Title: Wingdale Vacation Home Rentals from CA $362: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Wingdale](https://expedia.ca/Wingdale-Hotels.d553248635975862760.Travel-Guide-Hotels)[Vacation Rentals in Wingdale](https://expedia.ca/Wingdale-Vacation-Rentals.d553248635975862760.Travel-Guide-VacationRentals)[Wingdale Car Rentals](https://expedia.ca/Car-Rentals-In-Wingdale.d553248635975862760.Car-Rental-Guide)[Wingdale Vacation Packages](https://expedia.ca/Wingdale.d553248635975862760.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/ccf149061fe165fab130b0cdc9acc5a3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Anna Arsenault # Wingdale Vacation Rentals ![](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 prices for these dates Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Wingdale Vacation Homes ![Exterior detail](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/3db87cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/e729bc4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/1e32801e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/1c3ab355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CT Gate House Goshen CT, Gate House Goshen CT Goshen 9.8/10 Exceptional (7) "The property was great and the house was huge even for all 12 of us " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan L. CA $165 CA $924 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Goshen-Hotels-Gate-House-Goshen-CT.h106031055.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110650000/110643700/110643700/9015258a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110650000/110643700/110643700/52b7436e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/111000000/110650000/110643700/110643700/6db641f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/111000000/110650000/110643700/110643700/8dd5c447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Escape -Strong Wi-Fi -Prime Location Poughkeepsie 7.4/10 Good (3) "The property was perfect for our little weekend getaway. It was very clean and cozy and the host Christina made it so easy for check in and was available for any questions. We would definitely stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea C. CA $137 CA $460 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Poughkeepsie-Hotels-Cozy-Escape-Strong-Wi-Fi-Prime-Location.h110643700.Hotel-Information) ![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/33b86b13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/d8805194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/3e0d1b85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/fd769a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Country outside the city " 3 bedrooms 2 full bathrooms Holmes 9.6/10 Exceptional (4) "Great house! We had a fantastic weekend!! Thank you so much " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) pamela w. CA $336 CA $881 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Holmes-Hotels-Country-Outside-The-City-3-Bedrooms-2-Full-Bathrooms.h109381685.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/89000000/88190000/88181200/88181115/280bea60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/89000000/88190000/88181200/88181115/21fb1fff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/89000000/88190000/88181200/88181115/8c15249f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88190000/88181200/88181115/cbf53a35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park Hopewell Junction 9.0/10 Wonderful (10) "We had a fantastic stay at The Chapel. It was just the fun, different kind of place we were looking for. Pat and Christine were great hosts. We really appreciated their suggestions of hikes and places to visit. We actually had our trip planned out before, but changed it due to their suggestions. We had NO regrets. The bed was super comfy and we loved the s'more makings. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Camille C. CA $213 CA $362 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Hopewell-Junction-Hotels-Cozy-1845-Chapel-Escape-Near-Appalachian-Trail-And-Fahnestock-Park.h88181115.Hotel-Information) ![Family House](https://images.trvl-media.com/lodging/71000000/70550000/70549400/70549365/ff59e7a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach nearby, beach towels, fishing](https://images.trvl-media.com/lodging/71000000/70550000/70549400/70549365/f37bc34c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/71000000/70550000/70549400/70549365/0802bc3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House | Terrace/patio](https://images.trvl-media.com/lodging/71000000/70550000/70549400/70549365/3527e7ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Las Flores Villa New Preston 10/10 Exceptional (1) CA $1,426 CA $2,201 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/New-Preston-Hotels-Las-Flores-Villa.h70549365.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/a7dbb900.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/8bc06f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/1b0ced6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/393a7982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike. Carmel Hamlet 9.8/10 Exceptional (12) "We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hannah P. CA $259 CA $530 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Carmel-Hotels-Lux-Bungalow-On-Gorgeous-Lake-Relax-Explore-Nearby-Towns-Ski-Kayak-Hike.h101941777.Hotel-Information) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/cde347d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/3089dd8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/8e1f1f20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/e34b64d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake New Fairfield 10/10 Exceptional (13) "The house worked very well for our family holiday. Very clean, had everything we needed " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Audrey P. CA $287 CA $730 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/New-Fairfield-Hotels-Peaceful-All-Season-Lake-Community-Home.h100167349.