---
title: "Book the Best ROMANTIC Hotels in Windham, NY from CA $96 - Windham Romantic Getaways | Expedia.ca"
description: "Let us help you find the perfect romantic gateaway in Windham, NY. Choose from 260 Windham most romantic hotels, reviewed and rated by couples like you. Book now and pay later on Expedia.ca!"
canonical: "https://www.expedia.ca/Windham-Hotels-Romantic-Hotel.0-0-d175529-tRomanticHotel.Travel-Guide-Filter-Hotels"
language: en-CA
market: CA
currency: CAD
prices_as_of: 2026-11-13T16:22:19Z
---

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- [Windham Travel Guide](https://www.expedia.ca/Windham.dx175529)
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# Find Romantic Hotels in Windham, NY from CA $96
![A calm river reflecting trees and a sunset sky.](https://images.trvl-media.com/place/175529/fc2bf419-6010-434c-b13a-65082a031298.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

[Check prices for these dates, December 13–14, 2026](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-12-13&endDate=2026-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic)

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## Our top choices for Windham romantic hotels

### [1\. Hotel Vienna](https://www.expedia.ca/Kingston-Hotels-Hotel-Vienna.h893228.Hotel-Information)

![A cabin with a deck, large windows, and a mountain backdrop.](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/75609405.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

- Location: Windham
- Guest rating: 9.4/10 (Exceptional, 914 reviews)
- Price: CA $160, CA $198 total, includes taxes & fees, Nov 22 - Nov 23, for Our top choices for Windham romantic hotels
- Review: Clean room and helpful staff, good location., by Hongtao

### [2\. Wylder Hotel Windham](https://www.expedia.ca/Windham-Hotels-Wylder-Hotel-Windham.h102239431.Hotel-Information)

![A building with a porch and a sign that reads "Main Lodge."](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/f5960849.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Windham
- Guest rating: 9/10 (Wonderful, 139 reviews)
- Price: CA $257, CA $349 total, includes taxes & fees, Nov 19 - Nov 20, for Our top choices for Windham romantic hotels
- Review: Room super clean and beautiful property!, by Daniela

### [3\. Studio 3 BEDS-SLP 3\. Downtown Windham. Next to the Ski Resort. Close to Hunter](https://www.expedia.ca/Windham-Hotels-Studio-3-BEDS-SLP-3-Downtown-Windham-Next-To-The-Ski-Resort-Close-To-Hunter.h29486819.Hotel-Information)

![A two-story building with large windows and a storefront.](https://images.trvl-media.com/lodging/30000000/29490000/29486900/29486819/w953h720x164y0-fef4ea98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Windham
- Guest rating: 9.2/10 (Wonderful, 46 reviews)
- Price: CA $96, CA $169 total, includes taxes & fees, Nov 15 - Nov 16, for Our top choices for Windham romantic hotels
- Review: Great, highly recommend, by Rebecca

### [4\. Eastwind Windham](https://www.expedia.ca/Windham-Hotels-Eastwind-Windham.h91907167.Hotel-Information)

![A cozy wooden interior with a sofa, coffee table, and a view of a deck and greenery outside.](https://images.trvl-media.com/lodging/92000000/91910000/91907200/91907167/bc680677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Windham
- Guest rating: 9.2/10 (Wonderful, 123 reviews)
- Price: CA $333, CA $402 total, includes taxes & fees, Nov 22 - Nov 23, for Our top choices for Windham romantic hotels
- Review: Loved the stay here as well as the friendly staff. Jamie who had helped us check in was very friendly, helpful and made us feel welcome. Location was very dog friendly. Our room was very clean, quiet and had a beautiful scene of nature. Nice place to choose for a quiet get away stay., by Danica

### [5\. The Haüs Windham](https://www.expedia.ca/Windham-Hotels-The-Haus-Windham.h91133132.Hotel-Information)

![A wooden cabin with a stone pathway leading to the entrance, surrounded by greenery.](https://images.trvl-media.com/lodging/92000000/91140000/91133200/91133132/2d007c2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Windham
- Guest rating: 8/10 (Very good, 40 reviews)
- Price: CA $208, CA $439 total, includes taxes & fees, Nov 16 - Nov 17, for Our top choices for Windham romantic hotels
- Review: Easy check in, nice layout of the apt, comfortable bed, nice to have a kitchen. Nearby lots of restaurants and mountain access. , by Erica

