Holiday Rentals in Windsor County

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Featured Holiday Rentals in Windsor County

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

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 €139
includes taxes & fees
27 Jul - 28 Jul
Queen Studio on the 2nd floor with outdoor heated pool 207
116 Two Double bed Standard Hotel room
Interior

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"
116 Two Double bed Standard Hotel room
118 Two Double bed Standard Hotel room
Pool

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."
118 Two Double bed Standard Hotel room
Two Double bed Standard Hotel room 218
Interior

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 €139
includes taxes & fees
20 Jul - 21 Jul
Two Double bed Standard Hotel room 218
Cozy Cavendish Bunk minutes to Okemo
Interior

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 €210
includes taxes & fees
20 Jul - 21 Jul
Cozy Cavendish Bunk minutes to Okemo
Two Double bed Standard Hotel room 219
Interior

Two Double bed Standard Hotel room 219

7.6 out of 10, Good, (4)
"Very clean and easy access."
The price is €139
includes taxes & fees
18 Aug - 19 Aug
Two Double bed Standard Hotel room 219
Sleep Woodstock - 2 Double Beds - Dog Friendly
Iron/ironing board, travel cot, WiFi, bed sheets

Sleep Woodstock - 2 Double Beds - Dog Friendly

The price is €169
includes taxes & fees
7 Aug - 8 Aug
Sleep Woodstock - 2 Double Beds - Dog Friendly
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Fridge, microwave, oven, stovetop

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 €492
includes taxes & fees
28 Jul - 29 Jul
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Whimsical Room & Private Bathroom in Historic Inn
Interior

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 €191
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!
Interior

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 €282
includes taxes & fees
21 Jul - 22 Jul
Okemo's Back Room - in the heart of the village on the shuttle route!
The Bridgewater House | Game Room | Hiking | Golf
Fridge, microwave, oven, stovetop

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 €497
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 €584
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
Terrace/patio

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 €554
includes taxes & fees
5 Aug - 6 Aug
Ski/MTB Home with Mountain Views near Killington/Woodstock/Green Mountain Trails
WhiSki Cabin - 12 Acres With a Mountain View!
Fridge, microwave, oven, stovetop

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 €870
includes taxes & fees
31 Jul - 1 Aug
WhiSki Cabin - 12 Acres With a Mountain View!
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Fridge, microwave, oven, stovetop

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 €354
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!
Terrace/patio

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 €381
includes taxes & fees
4 Aug - 5 Aug
Charming Chester Farmhouse – peaceful and close to everything!
NEW Hot Tub/Lakeview/Pool Table/Okemo Ski House
Outdoor dining

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

The price is €800
includes taxes & fees
22 Jul - 23 Jul
NEW Hot Tub/Lakeview/Pool Table/Okemo Ski House
Beautifully Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Exterior

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 €418
includes taxes & fees
29 Jul - 30 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 €593
includes taxes & fees
23 Jul - 24 Jul
RoundTop Chalet- Hot Tub, Grill, Hiking!
New Ludlow Village Home with Stunning Okemo Mountain View
Fridge, microwave, oven, stovetop

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 €477
includes taxes & fees
1 Aug - 2 Aug
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free