Holiday Rentals in Windsor County

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Featured Holiday Rentals in Windsor County

Relax in a spacious living area with a brick fireplace, wicker chairs, and a sliding glass door to an outdoor space.

"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...

includes taxes & fees

28 Jul - 29 Jul

Relax in this spacious room with a brick fireplace, large windows, and a door to the outdoor pool area.

"The place was an ok place to "crash" after a day of out side activities. The rug needs to be replaced or shampooed. The beds are not very comfortable. "

includes taxes & fees

28 Jul - 29 Jul

Relax in this serene room with a backyard view, featuring a pool and a brick fireplace.

"The place is good. It was our first time here and enjoyed our stay. The brook overlooking our window made the day"

includes taxes & fees

28 Jul - 29 Jul

Enjoy meals in the spacious dining area adjacent to the kitchen, featuring a wooden table and chairs.

"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!"

Enjoy cooking in this well-equipped kitchen with a central island and stainless steel appliances.

"We celebrated my sister's 80th birthday at Blueberry Hill. It was very quiet, pleasant and perfect for our family."

includes taxes & fees

16 Jul - 17 Jul

Cozy retreat with a kitchenette, comfortable bed, and workspace.

includes taxes & fees

28 Jul - 29 Jul

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.

"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!!"

includes taxes & fees

20 Jul - 21 Jul

Enjoy a cozy atmosphere with a brick fireplace, large windows, and artwork-adorned walls.

"Very clean and easy access."

includes taxes & fees

16 Jul - 17 Jul

Cozy living room with a fireplace, comfortable seating, and a television.

Relax in this stylish living room with a flat-screen TV, entertainment unit, and comfortable seating area.

"Perfect location. Charming place to stay. Very clean. Great view of the creek."

includes taxes & fees

21 Jul - 22 Jul

Relax in this elegantly furnished living room with a tufted leather armchair, sofa, and classic coffee table.

"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!"

includes taxes & fees

20 Jul - 21 Jul

Enjoy cooking in this well-equipped kitchen with a microwave, oven, and dishwasher.

"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."

includes taxes & fees

16 Jul - 17 Jul

includes taxes & fees

4 Aug - 5 Aug

Cozy cabin with a warm atmosphere, featuring a comfortable seating area and a washing machine for added convenience.

includes taxes & fees

18 Jul - 19 Jul

Relax in the serene outdoor seating area surrounded by lush greenery and vibrant flowers.

"Great location. Beautiful house. All the amenties. We came up for a ski trip and it was perfect. "

includes taxes & fees

30 Jul - 31 Jul

Enjoy outdoor cooking on the UNITA deck, equipped with a grill and firewood.

"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."

Enjoy cooking in this well-equipped kitchen with a central island, appliances, and ample countertop space.

"Great location and house was very nice."

includes taxes & fees

17 Jul - 18 Jul

Enjoy cooking in this well-equipped kitchen with a central island, microwave, oven, and refrigerator.

"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. "

includes taxes & fees

27 Jul - 28 Jul

Stunning two-story home with a cozy front porch and white picket fence.

"We had a great stay at this home for a long weekend skiing at Okemo. "

includes taxes & fees

17 Jul - 18 Jul

Enjoy a serene forest view from this deck with a table and chairs, shaded by an umbrella.

includes taxes & fees

16 Jul - 17 Jul

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Find out more about Windsor County

Holiday Homes in Windsor County

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Recent reviews in Windsor County

5/5 Excellent

"Helpfulness of the staff was first class"

A verified traveller stayed at On The River Inn

Posted 1 day ago

5/5 Excellent

"This is a lovely property in the town of Woodstock. We enjoyed our time there (and all the space in our room!). I left something in our room and did not realize it until the next day. I called the property to ask if anything had been found. They soon got back to me that they had my item and would mail it to me - which they did. I'm extremely grateful!"

A verified traveller stayed at The Shire Woodstock

Posted 4 days ago

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Holiday Rentals in Windsor County

Change your mind

Treat yourself

Be picky

Featured Holiday Rentals in Windsor County

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

Cedarbrook Hotel Room 2 Doubles 119

116 Two Double bed Standard Hotel room

Cozy Cavendish Bunk minutes to Okemo

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Sleep Woodstock - 2 Double Beds - Dog Friendly

Two Double bed Standard Hotel room 218

Two Double bed Standard Hotel room 219

Sleep Woodstock - Deluxe Suite

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

Whimsical Room & Private Bathroom in Historic Inn

The Bridgewater House | Game Room | Hiking | Golf

Acres & Views! Firepit, BBQ | Bayley Way Getaway

Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

Charming Chester Farmhouse – peaceful and close to everything!

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

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

WhiSki Cabin - 12 Acres With a Mountain View!

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

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

Find out more about Windsor County

Holiday Homes in Windsor County

Recent reviews in Windsor County

On The River Inn

The Quechee Inn at Marshland Farm

Sleep Woodstock Motel

Lincoln Inn & Gallery

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Fullerton Inn

The Shire Woodstock

Norwich Inn

Align Inn Vermont