A river flowing through a forest with autumn foliage.

Vacation Homes in Windsor County

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Windsor County vacation homes

A wooden cabin with a deck, a barbecue grill, and a glass door leading to an interior with a dining area.

1. Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Ludlow
9.6 out of 10, Exceptional, (146 reviews)
"The property was amazing, and the location was perfect! You’re close enough to town and other amenities, but once you arrive, it feels like you’re tucked away in the woods with plenty of privacy.The property was clean and had everything we needed for our stay. The kids had a great time exploring and enjoying the outdoor space. The fire pit was a highlight for us—we loved making s’mores, and it was a nice bonus that firewood was provided.We had a fantastic stay and would definitely book this...
United States
Aaron M.
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
A spacious living room with a large sofa, a coffee table, and a bookshelf filled with books and decorative items.

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

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
Woodstock
9.8 out of 10, Exceptional, (251 reviews)
"Great spot, in a lovely location! "
United States
Beth W.
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
A dining area with a wooden table, chairs, a chandelier, a window with curtains, and a cabinet with bottles.

3. The Dorothy-10 minutes from Okemo- freshly renovated

The Dorothy-10 minutes from Okemo- freshly renovated
Cavendish
9.6 out of 10, Exceptional, (8 reviews)
"Charming place – – wonderful, responsive hosts. "
United States
Richard P.
The Dorothy-10 minutes from Okemo- freshly renovated
A lakeside view with Adirondack chairs and a bench, surrounded by autumn foliage and a stone wall.

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

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town
Woodstock
10.0 out of 10, Exceptional, (68 reviews)
"Gorgeous setting wonderful accommodations stars in the sky were amazing delightful host want to come back"
United States
Lee L.
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town
A cozy living room with a stone fireplace, a comfortable armchair, and a wooden coffee table.

5. Rustic home with a private hot tub, cable, & washer/dryer

Rustic home with a private hot tub, cable, & washer/dryer
Plymouth
9.6 out of 10, Exceptional, (67 reviews)
"House was great and well located for skiing at both Killington and Okemo"
United States
Mike M.
Rustic home with a private hot tub, cable, & washer/dryer
A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

6. New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View
Ludlow
10.0 out of 10, Exceptional, (22 reviews)
"The perfect stop on the way to UVM. Super clean! Walkable eateries & a beautiful view. Thank you!"
United States
Tara
The price is AED 985
AED 2,184 total
includes taxes & fees
20 Oct - 21 Oct
New Ludlow Village Home with Stunning Okemo Mountain View
A spacious kitchen with a large island, wooden cabinets, and a built-in oven. There is a dining area with a sofa and chairs, and a fireplace.

7. Charming VT ski retreat with hot tub, pool, fire pit & endless mountain views

Charming VT ski retreat with hot tub, pool, fire pit & endless mountain views
Weston
10.0 out of 10, Exceptional, (21 reviews)
"The four of us had a lovely stay here. Julia is a fantastic host. The house is very big, 3 couples can stay comfortably in the 3 upstairs bedrooms, plus there is another smaller room with bunk beds in the basement. The bedrooms, living room, family room are all big, comfortable and very tastefully furnished. We enjoyed the hot tub and the fire pit, and you also get a lovely view of the hills from there. Strongly recommended."
United States
barun
Charming VT ski retreat with hot tub, pool, fire pit & endless mountain views
A two-story house surrounded by autumn foliage, with a body of water in the foreground.

8. Waterfront House on Dewey Pond, Quechee

Waterfront House on Dewey Pond, Quechee
Hartford
10.0 out of 10, Exceptional, (13 reviews)
"The house was fabulous. Quirky and fun, antique but well maintained and appointed, with a glorious back deck with a spectacular view."
United States
Rowland M.
Waterfront House on Dewey Pond, Quechee
A cozy living room with a fireplace, wooden ceiling, and a large TV screen.

9. Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table

Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table
Ludlow
9.8 out of 10, Exceptional, (127 reviews)
"We were a party of 10 and have a great overall stay. Everything was as described and checking in and out was secure and simple. Would come again and recommend to others!"
United States
Muddasar J.
Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table
Three wall-mounted dispensers labeled with different hair care products: shampoo, conditioner, and body wash.

10. Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock

Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock
Hartford
10.0 out of 10, Exceptional, (179 reviews)
"Clean, well maintained property. Perfect decor for a quaint Vermont town."
United States
Joann
The price is AED 672
AED 1,573 total
includes taxes & fees
25 Oct - 26 Oct
Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock
A spacious living area with a high ceiling, skylights, a fireplace, a TV, and a large sliding glass door to a deck.

