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Vacation Homes in Windsor

Our top choices for Windsor vacation homes

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

2.0 star property
8.8 out of 10, Excellent, (8)
"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 ¥31,758
¥54,073 total
includes taxes & fees
Sep 29 - Sep 30
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, (44)
"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

Breathtaking 44+ Acre Country Estate

10.0 out of 10, Exceptional, (36)
"Great place, great setup and property "
Breathtaking 44+ Acre Country Estate

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

9.8 out of 10, Exceptional, (10)
"We had a nice stay. The house was as described. "
Steps from En-Joie Golf - 3BR Bungalow, Pet-Friendly w/ AC & WiFi

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

Peruvian-Lily Cosy Retreat Unit A Room 5

Peruvian-Lily Cosy Retreat Unit A Room 5

2 Story Loft House With Massage Chair

2.0 star property
9.6 out of 10, Exceptional, (5)
"Great place. Clean and quiet. "
2 Story Loft House With Massage Chair

FRENCH WOODS FARMHOUSE | TimeOut NY's Pick in Hancock

10.0 out of 10, Exceptional, (42)
"We had a great time with kids, friends and dogs alike! The house was beautiful and even bigger than the photos suggested. The dogs loved the outside area and pond to play. It was a great stay!"
FRENCH WOODS FARMHOUSE | TimeOut NY's Pick in Hancock

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

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

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.

Jones Oaks: rural, private, kid friendly, near D&H Rail Trail, Elk Mtn

10.0 out of 10, Exceptional, (4)
"This property gave me and my 8 friends plenty of place for sleeping and living. The distance from the mountain was a perfect short drive and we really enjoyed our time up there."
Jones Oaks: rural, private, kid friendly, near D&H Rail Trail, Elk Mtn

Grand Monarch! Luxury Boutique Living! Best for Extended Stays.

2.5 star property
10.0 out of 10, Exceptional, (1)
"Great place to stay very clean and secured"
Grand Monarch! Luxury Boutique Living! Best for Extended Stays.

Tranquil, Stylish Elk Mountain Home with Lake Access

10.0 out of 10, Exceptional, (16)
"Excellent experience, clean and well maintained property."
Tranquil, Stylish Elk Mountain Home with Lake Access

NEW charming 2-bedroom house in Pleasant Mount

10.0 out of 10, Exceptional, (1)
NEW charming 2-bedroom house in Pleasant Mount

Flagview Lodge - Cozy Apartment with a View

10.0 out of 10, Exceptional, (1)
"I love the entire day. It was fantastic from the inside to the outside. My best part of this whole trip wants to view makes you feel like the top of the world, the quietness, the wildlife being able to see."
The price is ¥14,647
¥40,438 total
includes taxes & fees
Sep 28 - Sep 29
Flagview Lodge - Cozy Apartment with a View

Indoor Pool,Largest Game Lodge,Sleeps 39

10.0 out of 10, Exceptional, (54)
"A group of us stayed for two nights and the property absolutely exceeded our expectations. Leah was a great communicator and I would absolutely recommend this property for a group to get away and enjoy all of the activities it has to offer."
Indoor Pool,Largest Game Lodge,Sleeps 39

DISCOUNT LAST MINUTE Elk Mountain Estate Manor in beautiful PA-Groups and Events

9.8 out of 10, Exceptional, (95)
"We booked at the last minute due to another rental falling through. The booking process was smooth and Laura was a gracious and amazing host. The property is beautiful and spacious! We can’t wait to visit again "
DISCOUNT LAST MINUTE Elk Mountain Estate Manor in beautiful PA-Groups and Events

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

10.0 out of 10, Exceptional, (34)
"4 rainy days of fishing. "
Waterfront house on the upper most portion of the West Branch Delaware.

Equinunk

2.0 star property
The price is ¥38,467
¥65,601 total
includes taxes & fees
Sep 24 - Sep 25
Equinunk
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

Find out more about Windsor

Find out more about Windsor

Windsor Vacation Homes information

Number of reviews
420
Accommodation
128 Vacation Homes
Lowest Price
¥40,438
Highest Price
¥65,601