### [6\. TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores](https://www.expedia.ca/Kingston-Hotels-Townhouse-Loft-30-Ft-Balcony-Mt-View6-Beds-Sleeps-6.h23592940.Hotel-Information)

![A two-story building with large windows and a storefront.](https://images.trvl-media.com/lodging/24000000/23600000/23593000/23592940/w953h720x164y0-af85ec27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Windham
- Guest rating: 8.8/10 (Excellent, 66 reviews)
- Price: CA $157, CA $265 total, includes taxes & fees, Nov 16 - Nov 17, for Our top choices for Windham romantic hotels
- Review: The pictures are not accurate. The two full and one twin bed are in one room upstairs, they are not separated as pictures would lead you to believe. Then three twins are in the living room with the couch, next to the dining room table and kitchen. The unit was dusty and not swept clean. There were dead bugs on the floor and party poppers from previous guest. I have never experienced something like this with Expedia, this was a zero star experience honestly., by April

### [7\. 1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mountain](https://www.expedia.ca/Windham-Hotels-1-Bedroom-Luxury-Suite-Full-Kitch-Haus-Windham.h97052664.Hotel-Information)

![A living room with a brick fireplace, leather sofa, and a flat-screen TV.](https://images.trvl-media.com/lodging/98000000/97060000/97052700/97052664/9df28976.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Windham
- Guest rating: 7.6/10 (Good, 5 reviews)
- Price: CA $212, CA $262 total, includes taxes & fees, Nov 16 - Nov 17, for Our top choices for Windham romantic hotels
- Review: Excellent accommodations, close to everything you could need. My wife and I had a perfect evening , by Anthony M.

### [8\. Beautiful Windham Chalet 2 minutes to Town and the Mountain](https://www.expedia.ca/Windham-Hotels-Beautiful-Windham-Chalet-2-Minutes-To-Town-And-The-Mountain.h27238630.Hotel-Information)

![A wooden deck with a railing, several lounge chairs, and a view of a green landscape.](https://images.trvl-media.com/lodging/28000000/27240000/27238700/27238630/w1125h750x104y0-75a795ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Windham
- Guest rating: 10/10 (Exceptional, 3 reviews)
- Price: CA $555, CA $899 total, includes taxes & fees, Nov 17 - Nov 18, for Our top choices for Windham romantic hotels
- Review: Very easy to check in and check out. Very excellent instructions and welcoming atmosphere. , by John K.

### [9\. 5BR Chalet Sleeps 12 with Jacuzzi, Sauna and Gym, 3 Min to Windham Mtn](https://www.expedia.ca/Windham-Hotels-NEW-OUTDOOR-HOT-TUB-5-BEDROOM3-BATH-CHALET-HAUS-WINDHAM.h96763957.Hotel-Information)

![A wooden boardwalk with a rope barrier, surrounded by autumn foliage.](https://images.trvl-media.com/lodging/97000000/96770000/96764000/96763957/58ce6920.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Windham
- Price: CA $519, CA $874 total, includes taxes & fees, Nov 30 - Dec 1, for Our top choices for Windham romantic hotels

### [10\. Duplex Suite with Jacuzzi, Steam Shower and Sauna, 3 Min to Windham Mtn](https://www.expedia.ca/Windham-Hotels-LUXURY-DUPLEX-SUITE-WITH-JACUZZI.h97052666.Hotel-Information)

![A spacious living room with a stone fireplace, wooden staircase, and modern furniture.](https://images.trvl-media.com/lodging/98000000/97060000/97052700/97052666/6f698b2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Windham
- Price: CA $265, CA $325 total, includes taxes & fees, Nov 16 - Nov 17, for Our top choices for Windham romantic hotels

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://www.expedia.ca/Hotel-Search?startDate=2026-11-27&endDate=2026-11-28&regionId=175529&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true)

