Holiday Rentals in Windsor County

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Featured Holiday Rentals in Windsor County

Idyllic Lakefront House Suited Two Families
Property grounds

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
Property grounds

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 €182
includes taxes & fees
1 Sept - 2 Sept
Treehouse at Wise Pines- SoBo
Amazing home on 90 acres - AC, fireplace & great mountain views
Fridge, microwave, oven, stovetop

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
Exterior

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
Interior

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 €294
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
Exterior detail

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
Lake

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
Terrace/patio

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
Exterior

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
Interior

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
Exterior

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 €416
includes taxes & fees
30 Sept - 1 Oct
Cozy Creekside Chalet centrally located near 4 ski resorts
Close to Lake & Golf & Pool | Newton Village 2A
TV, fireplace, offices

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

Close to Lake & Golf & Pool | Newton Village 2A
Woodstock Village Carriage House
Exterior

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
Fridge, microwave, oven, stovetop

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
Exterior

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.
Exterior

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
Outdoor dining

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
Microwave, oven, stovetop, coffee/tea maker

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
Fridge, microwave, oven, stovetop

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
Fridge, microwave, oven, stovetop

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

Holiday Homes in Windsor County

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