $190 CA $298 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.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) ![Interior](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/d4318cc7.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) ![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 (159) "Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paulina CA $232 CA $266 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Norfolk-Hotels-Blackberry-River-Inn.h95991149.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) ![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) ![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) ![Interior](https://images.trvl-media.com/lodging/34000000/33700000/33696800/33696708/febcf9d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Nest Hudson Hudson 9.6/10 Exceptional (208) "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) ![Loft, Private Bathroom (Skylight Loft)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/48ea2807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/eb4406db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/86910798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Victorian Room)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/49947e81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brook Farm Inn Lenox 9.4/10 Exceptional (162) "Comfortable, quiet, convenient location, very friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan [](https://www.expedia.ca/Lenox-Hotels-Brook-Farm-Inn.h1196186.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) ![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) ![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) ![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) ### Diamond Mills Resort Saugerties 9.4/10 Exceptional (343) "Amazing view from the room. We had a great stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Adam CA $379 CA $460 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Kingston-Hotels-Diamond-Mills-Hotel-Tavern.h4672738.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=2025-12-06&endDate=2025-12-07®ionId=183683&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_183683) ## Top Hillsdale Hotel Reviews ![ 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) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Everything was amazing my bf did get a beer at the bar that was expired but everything else was amazing " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "Clean, pleasant staff and good breakfast. " [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "I love the ambience - historic and comfortable and excellent food. " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Hillsdale? > If you and your partner need some romantic time away, we've got just the ticket. If you'd like to explore some of the area's notable sights, you might make a stop by Catamount Aerial Adventure Park, Catamount Ski Area, or Copake Lake. If you're interested in staying near a certain attraction, you can sort properties by neighborhood and proximity to top sights, so you'll be able to see everything on your list. ### When is the best time of year for a romantic getaway to Hillsdale? > If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Hillsdale: The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Hillsdale are January, March, February, and November, with each month seeing an average of 7 inches of snowfall. ### What is there to do in Hillsdale? > There's nothing better than seeing a new destination with your sweetheart, so consider checking out all there is to see and do in Hillsdale. You might consider a visit to Catamount Aerial Adventure Park, Catamount Ski Area, or Copake Lake. ### What's the best way to get to Hillsdale and around town during my romantic getaway? > These transportation options in Hillsdale might help your romantic trip go off without a hitch: If you're looking to fly to Hillsdale, the closest major airport is Hudson, NY (HCC-Columbia County), located 12.5 mi (20.1 km) from the city center. If you'd like to explore around the area, you may want to rent a car for your trip. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - 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) - [Ski Hotels in Albany](https://www.expedia.ca/Albany-Hotels-Ski-Hotel.0-0-d603260-tSkiHotel.Travel-Guide-Filter-Hotels) - 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