## Top Windham Hotel Reviews

### [Hotel Vienna](https://www.expedia.ca/Kingston-Hotels-Hotel-Vienna.h893228.Hotel-Information)

![A cabin with a deck, large windows, and a mountain backdrop.](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/75609405.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 107 State Route 296, Windham, NY, 12496, US
- Location: Windham
- Star rating: 3/5
- Guest rating: 9.4/10 (914 reviews)
- Review: Nice people and clean hotel, by Habib, May 24, 2024, rated 10/10 Excellent

### [The Winwood Condominiums](https://www.expedia.ca/Kingston-Hotels-Winwood-Inn-Condominiums.h15409739.Hotel-Information)

![A two-story building with a balcony, surrounded by well-maintained lawns and trees.](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/06763b2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Windham
- Review: Small kitchenette fully equipped. Lots of parking and near gas station/market for essentials. Great stay!, by Jean-Frédéric, April 21, 2026, rated 10/10 Excellent

### [Hotel Mountain Brook](https://www.expedia.ca/Tannersville-Hotels-Hotel-Mountain-Brook.h2256189.Hotel-Information)

![A wooden cabin interior with a bed, a desk, a television, and a large window.](https://images.trvl-media.com/lodging/3000000/2260000/2256200/2256189/7fb1470a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Tannersville
- Review: Super fun stay, had a great room, the outside firepit is a nice touch, breakfast was amazing!! Would go again, love the Catskills!, by Julien, June 25, 2026, rated 10/10 Excellent

### [Twin Gables of Woodstock](https://www.expedia.ca/Kingston-Hotels-Twin-Gables-Of-Woodstock.h42299613.Hotel-Information)

![A two-story house with a front entrance, a staircase, and a signboard.](https://images.trvl-media.com/lodging/43000000/42300000/42299700/42299613/7ddebc2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Woodstock
- Review: Cute property!, by Paola, July 14, 2026, rated 10/10 Excellent

### [Mountain Treasure B&B](https://www.expedia.ca/Kingston-Hotels-Mountain-Treasure-Bed-And-Breakfast.h6206677.Hotel-Information)

![A park with Adirondack chairs and a table, surrounded by trees.](https://images.trvl-media.com/lodging/7000000/6210000/6206700/6206677/8fd68d95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Maplecrest
- Review: We wished to spend some time in the Catskills and were looking for a countryside setting. The B&B building is very old and a former tavern in olden days which has been totally renovated. The rooms are small but comfortable. We took the opportunity to upgrade to a king size in order to obtain a little larger room. Our host was very welcoming and pleasant and was able to give information on interesting drives, hikes and restaurants., by Alice, November 3, 2014, rated 10/10 Excellent

### [Woodstock Way Hotel](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Way-Hotel.h91577819.Hotel-Information)

![A wooden cabin with large windows overlooking a forested area with a waterfall.](https://images.trvl-media.com/lodging/92000000/91580000/91577900/91577819/f0a67aac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Woodstock
- Review: Awesome property, cute town and excellent service., by Daryn, September 23, 2025, rated 10/10 Excellent

### [Hunter Lodge, a Bluebird by Lark](https://www.expedia.ca/Kingston-Hotels-The-Hunter-Inn.h64238678.Hotel-Information)

![A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.](https://images.trvl-media.com/lodging/65000000/64240000/64238700/64238678/39016ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Hunter
- Review: Great, good value place to stay, breakfast included was nice too., by David, August 6, 2026, rated 10/10 Excellent

### [Kaatskill Mountain Club & Condos by Vail Resorts](https://www.expedia.ca/Kingston-Hotels-Hunter-Mountain-Resort.h57228597.Hotel-Information)

![A large hotel with multiple floors, a parking lot, and a mountainous backdrop.](https://images.trvl-media.com/lodging/58000000/57230000/57228600/57228597/62d71aed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Hunter
- Review: Front desk staff was really pleasant when checking in! The rooms felt a bit dated, but everything was nice and clean!, by Adrian, August 4, 2025, rated 10/10 Excellent

## Frequently Asked Questions

### Searching for romantic hotels in Windham?

Are you looking for a romantic getaway? Our guests also enjoy Windham for its coffeehouses, skiing, and mountain views. If you'd like to explore some of the area's notable sights, you might make a stop by Windham Country Club, Windham Mountain Resort, or Windham Vineyards and Winery. If you're interested in staying close to a particular destination, you can sort properties by neighborhood or distance to top sights, so you and your partner will get to see everything on your list.

