Windsor County Holiday Rentals

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Top Cities in Windsor County

Top Holiday Rentals Destinations in Windsor County

Idyllic Lakefront House Suited Two Families

9.6 out of 10, Exceptional, (162)
"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

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

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

9.8 out of 10, Exceptional, (174)
"Gorgeous log home , spacious, cozy , fun and comfortable ."
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Converted Carriage Barn | The Carriage House Unit1

9.8 out of 10, Exceptional, (20)
"Charming, comfortable, beautiful place. Felt like home and was everything you could want from a converted barn in Vermont!"
Converted Carriage Barn | The Carriage House Unit1

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 NZ$575
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, (90)
"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

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

9.8 out of 10, Exceptional, (17)
"We loved the house and especially the location. The views are beautiful and the proximity to town, the mountain and parks make it a fantastic spot to stay."
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

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

10.0 out of 10, Exceptional, (140)
"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

Treehouse at Wise Pines- NoBo

9.8 out of 10, Exceptional, (11)
"Unique settings. Loved the accommodations "
The price is NZ$349
includes taxes & fees
19 Aug - 20 Aug
Treehouse at Wise Pines- NoBo

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

10.0 out of 10, Exceptional, (54)
"Margarete and Alice welcomed us upon arrival. The house was the quintessential New England home! It was super clean, our bed was very comfortable with soft welcoming linens. The views are incredible, and the property provided much needed peace and tranquility. The weather was not the best but we managed to find plenty to do in the area. Alice, Margarete's black lab, took us for a hike on the property. She was an excellent playful guide! We look forward to returning to this peaceful retreat in...
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

Hawks Mountain Farm, full apartment on a working farm.

9.8 out of 10, Exceptional, (42)
"Very nice place "
Hawks Mountain Farm, full apartment on a working farm.

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

Woodstock Village Carriage House

9.6 out of 10, Exceptional, (93)
"Location was great!!"
Woodstock Village Carriage House

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

9.8 out of 10, Exceptional, (219)
"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.

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

10.0 out of 10, Exceptional, (109)
"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

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

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

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

Sleep Woodstock - 2 Double Beds - Dog Friendly

10.0 out of 10, Exceptional, (1)
"The property is exactly as represented. It’s super clean. Comfortable beds. Bathrooms are updated and nice. It’s right across from a beautiful river and close proximity to quaint downtown Woodstock or nearby Killington. Felt safe and homey. Great communication from property owner. Would recommend! "
The price is NZ$321
includes taxes & fees
21 Aug - 22 Aug
Sleep Woodstock - 2 Double Beds - Dog Friendly

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
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