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/2af1ac8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/86da8ea2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/1bd3c0a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/fbb02298.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo Fishkill 9.8/10 Exceptional (41) "Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa B. CA $363 CA $469 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Fishkill-Hotels-Large-Relaxing-Family-Retreat-In-The-Hudson-Valley-With-Theatre-And-Gazebo.h111183358.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/119000000/118950000/118948100/118948037/0f90797e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118950000/118948100/118948037/8115f95e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118950000/118948100/118948037/1e6ca1a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118950000/118948100/118948037/0fb9360c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleeps 10 - Private Dock, Sauna, Outdoor Dining Danbury 10/10 Exceptional (4) "Great house and views of the lake. Very modern and comfortable with everything you need. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ronald L. CA $440 CA $1,175 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Danbury-Hotels-Sleeps-10-Private-Dock.h118948037.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120670000/120662200/120662144/18bc41ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120670000/120662200/120662144/fd92cdbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120670000/120662200/120662144/866b4112.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/121000000/120670000/120662200/120662144/9ccdb1d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunkissed Escape Bright Sunroom + Hammock Fun Poughkeepsie CA $329 CA $524 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Poughkeepsie-Hotels-Sunkissed-Escape-Bright-Sunroom-Hammock-Fun.h120662144.Hotel-Information) ![Dining tables](https://images.trvl-media.com/lodging/113000000/112590000/112584800/112584776/7d1ae479.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/113000000/112590000/112584800/112584776/377f36e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/113000000/112590000/112584800/112584776/f326c1ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112590000/112584800/112584776/0da715d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chestnut on Willow Lake Fishkill 9.4/10 Exceptional (3) "We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Doria W. CA $561 CA $816 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Fishkill-Hotels-Charming-3-Bedroom-Cottage-In-Wonderful-Fishkill.h112584776.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/105000000/104760000/104752000/104751955/cef7f580.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/105000000/104760000/104752000/104751955/fc31b289.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104760000/104752000/104751955/6584c339.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104760000/104752000/104751955/48ee7521.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The George is an elegant restored home in the Hudson Valley Stanfordville 9.2/10 Wonderful (5) "Wonderful property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marie S. CA $808 CA $1,299 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Stanfordville-Hotels-The-George-Is-An-Elegant-Restored-Home-In-The-Hudson-Valley.h104751955.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/cb8efd3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/d975f5d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/ac949794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/3a77d3b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Whispering Estate Guest House - A Romantic Countryside Getaway Goshen 10/10 Exceptional (4) "Beautiful property and great location. A true retreat. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea B. CA $1,122 CA $1,641 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Goshen-Hotels-Charming-Retreat-At-Stone-Hill-Estate-Nature-Meets-Luxury.h118467341.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/111000000/110240000/110235900/110235845/64ef1018.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/111000000/110240000/110235900/110235845/58e2ced5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/111000000/110240000/110235900/110235845/21e387b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/111000000/110240000/110235900/110235845/19262122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Dock & Pool - Candlewood Lake New Milford 10/10 Exceptional (4) "We had a wonderful stay! The host was incredibly responsive and made everything easy from start to finish. The location was perfect for a wedding at Candlewood Lake Inn—just a short drive and super convenient. The house was comfortable, clean, and a great fit for our group of four adults and two kids. We had plenty of space to relax and enjoy the weekend. Highly recommend this spot for anyone visiting the area!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Craig B. CA $447 CA $1,201 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/New-Milford-Hotels-The-Candlewood-Lake-Retreat-Private-Dock-Pool.h110235845.