Windsor County Holiday Rentals

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Top Cities in Windsor County

Our top choices for Windsor County holiday rentals

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is NZ$3,156
includes taxes & fees
1 July - 2 July
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

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 NZ$492
includes taxes & fees
10 June - 11 June
Brook Road Cabin

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 NZ$344
includes taxes & fees
10 June - 11 June
Mountain Green

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

Pinnacle E08

Pinnacle E08
3.5 star property
Killington
The price is NZ$792
includes taxes & fees
26 June - 27 June
Pinnacle E08

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 NZ$672
includes taxes & fees
10 June - 11 June
Long Trail House at Stratton Mountain Resort

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

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 NZ$487
includes taxes & fees
10 June - 11 June
Robert Frost Mountain Cabins

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 NZ$307
includes taxes & fees
15 June - 16 June
Bridges Resort

Blue Haven 3 Bedroom Home

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

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 NZ$698
includes taxes & fees
26 June - 27 June
Trail Creek 05

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 NZ$794
includes taxes & fees
26 June - 27 June
Pinnacle C16

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 NZ$745
includes taxes & fees
27 June - 28 June
Whiffletree C2

Colony Club C12

Colony Club C12
3.5 star property
Killington
The price is NZ$1,130
includes taxes & fees
26 June - 27 June
Colony Club C12

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is NZ$1,322
includes taxes & fees
10 June - 11 June
Breakaway House by Killington Vacation Rentals

Pinnacle F21

Pinnacle F21
3.5 star property
Killington
The price is NZ$986
includes taxes & fees
26 June - 27 June
Pinnacle F21

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

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 NZ$607
includes taxes & fees
26 June - 27 June
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

Find out more about Windsor County

Everything you need to know about Windsor County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor County holiday rentals we have selected for you start as low as NZ$534 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor County rentals

At Expedia, we put the best Windsor County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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