Title: Wingdale B&B: Find the Best Bed and Breakfast from CA $223 | 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 # Find a Bed and Breakfast in Wingdale from CA $223 - ![](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 [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Wingdale B&B ![Aerial view](https://images.trvl-media.com/lodging/15000000/14910000/14909300/14909243/341b20f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/15000000/14910000/14909300/14909243/48d818fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/15000000/14910000/14909300/14909243/eadec9fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/15000000/14910000/14909300/14909243/bb0114e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Millbrook Country House Bed & Breakfast Millbrook 9.0/10 Wonderful (79) "It was a very nice stay. The host went out of his way to make sure you had everything you needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ken CA $316 CA $358 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Poughkeepsie-Hotels-Millbrook-Country-House-Bed-Breakfast.h14909243.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/4000000/3810000/3808200/3808185/e8b5deeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/4000000/3810000/3808200/3808185/ecd921fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/4000000/3810000/3808200/3808185/f00c5b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/4000000/3810000/3808200/3808185/04187aee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jenny's Country Manor Red Hook 7.6/10 Good (133) "A beautiful country inn. Very comfortable and just like home " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew CA $197 CA $223 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Stanfordville-Hotels-Jennys-Country-Manor.h3808185.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99920000/99919400/99919328/1ca7ca84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/100000000/99920000/99919400/99919328/79502799.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Traditional Twin Room | Living area](https://images.trvl-media.com/lodging/100000000/99920000/99919400/99919328/49be28f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99920000/99919400/99919328/8f5460b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### it's a good thing Clinton Corners 8.0/10 Very good (24) "Wonderful stay and wonderful hosts! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniela-Cristina [](https://www.expedia.ca/Clinton-Corners-Hotels-Its-A-Good-Thing.h99919328.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/23000000/22230000/22227200/22227121/ddc846d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/23000000/22230000/22227200/22227121/de707444.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Accessible (The Smithfield Room)](https://images.trvl-media.com/lodging/23000000/22230000/22227200/22227121/e3593a4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/23000000/22230000/22227200/22227121/6cdeed48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Pine Plains Pine Plains 9.8/10 Exceptional (297) "Very nice spacious room and a good value." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Theodore CA $348 CA $394 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Pine-Plains-Hotels-Inn-At-Pine-Plains.h22227121.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/2000000/1050000/1046900/1046891/b1d5aed6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Room, 1 King Bed, Jetted Tub](https://images.trvl-media.com/lodging/2000000/1050000/1046900/1046891/5cda1bfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Room, 1 King Bed, Jetted Tub](https://images.trvl-media.com/lodging/2000000/1050000/1046900/1046891/1b68d1f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1050000/1046900/1046891/568f56b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homestead Inn New Milford 9.2/10 Wonderful (192) "Everything was as noted with a friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Colby CA $339 CA $390 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Danbury-Hotels-Homestead-Inn.h1046891.Hotel-Information) ![Hiking](https://images.trvl-media.com/lodging/18000000/17910000/17902100/17902038/c194d854.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/18000000/17910000/17902100/17902038/e86f8756.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/18000000/17910000/17902100/17902038/731ceae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/18000000/17910000/17902100/17902038/6ae0b5c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Journey Inn Bed & Breakfast Hyde Park 9.6/10 Exceptional (334) "The owners are lovely and breakfast was wonderful. It's 10 mins from Rhinebeck with lots of good restaurants which they recommended. Lovely stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mindy CA $315 CA $356 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Poughkeepsie-Hotels-Journey-Inn-Bed-Breakfast.h17902038.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/b528caee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/bd8601b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/677d2235.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/aeb97fc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away, Clinton Corners 8.2/10 Very good (11) "Beautiful, comfortable house on a lovely property. Hosts were very friendly and welcoming. Would definitely return and recommend to friends and family." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret CA $197 CA $274 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Poughkeepsie-Hotels-Private-Bed-Bath-On-Secluded-30-Acre-Farm.h67268558.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68780000/68773100/68773092/8e24845d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68780000/68773100/68773092/1941c471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68780000/68773100/68773092/f31a431f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68780000/68773100/68773092/6d7fbb92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private room on secluded 7 acres , access to entire house including patio, porch Clinton Corners 8.6/10 Excellent (30) "My wife and I enjoyed this very old and charming home and our host Lynn. There was so much to do nearby with the mansions and FDR Museum/Library." