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, (15 reviews)
"This property was extremely beautiful and peaceful. Loved being able to walk around the farm and say hi to the animals. The views of the mountains from the cabin or gorgeous, we enjoyed having our coffee on the porch each morning. Having fresh eggs and scones in our cabin upon arrival was a very nice surprise. Will definitely be staying there again."
United States
Brenda
The price is CA $158
CA $248 total
includes taxes & fees
Nov 17 - Nov 18
Fat Sheep Farm & Cabins
A sunroom with wicker furniture, large windows, and string lights.

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

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.6 out of 10, Exceptional, (21 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is CA $210
CA $328 total
includes taxes & fees
Nov 16 - Nov 17
Addie's Place: A Quiet and Quirky Guesthouse
A grassy backyard with a white fence, a wooden deck, and a house.

3. 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 $151
CA $284 total
includes taxes & fees
Nov 8 - Nov 9
Bridgewater Living - Ben&Jerry Suite
A wooden deck with a covered seating area, a grill, and string lights.

4. Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (16 reviews)
"Our stay in this tiny home was perfect! Very cozy and private. The host was very responsive and everything was exactly as described."
United States
Kat V.
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
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
9.2 out of 10, Wonderful, (9 reviews)
"Plenty of room beautiful view"
United States
Anthony A.
The price is CA $395
CA $720 total
includes taxes & fees
Nov 8 - Nov 9
180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
A cabin interior with a wooden staircase, a kitchen with modern appliances, and large windows offering a forest view.

6. Cozy Resort Cabin! Hot-Tub Sauna Fire Pit Trails

Cozy Resort Cabin! Hot-Tub Sauna Fire Pit Trails
Cavendish
10.0 out of 10, Exceptional, (58 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 $281
CA $559 total
includes taxes & fees
Nov 11 - Nov 12
Cozy Resort Cabin! Hot-Tub Sauna Fire Pit Trails
A cozy living room with a leather couch, a fireplace, and a television.

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 $414
CA $726 total
includes taxes & fees
Nov 9 - Nov 10
Cabin on the hill Ascutney Vt - 4 bedrooms
A red house with a gravel driveway and lush greenery.

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

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is CA $296
CA $835 total
includes taxes & fees
Nov 8 - Nov 9
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A modern kitchen with stainless steel appliances, a wooden dining table set for four, and a seating area with a sofa and chairs.

9. Cozy Village Condo-Okemo Shuttle

Cozy Village Condo-Okemo Shuttle
Ludlow
9.8 out of 10, Exceptional, (89 reviews)
"Great place to stay, very easy to get to. A cozy and comfortable place, that is always clean. There are postings and labels throughout, which is very helpful. Hosts are great and make the experience very easy. Oh and the bed is amazing!!"
United States
Vanessa W.
The price is CA $118
CA $356 total
includes taxes & fees
Nov 8 - Nov 9
Cozy Village Condo-Okemo Shuttle
A backyard with a hot tub, fire pit, and outdoor seating.

10. Brookside Cabin + Hot Tub | Woodstock & Killington

Brookside Cabin + Hot Tub | Woodstock & Killington
Bridgewater
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful property on a nice quiet stream. House was super clean and had everything we needed. We took the dogs and they had fun with us around town and playing in the stream."
United States
tom b.
Brookside Cabin + Hot Tub | Woodstock & Killington
A large house with a fire pit and outdoor seating.

11. 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, (4 reviews)
"We loved the farmhouse. It was very charming and cozy. Plenty of space for us and exactly as advertised. We would definitely stay here again. Thank you"
United States
Lisa G.
The price is CA $303
CA $692 total
includes taxes & fees
Nov 22 - Nov 23
Pet Friendly | Game Room | Minutes to Woodstock and Killington
A modern cabin with a deck, surrounded by a forest.

12. 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 $436
CA $1,211 total
includes taxes & fees
Nov 10 - Nov 11
Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
A cozy living room with a fireplace, a black leather sofa, and a television mounted above it.

13. Village Fireplace Shuttle Boot Warmers

Village Fireplace Shuttle Boot Warmers
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
"Great location right in town and close to Okemo."
United States
Justin P.
The price is CA $252
CA $581 total
includes taxes & fees
Nov 22 - Nov 23
Village Fireplace Shuttle Boot Warmers
A covered porch with wicker furniture, a table, and chairs.

14. Renovated Vermont Retreat with mountain views near Okemo & Killington for 6

Renovated Vermont Retreat with mountain views near Okemo & Killington for 6
Cavendish
10.0 out of 10, Exceptional, (3 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 $227
CA $700 total
includes taxes & fees
Nov 9 - Nov 10
Renovated Vermont Retreat with mountain views near Okemo & Killington for 6
A rustic cabin with a wooden deck, surrounded by dense greenery and a rocky landscape.

15. 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 $307
CA $638 total
includes taxes & fees
Nov 8 - Nov 9
Gnome Home Mountain Ski Chalet w/Sauna Killington
A rectangular pool with a glass enclosure, surrounded by lounge chairs and umbrellas, set in a landscaped area with trees.

16. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (26 reviews)
"Great location, and comfortable for the whole family. Everyone in the enjoyed the open living room and dining room, plus the privacy of their own bedroom space. "
United States
Ania H.
The price is CA $421
CA $719 total
includes taxes & fees
Nov 8 - Nov 9
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
A cozy living room with a brick fireplace, comfortable seating, and large windows offering a view of the outdoors.

17. Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Bridgewater
8.8 out of 10, Excellent, (3 reviews)
"Great place for a ski weekend"
United States
Kathryn F.
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

18. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
The price is CA $81
CA $315 total
includes taxes & fees
Nov 12 - Nov 13
Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge
A multi-story building with a central staircase, outdoor picnic tables, and a clear sky.

19. 2BR Duplex Villa w/ Balcony | Game Room + Fire Pit

2BR Duplex Villa w/ Balcony | Game Room + Fire Pit
Brownsville
The price is CA $326
CA $391 total
includes taxes & fees
Nov 10 - Nov 11
2BR Duplex Villa w/ Balcony | Game Room + Fire Pit
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (114 reviews)
"Wendi was very responsive when I had questions. We enjoyed our weekend getaway. Great location we walked into town to the Farmers Market Sunday."
United States
Tina l.
The price is CA $288
CA $647 total
includes taxes & fees
Nov 17 - Nov 18
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
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

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Fantastic stay at Woodstock Inn this week! The room and property were spotless, and the staff was incredibly kind and welcoming. The spa was beautiful, the food at Red Rooster was excellent, and the athletic center, pool, and hot tub were all great. The entire property has a quiet, peaceful atmosphere that makes it easy to relax and unwind. Would absolutely recommend!"
Alexander 3-night trip
Posted 6 hours ago
Woodstock Inn & Resort

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 $248 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.