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Apr 17 - Apr 19

Top Cities in Windsor County

Woodstock featuring a house
Cabin RentalsCabin Rentals

Woodstock

Woodstock

Our top choices for Windsor County cabin rentals

Exterior detail
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

Cabin in Ludlow

Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore
10.0 out of 10, Exceptional, (96)
"Weather was great we enjoyed our stay. Very clean & comfortable."
United States
James h.
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore
Exterior
Luxurious Mountain Cabin near Okemo with High-End Modern Amenities for up to 12

Cabin in Ludlow

Luxurious Mountain Cabin near Okemo with High-End Modern Amenities for up to 12
10.0 out of 10, Exceptional, (88)
"Second time staying here—it’s a wonderful spot!"
United States
Paul T.
Luxurious Mountain Cabin near Okemo with High-End Modern Amenities for up to 12
Exterior
The Cabin that brings people together

Cabin in Bridgewater

The Cabin that brings people together
9.6 out of 10, Exceptional, (82)
"This was our 3rd visit for an annual family reunion. Nice house with great space, and the yard is a great space to really spread out. The manager is very responsive and checks in periodically; they really want you to have a great stay. I highly recommend this vacation rental, and we’ll be back!"
United States
Peter L.
The Cabin that brings people together
Exterior
Amazing home on 90 acres - AC, fireplace & great mountain views

Cabin in Quechee

Amazing home on 90 acres - AC, fireplace & great mountain views
9.0 out of 10, Wonderful, (45)
"It was in the woods but close to shops also. It was peaceful. We loved the covered screened in porch."
United States
Cherry H.
Amazing home on 90 acres - AC, fireplace & great mountain views
Exterior
Countryside, lakefront cabin with kayaks, stone fireplace, balcony, & fast WiFi

Cabin in Ludlow

Countryside, lakefront cabin with kayaks, stone fireplace, balcony, & fast WiFi
9.0 out of 10, Wonderful, (22)
"Wonderful house and property for activity as well as relaxation. "
United States
Paula M.
Countryside, lakefront cabin with kayaks, stone fireplace, balcony, & fast WiFi
Exterior
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Cabin in Cavendish

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
2.0 star property
10.0 out of 10, Exceptional, (11)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
$361 nightly
The price is $395
Jan 7 - Jan 8, 2026
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Exterior
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Cabin in Ludlow

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
9.8 out of 10, Exceptional, (181)
"Great stay, for a golf trip with 12 guys, there was plenty of room for everyone, would definitely recommend and will be trying to come back and stay as well!"
United States
Matt C.
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Exterior
Treehouse at Wise Pines- SoBo

Cabin in Woodstock

Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, (24)
"I was on an adventure with my young daughter and was looking for something unique. This was perfect. The common building was beautiful and had a great bathroom and other amenities if needed."
United States
scott b.
$171 nightly
The price is $187
Jan 7 - Jan 8, 2026
Total with taxes and fees
Treehouse at Wise Pines- SoBo
Exterior detail
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Cabin in Cavendish

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
10.0 out of 10, Exceptional, (32)
"We really enjoyed our stay. Beautiful cabins with plenty of space for the two of us. Nice treats when we arrived! Very good communication with our host. And very private. We really enjoyed the hot tub!"
United States
Wayne U.
$361 nightly
The price is $395
Jan 7 - Jan 8, 2026
Total with taxes and fees
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Exterior
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Cabin in Chester

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
10.0 out of 10, Exceptional, (23)
"Loved being tucked away in the wilderness. Owners were very responsive. "
United States
Katy B.
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Exterior
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

Cabin in Ludlow

Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
9.8 out of 10, Exceptional, (144)
"We enjoyed our stay at the chalet! "
United States
Kimberly R.
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Exterior
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Cabin in Sharon

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
10.0 out of 10, Exceptional, (3)
"Very welcoming, awesome weekend getaway."
United States
Zachary B.
$252 nightly
The price is $282
Jan 13 - Jan 14, 2026
Total with taxes and fees
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Exterior
Cozy Log Cabin Short Drive to Okemo & Killington

Cabin in Cavendish

Cozy Log Cabin Short Drive to Okemo & Killington
9.8 out of 10, Exceptional, (6)
"The hosts were as great as the place. The cabin was nicely furnished and sitting by the stream was so pleasant I never got to try out the swing on the porch. I would highly recommend this rental."
United States
beth T.
Cozy Log Cabin Short Drive to Okemo & Killington
Exterior
The Little Red Cabin! Less than 15 minutes to Okemo! Close to Everything VT!

