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

Search the Best Cabins in Windsor

Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Windsor cabin rentals

Exterior

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
$290 nightly
The price is $316
Sep 1 - Sep 2
Total with taxes and fees
Fat Sheep Farm & Cabins
Exterior

2. Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
$468 nightly
The price is $529
Aug 16 - Aug 17
Total with taxes and fees
Cabin on the hill Ascutney Vt - 4 bedrooms
Exterior

3. Stylish Designer Loft And Adventure Hub With EV Charger Near Woodstock & Okemo

Stylish Designer Loft And Adventure Hub With EV Charger Near Woodstock & Okemo
West Windsor
10.0 out of 10, Exceptional, (1 review)
"Yes, our stay was very nice! Beautiful cabin, very clean ! "
United States
Alicja
$434 nightly
The price is $486
Sep 13 - Sep 14
Total with taxes and fees
Stylish Designer Loft And Adventure Hub With EV Charger Near Woodstock & Okemo
Exterior

4. Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (23 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
$286 nightly
The price is $311
Aug 30 - Aug 31
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Exterior

5. Scandi-Chic Luxury Loft Near Okemo With Solo Stove And EV Charger

Scandi-Chic Luxury Loft Near Okemo With Solo Stove And EV Charger
West Windsor
10.0 out of 10, Exceptional, (3 reviews)
"It was really great"
United States
Christopher W.
Scandi-Chic Luxury Loft Near Okemo With Solo Stove And EV Charger
Exterior

6. Designer Cabin With Solo Firepit Near Ski Trails - Ascutney Lofts

Designer Cabin With Solo Firepit Near Ski Trails - Ascutney Lofts
West Windsor
$435 nightly
The price is $491
Sep 13 - Sep 14
Total with taxes and fees
Designer Cabin With Solo Firepit Near Ski Trails - Ascutney Lofts
Exterior

7. High-End Loft - Cozy Firepit, Hiking and Biking Trails, Near Okemo

High-End Loft - Cozy Firepit, Hiking and Biking Trails, Near Okemo
West Windsor
$439 nightly
The price is $492
Sep 13 - Sep 14
Total with taxes and fees
High-End Loft - Cozy Firepit, Hiking and Biking Trails, Near Okemo
Exterior

8. Luxury Loft With Solo Fire Pit & Trails Close to Okemo & Ascutney EV Charger

Luxury Loft With Solo Fire Pit & Trails Close to Okemo & Ascutney EV Charger
West Windsor
10.0 out of 10, Exceptional, (1 review)
"Yulia was a great host. Very responsive and accomodating. The cabin was very clean, new, and plenty of space for our family. Very nice to come home to after a day of skiing. "
United States
David N.
$472 nightly
The price is $528
Sep 1 - Sep 2
Total with taxes and fees
Luxury Loft With Solo Fire Pit & Trails Close to Okemo & Ascutney EV Charger
Exterior detail

9. Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (48 reviews)
"We had a fantastic stay! Can’t wait to return for a summer or fall trip. Cabin was wonderful, clean and full of amenities. It is a plus having access to laundry services."
United States
John H.
$368 nightly
The price is $397
Aug 16 - Aug 17
Total with taxes and fees
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Exterior

10. Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (18 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.
$349 nightly
The price is $376
Aug 19 - Aug 20
Total with taxes and fees
Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Exterior

11. 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, (1 review)
"Lovely cabin, as described. Very clean and comfortable. Our only comments, which are not criticisms, but suggestions are: 1). Post the wifi password. We only got the password in an older communication and, fortunately one of us had that open on an older message and could see it. Otherwise, there was no cell service and we were unable to find it. 2) Leave some towels in the bathroom instead of all in the front linen closet. Thanks for a great stay."
United States
Peter C.
$760 nightly
The price is $859
Sep 7 - Sep 8
Total with taxes and fees
Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
Exterior

12. 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.
$391 nightly
The price is $442
Aug 19 - Aug 20
Total with taxes and fees
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Exterior

13. 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, (170 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.
$331 nightly
The price is $371
Aug 17 - Aug 18
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior

14. 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, (13 reviews)
"Very welcoming, awesome weekend getaway."
United States
Zachary B.
$285 nightly
The price is $319
Sep 7 - Sep 8
Total with taxes and fees
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Exterior

15. Brook Road Cabin

Brook Road Cabin
Goshen
9.6 out of 10, Exceptional, (18 reviews)
"Would go back!"
United States
Elizabeth C.
$298 nightly
The price is $323
Aug 16 - Aug 17
Total with taxes and fees
Brook Road Cabin
Exterior

16. 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, (25 reviews)
"It was excellent… missing tissues and address was confusing.. but would stay again in a heartbeat!! "
United States
Nancy L.
$446 nightly
The price is $484
Sep 8 - Sep 9
Total with taxes and fees
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Exterior

17. Cozy Private Cabin in Andover - Fireplace & Hot tub

Cozy Private Cabin in Andover - Fireplace & Hot tub
Andover
$605 nightly
The price is $678
Sep 11 - Sep 12
Total with taxes and fees
Cozy Private Cabin in Andover - Fireplace & Hot tub
Exterior

18. 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.
$1,227 nightly
The price is $1,387
Aug 31 - Sep 1
Total with taxes and fees
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
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 Hotel Reviews

