Windsor County Vacation Rentals

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Our top choices for Windsor County vacation rentals

Front of property

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is P70,632
P112,253 total
includes taxes & fees
Jun 24 - Jun 25
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
Interior

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is P15,561
P27,137 total
includes taxes & fees
Jul 1 - Jul 2
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Exterior

Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
10.0 out of 10, Exceptional, (41 reviews)
"Very nice place great owner"
United States
Joe
Robert Frost Mountain Cabins
Outdoor spa tub

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (83 reviews)
"Nice place and great location!!!"
United States
William
The price is P21,214
P26,369 total
includes taxes & fees
Jul 5 - Jul 6
Long Trail House at Stratton Mountain Resort
Aerial view

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (25 reviews)
"I enjoy the location "
United States
troy
The price is P3,633
P12,512 total
includes taxes & fees
Jul 8 - Jul 9
Mountain Green
Living room

Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
7.8 out of 10, Good, (9 reviews)
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
United States
Jill
The price is P10,490
P17,484 total
includes taxes & fees
Jun 24 - Jun 25
Brook Road Cabin
Interior

Colony Club C12

Colony Club C12
3.5 star property
Killington
Colony Club C12
Living area

Blue Haven 3 Bedroom Home

Blue Haven 3 Bedroom Home
3.0 star property
Killington
Blue Haven 3 Bedroom Home
Private kitchen

Bridges Resort

Bridges Resort
2.0 star property
Warren
8.0 out of 10, Very Good, (25 reviews)
"close to the mountain"
United States
Brian Shultis
The price is P3,929
P10,845 total
includes taxes & fees
Jul 6 - Jul 7
Bridges Resort
Interior

Trail Creek 05

Trail Creek 05
3.5 star property
Killington
10.0 out of 10, Exceptional, (2 reviews)
"I ended up getting changed to another property trail creek 80. I wish I could give 10 stars! This place is amazing! Clean quiet spacious and so much more. I want to already book this same place for next years Spartan race!! Thank you for having an amazing property "
United States
Kimberly
The price is P10,423
P24,634 total
includes taxes & fees
Jun 26 - Jun 27
Trail Creek 05
Interior

Pinnacle C16

Pinnacle C16
3.0 star property
Killington
8.8 out of 10, Excellent, (3 reviews)
"Ski trip - warm, cozy, quiet, 2 min ride on free shuttle bus to base."
United States
Steve
The price is P9,034
P26,570 total
includes taxes & fees
Jun 26 - Jun 27
Pinnacle C16
Pool

Pinnacle F21

Pinnacle F21
3.5 star property
Killington
Pinnacle F21
Living area

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is P10,948
P45,206 total
includes taxes & fees
Jun 24 - Jun 25
Breakaway House by Killington Vacation Rentals
Property grounds

Whiffletree C2

Whiffletree C2
3.5 star property
Killington
4.0 out of 10, (1 review)
"It would be good if they informed you that the unit is a walkout basement unit. Also out key code did not work when we arrived. Answering service gave us the cleaning peoples code that only worked once. day 2 we had to call and get a third code. "
United States
Gregory
The price is P9,212
P25,348 total
includes taxes & fees
Jun 27 - Jun 28
Whiffletree C2
Interior

Hemlock Ridge 6A

Hemlock Ridge 6A
3.5 star property
Killington
8.0 out of 10, Very Good, (1 review)
"Everything was good except minor confusion with the lock code. But response was quick, and the issue was resolved."
United States
Leonid
Hemlock Ridge 6A
Pool

Trail Creek by Killington Vacation Rentals

Trail Creek by Killington Vacation Rentals
2.0 star property
Killington
Trail Creek by Killington Vacation Rentals
Interior

Pinnacle E15

Pinnacle E15
3.5 star property
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Great location and close to restaurants in Killington. "
United States
Kevin
The price is P6,735
P20,462 total
includes taxes & fees
Jun 26 - Jun 27
Pinnacle E15
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 County Hotel Reviews

Sleep Woodstock Motel

Sleep Woodstock Motel

10/10 Excellent
"The motel had snacks, coffee, free laundry and other supplies you could help yourself to as needed. They had a picnic area that included a bonfire pit with fire supplies and smore supplies, all free. They had a variety of games and a small kitchen stocked with necessities that a family could utilize to make their stay more affordable. It was amazing. Staff were off site which was more difficult after a smoke detector failed but did answer the phone and supported. Fabulous!"
JoEllen 3-night trip
Posted 10 hours ago
Sleep Woodstock Motel

Find out more about Windsor County

Holiday Apartments in Windsor County

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