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Search the Best Cabins in Windsor

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Windsor cabin rentals

A white building with a window, surrounded by trees and forest.

1. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (41 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
$378 nightly
The price is $422
Nov 9 - Nov 10
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A log cabin with large windows and a wooden deck.

2. Bear Creek Cabin

Bear Creek Cabin
Charlemont
9.8 out of 10, Exceptional, (55 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
$512 nightly
The price is $572
Nov 11 - Nov 12
Total with taxes and fees
Bear Creek Cabin
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Very centrally located. Right next to a good little market. Very reasonable price for an apartment like room."
Holly 3-night trip
Posted 17 hours ago
Berkshire Mountain Lodge

Find out more about Windsor

Windsor Cabin Rentals information

Number of reviews
96
Accommodation
29 Cabin Rentals
Lowest Price
$422
Highest Price
$572

Frequently asked questions

What are the best cabins near Windsor?
Escape to the outdoors without having to rough it at one of our 304 cabins in and around Windsor. Whether you have relaxation or adventure on your itinerary, Log Cabin Living On The Esopus Creek offers both. Alternatively, spend your vacation at Private And Artistic Cabin, Pet Friendly and kick back among wonderful natural surroundings.
Are there cheap cabins in Windsor?
Whether you'd prefer to stay next to the water or moments from a mountain, we have a great variety of cheap cabins in Windsor to suit. Priced from $422 to $572 per night, your perfect cabin is waiting 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 near Windsor?
If you've ever yearned to squirrel yourself away in a cabin up in the mountains with only nature and awesome views to keep you company, you're definitely not alone. Cabin - Charming, Quiet, River Front is a magnet for guests who want to get away from it all. This mountain cabin near Windsor features many comforts, such as snowsport activities and skiing facilities. Also consider This Is It Fabulous Vermont Cabin W. A wood stove, winery tours and lots of opportunities to explore the surrounding wilderness make it a favorite with travelers.
What are the best river cabins near Windsor?
If you're seeking a cozy retreat surrounded by water, a Windsor river cabin is an awesome choice. Settle in at Cabin - Charming, Quiet, River Front and let any stresses float away downstream. Amenities here include snowsport activities and skiing facilities. Another superb riverside retreat is Cabin - Romantic Retreat. It offers on-site watersports, snowsport activities and more.
What are the best cabins with pools near Windsor?
Staying in a cabin rental with a pool adds even more fun to your vacation. If you're chasing one near Windsor, Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna has useful amenities like a swimming pool and a porch to make your poolside escape even more awesome. Cabin - Romantic Retreat is another top pick and features on-site watersports and a swimming pool.
Can I find beach cabins near Windsor?
Wake up and be steps from the shoreline when you book a Windsor beach cabin rental. Sun, fun and relaxation should be your top priorities at Cabin - Relax, Reconnect And Enjoy. This seaside stay comes with on-site watersports and children's activities. Or, drop your beach bag down and spend your break at Lakefront - King - Petsok - W And D. Amenities here include on-site watersports and clothes washing facilities.
What are the best weekend cabin rentals in Windsor?
If you're yearning to spend a couple of restful days surrounded by nature, Cabin - Charming, Quiet, River Front has your name on it. Head here for a weekend and make use of amenities including a patio and a firepit. Another top escape is This Is It Fabulous Vermont Cabin W. Offering a patio, a firepit and plenty of chill vibes, you'll go home feeling all brand new.
What are the best cabin prices in Windsor?
If you'd prefer to spend less on your stay, we've got some incredible deals on Windsor cabins that won't put a hole in your vacation budget. Like the sound of $422 per night?
Can I find log cabins in Windsor?
Begin your day with a coffee in your peaceful log cabin and then try some snow shoeing and shore fishing. Sound like your dream vacation? Then check out Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna. Another getaway that offers ample charm and warmth is Luxury Secluded Catskill Log Cabin On Creek. Activities like boating and cross-country skiing will add to the fun times here.
What are the highest-rated cabins in Windsor?
Expedia adventurers just keep returning to Cabin - Artist's Camp On Lake Mahkeenac. This knockout features a host of amenities like a patio and a fireplace. It won't take you too long to understand why Cabin With 3 Acres, Tennis Courts: By 4 Ski Mtns is also a hit with visitors. Conveniences like a porch and a tennis court help make it a winner.
Why should I book a cabin in Windsor?
Affordability, rustic charm, nature-filled surroundings — there are loads of reasons for you to choose a Windsor cabin. Get far away from the clamor of the city and wake up to the sweet sound of birdsong. There's mountains of adventure on your doorstep too. Whether you're on vacation with friends, family or your special someone, you'll discover the perfect cabin on Expedia.
What are the top nature cabins in Windsor?
Featuring plenty of creature comforts and charm, Cabin - Charming, Quiet, River Front is one of our leading nature cabins in Windsor. But with countless things to see and do close by, make sure you don't spend too much time relaxing indoors. Activities including nearby sailing and nearby mountain biking are on the to-do list here. Cabin - Romantic Retreat is another getaway where you can get back to nature. Nearby motor boating and nearby kayaking are a couple of enjoyable ways to do it.
What are some of the best cabins near National Shrine of the Divine Mercy in Windsor?
Mother Nature will be your closest neighbor at a cabin in National Shrine of the Divine Mercy. Cozy Stockbridge Cabin - Walk To Beach And Lake is a top pick. This place is also big on adventure, with nearby hiking and biking trails and nearby kayaking among the things to do close by. Also consider Cabin - Artist's Camp On Lake Mahkeenac. Go exploring and then head back to your cabin to enjoy its comforts.

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