Vacation Rentals in Windsor County

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Our top choices for Windsor County vacation rentals

Exterior

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is ￥86,423
￥161,969 total
includes taxes & fees
Apr 5 - Apr 6
Cozy Vermont Cabin · Mountain Views · Near Okemo
Outdoor pool, a heated pool

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (23 reviews)
"Amazing place! "
United States
Tara
The price is ￥48,093
￥84,387 total
includes taxes & fees
Apr 1 - Apr 2
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Property grounds

Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo
Woodstock
9.6 out of 10, Exceptional, (15 reviews)
"Cleanness, quiet, and friendly "
United States
Zhongchun
The price is ￥23,972
￥30,067 total
includes taxes & fees
Apr 1 - Apr 2
Treehouse at Wise Pines- NoBo
Interior

Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
10.0 out of 10, Exceptional, (9 reviews)
"Perfect size and location! "
United States
Lyn H.
The price is ￥19,237
￥35,324 total
includes taxes & fees
Apr 26 - Apr 27
Addie's Place: A Quiet and Quirky Guesthouse
House (5 Bedrooms) | Front of property

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is ￥235,335
￥339,224 total
includes taxes & fees
Apr 1 - Apr 2
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
Fridge, microwave, oven, stovetop

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (108 reviews)
"We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo."
United States
Hannah M.
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Indoor pool

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo
Okemo Village
10.0 out of 10, Exceptional, (12 reviews)
"We had a great time , the location was amazing and the owner responded very quickly for any questions or concerns "
United States
Thomas B.
The price is ￥31,902
￥78,982 total
includes taxes & fees
Apr 1 - Apr 2
Cozy Slopeside Escape - Ski-In/Out Condo at Okemo
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, (17 reviews)
"It was an amazing experience! "
United States
Gruha
The price is ￥27,269
￥48,848 total
includes taxes & fees
Apr 1 - Apr 2
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Indoor pool

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Okemo Village
10.0 out of 10, Exceptional, (64 reviews)
"The host is extremely friendly and accommodating! The place is large and didn’t feel cramped with two adults and five male teenagers! Perfect in every way, clean, well stocked, and easy access to the slopes!"
United States
Nina
The price is ￥80,155
￥144,920 total
includes taxes & fees
Apr 26 - Apr 27
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
Beautiful Village Home, Short Walk to Restaurants, Shops, On 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, (107 reviews)
"Great Condo. We had plenty of space. Wendi was very responsive and even accommodated us checking in an hour early when we arrived in town. We would definitely come back. "
United States
Barbara M.
The price is ￥22,123
￥46,025 total
includes taxes & fees
Apr 20 - Apr 21
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Smart TV, fireplace

Ski Haven: 1-Bed Ski-in/out Condo, Okemo Base Area

Ski Haven: 1-Bed Ski-in/out Condo, Okemo Base Area
Clock Tower Base Area
10.0 out of 10, Exceptional, (13 reviews)
"Great communication, ski in/out location"
United States
Robin
The price is ￥23,886
￥65,214 total
includes taxes & fees
Apr 5 - Apr 6
Ski Haven: 1-Bed Ski-in/out Condo, Okemo Base Area
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 ￥35,268
￥44,592 total
includes taxes & fees
Apr 12 - Apr 13
Okemo | Studio Condo + Loft | Near Slopes + Pool
Dining

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, (16 reviews)
"The house still smells new! Really clean and all the couches and chairs were comfortable. Great view of Okemo."
United States
Alex
The price is ￥47,772
￥102,168 total
includes taxes & fees
Apr 19 - Apr 20
New Ludlow Village Home with Stunning Okemo Mountain View
Dining

Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.6 out of 10, Exceptional, (18 reviews)
"House was in a perfect location. The town was adorable. "
United States
Michelle A.
The price is ￥33,344
￥67,689 total
includes taxes & fees
Apr 1 - Apr 2
Charming Chester Farmhouse near Near VT Slopes
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, (8 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is ￥19,798
￥45,696 total
includes taxes & fees
Apr 1 - Apr 2
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Property grounds

Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington
Stockbridge
10.0 out of 10, Exceptional, (4 reviews)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
The price is ￥35,974
￥81,148 total
includes taxes & fees
Apr 28 - Apr 29
Gnome Home Mountain Ski Chalet w/Sauna Killington
Outdoor dining

2BR Exec Condo + Close to All Amenities | Biking

2BR Exec Condo + Close to All Amenities | Biking
Jackson Gore Base Area
10.0 out of 10, Exceptional, (1 review)
"Best amenities at ski on/off at Okemo that we have stayed at. Condo is a great size too. Large common area allows for lots of quality time with family."
United States
John M.
The price is ￥92,178
￥113,895 total
includes taxes & fees
Apr 10 - Apr 11
2BR Exec Condo + Close to All Amenities | Biking
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, (1 review)
"House was perfect! Well appointed with everything you need. Beds very comfortable and very clean. Host was very responsive and was there if you needed anything. Will definitely stay again. "
United States
Stephen S.
The price is ￥36,070
￥97,315 total
includes taxes & fees
Apr 1 - Apr 2
Terrific 3-bedroom cottage with AC in charming Cavendish
4 bedrooms, free WiFi, bed sheets

Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups

Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups
Stockbridge
9.0 out of 10, Wonderful, (2 reviews)
"The host was very responsive! The house was very clean when we came and had everything we needed."
United States
Angela W.
The price is ￥54,993
￥158,419 total
includes taxes & fees
Apr 1 - Apr 2
Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups
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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

8/10 Good
"Have stayed here many times. Close to town and Okemo. Very convenient."
Richard 2-night trip
Posted 3 hours ago
Pointe at Castle Hill Resort

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Vacation Apartments in Windsor County

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