Title: Book the Best Woodstock LUXURY Hotels - Upscale Hotels in Woodstock, NY | Expedia.ca [Hotels in Woodstock](https://expedia.ca/Woodstock-Hotels.d176573.Travel-Guide-Hotels)[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)[Woodstock Car Rentals](https://expedia.ca/Car-Rentals-In-Woodstock.d176573.Car-Rental-Guide)[Woodstock Vacation Packages](https://expedia.ca/Woodstock.d176573.Destination-Travel-Guides) ![Beautiful View. Woodstock, NY. 3h round trip with moderate walking speed. ](https://images.trvl-media.com/place/176573/a7db89cb-5afe-472b-a15c-8ee21e2a7f49.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Marina Timo # Find luxury hotels in Woodstock, NY - ![](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 Woodstock Luxury Hotels Tonight [Nov 14 - Nov 15](https://www.expedia.ca/Hotel-Search?regionId=176573&startDate=2025-11-14&endDate=2025-11-15&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Nov 15 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=176573&startDate=2025-11-15&endDate=2025-11-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=176573&startDate=2025-11-14&endDate=2025-11-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=176573&startDate=2025-11-21&endDate=2025-11-23&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Woodstock Luxury Hotels ## Top Woodstock Hotel Reviews ![Americas Best Value Inn New Paltz](//images.trvl-media.com/lodging/1000000/900000/897900/897882/1c07aec9_y.jpg) ### Americas Best Value Inn New Paltz 10/10 Excellent "Excellent" [](https://expedia.ca/Poughkeepsie-Hotels-Americas-Best-Value-Inn-New-Paltz.h897882.Hotel-Information) ![Residence Inn by Marriott Kingston](//images.trvl-media.com/lodging/16000000/15720000/15715300/15715238/3f674783_y.jpg) ### Residence Inn by Marriott Kingston 10/10 Excellent "Very clean very comfortable " [](https://expedia.ca/Kingston-Hotels-Residence-Inn-By-Marriott-Kingston.h15715238.Hotel-Information) ![Hampton Inn Kingston](//images.trvl-media.com/lodging/2000000/1670000/1662000/1661941/21cb7965_y.jpg) ### Hampton Inn Kingston 10/10 Excellent "Nice clean room, nice persons at counter, good breakfast." [](https://expedia.ca/Kingston-Hotels-Hampton-Inn-Kingston.h1661941.Hotel-Information) ![Quality Inn Hyde Park Poughkeepsie North](//images.trvl-media.com/lodging/1000000/910000/906700/906700/ea4bff95_y.jpg) ### Quality Inn Hyde Park Poughkeepsie North 10/10 Excellent "GOOD STAY" [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Hyde-Park-Poughkeepsie-North.h906700.Hotel-Information) ## Frequently asked questions ### What are the top-rated luxury hotels in Woodstock? > In Woodstock, the [Woodstock Way Hotel](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Way-Hotel.h91577819.Hotel-Information) is consistently celebrated for its exceptional quality. > > > > The 4-star Woodstock Way Hotel, with a 9.6 rating, is known for its premium bedding and designer toiletries, ensuring a comfortable stay. Customers frequently praise its location, which offers both a resort and river view, and its proximity to a shopping district. The presence of a fireplace in many rooms adds to the hotel's unique character. ### Which area of Woodstock is best to stay in for luxury hotels? > For luxury hotels in Woodstock, the best area to stay is generally around the town centre, particularly along Tinker Street and the surrounding quieter lanes. > > > > This area forms the heart of Woodstock and offers a blend of upscale accommodation and easy access to the town's key features. Tinker Street itself is the main thoroughfare, lined with unique shops, art galleries, and restaurants. While it can be busy, many luxury properties are set back slightly on side streets, providing a more peaceful experience while still being moments from the action. You'll find properties that focus on high-end design and comfort, often incorporating natural elements and local art. > > > > Couples looking for a refined getaway will find this area particularly appealing. The proximity to fine dining, boutique shopping, and cultural venues like the Woodstock Artists Association & Museum means there's always something enjoyable to do. Many luxury hotels here offer amenities such as spas, high-end fitness equipment, and exquisite dining options on-site, great for a relaxing and indulgent stay. ### How much does a luxury hotel in Woodstock cost? > Luxury hotel prices in Woodstock vary, but you can find a great deal on Expedia. To find the best prices on luxury stays, be flexible with your dates—typically, off-peak and mid-week stays are cheaper. Sort your search results by "Price: low to high" to see our lowest rates. ### Which luxury hotels in Woodstock are good for families? > For families seeking luxury accommodation in Woodstock, the [Woodstock Way Hotel](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Way-Hotel.h91577819.Hotel-Information) is an excellent option. > > > > The 4-star Woodstock Way Hotel, with a 9.6 rating, offers rooms with premium bedding and designer toiletries, ensuring comfort for all guests. Reviewers frequently highlight the hotel's great location and beautiful surroundings, making it a convenient base for family activities. Many rooms also feature a fireplace and rainfall showerhead, adding to the comfort. ### Which luxury hotels in Woodstock are good for couples? > For couples seeking a luxury hotel in Woodstock, [Woodstock Way Hotel](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Way-Hotel.h91577819.Hotel-Information) is a distinguished option. > > > > The 4-star Woodstock Way Hotel, with an impressive 9.6 rating, offers a refined experience with premium bedding, designer toiletries, and Egyptian cotton sheets. Many rooms feature a fireplace, and guests can enjoy resort or river views. Its location within a shopping district and proximity to concerts or live shows add to its appeal. Our customers frequently praise the hotel's clean rooms, helpful staff, and beautiful amenities and surroundings. ### What luxury activities and experiences are there in Woodstock? > The best area to stay in Woodstock for luxury activities and experiences is the village centre itself, particularly around Tinker Street and Rock City Road. > > > > This area is the heart of Woodstock, offering a refined blend of arts, culture, and upscale amenities. Tinker Street is the main thoroughfare, lined with art galleries, boutique shops, and a variety of dining options. You'll find many of the town's most sought-after experiences within a short stroll. > > > > Couples looking for a high-end getaway will particularly enjoy this area. They can indulge in private art lessons at local studios, enjoy curated tasting menus at fine dining establishments, or relax with bespoke spa treatments. The proximity to the historic Byrdcliffe Arts Colony also offers opportunities for private tours or workshops. > > > > For those interested in wellness and relaxation, several upscale retreats and spas are located just outside the immediate village centre but are easily accessible. ### How can I save on a luxury hotel in Woodstock with Expedia? > There are plenty of ways to save on a luxury hotel in Woodstock. Unlock our lowest prices by joining [One Key™](https://www.expedia.ca/welcome-one-key), Expedia's travel rewards program. It's free and easy to sign up, and you can access member perks too. Typically, booking in advance will help you save on your luxury hotel booking. If you're feeling spontaneous, be sure to check for last-minute deals. ### Is it cheaper to book a luxury Woodstock hotel and flights as a package? > Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect [travel package](https://www.expedia.ca/Woodstock.d176573.Destination-Travel-Guides). ### Can I cancel my luxury hotel reservation on Expedia? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. 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