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Compare 248 Vacation Homes in Wingdale with updated reviews, rates, and availability.

Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Private kitchen
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
10.0 out of 10, Exceptional, (7)
"Absolutely loved our stay! The house was cozy, comfortable, and well-equipped. The host was responsive and made sure everything was just right. Highly recommend!!"
The price is SAR 1,872
SAR 3,435 total
includes taxes & fees
4 Oct - 5 Oct
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Main deck w/ grill & sweeping lake views. Baby/dog gate at deck stairs.
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (64)
"The good: We had a great time staying here. The first and second floor are beautiful and very well maintained. Both bathrooms and three bedrooms are very clean and have more than enough bath and beach towels. The fire pit and kayaks are also a great touch. The water is just steps away and the view is excellent. Just be sure to bring your own propane and firewood. What could be better? Communication with the host left a lot to be desired. I’m still not sure who runs the property. There are two...
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Private kitchen
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (26)
"Great house well appointed driveway could use some work and twin bathroom needs shower curtain and towel bars - we’ll stay again on another visit location is perfect very convenient "
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Lakeview Estate - Chef's Kitchen - NYC Getaway
Outdoor dining
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (21)
"Great stay for 50th birthday "
Lakeview Estate - Chef's Kitchen - NYC Getaway
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Outdoor dining
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
10.0 out of 10, Exceptional, (40)
"We had such a great time! The views are stunning and the house has everything you need to enjoy your stay. The host Kerry was so helpful; we had a small issue with the shower and she had a plumber over within the hour to resolve it. Can’t wait to come back next summer! "
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Charming 1870 cape cottage in Litchfield
Outdoor dining
Charming 1870 cape cottage in Litchfield
10.0 out of 10, Exceptional, (32)
"Jeff was so responsive throughout the entire process of getting this VRBO. I was able to get ready for my wedding with our small group and it was such an incredibly beautiful place to do it. The property is gorgeous. The cottage is wonderful, well lit, and charming for sure. We will definitely be returning! "
Charming 1870 cape cottage in Litchfield
Spacious 4-BR house in lake community with beach access and swim-in-place spa.
Property grounds
Spacious 4-BR house in lake community with beach access and swim-in-place spa.
2.0 star property
Spacious 4-BR house in lake community with beach access and swim-in-place spa.
Spectacular Short Term Vacation Rental in Kent
Exterior
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Bathroom
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (71)
"Hoyse is in a beautiful location and was very clean. The host was responsive and helpful. I would give it 5 stars if it actually had 3 bedrooms."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
The Goshen Glass Chalet
The Goshen Glass Chalet
9.4 out of 10, Exceptional, (24)
"Everything was clean, and was a very comfortable home for friends and family."
The Goshen Glass Chalet
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Property grounds
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
10.0 out of 10, Exceptional, (12)
"The house is huge and is very well equiped. Owners are very responsive to any questions or issues. Wonderful stay for the family."
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
The Queen City Cottage
Living area
The Queen City Cottage
7.4 out of 10, Good, (16)
"My wife and I, along with my two daughters and grandchildren stayed at the Queen City Cottage for 4 nights. We needed to add an extra day at the last minute and Marissa was very responsive and accommodating. The house was clean upon our arrival and entry was a breeze. It's a bedroom, 1.5 bath, with extra bathroom in basement in laundry room. Location wa great! Restaurants and shopping minutes away. Outdoor space was tranquil with table and chairs under covered back porch. Wifi was fine, TV had...
The Queen City Cottage
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
Relax in the new, spacious hot tub on the large patio constructed in Fall 2023.
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
9.8 out of 10, Exceptional, (22)
"We were in the area for a family wedding. The house was as advertised. It was clean and the kitchen well equipped. We will stay again when in the area."
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
Private Annex/Former Artist Studio
Room
Private Annex/Former Artist Studio
10.0 out of 10, Exceptional, (42)
"Everything was inviting, lovely, charming."
Private Annex/Former Artist Studio
Mountain View Getaway
Breathtaking Mountain Views.
Mountain View Getaway
10.0 out of 10, Exceptional, (41)
"This is our second year staying with at Karen and Larry’s property and it did not disappoint. They are incredible hosts and their home is conveniently located near the Lime Rock Track (less than 3 miles). It’s a beautiful and peaceful setting and extremely comfortable home. We highly recommend."
Mountain View Getaway
FREE EV charger and NEMA plug! Breathtaking scenery.
FREE EV charger and NEMA plug! Breathtaking scenery.
2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house with more features than we expected, clean and accommodating "
FREE EV charger and NEMA plug! Breathtaking scenery.
Beacon Area Vacation Rental with Heated Pool!
Lagrangeville Vacation Rental | 5BR | 3BA | 4,000 Sq Ft | Steps Required
Beacon Area Vacation Rental with Heated Pool!
10.0 out of 10, Exceptional, (10)
"Property worked very well for us. Pool was great. (Couple of notes: The stay listed above is slightly incorrect. We arrived on Wed Jun 26 and left on Sun June 30). We requested additional chairs for the pool area from the owner but they were never delivered."
Beacon Area Vacation Rental with Heated Pool!
Traveling Nurse or Business Professional
Exterior
Traveling Nurse or Business Professional
10.0 out of 10, Exceptional, (7)
"The neighborhood was clean, upscale, and beautifully kept. It came with Candlewood Beach access. The second story suite was gorgeous, clean, and well apportioned. The bed was comfortable. The whole house was well maintained and a wonderful,"homey" feel to it. The Hostess was friendly, cheerful, and very accommodating. The house is on the hillside leading to Lake Candlewood. As can be imagined, the views from the windows were outstanding."
Traveling Nurse or Business Professional
The Queen City Cottage
Living area
The Queen City Cottage
9.0 out of 10, Wonderful, (8)
"I moved to the Hudson Valley and needed a place to call home during house hunting and closing on new home! This was the perfect place! Centrally located to the east side of the Hudson River!! The house met all my needs for 2 months! The communication with property manager was wonderful! I would highly recommend this property!"
The Queen City Cottage
Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT
Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT
9.8 out of 10, Exceptional, (10)
"Amenities galore in this well equipped beautiful home! Everyone was happily entertained with the many water play options and many indoor games and activities. The dock and lake were frequently used by all as we also rented a pontoon boat. Wonderful location for our large family to spend time together!"
Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT
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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.
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Other property types in Wingdale

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Main deck w/ grill & sweeping lake views. Baby/dog gate at deck stairs.
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (64)
"The good: We had a great time staying here. The first and second floor are beautiful and very well maintained. Both bathrooms and three bedrooms are very clean and have more than enough bath and beach towels. The fire pit and kayaks are also a great touch. The water is just steps away and the view is excellent. Just be sure to bring your own propane and firewood. What could be better? Communication with the host left a lot to be desired. I’m still not sure who runs the property. There are two...
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Spectacular Short Term Vacation Rental in Kent
Exterior
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Bathroom
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (71)
"Hoyse is in a beautiful location and was very clean. The host was responsive and helpful. I would give it 5 stars if it actually had 3 bedrooms."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
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.