Windsor County Holiday Rentals

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Our top choices for Windsor County holiday 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 S$2,362
includes taxes & fees
6 Jul - 7 Jul
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
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 S$368
includes taxes & fees
10 Jun - 11 Jun
Brook Road Cabin
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 S$257
includes taxes & fees
17 Jun - 18 Jun
Mountain Green
Interior

Killington Center Inn & Suites by Killington VR - 1 Bedrooms

Killington Center Inn & Suites by Killington VR - 1 Bedrooms
3.0 star property
Killington
2.0 out of 10, (1 review)
"This place does not have clean water. The water that comes from the faucets is brown and there are notices on the doors about high levels of carcinogens. "
United States
Tyler
Killington Center Inn & Suites by Killington VR - 1 Bedrooms
Interior

Pinnacle E08

Pinnacle E08
3.5 star property
Killington
The price is S$594
includes taxes & fees
26 Jun - 27 Jun
Pinnacle E08
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 S$509
includes taxes & fees
10 Jun - 11 Jun
Long Trail House at Stratton Mountain Resort
Interior

Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country

Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country
2.0 star property
Killington
Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country
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
The price is S$364
includes taxes & fees
10 Jun - 11 Jun
Robert Frost Mountain Cabins
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 S$230
includes taxes & fees
10 Jun - 11 Jun
Bridges Resort
Living area

Blue Haven 3 Bedroom Home

Blue Haven 3 Bedroom Home
3.0 star property
Killington
Blue Haven 3 Bedroom Home
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 S$522
includes taxes & fees
27 Jun - 28 Jun
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 S$593
includes taxes & fees
26 Jun - 27 Jun
Pinnacle C16
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 S$557
includes taxes & fees
27 Jun - 28 Jun
Whiffletree C2
Interior

Colony Club C12

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

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is S$985
includes taxes & fees
10 Jun - 11 Jun
Breakaway House by Killington Vacation Rentals
Pool

Pinnacle F21

Pinnacle F21
3.5 star property
Killington
The price is S$736
includes taxes & fees
26 Jun - 27 Jun
Pinnacle F21
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
The price is S$794
includes taxes & fees
26 Jun - 27 Jun
Hemlock Ridge 6A
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 S$455
includes taxes & fees
26 Jun - 27 Jun
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

The Hartness House

The Hartness House

10/10 Excellent
"Quaint stay in Springfield, VT in a 1904 built mansion which is a National Historic Landmark. Wonderful room in the attached hotel adjacent to the mansion. The rooms were beautiful and the mansion itself had a coffee & drink station in a beautiful reading room complete with grand piano, 1920s-era music, and a library. The property is quiet but close to the downtown. It's a 12 minute walk to the downtown area. The Copper Fox is a must try restaurant. The atmosphere and experience can't be beat. My wife and I will be returning in the future."
Dan 1-night trip
Posted 15 hours ago
The Hartness House