A river flowing through a forest with autumn foliage.

Windsor County Vacation Rentals

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Top Cities in Windsor County

A street with historic buildings, including a diner and a Blue Star Trading Company.
Vacation RentalsVacation Rentals

Ludlow

Ludlow

Our top choices for Windsor County vacation rentals

A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

1. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views! "
United States
Jessica
The price is CA $179
CA $272 total
includes taxes & fees
Nov 2 - Nov 3
Fat Sheep Farm & Cabins
A cozy living room with a sectional sofa, a fireplace, a flat-screen TV, and a bookshelf.

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

Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock
Hartford
10.0 out of 10, Exceptional, (178 reviews)
"Clean, well maintained property. Perfect decor for a quaint Vermont town."
United States
Joann
The price is CA $261
CA $608 total
includes taxes & fees
Oct 25 - Oct 26
Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock
A sunroom with wicker furniture, large windows, and string lights.

3. Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.6 out of 10, Exceptional, (19 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is CA $185
CA $331 total
includes taxes & fees
Oct 27 - Oct 28
Addie's Place: A Quiet and Quirky Guesthouse
A two-story house with a porch, surrounded by a well-maintained lawn and dense trees.

4. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
10.0 out of 10, Exceptional, (1 review)
"Swati, my host, helped me when I had difficulties with tech issues and my stay was as smooth as silk. Thanks!"
United States
Sylvia F.
The price is CA $171
CA $330 total
includes taxes & fees
Nov 3 - Nov 4
Bridgewater Living - Ben&Jerry Suite
A room with a large sliding glass door leading to a balcony with a wooden deck and a scenic view of the countryside.

5. 180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub

180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
Hartford
9.0 out of 10, Wonderful, (8 reviews)
"Plenty of room beautiful view"
United States
Anthony A.
The price is CA $407
CA $782 total
includes taxes & fees
Oct 26 - Oct 27
180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
A wooden cabin with large windows, a door, and a small porch with Adirondack chairs.

6. Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit

Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (54 reviews)
"The cabins are amazing, everything you need for a great weekend! I will be back for sure!"
United States
Joe C.
The price is CA $286
CA $582 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit
A person standing on a sandy beach by a river with trees in the background.

7. Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
10.0 out of 10, Exceptional, (1 review)
"The Cabin in the Woods looks very rustic on the outside, but a cabin ine the woods should. Inside was a pleasant surprise. Full kitchen, large leather wrap around sofa to watch the LARGE flat-screen TV, large dining room table, 4 bedrooms, and 2 full baths made this a perfect get away place."
United States
Alvin
The price is CA $420
CA $778 total
includes taxes & fees
Oct 19 - Oct 20
Cabin on the hill Ascutney Vt - 4 bedrooms
A stone fire pit with a fire burning in a garden setting.

8. Spacious home on picturesque grounds with stunning views. Quechee - Woodstock

Spacious home on picturesque grounds with stunning views. Quechee - Woodstock
Hartford
10.0 out of 10, Exceptional, (92 reviews)
"Excellent communication and gorgeous area"
United States
Lauren R.
The price is CA $1,280
CA $2,248 total
includes taxes & fees
Oct 19 - Oct 20
Spacious home on picturesque grounds with stunning views. Quechee - Woodstock
A picnic table and a fire pit by a lake with a forest in the background.

9. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is CA $213
CA $426 total
includes taxes & fees
Oct 15 - Oct 16
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A large indoor swimming pool with clear lanes, wooden beams, and seating areas.

10. Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8

Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
Hartford
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful and well appointed abode - super cozy!"
United States
Nina S.
The price is CA $422
CA $1,265 total
includes taxes & fees
Oct 28 - Oct 29
Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
A covered porch with wicker furniture, a table, and chairs.

11. Renovated Vermont Retreat with mountain views near Okemo & Killington for 8

Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is CA $253
CA $779 total
includes taxes & fees
Nov 4 - Nov 5
Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
A dining area with a wooden table, black chairs, a hanging light fixture, and a colorful rug.

12. Renovated Farmhouse between Woodstock & Killington

Renovated Farmhouse between Woodstock & Killington
Bridgewater
10.0 out of 10, Exceptional, (4 reviews)
"We only stayed there one night because our rental was not available. The property was very clean and bright. Great for short term stay."
United States
Irene M.
Renovated Farmhouse between Woodstock & Killington
A rustic cabin with a wooden deck, surrounded by dense greenery and a rocky landscape.

13. Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington
Stockbridge
10.0 out of 10, Exceptional, (7 reviews)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
The price is CA $336
CA $741 total
includes taxes & fees
Nov 2 - Nov 3
Gnome Home Mountain Ski Chalet w/Sauna Killington
A large house with a fire pit and outdoor seating.

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

Pet Friendly | Game Room | Minutes to Woodstock and Killington
Bridgewater
10.0 out of 10, Exceptional, (3 reviews)
"Great house with fun decorations. Comfortable with lots of room; full kitchen with ample dining area. Loved the coffee available and the sound machine in the bedroom- great conveniences! Communication around booking were great with easy check in and check out."
United States
Susan S.
The price is CA $337
CA $803 total
includes taxes & fees
Nov 3 - Nov 4
Pet Friendly | Game Room | Minutes to Woodstock and Killington
A compact kitchen with a refrigerator, stove, microwave, and sink.

15. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A two-story house with a deck, surrounded by dense forest.

16. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Chester
10.0 out of 10, Exceptional, (5 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is CA $767
CA $1,437 total
includes taxes & fees
Oct 19 - Oct 20
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
A spacious living room with a stone fireplace, wooden furniture, and large windows.

17. Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Plymouth
9.8 out of 10, Exceptional, (24 reviews)
"convenient to okemo"
United States
marcus l.
The price is CA $261
CA $960 total
includes taxes & fees
Nov 5 - Nov 6
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
A wooden deck with a hot tub, outdoor seating, and a view of a forested hillside.

18. Killington Cabin, Hot Tub & Foliage Views!

Killington Cabin, Hot Tub & Foliage Views!
Stockbridge
9.6 out of 10, Exceptional, (27 reviews)
"Everything was perfect!. Really enjoyed our stay"
United States
Kinshasa F.
Killington Cabin, Hot Tub & Foliage Views!
A wooden deck with a hot tub, outdoor seating, and a view of a forested hillside.

19. Killington Cabin, Hot Tub & Foliage Views!

Killington Cabin, Hot Tub & Foliage Views!
3.0 star property
Stockbridge
Killington Cabin, Hot Tub & Foliage Views!
A covered porch with white rocking chairs, a wooden deck, and a view of trees and hills.

20. 2BR Duplex Villa w/ Balcony | Game Room + Fire Pit

2BR Duplex Villa w/ Balcony | Game Room + Fire Pit
Brownsville
The price is CA $317
CA $401 total
includes taxes & fees
Nov 1 - Nov 2
2BR Duplex Villa w/ Balcony | Game Room + Fire Pit
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

Align Inn Vermont

Align Inn Vermont

10/10 Excellent
"Room was comfortable. Staff was very nice."
Bonny 1-night trip
Posted 1 hour ago
Align Inn Vermont

Find out more about Windsor County

Everything you need to know about Windsor County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor County vacation rentals we have selected for you start as low as CA $272 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor County rentals

At Expedia, we put the best Windsor County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.