Photo by Anna Arsenault

Holiday Homes in Wingdale

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Wingdale

Our top choices for Wingdale holiday homes

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (28)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.8 out of 10, Exceptional, (29)
"Great place for a quiet stay"
The price is AU$513
includes taxes & fees
21 Sept - 22 Sept
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Lake Oasis with Firepit, Game room and Kayaks

8.8 out of 10, Excellent, (3)
"Our weekend at Rory’s home was everything and then some. The hospitality was truly unmatched. Rory bought us a new grill, provided pizza, and gave us fantastic suggestions to go do in the area. There was so much to do around the house between using the kayaks during the day and ending the night by the bonfire. I highly recommend staying here for a weekend getaway, reunion, or even to just unwind and get away from the city. 10/10 experience, would absolutely stay here again! "
Lake Oasis with Firepit, Game room and Kayaks

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (87)
"It was very nice "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

9.0 out of 10, Wonderful, (21)
"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Charming 1870 cape cottage in Litchfield

10.0 out of 10, Exceptional, (54)
"My family and I enjoyed our stay and their hospitality!"
Charming 1870 cape cottage in Litchfield

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (45)
"Wonderful property with a great location."
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

Modern NY Home w/ Views By Hudson Valley Hiking!

9.8 out of 10, Exceptional, (25)
"Amazing..superClean and so accommodating. Needed a few things for graduation and they made it happened since we are from Wisconsin This was the best Vrbo ever. "
Modern NY Home w/ Views By Hudson Valley Hiking!

Woodland A-Frame

10.0 out of 10, Exceptional, (2)
"Nice, clean place out in the woods. Enjoyed our stay and had no issues. Host responded quickly and check-in/out was refreshingly simple. Our kid enjoyed the supply of children’s books. "
Woodland A-Frame

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Lakefront Fall Foliage in New England Just 2 Hours From NYC

10.0 out of 10, Exceptional, (80)
"Great place! Loved waking up to a water view. Very peaceful."
Lakefront Fall Foliage in New England Just 2 Hours From NYC

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

10.0 out of 10, Exceptional, (11)
"The house worked very well for our family holiday. Very clean, had everything we needed "
The price is AU$1,004
includes taxes & fees
2 Sept - 3 Sept
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Litchfield County Four Season Country Paradise

9.6 out of 10, Exceptional, (48)
"Overall rating 5/5. I would recommend this home to other families and would stay again. "
Litchfield County Four Season Country Paradise

Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

10.0 out of 10, Exceptional, (26)
"The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed"
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

The House In Highland- Secluded Retreat

10.0 out of 10, Exceptional, (9)
"Perfect stay while visiting Marist. "
The House In Highland- Secluded Retreat

Serene Hudson Valley Escape w/ Pool & Grill

10.0 out of 10, Exceptional, (3)
"Beautiful home and great host!"
Serene Hudson Valley Escape w/ Pool & Grill

NEW Candlewood Lake 3BR 2BA Direct Waterfront Home~ Dock~Fire Pit~Sunset Views!

10.0 out of 10, Exceptional, (13)
"What a lovely and well appointed place to stay! My only quibble was that the pictures just don’t do the property justice. We will definitely be back!"
NEW Candlewood Lake 3BR 2BA Direct Waterfront Home~ Dock~Fire Pit~Sunset Views!

Fire Pit + On-Site Pond: Hudson Valley Home!

9.2 out of 10, Wonderful, (15)
"I recommend this property to all you peace and nature lovers! We spent 10 days here and found it to be exceptional - the cabin, the host, and the surroundings."
Fire Pit + On-Site Pond: Hudson Valley Home!

Walk to Putnam Lake: Updated Home w/ Deck

2.0 out of 10, (1)
"Upon opening front door, first floor was visually appealing. Quickly the smell of air freshener and stail wet dog overwhelmed. Upon exploring the bedrooms the "guest room" was lacking all beding and window coverings. Master bedroom as advertised has walk in closets. However these are unusable due to 4 feet of home owners items piled within. Upon futher inspection every closet in the home contained piles of home owners belongings. Provided within the master bathroom were 4 towels, no hand towels...
Walk to Putnam Lake: Updated Home w/ Deck

Spacious 4BD Country Gem - Fire Pit & Chill Vibes

9.8 out of 10, Exceptional, (7)
"We had a lovely time at the Gemstone House. There was plenty of room for our family of five, and every detail was attended to. We will come back!"
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Wingdale Hotel Reviews

Find out more about Wingdale

Find out more about Wingdale

Wingdale Holiday Homes information

Number of reviews
39
Accommodation
326 Holiday Homes
Lowest Price
AU$513
Highest Price
AU$1,004

Explore a world of travel with Expedia

Explore a world of travel with Expedia