Title: Book the Best ROMANTIC Hotels in Windsor, VT from CA $182 - Windsor Romantic Getaways | Expedia.ca [Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d7881.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d7881.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.ca/Cheap-Flights-To-Windsor.d7881.Travel-Guide-Flights)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d7881.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.ca/Windsor.d7881.Destination-Travel-Guides) ![Cornish Windsor Covered Bridge](https://images.trvl-media.com/place/183560/cb657638-a45b-4260-96ba-18d22ff7fd4b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Romantic Hotels in Windsor, VT from CA $182 - ![](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 Windsor Romantic Hotels Tonight [Nov 7 - Nov 8](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2025-11-07&endDate=2025-11-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Nov 8 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2025-11-08&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Top Windsor Romantic Hotels ![Meeting facility](https://images.trvl-media.com/lodging/22000000/21500000/21490500/21490448/0ffc6821.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21500000/21490500/21490448/fba83d9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/22000000/21500000/21490500/21490448/1bac12bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/22000000/21500000/21490500/21490448/e2e8ee06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Hanover Lebanon Lebanon 9.0/10 Wonderful (1000) "Clean hotel, friendly staff and great area! Loved it and would highly recommend!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raymond Alan CA $167 CA $182 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Lebanon-Hotels-Hilton-Garden-Inn-HanoverLebanon.h21490448.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/36000000/35090000/35089600/35089593/cc154186.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/36000000/35090000/35089600/35089593/56da22f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/36000000/35090000/35089600/35089593/e721d264.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/36000000/35090000/35089600/35089593/e9bfe6a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brook Road Inn Goshen 8.6/10 Excellent (243) "I loved how comfortably I was able to sleep in their bed. The property was beautiful and well maintained. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Haley [](https://www.expedia.ca/Goshen-Hotels-Brook-Road-Inn.h35089593.Hotel-Information) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/3cca622a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/72849c1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/18beef69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Mountain Inn at Killington Killington 9.2/10 Wonderful (934) "Excellent hotel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristan CA $169 CA $195 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/403a8548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/0dbf9fa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Billiards](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/b1730c3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/2b1767e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Killington Mountain Lodge, Tapestry Collection by Hilton Killington 7.4/10 Good (1001) "Room was spotless and comfortable. Dog friendly, hassle free stay. Cleanliness was top tier, and staff was fantastic!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Desiree CA $184 CA $202 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ![1 bedroom, premium bedding, desk, blackout drapes](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970529/d5b8706f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970529/bca550da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970529/490f03e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free continental breakfast](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970529/0f2bf37c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Common Man Inn & Restaurant Claremont 9.6/10 Exceptional (369) "Great place to stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Candace M CA $177 CA $192 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Claremont-Hotels-The-Common-Man-Inn-Restaurant.h2970529.Hotel-Information) ![Breakfast, lunch, dinner served; local cuisine ](https://images.trvl-media.com/lodging/4000000/3980000/3974400/3974306/1703a489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, 1 King Bed](https://images.trvl-media.com/lodging/4000000/3980000/3974400/3974306/5b06bb26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3980000/3974400/3974306/bf81da74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3980000/3974400/3974306/12ba4ad3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hanover Inn Dartmouth Hanover 9.6/10 Exceptional (881) "Lovely property perfectly situated facing the campus. Friendly, helpful staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard P [](https://www.expedia.ca/Lebanon-Hotels-Hanover-Inn-Dartmouth.h3974306.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/1d2c94d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/96a629e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna, aromatherapy, hot stone massages, deep-tissue massages](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/a736e5ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pointe at Castle Hill Resort Cavendish 8.8/10 Excellent (912) "Nice clean room and friendly staff. I was there off season (early November) so some restaurants weren’t open but there were still plenty of options. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew CA $182 CA $208 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/bb7b6824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/aa061d2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/1525a0b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Room with Spa Bath](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/ad9a6e84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Weathersfield Perkinsville 9.8/10 Exceptional (70) "Comfortable room and tasty dinner. Very well run." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew [](https://www.expedia.ca/Perkinsville-Hotels-The-Inn-At-Weathersfield.h1154949.Hotel-Information) ![Game room](https://images.trvl-media.com/lodging/3000000/2050000/2042700/2042604/2cff4a08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/3000000/2050000/2042700/2042604/6274eb11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Multiple Beds, Private Bathroom](https://images.trvl-media.com/lodging/3000000/2050000/2042700/2042604/bf739072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2050000/2042700/2042604/f20a7a36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dexter's Inn Sunapee 8.8/10 Excellent (70) "This was my 3rd time staying at Dexter’s Inn and hopefully not the last. It is a wonderful inn with easy access to Mount Sunapee. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa CA $349 CA $379 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Sunapee-Hotels-Dexters-Inn.h2042604.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/06298210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/61c9c6e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/978b1784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG Brownsville 9.0/10 Wonderful (771) "Strongly recommend and will go back again!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Craig CA $182 CA $218 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.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=2025-11-21&endDate=2025-11-22®ionId=7881&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Windsor Hotel Reviews ## Frequently asked questions ### Searching for romantic hotels in Windsor? > Are you in need of a romantic escape? If you want to explore the area, you might head to Harpoon Brewery, Mt Ascutney State Park, or Connecticut River. If you'd like to stay close to 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 Windsor? > If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Windsor: The hottest months are usually July and August with an average temp of 62°F, while the coldest months are January and February with an average of 22°F. The snowiest months in Windsor are March, January, November, and February, with each month seeing an average of 15 inches of snowfall. ### What is there to do in Windsor? > There's nothing better than experiencing a new place with your sweetheart, so consider taking time to discover all there is to see and do in Windsor. You might think about stopping by Harpoon Brewery, Mt Ascutney State Park, or Connecticut River while you're seeing the sights. ### What's the best way to get to Windsor and around town during my romantic getaway? > This information about transportation options in Windsor might help your romantic trip get off to a smooth start: To get to Windsor, you can fly into Lebanon, NH (LEB-Lebanon Municipal), which is the closest major airport, located 10.7 mi (17.3 km) from the city center. 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