Photo by Kim Knox Beckius

Find Cabins in Winsted for Rent from CA $754

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Browse Select Winsted Cabin Rentals

Cozy & Chic Cabin by the Lake, with access to private Beach!
Exterior

Cozy & Chic Cabin by the Lake, with access to private Beach!

10.0 out of 10, Exceptional, (17)
"great chic house, very clean"
Cozy & Chic Cabin by the Lake, with access to private Beach!
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, (209)
"The Cabin Had All The Amenities You Would Need and With A Quiet and Serene Area. For Me It Was Relaxing Stay!"
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Berkshires Cabin 2 Mi to Appalachian Trail!
TV, fireplace, books

Berkshires Cabin 2 Mi to Appalachian Trail!

9.6 out of 10, Exceptional, (10)
"The hosts were extremely responsive and helpful, providing us with hiking ideas, questions regarding the house and suggesting best shopping spots for incidentals. The living room was cozy, seating five comfortably. The kitchen was well stocked so cooking a Thanksgiving meal was a pleasure. We thoroughly enjoyed ourselves."
Berkshires Cabin 2 Mi to Appalachian Trail!
'The Mill River Cabin’ w/ Fireplace & River View!
TV, streaming services

'The Mill River Cabin’ w/ Fireplace & River View!

9.8 out of 10, Exceptional, (37)
"The Mill River Cabin is the perfect location for a vacation focused on relaxation and communing with nature! We recently enjoyed a beautiful fall week at this property. Highlights included time spent on the deck overlooking the Konkapot River, evening campfires, hiking the large number/variety of trails very nearby, Hancock Shaker Village and the Norman Rockwell Museum. This rustic cabin has everything you need to make for an enjoyable stay. It's a good idea to bring your food and other...
'The Mill River Cabin’ w/ Fireplace & River View!
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.8 out of 10, Exceptional, (38)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Serene Acreage - Pond - Hiking Trails Nearby
Terrace/patio

Serene Acreage - Pond - Hiking Trails Nearby

10.0 out of 10, Exceptional, (6)
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby
Tolland Cabin w/ Private Hot Tub & Grill!
Fridge, microwave, stovetop, dishwasher

Tolland Cabin w/ Private Hot Tub & Grill!

9.4 out of 10, Exceptional, (12)
"I want to preface my review by stating we had a wonderful time. We needed a getaway to unplug and relax and we were able to do just that. The area was beautiful, nature-plenty, quiet, secluded. There were a few unexpected glitches but nothing that we couldn't improvise around. Having said that, the listing said queen size beds, but they were only full, so my husband and I stayed in separate rooms which was sad . We also felt the people that prepped the home for our stay, must have ran short of...
Tolland Cabin w/ Private Hot Tub & Grill!
Romantic and Secluded Berkshire's Gem
Fridge, microwave, oven, stovetop

Romantic and Secluded Berkshire's Gem

9.8 out of 10, Exceptional, (12)
"I recently had the pleasure of staying at a charming cabin in the woods, and it was an unforgettable experience! From the moment we arrived, we were greeted by the serene beauty of nature all around us. The cabin was cozy, beautifully decorated, and equipped with everything we needed for a comfortable stay. I highly recommend this cabin for anyone looking to escape the hustle and bustle of everyday life. It’s the perfect blend of comfort and adventure, and I can’t wait to return for another...
Romantic and Secluded Berkshire's Gem
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Aerial view

Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard

9.6 out of 10, Exceptional, (8)
"We had such a wonderful long weekend away that this home. Everything was exactly as pictured. Home was clean and so welcoming. Location was perfect for all that Great Barrington has to offer. The wraparound deck and fireplace made it all the more special. Communication was excellent and we got quick replies to any questions that came up. I would definitely recommend staying here and would happily return."
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK
Aerial view

LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

9.6 out of 10, Exceptional, (5)
"Beautiful lake, traditional charming cottage- great get-away"
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK
A-Frame Cabin w/ Furnished Deck in Becket!
Exterior

A-Frame Cabin w/ Furnished Deck in Becket!

8.4 out of 10, Very good, (6)
"This A-frame cabin was the perfect location for some Berkshire R&R. Close to so many of western MA's greatest attractions, we had a great time visiting Tanglewood and museums, and touring local towns and restaurants. The property was clean, as described, and very comfortable. Communicating with our hosts was very simple. We will be happy to return!"
A-Frame Cabin w/ Furnished Deck in Becket!
Guesthouse Cabin vacation rentals in Berkshire County
Exterior

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (5)
"Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private. "
The price is CA $754
CA $1,282 total
includes taxes & fees
Jan 1 - Jan 2, 2025
Guesthouse Cabin vacation rentals in Berkshire County
East Otis Reservoir Cabin w/ Porch - Walk to Lake!
TV, fireplace, DVD player

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

8.4 out of 10, Very good, (8)
"Lovely cottage. Very clean. Everything we needed. We had a great time!"
East Otis Reservoir Cabin w/ Porch - Walk to Lake!
Great Family Cabin in the woods on a lake.
Interior

Great Family Cabin in the woods on a lake.

