Windsor County Holiday Rentals

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Featured Windsor County Holiday Rentals

Queen Studio on the 2nd floor with outdoor heated pool 207
Relax in a spacious living area with a brick fireplace, wicker chairs, and a sliding glass door to an outdoor space.

Queen Studio on the 2nd floor with outdoor heated pool 207

8.0 out of 10, Very good, (5)
"Overall a good option for a visit to Killington if you don’t need to be on the access road. The outdoor heated pool was a really nice way to relax after a day of skiing. If you don’t want to drive, there is a pretty good restaurant across the street. The only slight concern is if more units than unit 207 are listed on VRBO (the unit we stayed in). I’m glad we had an upstairs unit because the floor was very squeaky. I was wondering if it was annoying the unit below us. With that minor detail...
The price is HK$816
HK$1,234 total
includes taxes & fees
28 Jul - 29 Jul
Queen Studio on the 2nd floor with outdoor heated pool 207
116 Two Double bed Standard Hotel room
Relax in this serene room with a backyard view, featuring a pool and a brick fireplace.

116 Two Double bed Standard Hotel room

8.6 out of 10, Excellent, (10)
"The place is good. It was our first time here and enjoyed our stay. The brook overlooking our window made the day"
The price is HK$816
HK$1,234 total
includes taxes & fees
27 Jul - 28 Jul
116 Two Double bed Standard Hotel room
118 Two Double bed Standard Hotel room
Relax by the serene pool surrounded by lush greenery and cherry blossom trees.

118 Two Double bed Standard Hotel room

9.0 out of 10, Wonderful, (2)
"We love staying here. So close to Killington, but also convenient. Clean, well maintained, and nicely furnished. Beautiful creek."
The price is HK$816
HK$1,234 total
includes taxes & fees
29 Jul - 30 Jul
118 Two Double bed Standard Hotel room
Two Double bed Standard Hotel room 218
Relax in this spacious room with a high ceiling, large windows, and a brick fireplace, offering a view of the backyard with a swimming pool and barbecue area.

Two Double bed Standard Hotel room 218

7.0 out of 10, Good, (2)
"The room was nice, clean and comfortable, but there was no coffee maker, no refrigerator, no microwave... we couldn't even make hot water in our room, let alone coffee. There wasn't even any coffee available in the lobby/office area in the morning! We had a restful stay, but if you're a morning coffee drinker, make sure you plan ahead for no coffee availability at all!!"
The price is HK$816
HK$1,236 total
includes taxes & fees
17 Aug - 18 Aug
Two Double bed Standard Hotel room 218
Cozy Cavendish Bunk minutes to Okemo
Enjoy meals in the spacious dining area adjacent to the kitchen, featuring a wooden table and chairs.

Cozy Cavendish Bunk minutes to Okemo

9.8 out of 10, Exceptional, (6)
"Very cozy and had all the essentials we needed for our trip! Check in and check out were easy, and it was perfect for our winter trip. It's a short drive to Okemo, which is super convenient - would definitely stay here again!"
The price is HK$989
HK$1,873 total
includes taxes & fees
27 Jul - 28 Jul
Cozy Cavendish Bunk minutes to Okemo
Two Double bed Standard Hotel room 219
Enjoy a cozy atmosphere with a brick fireplace, large windows, and artwork-adorned walls.

Two Double bed Standard Hotel room 219

7.6 out of 10, Good, (4)
"Very clean and easy access."
The price is HK$816
HK$1,234 total
includes taxes & fees
3 Aug - 4 Aug
Two Double bed Standard Hotel room 219
Sleep Woodstock - 2 Double Beds - Dog Friendly
Cozy retreat with a kitchenette, comfortable bed, and workspace.

Sleep Woodstock - 2 Double Beds - Dog Friendly

The price is HK$1,071
HK$1,503 total
includes taxes & fees
7 Aug - 8 Aug
Sleep Woodstock - 2 Double Beds - Dog Friendly
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Enjoy cooking in this well-equipped kitchen with a central island and stainless steel appliances.

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

9.4 out of 10, Exceptional, (16)
"We celebrated my sister's 80th birthday at Blueberry Hill. It was very quiet, pleasant and perfect for our family."
The price is HK$1,436
HK$4,343 total
includes taxes & fees
21 Jul - 22 Jul
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Whimsical Room & Private Bathroom in Historic Inn
Relax in this elegantly furnished living room with a tufted leather armchair, sofa, and classic coffee table.