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/105000000/104380000/104373800/104373791/w1436h1440x0y0-175a22f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cookware/dishes/utensils](https://images.trvl-media.com/lodging/105000000/104380000/104373800/104373791/239d3285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cookware/dishes/utensils](https://images.trvl-media.com/lodging/105000000/104380000/104373800/104373791/46f74edf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/105000000/104380000/104373800/104373791/16dfe03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Awesome Lake Home with tons of fun! New Fairfield 9.4/10 Exceptional (3) "Great spot " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mike P. CA $631 CA $1,073 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/New-Fairfield-Hotels-Awesome-Lake-Home-With-Tons-Of-Fun.h104373791.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120390000/120384900/120384809/75b18da9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120390000/120384900/120384809/9c93ce23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/121000000/120390000/120384900/120384809/f3de8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120390000/120384900/120384809/62a1e2aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY Poughkeepsie 10/10 Exceptional (1) "Great host" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lindsey F. CA $453 CA $1,112 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Poughkeepsie-Hotels-Stunning-5-Bedroom-House-With-AC-Heat-In-Charming-Poughkeepsie-NY.h120384809.Hotel-Information) ![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/105000000/104860000/104859300/104859237/c865fa7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/105000000/104860000/104859300/104859237/b491d7c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104860000/104859300/104859237/650aad1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104860000/104859300/104859237/0ed722f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Hudson Valley Estate Hyde Park CA $2,103 CA $2,841 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Hyde-Park-Hotels-Historic-Hudson-Valley-Estate.h104859237.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103310000/103302500/103302422/0c5094d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103310000/103302500/103302422/5351c67d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103310000/103302500/103302422/0ce6becf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103310000/103302500/103302422/19bef9d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious New Luxurious holiday house in lovely Hudson Valley Poughkeepsie 9.8/10 Exceptional (19) "The house is gorgeous. It’s large and very well laid out. Two of the bedrooms are absolutely huge. All six of us were extremely happy with our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Suzanne S. CA $536 CA $984 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Poughkeepsie-Hotels-Spacious-New-5-Bedroom-Holiday-House-In-Lovely-Hudson-Valley.h103302422.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107260000/107252800/107252704/89f3b131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107260000/107252800/107252704/7a401864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107260000/107252800/107252704/4b00451d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107260000/107252800/107252704/51ce249e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Converted Barn with Hot Tub! Hyde Park 9.6/10 Exceptional (5) "The house has a big open floor plan with extra large windows letting light and views in. The bedrooms are comfortable and the kitchen is well equipped. Big playroom was heaven for our toddler. Highly recommend.this property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert P. CA $1,260 CA $1,839 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Hyde-Park-Hotels-Modern-Converted-Barn-With-Hot-Tub.h107252704.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/74000000/73240000/73234400/73234362/463b69eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/74000000/73240000/73234400/73234362/82940c1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73240000/73234400/73234362/caa61cf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73240000/73234400/73234362/23d38d58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Lake Retreat; Dock, Game Room & Firepit New Milford 10/10 Exceptional (47) "Everything was great! Thank you!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ari W. CA $893 CA $1,707 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/New-Milford-Hotels-Candlewood-Lake-Luxurious-Family-Waterfront-Retreat.h73234362.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=2025-11-02&endDate=2025-11-03®ionId=553248635975862760&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWingdale-Private-Vacation-Homes.d553248635975862760-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWingdale-Private-Vacation-Homes.d553248635975862760-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Wingdale Hotel Reviews ![Hampton Inn & Suites Poughkeepsie](//images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg) ### Hampton Inn & Suites Poughkeepsie 10/10 Excellent "Good" [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![Microtel Inn & Suites by Wyndham Bethel/Danbury](//images.trvl-media.com/lodging/1000000/580000/579300/579216/ef7dd368_y.jpg) ### Microtel Inn & Suites by Wyndham Bethel/Danbury 10/10 Excellent "Good" [](https://expedia.ca/Danbury-Hotels-Microtel-Inn-Suites-By-Wyndham-BethelDanbury.h579216.Hotel-Information) ![Home2 