Windsor Holiday House Rentals from AU$424: Search Holiday Homes

A snow-covered river valley with a bridge and a town.

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Our top choices for Windsor holiday homes

A cozy living room with a sectional sofa, a fireplace, a flat-screen TV, and a bookshelf.

1. Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock

Hartford

Joann

includes taxes & fees

25 Oct - 26 Oct

A room with a bunk bed, a dresser, a lamp, and a window with a view of greenery.

2. Peaceful Stay w/ Pond & Massage Chair | Near Okemo

Ludlow

includes taxes & fees

5 Oct - 6 Oct

A room with a large sliding glass door leading to a balcony with a wooden deck and a scenic view of the countryside.

3. 180-degree panoramic views of Vermont's mountains from the living room and Deck

Hartford

Anthony A.

includes taxes & fees

26 Oct - 27 Oct

A wooden cabin with a balcony, surrounded by trees.

4. Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Newport

Naydene G.

includes taxes & fees

12 Oct - 13 Oct

A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

5. Lakefront Family Fun Retreat

Newport

Ann R.

includes taxes & fees

3 Nov - 4 Nov

A large house with a fire pit and outdoor seating.

6. Pet Friendly | Game Room | Minutes to Woodstock and Killington

Bridgewater

Susan S.

includes taxes & fees

1 Nov - 2 Nov

A two-story house with a deck, surrounded by dense forest.

7. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

Chester

pauline

includes taxes & fees

5 Oct - 6 Oct

A yellow building with a porch and a sign that reads "Brook Road Inn."

8. Brook Road Condo

Goshen

Meghan B.

includes taxes & fees

19 Oct - 20 Oct

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Top Windsor Hotel Reviews

Align Inn Vermont

10/10 Excellent

"Great place"

The Shire Woodstock

10/10 Excellent

"We had Deluxe King River view - deluxe has a fireplace and shares a balcony with rocking chairs. The room was great except a couple little maintenance issues (I told the front desk and hope they fix). And it’s a great location walkable to downtown, great views of river and hills, and the inn has fire pits ready to go. Too bad coffee makers are in the hallway, not in the room, and there’s no breakfast (they said they might start next year). We went nearby for breakfast, and a good market is just across the street."

White River Inn and Suites

10/10 Excellent

"My room was cozy, quiet, and clean. It was a restful stay, and was much-needed during my business trip. Special shout-out to Tianna at the front desk; she was so kind, helpful, and always had a smile on her face. Every time I passed by, she'd greet me with a warm, "hello!" I will happily stay here again for future business trips!"

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"My daughter and I were looking for someplace to meet in the middle… one coming from upstate New York and one coming from Massachusetts.This was not the first hotel we looked at. Fortunately it is the one we stayed at! The facility is very nice, even though older still very well maintained. Staff was exceptional! The location was perfect for just a fun getaway weekend. The downtown area has some lovely restaurants and shops but the restaurant at the resort was also very good. We enjoyed the area so much. We're talking about going again in the winter, even though neither of us have skied in ages!"

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews	357
Accommodation	811 Holiday Homes
Lowest Price	AU$424
Highest Price	AU$1,428

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor holiday homes

1. Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock

2. Peaceful Stay w/ Pond & Massage Chair | Near Okemo

3. 180-degree panoramic views of Vermont's mountains from the living room and Deck