Windsor Vacation Rentals

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Browse Select Windsor Vacation Homes

Our top choices for Windsor vacation homes

Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.

2.0 star property
9.6 out of 10, Exceptional, (4)
"Wanted a quiet rural location for family conversation, a good view, and great food. This was a perfect location and truly enjoyed by all. "
The price is CA $298
CA $508 total
includes taxes & fees
Aug 24 - Aug 25
Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.

Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing

10.0 out of 10, Exceptional, (38)
"Enjoyed our stay, unfortunately it rained so couldn’t enjoy the outside space. "
Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing

Waterfront house on the upper most portion of the West Branch Delaware.

10.0 out of 10, Exceptional, (32)
"This is our 3rd year staying here. It’s a great property and a great location !! We’ll be back next year!!!"
Waterfront house on the upper most portion of the West Branch Delaware.

Binghamton's Beautiful Riverside Drive Living!

10.0 out of 10, Exceptional, (11)
"This was the perfect house for our trip! This house was meant for entertaining for sure. We were comfortable and able to actually host a family dinner! Everyone loved the house and space! This is a definite stay again! "
Binghamton's Beautiful Riverside Drive Living!

2 Story Loft House With Massage Chair

2.0 star property
9.0 out of 10, Wonderful, (2)
"Great place. Clean and quiet. "
2 Story Loft House With Massage Chair

Charming & Private Delaware Riverfront Home near Callicoon NY

9.8 out of 10, Exceptional, (181)
"Once again we thoroughly enjoyed our stay at Joe's. The owner and property manager are very nice people. I highly recommend this property if you enjoy the river and other outdoor opportunities. Thanks again!"
Charming & Private Delaware Riverfront Home near Callicoon NY

12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos

9.8 out of 10, Exceptional, (29)
"We really enjoyed our stay. The place is even better than the pictures and the host Julia was excellent."
12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos

Steps from En-Joie Golf - 3BR Bungalow, Pet-Friendly w/ AC & WiFi

9.8 out of 10, Exceptional, (10)
"Perfect"
Steps from En-Joie Golf - 3BR Bungalow, Pet-Friendly w/ AC & WiFi

FRENCH WOODS FARMHOUSE | TimeOut NY's Pick in Hancock

10.0 out of 10, Exceptional, (41)
"good times - great property in a secluded location :)"
FRENCH WOODS FARMHOUSE | TimeOut NY's Pick in Hancock

!!LAKEFRONT house with baby goats!!

9.8 out of 10, Exceptional, (17)
"We loved the house. "
!!LAKEFRONT house with baby goats!!

Charm by the Lake! Elk Mountain Lake house & Ski lodge.

2.0 star property
9.0 out of 10, Wonderful, (2)
"It was okay, the main bathroom got clogged quickly, silverwear wasnt cleaned properly, fridge wasnt working correctly the first few hours, needs kayaks since its by the lake, also has no air conditioner."
Charm by the Lake! Elk Mountain Lake house & Ski lodge.

Lakeside Gem: Hot Tub & Game Room in Hancock

9.8 out of 10, Exceptional, (45)
"Great host, great property, great stay. Secluded, big, well put together and comfortable. Would highly recommend and will 100% be staying again."
Lakeside Gem: Hot Tub & Game Room in Hancock

Sweet comfy duplex house

2.4 out of 10, (6)
"Very dirty most lights were led light bars bugs crawling Outlets broken "
Sweet comfy duplex house

NEW charming 2-bedroom house in Pleasant Mount

NEW charming 2-bedroom house in Pleasant Mount

Catskills Modern Comfort Home Mountainous Backdrop

8.2 out of 10, Very good, (11)
"Perfect place for a quiet vacation while social distancing. House was very welcoming and clean, We really enjoyed the arcade games for kids and adults in the livingroom. Deck are amazing space with grill, firepit and nice lights to turn on at night. Thanks Matthew!"
Catskills Modern Comfort Home Mountainous Backdrop

Tranquil, Stylish Elk Mountain Home with Lake Access

10.0 out of 10, Exceptional, (15)
"Excellent experience, clean and well maintained property."
Tranquil, Stylish Elk Mountain Home with Lake Access

Waterfront Properties vacation rental

9.8 out of 10, Exceptional, (62)
"We stayed here and it was a true paradise, very quiet and very very pretty. The cottage is on a really nice bend in the river, you can sit on the front porch and just watch it go by. The place is newly updated, very clean and presentable. We would stay here again. Also, check out Animal Adventure Park 5 min away."
The price is CA $173
CA $433 total
includes taxes & fees
Sep 16 - Sep 17
Waterfront Properties vacation rental

Western Catskills Paradise - Four-Season Mountaintop Retreat

9.8 out of 10, Exceptional, (61)
"Would recommend to anyone. Our family stayed here in 2014. Upgrades on furniture since then we're great. Beds were all comfort, which is huge for us since we used them all. Three generations of us enjoyed the property, house and that fantastic view. What was our family farm (1940’s) could be seen across the valley making it extra special. Thank you to our awesome hosts. Your place allowed us to gather together for a tough weekend."
Western Catskills Paradise - Four-Season Mountaintop Retreat

1 Mi to Dtwn: Colorful Binghamton Home

6.8 out of 10, (3)
"Warm environment for a family stay during Christmas to visit family."
1 Mi to Dtwn: Colorful Binghamton Home

New York Abode: 2 Mi to Binghamton University!

9.0 out of 10, Wonderful, (4)
"the only complait about this property, is there was only two bath towels. also there was only four forks"
New York Abode: 2 Mi to Binghamton University!
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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Top Windsor Hotel Reviews