Suites By Hilton Poughkeepsie](//images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/7472348e_y.jpg) ### Home2 Suites By Hilton Poughkeepsie 10/10 Excellent "Clean room" [](https://expedia.ca/Poughkeepsie-Hotels-Home2-Suites-By-Hilton-Poughkeepsie.h103394153.Hotel-Information) ![Ethan Allen Hotel](//images.trvl-media.com/lodging/1000000/850000/848400/848360/9fd70ba0_y.jpg) ### Ethan Allen Hotel 10/10 Excellent "Close to highway " [](https://expedia.ca/Danbury-Hotels-Ethan-Allen-Hotel.h848360.Hotel-Information) ![Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG](//images.trvl-media.com/lodging/1000000/700000/690800/690766/f70c64c6_y.jpg) ### Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG 10/10 Excellent "Space was great" [](https://expedia.ca/Danbury-Hotels-Holiday-Inn-Express-Hotel-Suites-Danbury-I-84.h690766.Hotel-Information) ![Holiday Inn Express Poughkeepsie by IHG](//images.trvl-media.com/lodging/1000000/20000/12200/12157/9d729415_y.jpg) ### Holiday Inn Express Poughkeepsie by IHG 10/10 Excellent "Clean room. Helpful staff. Breakfast was a typical Holiday Inn Express buffet - adequate and replenished as needed. No nearby restaurants so we had to drive 7-8 minutes to get dinner, which wasn’t a big inconvenience. We were there on a Sunday night and many places were closed. " [](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.Hotel-Information) ![HYATT house Fishkill/Poughkeepsie](//images.trvl-media.com/lodging/2000000/1340000/1336000/1335929/4a7fc30b_y.jpg) ### HYATT house Fishkill/Poughkeepsie 10/10 Excellent "Very nice set of rooms. Quite comfortable bed, the best we slept in all week. L shaped Sofa was great." [](https://expedia.ca/Poughkeepsie-Hotels-HYATT-House-FishkillPoughkeepsie.h1335929.Hotel-Information) ![DoubleTree by Hilton Poughkeepsie Convention Center](//images.trvl-media.com/lodging/1000000/20000/14600/14563/acc87956_y.jpg) ### DoubleTree by Hilton Poughkeepsie Convention Center 10/10 Excellent " I wouldn’t consider it a unique venue, but the staff was efficient and hospitable and the hotel was clean and comfortable. We appreciated the free parking. The parking lot to hotel elevators was a bit convoluted. " [](https://expedia.ca/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.Hotel-Information) ![Hotel Zero Degrees Danbury](//images.trvl-media.com/lodging/17000000/16270000/16263900/16263812/1fb60e7f_y.jpg) ### Hotel Zero Degrees Danbury 10/10 Excellent "We always stay here on our trips to CT. No complaints!" [](https://expedia.ca/Danbury-Hotels-Hotel-Zero-Degrees-Danbury.h16263812.Hotel-Information) ## Find out more about Wingdale ## Wingdale Vacation Homes information | Number of reviews | 178 | | --- | --- | | Accommodation | 306 Vacation Homes | | Lowest Price | CA $362 | | Highest Price | CA $2,841 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [5 Star Hotels in Millbrook](https://www.expedia.ca/5Star-Millbrook-Hotels.s50-0-d6051715.Travel-Guide-Filter-Hotels) - [B&B in Amenia](https://www.expedia.ca/Amenia-Bed-And-Breakfast.d183634-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Inns in Amenia](https://www.expedia.ca/Amenia-Inns.d183634-aaInns.Travel-Guide-Accommodation) - [Resorts in Amenia](https://www.expedia.ca/Amenia-Resort-Hotels.d183634-aaResortHotels.Travel-Guide-Accommodation) - [Chalets in Appalachian Trail](https://www.expedia.ca/Appalachian-Trail-Chalets.d553248635947269058-aaChalets.Travel-Guide-Accommodation) - 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[Wassaic Hotels](https://www.expedia.ca/Wassaic-Hotels.d553248635975849032.Travel-Guide-Hotels) - [Flights to New York](https://www.expedia.ca/Cheap-Flights-To-New-York.d178293.Travel-Guide-Flights) - [Flights to Patterson](https://www.expedia.ca/Cheap-Flights-To-Patterson.d6190610.Travel-Guide-Flights) - [Flights from Lagrangeville](https://www.expedia.ca/lp/flights/3000350983/flights-from-lagrangeville) - [Flights from Verbank](https://www.expedia.ca/lp/flights/3000351329/flights-from-verbank) - [Flights from Wassaic](https://www.expedia.ca/lp/flights/553248635975849032/flights-from-wassaic) - [Flights from Millbrook](https://www.expedia.ca/lp/flights/6051715/flights-from-millbrook) - [Flights from Patterson](https://www.expedia.ca/lp/flights/6190610/flights-from-patterson) - [Flights from Toronto (YYZ) to New York (NYC)](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york) - [Visit Dover Plains](https://www.expedia.ca/Dover-Plains.dx183663) - [Visit Hopewell Junction](https://www.expedia.ca/Hopewell-Junction.dx55760) - [John Kane House](https://www.expedia.ca/John-Kane-House-Pawling.d6258690.Vacation-Attraction) - [Visit Millbrook](https://www.expedia.ca/Millbrook.dx6051715) - [Stormville Airport Antique Show & Flea Market](https://www.expedia.ca/Stormville-Airport-Antique-Show-Flea-Market-Stormville.d553248621532664682.Vacation-Attraction) - [Visit Stormville](https://www.expedia.ca/Stormville.dx3000449638) - [Car rental Millbrook](https://www.expedia.ca/Car-Rentals-In-Millbrook.d6051715.Car-Rental-Guide) - [Car rental Patterson](https://www.expedia.ca/Car-Rentals-In-Patterson.d6190610.Car-Rental-Guide) - [Car rental Pawling](https://www.expedia.ca/Car-Rentals-In-Pawling.d6278767.Car-Rental-Guide) - [Millbrook Vacation Rentals](https://www.expedia.ca/Millbrook-Vacation-Rentals.d6051715.Travel-Guide-VacationRentals) - [Things to do in Millbrook](https://www.expedia.ca/Things-To-Do-In-Millbrook.d6051715.Travel-Guide-Activities) - [Book Vacation Homes in Wingdale on Expedia.com](https://www.expedia.com/Wingdale-Private-Vacation-Homes.d553248635975862760-aaPrivateVacationHomes.Travel-Guide-Accommodation)