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kip L. CA $211 CA $291 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Clinton-Corners-Hotels-Private-Room-On-Secluded-7-Acres.h68773092.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/31000000/30530000/30528700/30528653/1d436988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/31000000/30530000/30528700/30528653/8e6a9ec3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/31000000/30530000/30528700/30528653/89b9b977.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/31000000/30530000/30528700/30528653/41817d7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn the Woods Bed and Breakfast Hyde Park 9.8/10 Exceptional (133) "Very spacious room. Host, Harry, is great and makes an excellent breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dwight CA $343 CA $388 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/Poughkeepsie-Hotels-Inn-The-Woods-Bed-And-Breakfast.h30528653.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=2025-11-19&endDate=2025-11-20®ionId=553248635975862760&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&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-Bed-And-Breakfast.d553248635975862760-aaBedAndBreakfast.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWingdale-Bed-And-Breakfast.d553248635975862760-aaBedAndBreakfast.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 "Service and staff was A+++++" [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.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 "Excellent comfortable rooms and staff" [](https://expedia.ca/Danbury-Hotels-Holiday-Inn-Express-Hotel-Suites-Danbury-I-84.h690766.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 "Great place to stay. Very quiet for sleeping." [](https://expedia.ca/Danbury-Hotels-Microtel-Inn-Suites-By-Wyndham-BethelDanbury.h579216.Hotel-Information) ![SureStay Plus Hotel by Best Western Highland Poughkeepsie](//images.trvl-media.com/lodging/1000000/920000/918800/918797/960f4844_y.jpg) ### SureStay Plus Hotel by Best Western Highland Poughkeepsie 10/10 Excellent "Property Clean, parking area well lit, room was clean, staffing pleasant- great place for family, will return. " [](https://expedia.ca/Poughkeepsie-Hotels-SureStay-Plus-Hotel-By-Best-Western-Highland-Poughkeepsie.h918797.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 "Spotless room, friendly staff, convenient parking and great location for events at Bardavon, Hudson pedestrian bridge in walking distance. We'd stay here again!" [](https://expedia.ca/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.Hotel-Information) ![Inn at Bellefield / Hyde Park, Residence Inn by Marriott](//images.trvl-media.com/lodging/100000000/99860000/99850800/99850733/w4000h2662x0y0-e2ffacae_y.jpg) ### Inn at Bellefield / Hyde Park, Residence Inn by Marriott 10/10 Excellent "Very nice hotel across the CIA It is a beautiful hotel Great rooms They have a great gym and laundry room Great location " [](https://expedia.ca/Hyde-Park-Hotels-Inn-At-Bellefield-Hyde-Park.h99850733.Hotel-Information) ![Hyatt Place Poughkeepsie / Hudson Valley](//images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/9bb388bd_y.jpg) ### Hyatt Place Poughkeepsie / Hudson Valley 10/10 Excellent "We have good time at the hotel. Nice and clean " [](https://expedia.ca/Poughkeepsie-Hotels-Hyatt-Place-Poughkeepsie.h37960419.Hotel-Information) ![Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection](//images.trvl-media.com/lodging/1000000/40000/35400/35389/d1cdaed7_y.jpg) ### Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection 10/10 Excellent "The staff could not have been friendlier or more helpful. I really enjoyed my stay here." [](https://expedia.ca/Danbury-Hotels-Heritage-Hotel.h35389.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) ## Find out more about Wingdale ## Wingdale B&B information | Number of reviews | 1,160 | | --- | --- | | Accommodation | 15 B&B | | Lowest Price | CA $223 | | Highest Price | CA $394 | ## Frequently asked questions ### Searching for B&Bs in Wingdale? > Whether you're traveling with your family and want a friendly place to stay, or you're traveling solo and hoping to make some connections, a B&B can be a good choice for many different types of travelers. If you're interested in playing some golf on your trip, Harlem Valley Golf Club is a good spot to tee off. ### Are you thinking about a B&B instead of a traditional hotel? > Every B&B has a unique charm. Whether it's a garden for guests to admire or a sunlit breakfast nook, the tiny details are what make bed and breakfasts a home away from home. ### What are the best B&Bs in Wingdale? > Below are some well-liked B&Bs in the surrounding area: [Homestead Inn](https://www.expedia.ca/Danbury-Hotels-Homestead-Inn.h1046891.Hotel-Information): 16 rooms. Situated 9.3 mi (15 km) from the heart of Wingdale. [Millbrook Country House Bed & Breakfast](https://www.expedia.ca/Poughkeepsie-Hotels-Millbrook-Country-House-Bed-Breakfast.h14909243.Hotel-Information): 4 rooms. Located 12.1 mi (19.4 km) from the core of Wingdale. Enjoy the free full breakfast and unique décor. ### What's the best time of year to book my B&B in Wingdale? > When you're planning your stay in Wingdale, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Wingdale are January, February, March, and April, with each month seeing an average of 7 inches of snowfall. ### What is there to do in Wingdale? > When you want to check out some attractions in town, you might consider a visit to Dover Veterans Memorial Library and Harlem Valley Golf Club. You might put Leather Hill Preserve and Pawling Nature Reserve on your list if you want to see more of the area. ### How can I get to and around Wingdale? > Mapping out your trip in and around Wingdale is easy with these transportation options. Fly into Danbury, CT (DXR-Danbury Municipal), which is located 19.4 mi (31.2 km) away from the city center. Otherwise, look for flights into Oxford, CT (OXC-Waterbury - Oxford), which is 25 mi (40.3 km) away. 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