Whimsical Room & Private Bathroom in Historic Inn

8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
The price is HK$1,091
HK$1,697 total
includes taxes & fees
20 Jul - 21 Jul
Whimsical Room & Private Bathroom in Historic Inn
Okemo's Back Room - in the heart of the village on the shuttle route!
Relax in this stylish living room with a flat-screen TV, entertainment unit, and comfortable seating area.

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

9.6 out of 10, Exceptional, (14)
"Perfect location. Charming place to stay. Very clean. Great view of the creek."
The price is HK$816
HK$2,572 total
includes taxes & fees
30 Jul - 31 Jul
Okemo's Back Room - in the heart of the village on the shuttle route!
The Bridgewater House | Game Room | Hiking | Golf
Enjoy cooking in this well-equipped kitchen with a microwave, oven, and dishwasher.

The Bridgewater House | Game Room | Hiking | Golf

9.4 out of 10, Exceptional, (6)
"My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington."
The price is HK$1,711
HK$4,545 total
includes taxes & fees
21 Jul - 22 Jul
The Bridgewater House | Game Room | Hiking | Golf
Acres & Views! Firepit, BBQ | Bayley Way Getaway
Terrace/patio

Acres & Views! Firepit, BBQ | Bayley Way Getaway

The price is HK$1,832
HK$5,211 total
includes taxes & fees
4 Aug - 5 Aug
Acres & Views! Firepit, BBQ | Bayley Way Getaway
Ski/MTB Home with Mountain Views near Killington/Woodstock/Green Mountain Trails
Enjoy outdoor cooking on the UNITA deck, equipped with a grill and firewood.

Ski/MTB Home with Mountain Views near Killington/Woodstock/Green Mountain Trails

10.0 out of 10, Exceptional, (2)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
The price is HK$1,845
HK$4,835 total
includes taxes & fees
4 Aug - 5 Aug
Ski/MTB Home with Mountain Views near Killington/Woodstock/Green Mountain Trails
WhiSki Cabin - 12 Acres With a Mountain View!
Enjoy cooking in this well-equipped kitchen with a central island, microwave, oven, and refrigerator.

WhiSki Cabin - 12 Acres With a Mountain View!

10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. "
The price is HK$4,232
HK$7,834 total
includes taxes & fees
18 Jul - 19 Jul
WhiSki Cabin - 12 Acres With a Mountain View!
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Enjoy cooking in this well-equipped kitchen with a central island, appliances, and ample countertop space.

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

9.8 out of 10, Exceptional, (100)
"Great location and house was very nice."
The price is HK$1,562
HK$3,290 total
includes taxes & fees
21 Jul - 22 Jul
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Charming Chester Farmhouse – peaceful and close to everything!
Relax in the serene outdoor seating area surrounded by lush greenery and vibrant flowers.

Charming Chester Farmhouse – peaceful and close to everything!

9.6 out of 10, Exceptional, (11)
"Great location. Beautiful house. All the amenties. We came up for a ski trip and it was perfect. "
The price is HK$1,688
HK$3,394 total
includes taxes & fees
4 Aug - 5 Aug
Charming Chester Farmhouse – peaceful and close to everything!
NEW Hot Tub/Lakeview/Pool Table/Okemo Ski House
Enjoy a serene forest view from this deck with a table and chairs, shaded by an umbrella.

NEW Hot Tub/Lakeview/Pool Table/Okemo Ski House

The price is HK$3,234
HK$7,167 total
includes taxes & fees
21 Jul - 22 Jul
NEW Hot Tub/Lakeview/Pool Table/Okemo Ski House
Beautifully Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Stunning two-story home with a cozy front porch and white picket fence.

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

9.8 out of 10, Exceptional, (84)
"We had a great stay at this home for a long weekend skiing at Okemo. "
The price is HK$1,586
HK$3,316 total
includes taxes & fees
21 Jul - 22 Jul
Beautifully Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
RoundTop Chalet- Hot Tub, Grill, Hiking!
Outdoor spa tub

RoundTop Chalet- Hot Tub, Grill, Hiking!

The price is HK$1,898
HK$4,962 total
includes taxes & fees
5 Aug - 6 Aug
RoundTop Chalet- Hot Tub, Grill, Hiking!
New Ludlow Village Home with Stunning Okemo Mountain View
Enjoy cooking in this well-lit kitchen with an oven, stainless steel dishwasher, and a convenient island with sink and countertop.

New Ludlow Village Home with Stunning Okemo Mountain View

10.0 out of 10, Exceptional, (6)
"Beautiful and clean place near Okemo with everything you need. "
The price is HK$2,812
HK$5,572 total
includes taxes & fees
28 Jul - 29 Jul
New Ludlow Village Home with Stunning Okemo Mountain View
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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