Windsor County Holiday Rentals

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Top Holiday Rentals Destinations in Windsor County

Idyllic Lakefront House Suited Two Families

9.6 out of 10, Exceptional, (165)
"We really enjoyed our stay at the lake house. We had great views of the lake and the kitchen was very well stocked. The beds were comfortable and the house was very clean and nicely decorated. Thank you for the incredible stay and we will be staying again!"
Idyllic Lakefront House Suited Two Families

Treehouse at Wise Pines- SoBo

9.8 out of 10, Exceptional, (21)
"The treehouse is super comfortable and spacious and the lodge was very cozy with everything you need! Breakfast was great too :)"
The price is AU$320
includes taxes & fees
1 Sept - 2 Sept
Treehouse at Wise Pines- SoBo

Amazing home on 90 acres - AC, fireplace & great mountain views

9.0 out of 10, Wonderful, (43)
"My favorite place to stay in the area. Love it! "
Amazing home on 90 acres - AC, fireplace & great mountain views

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (175)
"Gorgeous log home , spacious, cozy , fun and comfortable ."
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

10.0 out of 10, Exceptional, (20)
"Thanks for a great stay!"
The price is AU$518
includes taxes & fees
8 Sept - 9 Sept
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

10.0 out of 10, Exceptional, (91)
"We needed a quiet place to stay in the woods. It was close to Ludlow shops/ restaurants and the Okemo Ski. "
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

10.0 out of 10, Exceptional, (141)
"Cute cabin close to Okemo and town! Really enjoyed our stay and would definitely return. "
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

2.0 star property
9.8 out of 10, Exceptional, (75)
"Beautiful area and gorgeous leaves. Liked having a weber grill."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

9.8 out of 10, Exceptional, (17)
"The property was as described, very clean, updated with a nice view. WeHad fun exploring the area.We enjoyed the fireplace while relaxing after hiking and exploring."
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Converted Carriage Barn | The Carriage House Unit2

9.6 out of 10, Exceptional, (4)
"Very cool conversion of an old barn. Very comfy and rather iconic. Because of the barn construction, there was an occasional encounter with a bug or two. Nicely located with many shops and restaurants nearby. The surrounding neighborhood of Quechee is very pleasant and kind of upscale country. Be aware there are no hangers/closets/ironing board/washer/dryer, so plan accordingly."
Converted Carriage Barn | The Carriage House Unit2

Cozy Creekside Chalet centrally located near 4 ski resorts

10.0 out of 10, Exceptional, (12)
"We spent a great week in Weston. Great location to ski Stratton. Hosts were very responsive. Would def go back."
The price is AU$733
includes taxes & fees
29 Sept - 30 Sept
Cozy Creekside Chalet centrally located near 4 ski resorts

Close to Lake & Golf & Pool | Newton Village 2A

Close to Lake & Golf & Pool | Newton Village 2A

Woodstock Village Carriage House

9.8 out of 10, Exceptional, (96)
"Location was great!!"
Woodstock Village Carriage House

Quechee Village Getaway | The Cottage on Main

9.8 out of 10, Exceptional, (18)
"We enjoyed our stay at the Cottage on Main. Nice house, very convenient location."
Quechee Village Getaway | The Cottage on Main

Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

10.0 out of 10, Exceptional, (110)
"Nice rental for our family and the owner was very rsponsive."
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

9.8 out of 10, Exceptional, (221)
"Our stay was amazing! The house offered everything we needed, was spacious and clean. Working with the owners was also easy. Would definitely recommend and stay again!"
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

8.6 out of 10, Excellent, (27)
"Cool location, perfect basic ski house"
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Spacious studio, dog-friendly, close to recreation, central a/c, TV, wifi

8.0 out of 10, Very good, (1)
"The loft space is cute. Just know there is another house that is also rented out and it’s right next to this garage loft. I didn’t expect it to be so close. "
Spacious studio, dog-friendly, close to recreation, central a/c, TV, wifi

Killington ski house

9.4 out of 10, Exceptional, (35)
"Property owner was excellent! We enjoyed our stay."
Killington ski house

Perfect Woodstock Getaway! Lovely Riverside Home

10.0 out of 10, Exceptional, (6)
"We had a wonderful weekend at Charlie's house. The property was clean and welcoming and the fenced in backyard was excellent for our dog Riley"
Perfect Woodstock Getaway! Lovely Riverside Home
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

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 favourite 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 depend 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 chosen for you start as low as AU$320 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.