### When is the best time of year for a romantic getaway to Windham?

If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Windham: The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Windham are January, March, December, and November, with each month seeing an average of 7 inches of snowfall.

### What is there to do in Windham?

There's nothing better than seeing a new place with your sweetheart, so consider checking out all that Windham has to offer. Couples looking for a little of everything will enjoy Windham for its coffeehouses, skiing, and mountain views. You might think about visiting Windham Country Club, Windham Mountain Resort, or Windham Vineyards and Winery.

### What’s the best way to get to Windham and around town during my romantic getaway?

This information about transportation options in Windham might help your romantic trip get off to a smooth start: To get to Windham, you can fly into Hudson, NY (HCC-Columbia County), which is the closest major airport, located 27.6 mi (44.4 km) from the city center. If you'd like to venture out around the area, you may want a rental car for your journey.

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- [Hunter Lodge](https://www.expedia.ca/Kingston-Hotels-The-Hunter-Inn.h64238678.Hotel-Information)
- [Cabin Rentals in Hunter](https://www.expedia.ca/Hunter-Cabins.d117507-aaCabins.Travel-Guide-Accommodation)
- [Kaatskill Mountain Club & Condos by Vail Resorts](https://www.expedia.ca/Kingston-Hotels-Hunter-Mountain-Resort.h57228597.Hotel-Information)
- [Adults Only Resorts & in Kingston](https://www.expedia.ca/Kingston-Hotels-Adults-Only-Resorts.0-0-d6056321-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
- [Perfect Lodge /w Gameroom Center of Hunter MT 11](https://www.expedia.ca/Hunter-Hotels-Perfect-Lodge-W-Gameroom-Center-Of-Hunter-MT-11.h113384779.Hotel-Information)
- [Cheap Hotels in Albany](https://www.expedia.ca/Albany-Hotels-Cheap-Hotels.0-0-d603260-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Albany](https://www.expedia.ca/Albany-Hotels-Luxury-Hotel.0-0-d603260-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Apartments in Medusa](https://www.expedia.ca/Medusa-Apartments.d3000449074-aaApartments.Travel-Guide-Accommodation)
- [The Garden House](https://www.expedia.ca/East-Jewett-Hotels-The-Garden-House-Ski-Hunter-Windham.h94732834.Hotel-Information)
- [Cheap Hotels in The Catskills](https://www.expedia.ca/The-Catskills-Hotels-Cheap-Hotels.0-0-d3000655690-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Lgbt Friendly Hotels in Hunter](https://www.expedia.ca/Hunter-Hotels-LGBT-Friendly-Hotel.0-0-d117507-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels)
- [Spa Hotels in Big Indian](https://www.expedia.ca/Big-Indian-Hotels-Spa-Hotel.0-0-d6060239-tSpaHotel.Travel-Guide-Filter-Hotels)
- [Hotels with Bar in Hudson](https://www.expedia.ca/Hudson-Hotels-Hotels-With-Bar.0-0-d55762-tHotelswithBar.Travel-Guide-Filter-Hotels)
- [A'neils Windham Ski Lodge & Family Retreat](https://www.expedia.ca/Kingston-Hotels-Aneils-West-Windham-House.h60036836.Hotel-Information)
- [Hunter Hotels](https://www.expedia.ca/Hunter-Hotels.d117507.Travel-Guide-Hotels)
- [Chalets in Durham](https://www.expedia.ca/Durham-Chalets.d553248635975930774-aaChalets.Travel-Guide-Accommodation)
- [Shandaken Inn](https://www.expedia.ca/Kingston-Hotels-Shandaken-Inn.h42761897.Hotel-Information)