Cabin in Cavendish

The Little Red Cabin! Less than 15 minutes to Okemo! Close to Everything VT!
9.8 out of 10, Exceptional, (113)
"Cabin was very clean with that back woods rustic appeal. Great place to get away and be one with nature. "
United States
ERIC G.
The Little Red Cabin! Less than 15 minutes to Okemo! Close to Everything VT!
Exterior
Spacious 5-bedroom cabin in charming Chester

Cabin in Chester

Spacious 5-bedroom cabin in charming Chester
Spacious 5-bedroom cabin in charming Chester
Exterior
Private 3-bedroom cabin with WiFi and backyard!

Cabin in Springfield

Private 3-bedroom cabin with WiFi and backyard!
10.0 out of 10, Exceptional, (1)
"Wonderful stay at this cabin! Large yard fairly closed off with trees that leaves room to run around! Pictures don’t do the property justice! Very kid/family friendly and very accommodating with a stocked up kitchen, lots of games in the living room, and really simple check out. Hosts gave us a list of great local spots and had a whole binder full of take out menus, tidbits for the house, and activities for the area. "
United States
Benjamin W.
Private 3-bedroom cabin with WiFi and backyard!
Exterior detail
Sage House at Camp Greenwood Vermont with Sauna

Cabin in Chester

Sage House at Camp Greenwood Vermont with Sauna
10.0 out of 10, Exceptional, (3)
"I had a great stay, kitchen is fully equipped. The place is clean and cozy. My dtay was very relaxing. Would definitely stay again."
United States
Hollis A.
Sage House at Camp Greenwood Vermont with Sauna
Exterior
Riverfront mountain view house w/ fireplace, firepit, decks, w/d, wifi, yard

Cabin in Cavendish

Riverfront mountain view house w/ fireplace, firepit, decks, w/d, wifi, yard
2.0 star property
Riverfront mountain view house w/ fireplace, firepit, decks, w/d, wifi, yard
Exterior
Log cabin near Okemo / Ludlow on 25 acres borders state forest w/trails nearby

Cabin in Chester

Log cabin near Okemo / Ludlow on 25 acres borders state forest w/trails nearby
10.0 out of 10, Exceptional, (27)
"This was our second time at this property and it remains a gem in a beautiful area!"
United States
Kristina R.
Log cabin near Okemo / Ludlow on 25 acres borders state forest w/trails nearby
Exterior
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!

Cabin in Chester

Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
9.8 out of 10, Exceptional, (73)
"It was a nice cabin- perfect for getting away for a few days and nice place to stay for access to skiing"
United States
Aaron C.
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
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

On The River Inn

On The River Inn

10/10 Excellent
"Rearaurant staff was top notch. "
Daniel 1-night trip
Posted 2 days ago
On The River Inn

Find out more about Windsor County

Windsor County Cabin Rentals information

Number of reviews
805
Accommodation
65 Cabin Rentals
Lowest Price
$187
Highest Price
$395

