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Cabin Rentals in Windsor County

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Top Cities in Windsor County

A river flowing through a rocky gorge with autumn foliage and a bridge in the background.
Cabin RentalsCabin Rentals

Quechee

Quechee
A coastal landscape with a sandy beach, dense forest, and a clear blue sea under a partly cloudy sky.
Cabin RentalsCabin Rentals

Cavendish

Cavendish

Our top choices for Windsor County cabin rentals

Exterior detail

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, (43 reviews)
"Great location, so well set up with many extra touches inside "
United States
Victoria H.
The price is AED 598
AED 1,085 total
includes taxes & fees
28 Jun - 29 Jun
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Exterior

Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Ludlow
9.8 out of 10, Exceptional, (150 reviews)
"Loved everything about this place. Perfect for a ski weekend at Okemo a few minutes away! We will definitely look to stay here again next winter!"
United States
Matt D.
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Exterior

Killington Area Escape w/ Deck, Views & Hot Tub!

Killington Area Escape w/ Deck, Views & Hot Tub!
Stockbridge
9.6 out of 10, Exceptional, (27 reviews)
"The cabin was warm and cozy. Very clean and well-stocked. Plenty of parking. It was perfect for our visit to Killington Resort. Matt was very accommodating, responded promptly, and provided all of the details we needed. Would definitely stay there again."
United States
Patti
Killington Area Escape w/ Deck, Views & Hot Tub!
Exterior

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, (15 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 AED 579
AED 1,063 total
includes taxes & fees
30 Jun - 1 Jul
Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Terrace/patio

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

Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore
Ludlow
10.0 out of 10, Exceptional, (101 reviews)
"Cozy cabin in perfect spot close to Okemo. Kitchen very well stocked and we made some delicious meals. Quiet and comfy beds, update bathrooms. Great stay! "
United States
Tracey H.
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore
Exterior

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

Brookside Cabin + Hot Tub | Woodstock & Killington

Brookside Cabin + Hot Tub | Woodstock & Killington
Bridgewater
10.0 out of 10, Exceptional, (6 reviews)
"Highly recommend, the house was not only aesthetically appealing, but very well stocked for our needs and more, owners are super attentive and just overall 5 stars without question. "
United States
Amber F.
Brookside Cabin + Hot Tub | Woodstock & Killington
Fridge, oven, stovetop, coffee/tea maker

Cozy Cabin near Okemo

Cozy Cabin near Okemo
Ludlow
9.4 out of 10, Exceptional, (12 reviews)
"Great little cabin. Perfect for our family. Cozy, clean, had everything we needed and convenient to Okemo. Seamless check-in and check-out. "
United States
Pamela M.
Cozy Cabin near Okemo
TV, fireplace, DVD player, foosball

Log Cabin home with Mt Ascutney views and pool table

Log Cabin home with Mt Ascutney views and pool table
Brownsville
9.8 out of 10, Exceptional, (100 reviews)
"House has everything a family can need or want. It was cozy and perfect. We had an amazing stay and highly recommend to others looking for a comfortable getaway with family and friends. "
United States
L & W W.
Log Cabin home with Mt Ascutney views and pool table
Exterior

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, (12 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Outdoor spa tub

Cozy A frame Cabin in Proctorsville

Cozy A frame Cabin in Proctorsville
Cavendish
10.0 out of 10, Exceptional, (6 reviews)
"Nice place to stay! Very cozy and private, lovely hot tub, plenty of room. Location is serene and made for the perfect VT experience. "
United States
Benjamin M.
Cozy A frame Cabin in Proctorsville
Exterior

Rustic cabin w/ mountain view & fireplace

Rustic cabin w/ mountain view & fireplace
Ludlow
9.4 out of 10, Exceptional, (52 reviews)
"Cozy mountain house! Good location to the mountain! "
United States
Curtis C.
Rustic cabin w/ mountain view & fireplace
Exterior

Andover Cabin Retreat w/ Hot Tub & Fireplace!

Andover Cabin Retreat w/ Hot Tub & Fireplace!
Andover
10.0 out of 10, Exceptional, (8 reviews)
"The amenities were perfect and the hot tub was a welcome addition to the home."
United States
Barbara P.
Andover Cabin Retreat w/ Hot Tub & Fireplace!
Exterior

Hike, Ski & Unwind: Cabin w/ Deck in Chester!

Hike, Ski & Unwind: Cabin w/ Deck in Chester!
Chester
Hike, Ski & Unwind: Cabin w/ Deck in Chester!
Exterior

Contemporary 4-BR Cabin 5-min to Okemo

Contemporary 4-BR Cabin 5-min to Okemo
Ludlow
Contemporary 4-BR Cabin 5-min to Okemo
Exterior

Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!

Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
Chester
9.8 out of 10, Exceptional, (73 reviews)
"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!
Exterior

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Ludlow
9.8 out of 10, Exceptional, (188 reviews)
"Great stay. Beautiful home! "
United States
diane p.
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Exterior

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

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Chester
9.8 out of 10, Exceptional, (24 reviews)
"I had a great stay! Everything was as shown and described in the listing. My only advice is-if you are staying there during mud season make sure you have a AWD/4WD vehicle-the road to the property can get pretty bad. "
United States
Molly L.
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Exterior

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, (19 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
The price is AED 592
AED 1,078 total
includes taxes & fees
30 Jun - 1 Jul
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Interior

The Cabin that brings people together

The Cabin that brings people together
Bridgewater
9.6 out of 10, Exceptional, (84 reviews)
"House was amazing. Not too far from the ski resort and held a large group very well. 10/10 would recommend."
United States
Dylan R.
The Cabin that brings people together
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

Hotel Coolidge

Hotel Coolidge

8/10 Good
"Definitely has character. Be prepared for a very slow check-in. The floors are very very slanted. They highlight a New England visual artist in their lobby. It is clean. I've never had this happen in the US before, but they required IDs from both adults. They do not offer breakfast, but rather give you a $4.50 voucher for nearby restaurants which start at $8 - 10 for breakfast sans coffee.. The hot water disappears while taking a shower - I think this might be because others are flushing. .."
Diane 1-night trip
Posted 1 hour ago
Hotel Coolidge