Photo by Rachel Samanyi
Holiday Rentals in Windsor County
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Our top choices for Windsor County holiday rentals
Cottage in Hartford
Addie's Place: A Quiet and Quirky Private Guesthouse10.0 out of 10, Exceptional, (4 reviews)
"Perfect size and location! "
Lyn H.
The price is €164
includes taxes & fees
25 Jan - 26 Jan
Cabin in Woodstock
Treehouse at Wise Pines- SoBo9.8 out of 10, Exceptional, (25 reviews)
"Friendly owners with a very comfortable and accommodating space.Very well thought out with a great common space .Hiking trails , fire pit , animals , fresh eggs and produce in season.Highly recommended!!"
Jo-Alice S.
The price is €161
includes taxes & fees
3 Feb - 4 Feb
Apartment in Bridgewater
Vermont Suite | 10 Min to Woodstock & Killington10.0 out of 10, Exceptional, (5 reviews)
"We had a lovely time in Woodstock Vermont. The Bridgewater Inn was cozy and perfect for our weekend get away"
Rosie L.
The price is €185
includes taxes & fees
26 Jan - 27 Jan
Cabin in Cavendish
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit10.0 out of 10, Exceptional, (11 reviews)
"Super easy check in, beautiful and peaceful. Will def be back "
Tyler S.
The price is €261
includes taxes & fees
27 Jan - 28 Jan
10.0 out of 10, Exceptional, (6 reviews)
"Cabin was spotless and exactly what I expected"
mark g.
The price is €289
includes taxes & fees
17 Feb - 18 Feb
Condo in Clock Tower Base Area
Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi8.6 out of 10, Excellent, (14 reviews)
"Excellent Location.. "
Juan Carlos L.
9.0 out of 10, Wonderful, (23 reviews)
"Great rate for a place with all the basics!"
Macgregor
The price is €241
includes taxes & fees
26 Jan - 27 Jan
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay! Beautiful spot tucked in the woods. Great host communication!"
Julie-Anne B.
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.
Find holiday rentals that suit your style
Cabins
Aparthotels
Save an average of 15% on thousands of hotels when you're signed in
Top Windsor County Hotel Reviews
Pointe at Castle Hill Resort
10/10 Excellent
Find out more about Windsor County
Holiday Homes in Windsor County
Search for holiday homes in Windsor County on Expedia.ie! You can easily find your home rentals, villas, holiday apartments in Windsor County using one of the methods below:
- View our selection of featured holiday homes in Windsor County
- Use the map to find apartments and other holiday rentals in the Windsor County neighbourhood you prefer
- Enter your travel dates to view the best deals on holiday homes in Windsor County while they last
Look no further and take a look at our great range of rental properties in Windsor County!