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Jul 4 - Jul 6
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Aug 22 - Aug 24

Cabin Rentals in Windsor

Bear Creek Cabin
Exterior

Bear Creek Cabin

9.8 out of 10, Exceptional, (30)
"Enjoyed our stay"
$524 nightly
The price is $585
Jun 29 - Jun 30
Total includes taxes and fees
Bear Creek Cabin
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Exterior

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

10.0 out of 10, Exceptional, (119)
"Had an amazing weekend in this beautiful cabin! Highly recommend staying here! Great host, amazing views, beautiful property!"
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Lakefront Westhampton Cabin w/ Beach + Kayaks!
Interior

Lakefront Westhampton Cabin w/ Beach + Kayaks!

10.0 out of 10, Exceptional, (8)
"Loved our stay. "
Lakefront Westhampton Cabin w/ Beach + Kayaks!
Berkshires Cabin 2 Mi to Appalachian Trail!
Dining

Berkshires Cabin 2 Mi to Appalachian Trail!

9.8 out of 10, Exceptional, (11)
"The cabin was pretty much all we could wish for to spend a few cozy days in the beautiful Berkshires! "
Berkshires Cabin 2 Mi to Appalachian Trail!
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

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

10.0 out of 10, Exceptional, (24)
"We had a great time in the cottage. It was perfectly cozy for our family of 6. The cottage has everything you need to have fun on a cold winter night. We especially enjoyed the hot tub and board games! Thanks for a lovely stay - we will come back in the summer!"
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Artist's Camp on Lake Mahkeenac
Sun loungers, beach towels

Artist's Camp on Lake Mahkeenac

9.6 out of 10, Exceptional, (18)
"Great location, comfortable, beautiful setting and nice porch! "
Artist's Camp on Lake Mahkeenac
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Terrace/patio

Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.

9.6 out of 10, Exceptional, (59)
"Great"
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Dadzpad Cabin in Stephentown
Fridge, microwave, oven, stovetop

Dadzpad Cabin in Stephentown

8.0 out of 10, Very Good, (1)
"House was clean and comfortably furnished. The kids enjoyed the arcade games and it was an overall good time. Only Issues were that the drive and walk ways were hidden in the snow and the house did not hold heat well "
Dadzpad Cabin in Stephentown
Cozy Stockbridge Cabin - Walk to Beach & Lake!
TV

Cozy Stockbridge Cabin - Walk to Beach & Lake!

9.4 out of 10, Exceptional, (8)
"Location of this property is near all things Stockbridge has to offer. Easy ride to Tanglewood Short ride to Lenox and Lee The cottage is an older gem Well stocked and lots of quirky charm"
Cozy Stockbridge Cabin - Walk to Beach & Lake!
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
TV, fireplace, DVD player, books

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

9.8 out of 10, Exceptional, (118)
"Great place to stay with friends and family. Will be visiting again!"
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
Lakefront House with Stunning Views and Great Room
Dining

Lakefront House with Stunning Views and Great Room

9.6 out of 10, Exceptional, (15)
"Beautiful setting. We had fun exploring the area and made good use of the kayaks to explore the lake."
Lakefront House with Stunning Views and Great Room
Charming 3-bedroom Cabin for nature lovers
Interior

Charming 3-bedroom Cabin for nature lovers

$327 nightly
The price is $363
Jul 15 - Jul 16
Total includes taxes and fees
Charming 3-bedroom Cabin for nature lovers
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (216)
"The house was small, cozy and even had a small stream that ran through the backyard and under the deck. It had everything we needed. A bigger TV in the living room but definitely be a big upgrade but that isn't the end of the world. Would stay here again. "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!
2 bedrooms, iron/ironing board, internet, bed sheets

Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!

9.0 out of 10, Wonderful, (30)
"Adorable cabin with a central location to see everything in the Pioneer Valley/ Berkshires/Greater Springfield areas. The cabin is perfect for playing games, fishing, exploring the nearby lake and state parks or just plain relaxing! Be sure to bring marshmallows for toasting in the fire pit. Enjoy!"
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Florida Mountain Log Cabin!
Living area

Florida Mountain Log Cabin!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Place was super clean. Beds were comfortable. Location was great."
$388 nightly
The price is $410
Jun 29 - Jun 30
Total includes taxes and fees
Florida Mountain Log Cabin!
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
Exterior

Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum

9.8 out of 10, Exceptional, (57)
"Great cabin on a beautiful lake. Scenic drive to all other attractions in the Berkshires (Lenox, Mt. Greylock, etc.). We enjoyed our stay!"
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
Vermont Lake Front Log Cabin Close to Mt. Snow
Exterior

Vermont Lake Front Log Cabin Close to Mt. Snow

10.0 out of 10, Exceptional, (66)
"The property was very nice, and the host was very accommodating and responsive. Would definitely stay here again. "
Vermont Lake Front Log Cabin Close to Mt. Snow
A-Frame Cabin w/ Furnished Deck in Becket!
Exterior

A-Frame Cabin w/ Furnished Deck in Becket!

8.4 out of 10, Very Good, (7)
"We had a wonderful stay in this adorable a frame!! Super cozy :)"
A-Frame Cabin w/ Furnished Deck in Becket!
Lakeshore cabin with private beach and dock
Exterior

Lakeshore cabin with private beach and dock

10.0 out of 10, Exceptional, (4)
"Took advantage of the peaceful setting and location to nearby attractions!"
Lakeshore cabin with private beach and dock
Modern Cabin Near Tanglewood
Property grounds

Modern Cabin Near Tanglewood

10.0 out of 10, Exceptional, (9)
"We had a great time staying in Lauren and Blake's cabin. It was very comfortable, clean and convenient and I would definitely stay there again. Thank you for being great hosts!"
Modern Cabin Near Tanglewood
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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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 $363 to $585 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.