A river flowing through a forest with autumn foliage.

Windsor County Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Our top choices for Windsor County holiday rentals

Terrace/patio

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (13 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is HK$1,266
HK$2,604 total
includes taxes & fees
30 Jul - 31 Jul
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Interior

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (20 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
The price is HK$1,376
HK$2,445 total
includes taxes & fees
28 Jul - 29 Jul
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Interior

Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.6 out of 10, Exceptional, (13 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is HK$1,176
HK$2,029 total
includes taxes & fees
4 Aug - 5 Aug
Addie's Place: A Quiet and Quirky Guesthouse
Property grounds

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

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"Lots of steps but great space. Blankets were dirty, which was the only downside. "
United States
serena m.
The price is HK$585
HK$2,088 total
includes taxes & fees
25 Jul - 26 Jul
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
TV

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Plymouth
9.8 out of 10, Exceptional, (24 reviews)
"convenient to okemo"
United States
marcus l.
The price is HK$1,441
HK$5,423 total
includes taxes & fees
25 Jul - 26 Jul
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Property grounds

Beautiful 3-bedroom house with AC in charming Bridgewater

Beautiful 3-bedroom house with AC in charming Bridgewater
Bridgewater
The price is HK$1,361
HK$3,852 total
includes taxes & fees
27 Jul - 28 Jul
Beautiful 3-bedroom house with AC in charming Bridgewater
TV, DVD player

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"The slope side condo was wonderful, warm and had everything we needed. Thank you, Amy"
United States
AMY K.
The price is HK$412
HK$1,831 total
includes taxes & fees
27 Jul - 28 Jul
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Exterior

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
9.0 out of 10, Wonderful, (26 reviews)
"Great location - walkable to small town. Very close drive to slopes"
United States
Keath
The price is HK$823
HK$2,066 total
includes taxes & fees
3 Aug - 4 Aug
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
TV

Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Very clean and comfortable for our family of 4. Great ski-in/ski-out location - easily accessible to all lifts. Highly recommend. "
United States
Carey S.
The price is HK$1,095
HK$3,487 total
includes taxes & fees
28 Jul - 29 Jul
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
TV, DVD player, books, video library

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
The price is HK$445
HK$2,271 total
includes taxes & fees
3 Aug - 4 Aug
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Golf

Well-appointed studio right downtown - less than a mile to Okemo Mountain

Well-appointed studio right downtown - less than a mile to Okemo Mountain
Ludlow
8.8 out of 10, Excellent, (13 reviews)
"This place was so close to Okemo, and walking distance to the local pub and restaurants."
United States
Brian
The price is HK$782
HK$2,421 total
includes taxes & fees
28 Jul - 29 Jul
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Golf

Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (33 reviews)
"the home was clean and very nice. "
United States
Frank R.
The price is HK$782
HK$1,818 total
includes taxes & fees
4 Aug - 5 Aug
Efficient condo near slopes with kitchenette & great location
Exterior

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
The price is HK$1,558
HK$5,261 total
includes taxes & fees
29 Jul - 30 Jul
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Interior

Ski Home/Arcade Mountain Views Near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
The price is HK$1,143
HK$4,725 total
includes taxes & fees
27 Jul - 28 Jul
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Interior

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is HK$2,227
HK$3,505 total
includes taxes & fees
28 Jul - 29 Jul
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Outdoor dining

Okemo | Studio Condo + Loft | Near Slopes + Pool

Okemo | Studio Condo + Loft | Near Slopes + Pool
Jackson Gore Base Area
10.0 out of 10, Exceptional, (2 reviews)
"Very conveinent check in, nice property."
United States
michael
The price is HK$1,626
HK$2,076 total
includes taxes & fees
30 Jul - 31 Jul
Okemo | Studio Condo + Loft | Near Slopes + Pool
Interior

Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is HK$1,764
HK$4,707 total
includes taxes & fees
26 Jul - 27 Jul
Terrific 3-bedroom cottage with AC in charming Cavendish
Terrace/patio

Okemo's Back Room - in the heart of the village on the shuttle route!

Okemo's Back Room - in the heart of the village on the shuttle route!
Ludlow
9.6 out of 10, Exceptional, (16 reviews)
"Cool building, right on main street. Building is undergoing renovation on back porches so some construction material and disruption. The kitchen was not well equiped and needs an update. However, the space is really cool, very open, big bedrooms, decent bedding. Shower is a little small but nice. Good value"
United States
jonathan w.
The price is HK$1,270
HK$3,154 total
includes taxes & fees
27 Jul - 28 Jul
Okemo's Back Room - in the heart of the village on the shuttle route!
Smart TV, fireplace, books

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
"Great location right in town and close to Okemo."
United States
Justin P.
The price is HK$1,474
HK$2,747 total
includes taxes & fees
17 Aug - 18 Aug
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Beach

Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
The price is HK$2,061
HK$3,959 total
includes taxes & fees
27 Jul - 28 Jul
Cabin on the hill Ascutney Vt - 4 bedrooms
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor County Hotel Reviews

Align Inn Vermont

Align Inn Vermont

8/10 Good
"A little dated but clean. staff was nice and helpful"
Chris 1-night trip
Posted 11 hours ago
Align Inn Vermont