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Compare 87 Cabin Rentals in Windsor with updated reviews, rates, and availability.

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"Very nice place only negative was the sauna did not work"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (206)
"Cozy and scenic property here with more than enough space, great spot with a dog, to go hiking, or just relax."
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Charming farmhouse, dog friendly, Appalachian trail access

7.2 out of 10, Good, (5)
"Pros: - Very responsive property management - Big house, great Vermont cabin feel - Clean bathrooms and great water pressure - Decently stocked kitchen - Beautiful location/ scenery Cons: - A bit hard to find (google maps gets confused) - We had many flies in kitchen and bedrooms - Heating issues (eventually fixed) - Access issues upon arrival (immediately fixed) - Have to remove your own trash when you leave"
Charming farmhouse, dog friendly, Appalachian trail access

Lakefront Cabin w/ Panoramic Water View & Access

9.0 out of 10, Wonderful, (9)
"Overall good rental but these are 3 minor issues: 1. A railing from the parking lot to the front door would help to walk down the steps. 2. Additional bath towels and wash clothes are needed. 3. A large stone is missing from the last deck step to the dock."
Lakefront Cabin w/ Panoramic Water View & Access

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (157)
"Two friends and I stayed at this house for the second year in a row. It has been a perfect place for us, being 10 minutes away from Grafton and 25 minutes from Okemo."
The price is AED 624
AED 1,345 total
includes taxes & fees
1 May - 2 May
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Treehouse at Wise Pines- SoBo

9.8 out of 10, Exceptional, (20)
"The place is everything it describes, however I missed the part where the bathrooms are in a separate building and they are shared. Thankfully for us there was nobody else staying there. Everything was very clean. Other than that I was satisfied. "
The price is AED 533
AED 663 total
includes taxes & fees
4 May - 5 May
Treehouse at Wise Pines- SoBo

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

10.0 out of 10, Exceptional, (14)
"This cabin property is amazing. The cabin itself is adorable and super comfortable. They were very thoughtful in creating these cabins and we had everything we needed, easy to find and use. It was beautiful and really relaxing to look out all the windows at the woods. We will definitely be trying to come back to enjoy this spot again. My only somewhat critical feedback would be that the couch isn’t super comfortable and they could use a few blankets. The bed was very comfortable but it’s warm in...
The price is AED 643
AED 1,131 total
includes taxes & fees
1 May - 2 May
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Cozy Quechee Corner Cabin

10.0 out of 10, Exceptional, (49)
"Great little spot for a get away. Has everything you need. Great location, clean and quiet. Owners are very receptive and easy to work with. Highly recommend. "
Cozy Quechee Corner Cabin

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

10.0 out of 10, Exceptional, (12)
"My family and I stayed for a ski weekend up at Mount Sunapee. The house was perfect for our needs and just a quick 5 minutes from the mountain. The hosts had thought of everything and we had a great experience! We will be back!"
The price is AED 771
AED 1,766 total
includes taxes & fees
1 May - 2 May
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

Luxe Quechee home on quiet road - chef’s kitchen, two-car garage, screened porch

8.6 out of 10, Excellent, (14)
"House is lovely and well appointed."
Luxe Quechee home on quiet road - chef’s kitchen, two-car garage, screened porch

Cozy cabin near skiing with free WiFi, game room, deck, & wood fireplace

9.0 out of 10, Wonderful, (109)
"Overall great stay and convenient to the mountain. This was our 2nd visit and would stay again. "
Cozy cabin near skiing with free WiFi, game room, deck, & wood fireplace

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

10.0 out of 10, Exceptional, (23)
"This lovingly built off-grid glamping cabin is drenched with sun! It’s absolutely gorgeous! The kids enjoyed pumping their own water and sledding down the front hill. Paris is an excellent hostess- she answered all our questions very promptly & thoroughly. We cant wait to come back! Thank you!!!"
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

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

10.0 out of 10, Exceptional, (88)
"Had a very relaxing time at this cabin. Everything was as described on listing. Very clean and excellent location. Very comfortable sitting by the fireplace after skiing Okemo all day! Would definitely stay here again! Nice and secluded but yet close to the mountain and stores if needed!"
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

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

10.0 out of 10, Exceptional, (7)
"The property is gorgeous!! I’m glad we stayed there! Clean and cozy. Love it!"
The price is AED 643
AED 1,131 total
includes taxes & fees
1 May - 2 May
Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Log Cabin home with Mt Ascutney views and pool table

9.8 out of 10, Exceptional, (88)
"We were very pleased with the amount of space and beautiful views that the home offered. It was comfortable, warm and inviting and the owner was very attentive to any questions we had."
Log Cabin home with Mt Ascutney views and pool table

Cozy 3-bedroom VT cabin minutes from Okemo

9.0 out of 10, Wonderful, (2)
"House was very nice. Very close to Okemo. Had everything we needed on a sweet lake with a sugar shack directly across. Layout is a little funky but worked just fine. Beds are very comfy. "
The price is AED 1,308
AED 2,349 total
includes taxes & fees
2 May - 3 May
Cozy 3-bedroom VT cabin minutes from Okemo

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

Vermont Cabin - Ski, Hike, Kayak, Leaf Peep - 5mins to Okemo, near quaint towns

9.8 out of 10, Exceptional, (11)
"What a great place to stay! The perfect comfy cozy house. Super close to Okemo mountain, quaint towns, and shops!! Kerry gave us many suggestions on places to visit and eat! Thank you for making our long weekend awesome!!"
Vermont Cabin - Ski, Hike, Kayak, Leaf Peep - 5mins to Okemo, near quaint towns

Brook Road Cabin

9.8 out of 10, Exceptional, (17)
"Visited our son at school and stayed the night away from campus. Great get away spot. Wonderful location. The outdoor deck was perfect."
The price is AED 591
AED 1,148 total
includes taxes & fees
1 May - 2 May
Brook Road Cabin

Contemporary 4-BR Cabin 5-min to Okemo

Contemporary 4-BR Cabin 5-min to Okemo
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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Other property types in Windsor

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"Very nice place only negative was the sauna did not work"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Crescent Cottage

10.0 out of 10, Exceptional, (25)
"This was our second stay at the cozy cottage amd was just as enjoyable as the first time . Glenn and Melanie are very responsive and like to makesure their guests are comfortable and happy . We loved waking up on the lake and enjoyed the back deck and firepit. We look forward to renting here again in the future. P"
Cozy Crescent Cottage

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (103)
"The community, this unit in particular, and its hosts are all spectacular beyond belief. There was one technical/communication glitch that can easily be remedied. Prior communications were encrypted in VRBO platform. When I arrived, I needed to access those in order to refresh my recollection on entry instructions. There's no cellular internet service in the area (need wi-fi connection). Unable to enter the unit, I likewise could not connect to the host-provided wi-fi. I had some of the...
Beautifully renovated with fireplace and coffee bar
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.