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

Search Windsor Cabins

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Windsor cabin 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 AU$308
includes taxes & fees
1 Nov - 2 Nov
Fat Sheep Farm & Cabins
A cabin with a deck, surrounded by dense forest.

2. 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 AU$752
includes taxes & fees
14 Oct - 15 Oct
Cabin on the hill Ascutney Vt - 4 bedrooms
A small red cabin with a door and windows, surrounded by autumn trees and a dirt ground.

3. Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub

Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
Cavendish
10.0 out of 10, Exceptional, (28 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
The price is AU$639
includes taxes & fees
27 Oct - 28 Oct
Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
A wooden cabin with large windows, a door, and a small porch with Adirondack chairs.

4. 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 AU$639
includes taxes & fees
27 Oct - 28 Oct
Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit
A small red cabin with a door and windows, surrounded by autumn trees and a dirt ground.

5. Upscale Cabin hot-tub, private fire pit, complimentary kayaks paddleboards

Upscale Cabin hot-tub, private fire pit, complimentary kayaks paddleboards
Cavendish
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful property, quiet and peaceful location. Enjoyed the access to the hot tub, and loved having a private fire pit."
United States
David V.
The price is AU$661
includes taxes & fees
26 Oct - 27 Oct
Upscale Cabin hot-tub, private fire pit, complimentary kayaks paddleboards
A blue single-story house with a red roof, a front door, and two windows.

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

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Ludlow
8.0 out of 10, Very good, (3 reviews)
"Great location and very cozy cottage. Well-appointed place to stay and accurately described in its listing. "
United States
jeremy a.
The price is AU$448
includes taxes & fees
4 Oct - 5 Oct
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A cabin with a snow-covered roof, surrounded by a forest.

7. 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, (2 reviews)
"Wonderful and well appointed abode - super cozy!"
United States
Nina S.
The price is AU$1,258
includes taxes & fees
26 Oct - 27 Oct
Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
A small cabin with a wooden exterior, a front porch, and a deck with chairs.

8. Brook Road Cabin

Brook Road Cabin
Goshen
9.6 out of 10, Exceptional, (18 reviews)
"Would go back!"
United States
Elizabeth C.
The price is AU$459
includes taxes & fees
4 Oct - 5 Oct
Brook Road Cabin
A red house with a covered porch and a chimney.

9. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (172 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
The price is AU$517
includes taxes & fees
12 Oct - 13 Oct
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A house with a stone foundation, a front porch, and a blue car parked in front.

10. Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Newbury
10.0 out of 10, Exceptional, (27 reviews)
"The place was clean and very comfortable"
United States
Pam D.
The price is AU$710
includes taxes & fees
14 Oct - 15 Oct
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
A two-story house with a snow-covered roof and a wooden deck.

11. Cabin at Killington Left: 4BR with Wood Stove, Deck and Hot Tub

Cabin at Killington Left: 4BR with Wood Stove, Deck and Hot Tub
Killington
9.4 out of 10, Exceptional, (22 reviews)
"Cozy, classic, basic, old school Killington condo. Loved the wood stove. Easy access to Killington area. "
United States
Leslie P.
Cabin at Killington Left: 4BR with Wood Stove, Deck and Hot Tub
A rustic wooden cabin with a porch, surrounded by autumn foliage.

12. NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!

NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
Killington
10.0 out of 10, Exceptional, (4 reviews)
"Location near gondola was clutch (short 1 min drive). Super clean and layout of cabin was perfect for our group. We had a fair amount of snow and icy weather and our host kept the road and driveway clear."
United States
Jeremy F.
The price is AU$1,838
includes taxes & fees
18 Oct - 19 Oct
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
The home sits beside a snow-covered ski trail. Access depends on snow conditions and trail operations.

13. Ski-In/Ski-Out Log Cabin on Great Eastern Trail | Hot Tub, Sauna, Game Room

Ski-In/Ski-Out Log Cabin on Great Eastern Trail | Hot Tub, Sauna, Game Room
Killington
The price is AU$2,286
includes taxes & fees
5 Oct - 6 Oct
Ski-In/Ski-Out Log Cabin on Great Eastern Trail | Hot Tub, Sauna, Game Room
A house with a sloped roof, a front porch, and a well-maintained lawn.

14. Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape

Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape
Killington
9.8 out of 10, Exceptional, (65 reviews)
"Amazing location, cozy cabin with plenty of beds for sleeping , owners were super responsive will def love to stay again!"
United States
Robert D.
The price is AU$970
includes taxes & fees
5 Oct - 6 Oct
Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape
A wooden building with a white door, a bear sculpture with a sign, and a window with a view of trees and mountains.

15. Roaring Bear Cabin: Secluded Killington Retreat with Hot Tub and Fire Pit

Roaring Bear Cabin: Secluded Killington Retreat with Hot Tub and Fire Pit
Killington
6.0 out of 10, (2 reviews)
"A beautiful, and very well-maintained property. We booked it specifically for the hot tub and fire pit combo and it did not disappoint! We were also pleasantly surprised to find plenty of dry firewood stacked and ready to go for us to use upon our arrival. I'd recommend this place to anyone wanting to get away for the weekend at any time of the year!"
United States
Justin A.
The price is AU$1,066
includes taxes & fees
5 Oct - 6 Oct
Roaring Bear Cabin: Secluded Killington Retreat with Hot Tub and Fire Pit
A two-story house with a snow-covered roof and a wooden deck.