The Shire Woodstock

The Shire Woodstock

8/10 Good
"The staff was helpful. The room was clean. There was some 1st floor construction that it would have been nice to know about prior to check in. It didn’t impact our stay but made things a bit dusty. Very conveniently located to downtown area."
Theresa 1-night trip
Posted less than an hour ago
The Shire Woodstock

Find out more about Windsor

Windsor Cabin Rentals information

Number of reviews
341
Accommodation
108 Cabin Rentals
Lowest Price
$311
Highest Price
$1,387

Frequently asked questions

What are the best cabins near Windsor?
Vacation in one of our 549 cabins in Windsor and you'll be rewarded with spectacular scenery, outdoor adventure and great memories. Cabin - Romantic Retreat: Mt. Views, Hot Tub is where life seems to slow down. Cabin - Close To Skiing, Hiking, Pvt Beach is another top pick if you'd love to spend time in Mother Nature.
Are there cheap cabins in Windsor?
Priced between $311 and $1,387 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?
After spending your day out and about in Mother Nature, come home to the impeccable comfort and style of a Windsor luxury cabin. Robert Frost Mountain Cabins is a perfect choice if you're in the mood to splash out and spoil yourself. You'll enjoy the top amenities here, such as pillow top mattresses and massage services. Cabin - Pollard Brook Condo In Great Lincoln is another popular stay. Make use of a swimming pool, a spa tub and a whole lot more.
What are the best river cabins near Windsor?
If you're searching for a comfy hideaway by the water, a Windsor river cabin is calling your name. Kick back at Warm And Inviting Jamaica Cabin W and let all your worries drift downstream. Handy amenities here include a wood stove and a firepit. Another awesome riverside getaway is Cabin - Camp David: Heart Of The Wht. Mtns. N. Lincoln Nh. Clean And Well Maintained. Guests have use of a wood stove, outdoor furniture and more.
What are the best cabins with pools near Windsor?
Slip on your board shorts or bikini and enjoy a relaxing dip whenever your heart desires when you stay at one of our cabin rentals with a pool. Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna ranks high among travelers. A swimming pool and a porch are some of the other amenities that'll help make your stay comfortable. Alternatively, spend your vacation at Welcome To Northaven Family - Friendly Lakefront Cabin In The White Mountains. As well as a great pool, this cabin comes with on-site watersports and a swimming pool.
Can I find beach cabins near Windsor?
Get a big dose of salty air and sunshine at Cabin - Close To Skiing, Hiking, Pvt Beach. One of our most popular Windsor beach cabins, it comes with on-site watersports and children's activities. You can also spend stress-free days by the sea at Renovated Cabin Overlooking Waterfall And Pond. On-site watersports and beach sun loungers will make your visit nice and comfy.
What are the best weekend cabin rentals in Windsor?
Whether you're planning a mini break with your beau or your besties, we'll help you locate the perfect weekend cabin getaway. One of our favorites? Private Lake - Front Cabin With Walk. Featuring a patio and a firepit, you'll adore the natural surroundings here. Shelving Rock Lodge On 54 Acres In Adirondack Park is another place where you can slow things down. Book a few nights at this escape which offers on-site watersports and a patio.
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 $311 a night?
Can I find log cabins in Windsor?
Start your day with a cup of joe in your cozy log cabin and then spend the rest of your time cross-country skiing and mountain biking. Sound like your idea of heaven? Then head for Cabin - Close To Skiing, Hiking, Pvt Beach. Another wooden escape that has lots of character and comfort is Lake George Custom Built Log Cabin. Activities like rafting and skiing only add to your experience here.
What are the highest-rated cabins in Windsor?
With an impressive rating, it's not hard to understand why Cabin - Birch Hill Hollow - Mt Snow And Pool Table is such a hit with vacationers. It offers useful amenities like a spa tub and a patio. Cabin - Beautiful Mt Area With Beautiful Scenic Views is another fabulous option. Conveniences including a patio and a firepit will help make your stay a comfy one.
Why should I book a cabin in Windsor?
For a nature-filled escape that won't cost the earth, you can't beat a cabin. Picture yourself waking up to the sounds of chirping birds and eating breakfast on a private deck surrounded by stunning vistas. Stay in a cabin in Windsor to escape the hectic routine of modern life. Whether they're by a lake, river, beach or mountain, cabins offer a relaxing, rustic experience for anyone needing a break.
What are the top nature cabins in Windsor?
If you can tear yourself away from the home comforts of Warm And Inviting Jamaica Cabin W, you'll find adventure everywhere. One of our finest nature cabins in Windsor, it offers terrific access to the great outdoors and amenities such as a barbecue grill and a firepit. Cabin - Camp David: Heart Of The Wht. Mtns. N. Lincoln Nh. Clean And Well Maintained is another recommendation. Rustic charm, a spa tub, a patio ... They're just a few things to love about this place.
What are some of the best cabins near Lake Sunapee in Windsor?
Rediscover the great outdoors without foregoing home comforts at a Lake Sunapee cabin. Fall asleep to the soothing sounds of Mother Nature and wake to pretty views at Lakefront Cabin With Panoramic Water View And Access. A lake view and a water view are some of the amenities you'll find here. Pinewood Lodge | Cozy Pet - Friendly Log Cabin 5 Min To Mt Sunapee is also popular with nature lovers. In addition to its gorgeous surroundings, it offers a firepit and a fireplace.

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