Frequently asked questions

Are there cheap cabins in Windsor County?
Whether you'd like to stay by the water or up a mountain, we have an awesome range of cheap cabins in Windsor County to suit your budget and style. Priced from $187 to $395 per night, your ideal cabin awaits you here.These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best mountain cabins in Windsor County?
Breathe in the cool mountain air at Cabin - Cozy Chalet, Lake Pauline, Lake Rescue. Located in Ludlow, a spectacular setting, a deck and a porch help make it one of the leading mountain cabins in Windsor County. A few weeks at Beautiful Log Cabin In Weston, Vt in Weston is sure to refresh your mind, body and soul. This mountainside stay also offers the creature comforts you need, such as snow sports gear and a microwave oven.
What are the best river cabins in Windsor County?
Whether you want to go fishing, swimming or simply drift off to sleep with the calming sounds of water, nothing compares to staying close to the river. Cabin - Cozy Chalet, Lake Pauline, Lake Rescue in Ludlow is an impressive waterside getaway. Handy amenities here include a wood stove and snowsport activities. Log Cabin In The Smokeshire Valley Area Of Chester in Chester is another favorite with travelers. It offers a wood stove, outdoor furniture and plenty of opportunities to enjoy yourself around the river.
What are the best cabins with pools in Windsor County?
Your favorite swimsuit is one thing you won't want to forget at Log Cabin - Cozy, Quaint And Scenic And Ready For Your Enjoyment. Its inviting pool demands lots of fun-filled days in the water. But there are loads of other things to like about this Chester escape, such as on-site watersports and a porch. Contemporary 4 - Bedroom Cabin 5 - Min To Okemo is another popular cabin rental with a pool in Windsor County. A fireplace and a barbecue grill make this Ludlow option even better.
What are some great cabins in Windsor County?
Travelers can't get enough of Cabin - Cozy Chalet, Lake Pauline, Lake Rescue. If you need a break from the fast pace of life, this Ludlow retreat is where you can step on the brakes. A porch and a firepit will help keep you in your comfort zone. Rediscover peace and quiet or go after adventure at The Little Red Cabin Less Than 15 Minutes To Okemo Close To Everything Vt. Located in Cavendish, a tennis court and a patio are among its many amenities.
What are the best weekend cabin rentals in Windsor County?
Whether you're organizing a short trip with your sweetheart or your whole family, we'll help you locate the perfect weekend cabin getaway. One superb example? Renovated Cabin Overlooking Waterfall And Pond. Featuring on-site watersports and a firepit, you'll appreciate waking up in nature here. Log Cabin - Cozy, Quaint And Scenic And Ready For Your Enjoyment is another popular place where you can slow things down. Spend a couple of nights at this retreat which offers on-site watersports and a swimming pool.
What are the highest-rated cabins in Windsor County?
There are some cabins that tick all the boxes. Log Cabin Retreat On 40 Acres is a prime example. With such an impressive rating, it comes with amenities such as a patio, a fireplace and more. Another fantastic option is Log Cabin Near Okemo / Ludlow On 25 Acres Borders State Forest W. A patio and a firepit are among the conveniences here.
What are the top things to see and do in Windsor County?
We hope you like exploring, because there's no shortage of things to do and see. For instance, Okemo Mountain Resort and Waterville Valley Resort. Fort Ticonderoga, Fort William Henry and Cannon Mountain Ski Area are other interesting attractions. And you won't want to forget about Franconia Notch State Park! Of course, squeezing all the major sights into your Windsor County getaway will be a lot easier with a car rental. You can add a set of wheels to your Expedia booking after deciding on your cabin.
Why should I book a cabin in Windsor County?
Affordability, nature-filled surroundings, rustic charm — there are countless great reasons to book a Windsor County cabin. Get far away from the cacophony of the city and rise with the sound of songbirds and wildlife. There's so much adventure right on your doorstep too. Whether you're on vacation with family members, friends or your other half, you'll discover the ideal cabin on Expedia.
What are the top nature cabins in Windsor County?
Featuring plenty of charm and home comforts, Cabin - Cozy Chalet, Lake Pauline, Lake Rescue is among our most sought-after nature cabins in Windsor County. But with a whole lot of things to see and do nearby, make sure you don't spend all your time chilling indoors. Activities such as paddle boating and nearby fishing await. New Secluded Log Cabin In The Mountains is another property where you can immerse yourself in nature. Nearby mountain biking and nearby hiking and biking trails are a few enjoyable ways to do it.
What are some of the best cabins near Killington Resort in Windsor County?
You'll have Mother Nature as a neighbor at a Killington Resort cabin. Killington Cabin - Left Unit: Great For Families is popular. This retreat also offers plenty of adventure, with nearby cross-country skiing and ice skating nearby among the fun things to do in the area. Also check out The Killington Cabin By Killington Vacation Rentals. Go exploring and then head back to your cabin to take advantage of its comforts.

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