Photo by Anna Arsenault

Book Wingdale Bed & Breakfast

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21
In one month
Jan 2 - Jan 4
In two months
Jan 30 - Feb 1

B&B in Wingdale

Aerial view
Millbrook Country House Bed & Breakfast

Millbrook Country House Bed & Breakfast

4.0 star property
Millbrook
9.0 out of 10, Wonderful, (81)
"Gracious host and great breakfast "
United States
Gerald
$198 nightly
The price is $224
Jan 4 - Jan 5, 2026
Total with taxes and fees
Millbrook Country House Bed & Breakfast
Dining
Homestead Inn

Homestead Inn

3.5 star property
New Milford
9.2 out of 10, Wonderful, (196)
"Everything was as noted with a friendly staff"
United States
Colby
$206 nightly
The price is $237
Jan 4 - Jan 5, 2026
Total with taxes and fees
Homestead Inn
Terrace/patio
it's a good thing

it's a good thing

4.5 star property
Clinton Corners
8.0 out of 10, Very Good, (24)
"Wonderful stay and wonderful hosts! "
United States
Daniela-Cristina
$141 nightly
The price is $160
Jan 1 - Jan 2, 2026
Total with taxes and fees
it's a good thing
Exterior
Jenny's Country Manor

Jenny's Country Manor

2.0 star property
Red Hook
7.6 out of 10, Good, (133)
"Jenny's was quaint and comfortable, with "
United States
Bill
$140 nightly
The price is $158
Dec 8 - Dec 9
Total with taxes and fees
Jenny's Country Manor
Property grounds
Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,

Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,

Clinton Corners
8.2 out of 10, Very Good, (11)
"The propert my, grounds and location is just charming. Hosts were stellar and welcoming. Accomodations warm and inviting."
United States
Dawn B.
$172 nightly
The price is $195
Dec 8 - Dec 9
Total with taxes and fees
Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,
Free daily continental breakfast
Inn at Pine Plains

Inn at Pine Plains

3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (301)
"Great stay"
United Kingdom
Katherine
$275 nightly
The price is $311
Dec 8 - Dec 9
Total with taxes and fees
Inn at Pine Plains
Exterior detail
Inn the Woods Bed and Breakfast

Inn the Woods Bed and Breakfast

3.5 star property
Hyde Park
9.8 out of 10, Exceptional, (136)
"Harry was great, room clean and fresh, breakfast amazing "
United States
Frank
$183 nightly
The price is $207
Dec 31 - Jan 1, 2026
Total with taxes and fees
Inn the Woods Bed and Breakfast
Hiking
Journey Inn Bed & Breakfast

Journey Inn Bed & Breakfast

4.0 star property
Hyde Park
9.6 out of 10, Exceptional, (338)
"Great staff, the breakfast was amazing, location to surrounding attractions was great! I would stay again!"
United States
Shawn
$224 nightly
The price is $253
Dec 8 - Dec 9
Total with taxes and fees
Journey Inn Bed & Breakfast
Property grounds
Private room on secluded 7 acres , access to entire house including patio, porch

Private room on secluded 7 acres , access to entire house including patio, porch

Clinton Corners
8.6 out of 10, Excellent, (30)
"It was just as advertised! Host was nice included fruit and coffee "
United States
matt w.
$183 nightly
The price is $207
Dec 8 - Dec 9
Total with taxes and fees
Private room on secluded 7 acres , access to entire house including patio, porch
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wingdale Hotel Reviews

Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North

10/10 Excellent
"The staff was very freindly and helpful. I thought this place was a great value. Clean room. Breakfast was good. I took advantage of the fitness room which was nice to have. Good location, close to restaurants and a grocery store. "
Mark 1-night trip
Posted 2 days ago
Quality Inn Hyde Park Poughkeepsie North

Find out more about Wingdale

Wingdale B&B information

Number of reviews
1,177
Accommodation
15 B&B
Lowest Price
$158
Highest Price
$311

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?
Check out this B&B in the surrounding area: Homestead Inn: 16 rooms. Situated 9.3 mi (15 km) from the heart of Wingdale.
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. If you'd like to explore around the area, you may want to rent a car for your trip.

Explore a world of travel with Expedia