16. Entire Killington Cabin Duplex: 8BR, Two Kitchens and Hot Tub

Entire Killington Cabin Duplex: 8BR, Two Kitchens and Hot Tub
Killington
10.0 out of 10, Exceptional, (18 reviews)
"great stay!"
United States
Patrick M.
The price is AU$3,030
includes taxes & fees
5 Oct - 6 Oct
Entire Killington Cabin Duplex: 8BR, Two Kitchens and Hot Tub
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

The Jackson

The Jackson

10/10 Excellent
"This property is beautiful, peaceful, friendly, welcoming and far enough away from the green for a noiseless stay. The wine, cheese and bites that start your evening are lovely and gives you the opportunity to meet other guests if you choose. Ms. Walton, the host, was friendly, helpful and warm. She made me feel right at home. A magnificent place to stay in Woodstock Vermont"
susan 2-night trip
Posted 8 hours ago
The Jackson

Find out more about Windsor

Windsor Cabin Rentals information

Number of reviews
427
Accommodation
105 Cabin Rentals
Lowest Price
AU$308
Highest Price
AU$3,030

Frequently asked questions

What are the best cabins near Windsor?
Experience the great outdoors without surrendering home comforts at one of our 552 cabins in and around Windsor. Whether you have adventure or relaxation on your itinerary, Cabin - Romantic Retreat: Mt. Views, Hot Tub delivers plenty of both. Alternatively, get cosy at Cabin - Close To Skiing, Hiking, Pvt Beach and kick back among beautiful surroundings.
Are there cheap cabins in Windsor?
Priced between AU$308 and AU$3,030 per night, getting away with friends or family is affordable and easy. Secure one of our cheap cabins in Windsor and enjoy some outdoorsy fun without breaking your budget.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 luxury cabins near Windsor?
Our Windsor luxury cabins offer the ultimate in comfort while staying in nature. You'll enjoy the upmarket amenities at Robert Frost Mountain Cabins. Pillow top mattresses and massage services help make this escape a top choice. Alternatively, settle back in luxury at Cabin - Pollard Brook Condo In Great Lincoln, which features a swimming pool and a spa tub.
What are the best river cabins near Windsor?
When you think of the word peaceful, a river cabin near Windsor should be the first thing that comes to mind. Waterfalls - View - Pond. Secluded Log Cabin Abuts Mt Snow. Ev Outlet is one place where you can rediscover your Zen. As well as its lovely surroundings, it comes with amenities such as a wood stove and snowsport activities. Warm And Inviting Jamaica Cabin W is another top pick. A wood stove and a firepit are some of the conveniences here.
What are the best cabins with pools near Windsor?
Staying in a cabin rental with a pool adds a whole new level of fun to your holiday. If you're seeking one near Windsor, Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna offers conveniences like a swimming pool and a porch to make your poolside getaway even more amazing. Waterfalls - View - Pond. Secluded Log Cabin Abuts Mt Snow. Ev Outlet is another top choice and features a porch and a patio.
Can I find beach cabins near Windsor?
Pack your favourite Hawaiian shirt and enjoy a more relaxed pace of life at Cabin - Close To Skiing, Hiking, Pvt Beach. This Windsor beach cabin rental has amenities such as on-site watersports and children's activities. Renovated Cabin Overlooking Waterfall And Pond also offers a sun-filled escape. Featuring on-site watersports and beach sun loungers, it's what beach holiday dreams are made of.
What are the best weekend cabin rentals in Windsor?
If you want to spend a handful of restful days immersed in nature, Private Lake - Front Cabin With Walk has your name on it. Settle down here for a weekend and enjoy access to conveniences such as a patio and a firepit. Another impressive option is Shelving Rock Lodge On 54 Acres In Adirondack Park. Offering on-site watersports, a patio and rare peace and quiet, you'll go home feeling brand spanking new.
What are the best cabin prices in Windsor?
If you'd rather save some cash on your stay, we've got some great deals on Windsor cabins that won't hurt your budget. Like the sound of AU$308 a night?
Can I find log cabins in Windsor?
If you pine for a more relaxed pace of life, you'll discover it at one of our log cabins in Windsor. For example, Lake George Custom Built Log Cabin. Spend your days here going boating and snow shoeing and then come home to enjoy its rustic charms. You can also take things slower at Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna. When you're ready to wander beyond your cosy digs, swimming and cross-country skiing opportunities are close by.
What are the highest-rated cabins in Windsor?
Expedia cabin travellers just keep coming back to Cabin - Birch Hill Hollow - Mt Snow And Pool Table. This top-notch option comes with a raft of handy amenities like a spa tub and a patio. It's not hard to figure out why Cabin - Beautiful Mt Area With Beautiful Scenic Views is also popular with travellers. Conveniences such as a patio and a firepit will help make your holiday the best one yet.
Why should I book a cabin in Windsor?
Affordability, outdoor activities, rustic charm — there's no end of great reasons to opt for a Windsor cabin. Leave behind the loud and lively city and wake up to the sounds of birds and wildlife. There's tons of adventure just a stone's throw away too. Whether you're taking a break with friends, relatives or your other half, you'll locate the perfect cabin on Expedia.
What are the top nature cabins in Windsor?
Our nature cabins in Windsor come in many budgets and styles, but there's one thing they all share — amazing access to the outdoors. Warm And Inviting Jamaica Cabin W lures plenty of nature lovers. Amenities such as a fireplace and a barbecue grill only make it better. Whether you want to get your feet into hiking boots or just put them up, you can do it at Cabin - Camp David: Heart Of The Wht. Mtns. N. Lincoln Nh. Clean And Well Maintained. Another top option, it comes with a patio and a spa tub.
What are some of the best cabins near Killington Resort in Windsor?
Killington Cabin - Left Unit: Great For Families is an outstanding option in Killington Resort. Ample creature comforts, a picturesque setting and activities such as nearby sledding and ice skating nearby help make it a traveller favourite. The Killington Cabin By Killington Holiday Rentals is another retreat where adventure and nature combine. Stay here and add nearby basketball and cycling to your must-do list.