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Windsor County Accommodation: Most Popular Cities to Stay

Top Holiday Rentals in Windsor County

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

Solitude Village at Okemo

4.0 star property
8.0 out of 10, Very good, (26)
"Beautiful Area. "
Solitude Village at Okemo

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

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

9.8 out of 10, Exceptional, (16)
"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

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

9.8 out of 10, Exceptional, (173)
"Gorgeous log home , spacious, cozy , fun and comfortable ."
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Treehouse at Wise Pines- SoBo

9.8 out of 10, Exceptional, (20)
"The treehouse is super comfortable and spacious and the lodge was very cozy with everything you need! Breakfast was great too :)"
The price is £156
includes taxes & fees
10 Aug - 11 Aug
Treehouse at Wise Pines- SoBo

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

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 £235
includes taxes & fees
11 Aug - 12 Aug
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Spacious condo with mountain view, fireplace, a/c, walk to Lake Pinneo

8.8 out of 10, Excellent, (3)
"It was very nice place to stay with family. Walking distance to lake pinneo and breakfast place skinny pancakes"
Spacious condo with mountain view, fireplace, a/c, walk to Lake Pinneo

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

9.0 out of 10, Wonderful, (72)
"Perfect location for a quick ski trip. "
The price is £192
includes taxes & fees
10 Aug - 11 Aug
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Charming Chester Farmhouse – peaceful and close to everything!

9.6 out of 10, Exceptional, (12)
"Great location. Beautiful house. All the amenties. We came up for a ski trip and it was perfect. "
The price is £322
includes taxes & fees
17 Aug - 18 Aug
Charming Chester Farmhouse – peaceful and close to everything!

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

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

9.8 out of 10, Exceptional, (218)
"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.

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

10.0 out of 10, Exceptional, (53)
"Cozy accommodations, great location, beautiful property, wonderful hosts."
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

Premier Woodstock Village Riverfront Home

Premier Woodstock Village Riverfront Home

Historic Charm, Located On the River - Rustic Chic

10.0 out of 10, Exceptional, (1)
"Amazing location and great house!! "
Historic Charm, Located On the River - Rustic Chic

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 £349
includes taxes & fees
5 Sept - 6 Sept
Cozy Creekside Chalet centrally located near 4 ski resorts

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

Woodstock Village Carriage House

9.6 out of 10, Exceptional, (92)
"Location was great!!"
Woodstock Village Carriage House

Sleep Woodstock - 2 Double Beds - Dog Friendly

The price is £161
includes taxes & fees
10 Aug - 11 Aug
Sleep Woodstock - 2 Double Beds - Dog Friendly
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