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

Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Plymouth
9.0 out of 10, Wonderful, (2 reviews)
"Nice place!!"
United States
Elisandro
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
A rustic interior with exposed wooden beams, a staircase, a dining area, and leather furniture.

12. Historic Farmhouse on Working VT Farm & Hot Tub

Historic Farmhouse on Working VT Farm & Hot Tub
Woodstock
10.0 out of 10, Exceptional, (12 reviews)
"The perfect VT farm house. Felt very authentic and is incredibly historic!"
United States
Michael C.
Historic Farmhouse on Working VT Farm & Hot Tub
A spacious living area with a large sofa, a television, and a bookshelf.

13. Quechee Meadows Home with Hot Tub & Fire Pit

Quechee Meadows Home with Hot Tub & Fire Pit
Quechee
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful property, great layout for a big group."
United States
Anastasia S.
Quechee Meadows Home with Hot Tub & Fire Pit
A garden with a stone wall, ferns, and flowering plants.

14. Cozy private country setting - 15 miles from Woodstock

Cozy private country setting - 15 miles from Woodstock
Royalton
10.0 out of 10, Exceptional, (41 reviews)
" Very clean and newly remodeled. It was a great place to stay. Nice layout, location. Host is very responsive to questions."
United States
Brian
Cozy private country setting - 15 miles from Woodstock
A snow-covered building with a clock tower, surrounded by other buildings with balconies.

15. Okemo Mountain Lodging by Vail Resorts

Okemo Mountain Lodging by Vail Resorts
3.5 star property
Clock Tower Base Area
7.6 out of 10, Good, (31 reviews)
"The unit was very clean. However, there was a distinct musty/moldy smell throughout the unit as if had been sitting for quite sometime. We did bring a scented candle to help and was able to use the fireplace which also helped with the smell. All and all, for an older unit, the stay was not bad, the neighbors were great and it was peaceful aling with a beautiful view. We would like to stay there again."
United States
Patricia
Okemo Mountain Lodging by Vail Resorts
A spacious kitchen with a stone fireplace, large windows, and a dining area with a long wooden table and chairs.

16. Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont

Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont
Hartford
10.0 out of 10, Exceptional, (21 reviews)
"Probably the best VRBO property we’ve ever stayed in….. well appointed, thick towels, pancake griddle, BBQ grill…..and Games…… thanks for the memories!"
United States
Margaret S.
Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont
A large swimming pool with multiple lanes, surrounded by lounge chairs and umbrellas, with a building featuring a red facade and a covered area in the foreground.

17. Charming house w/ privacy, bbq, seasonal balcony, hammock, fire pit, w/d, wifi

Charming house w/ privacy, bbq, seasonal balcony, hammock, fire pit, w/d, wifi
Quechee
8.8 out of 10, Excellent, (6 reviews)
"Place was very clean, mattresses in very good condition and comfortable, clean linens."
United States
Joyce G.
Charming house w/ privacy, bbq, seasonal balcony, hammock, fire pit, w/d, wifi
A wooden deck in a forest with a staircase leading up to it.

18. Custom-built Tiny House on forested lot near Quechee

Custom-built Tiny House on forested lot near Quechee
Hartland
9.8 out of 10, Exceptional, (79 reviews)
"The property was as described. The only recommendation would be to put a shade in the bathroom. The hot tub was wonderful!!! We really enjoyed our stay. It is very close to Woodstock and other restaurants/shopping."
United States
Robert
Custom-built Tiny House on forested lot near Quechee
A large house with a fire pit and outdoor seating.

19. Pet Friendly | Game Room | Minutes to Woodstock and Killington

Pet Friendly | Game Room | Minutes to Woodstock and Killington
Bridgewater
10.0 out of 10, Exceptional, (3 reviews)
"Great house with fun decorations. Comfortable with lots of room; full kitchen with ample dining area. Loved the coffee available and the sound machine in the bedroom- great conveniences! Communication around booking were great with easy check in and check out."
United States
Susan S.
The price is AED 735
AED 1,917 total
includes taxes & fees
20 Oct - 21 Oct
Pet Friendly | Game Room | Minutes to Woodstock and Killington
A snow-covered deck with a wooden railing, a large window, and a tree in the background.

20. Quaint lakefront home with a fire pit and beautiful views

Quaint lakefront home with a fire pit and beautiful views
Ludlow
9.4 out of 10, Exceptional, (105 reviews)
"Cozy cabin and great location to okemo "
United States
Harry M.
Quaint lakefront home with a fire pit and beautiful views
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

Hotel Coolidge

Hotel Coolidge

10/10 Excellent
"Good rooms. Old hotel with unique character. Well located for dining venues."
joe 1-night trip
Posted 4 hours ago
Hotel Coolidge

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