- [Windham Hotels](https://www.expedia.ca/Windham-Hotels.d175529.Travel-Guide-Hotels)
- [Aparthotels in Preston Hollow](https://www.expedia.ca/Preston-Hollow-Apart-Hotels.d553248634999030445-aaApartHotels.Travel-Guide-Accommodation)
- [Cheap Hotels in Hudson](https://www.expedia.ca/Hudson-Hotels-Cheap-Hotels.0-0-d55762-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Hunter Views + Stone Fireplace](https://www.expedia.ca/Hunter-Hotels-Hunter-Mountain-View-Cabin.h94931600.Hotel-Information)
- [Riedlbauer's Resort](https://www.expedia.ca/Kingston-Hotels-Riedlbauers-Resort.h9211510.Hotel-Information)
- [Authentic 1940s Pullman Train Car Nestled in Bucolic Catskill Woods](https://www.expedia.ca/East-Durham-Hotels-Authentic-1940s-Pullman-Train-Car-Nestled-In-Bucolic-Catskill-Woods.h121746483.Hotel-Information)
- [Pet-Friendly Hotels in Windham](https://www.expedia.ca/Windham-Hotels-Pet-Friendly-Hotel.0-0-d175529-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [B&B in Town of Durham](https://www.expedia.ca/Town-Of-Durham-Bed-And-Breakfast.d553248635976001991-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cheap Hotels in Kingston](https://www.expedia.ca/Kingston-Hotels-Cheap-Hotels.0-0-d6056321-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Starlite Motel](https://www.expedia.ca/Kingston-Hotels-Starlite-Motel.h10109815.Hotel-Information)
- [Pet-Friendly Hotels in Boiceville](https://www.expedia.ca/Boiceville-Hotels-Pet-Friendly-Hotel.0-0-d81287-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [5 Star Hotels in Haines Falls](https://www.expedia.ca/5Star-Haines-Falls-Hotels.s50-0-d183680.Travel-Guide-Filter-Hotels)
- [Flights from Toronto (YYZ) to Albany (ALB)](https://www.expedia.ca/lp/flights/yyz/alb/toronto-to-albany)
- [Flights to Hunter](https://www.expedia.ca/Cheap-Flights-To-Hunter.d117507.Travel-Guide-Flights)
- [Flights from Preston Hollow](https://www.expedia.ca/lp/flights/553248634999030445/flights-from-preston-hollow)
- [Mohonk Preserve Visitor Center](https://www.expedia.ca/Mohonk-Preserve-Visitor-Center-New-Paltz.d553248621532664628.Vacation-Attraction)
- [Catskill State Park](https://www.expedia.ca/Catskill-State-Park-New-York.d6335979.Vacation-Attraction)
- [Visit Windham](https://www.expedia.ca/Windham.dx175529)
- [Visit Acra](https://www.expedia.ca/Acra.dx183633)
- [Visit East Durham](https://www.expedia.ca/East-Durham.dx183665)
- [Visit Elka Park](https://www.expedia.ca/Elka-Park.dx553248635974530560)
- [Windham Mountain Resort](https://www.expedia.ca/Windham-Mountain-Resort-Windham.d6087209.Vacation-Attraction)
- [Hunter Vacations](https://www.expedia.ca/Hunter.d117507.Destination-Travel-Guides)
- [Avis Rental Cars in Hunter](https://www.expedia.ca/Avis-Car-Rentals-In-Hunter.d117507-c41.Car-Rental-Guide-Suppliers)
- [Windham Vacation Rentals](https://www.expedia.ca/Windham-Vacation-Rentals.d175529.Travel-Guide-VacationRentals)
- [Things to do in Albany](https://www.expedia.ca/Things-To-Do-In-Albany.d603260.Travel-Guide-Activities)
- [Things to do in Maplecrest](https://www.expedia.ca/Things-To-Do-In-Maplecrest.d6268398.Travel-Guide-Activities)
- [Things to do in Windham](https://www.expedia.ca/Things-To-Do-In-Windham.d175529.Travel-Guide-Activities)
- [Things to do in East Durham](https://www.expedia.ca/Things-To-Do-In-East-Durham.d183665.Travel-Guide-Activities)

## Other language versions

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