10.0 out of 10, Exceptional, (2)
"We love this place as the lake is extremely quiet and clean. The house has a great living room with lots of charm and plenty of bathroom and bedroom space. I wish I had something bad to say because we could keep it to ourselves, but I do not."
Great Family Cabin in the woods on a lake.
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Fridge, microwave, stovetop, dishwasher

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

10.0 out of 10, Exceptional, (5)
"This was a great, beautiful property to stay at. We are section hiking the AT and even went into NYC by train for a day. There were 6 of us and we were very comfortable. "
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Dining

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

9.0 out of 10, Wonderful, (12)
"We had a wonderful time at the cabin by the lake. Beautiful views in the Morning!! Loved it."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Fantastic cottage in the Berkshire Mountains
Fridge, oven, stovetop, dishwasher

Fantastic cottage in the Berkshire Mountains

10.0 out of 10, Exceptional, (1)
"This cabin is very well-maintained with all the amenities you could ask for... especially no cable TV, and the owner David is responsive and pleasant! It is the perfect place to unplug, unwind and reconnect with life, nature and whoever you're traveling with. The house is an easy 30 minutes to Tanglewood and 20 minutes to Great Barrington so there is plenty to see and do without feeling like always being in the car. We got takeout from a delicious Thai restaurant (Siam Square) in Great...
Fantastic cottage in the Berkshire Mountains
Cabin in the woods w cedar Hot Tub + private pond
Outdoor spa tub

Cabin in the woods w cedar Hot Tub + private pond

Cabin in the woods w cedar Hot Tub + private pond
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 Winsted

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Property grounds

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

9.2 out of 10, Wonderful, (37)
"We loved the brilliant use of space and all the amenities in this cozy hideaway. My husband, who owns a Professional Organization business, was very pleased and impressed by the clever use of various storage options. The walkways were attractively and effectively lit up for evening strolls and dog walking. All instructions were clearly communicated and our stay was lovely"
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Family House On Highland Lake with Dock
Fridge, microwave, oven, stovetop

Family House On Highland Lake with Dock

10.0 out of 10, Exceptional, (23)
"Stayed for labor day with family from out of state. Plenty of room for 4 adults and 4 kids, Could have easily fit more. Had a great time on the dock and having fires in the back yard. "
Family House On Highland Lake with Dock
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (200)
"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"
Peace and quiet on the lake
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.

Frequently asked questions

What are the best cabins near Winsted?
Book one of our 202 cabins in Winsted and you’ll be rewarded with breathtaking scenery, outdoor fun and long-lasting memories. Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! is one place where the rhythms of life seem to slow down. Log Cabin Living on the Esopus Creek is another popular choice if you’re craving time out in nature.
Are there cheap cabins near Winsted?
Priced from CA $754 to CA $754 per night, getting away with friends or family is affordable and easy. Book one of our cheap cabins near Winsted and enjoy an adventure-filled escape without blowing 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 mountain cabins near Winsted?
If you’re craving fresh air and stunning views, escape the city and stay in a Winsted mountain cabin. Experience nature without roughing it at Charming, Quiet, River Front. This lofty rental has all you need for an idyllic getaway, such as nearby wildlife walks and snowsport activities. Alternatively, experience mountain life at ROMANTIC LAKE RETREAT. It comes with nearby wildlife walks, a deck and more.
What are the best river cabins near Winsted?
When you think of the word relaxing, a river cabin near Winsted should be the first thing that comes to mind. Charming, Quiet, River Front is one place where you can find some serenity. In addition to its beautiful surroundings, it comes with amenities such as nearby wildlife walks and snowsport activities. ROMANTIC LAKE RETREAT is another appealing option. On-site watersports and nearby wildlife walks are among the conveniences that await you here.
What are the best cabins with pools near Winsted?
Staying in a cabin rental with a pool adds a level of fun to your vacation. If you’re looking for one near Winsted, ROMANTIC LAKE RETREAT has amenities like on-site watersports and a swimming pool to make your poolside escape even more memorable. Country Cabin in Woodstock, NY- Cozy and Pet Friendly is also popular and features a swimming pool and a barbecue grill.
Can I find beach cabins near Winsted?
Pack your Hawaiian shirts and spend your seaside getaway at Relax, reconnect and enjoy!. This Winsted beach cabin comes with on-site watersports and clothes washing facilities. Rustic Lakeside Cabin at White Gate Farm also delivers a sun-soaked stay. Featuring on-site watersports and beach sun loungers, it was made for carefree days by the shore.
What are the best weekend cabin rentals in Winsted?
If you can’t wait to spend a couple of relaxing days immersed in nature, Charming, Quiet, River Front is the perfect place. Put your bags down here for a long weekend and make use of amenities such as a patio and a firepit. Another fantastic option is ROMANTIC LAKE RETREAT. Offering on-site watersports, a swimming pool and plenty of peace and quiet, you’ll go home feeling all brand new.
What are the best cabin prices near Winsted?
Whether you’re pinching your pennies or want to splash out on your next vacation, you’ll find what you’re after with Expedia. At the moment, you can score a Winsted cabin from CA $754 per night.This price was 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.
Can I find log cabins in Winsted?
Nostalgic, cozy and offering a more laid-back way of life, log cabins have an enduring appeal. Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! is an ideal example in Winsted. On-site watersports and a porch are among its many amenities. Luxury secluded Catskill log cabin on creek-ski hike great restaurants mins away also offers respite from the routine. Make the most of its gorgeous location and amenities including a porch and a firepit.
What are the highest-rated cabins in Winsted?
Travelers just keep going back to A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything. This hot spot comes with lots of amenities like on-site watersports and a barbecue grill. It won’t take you a long time to work out why Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating is also a traveler favorite. Conveniences like a firepit and on-site watersports will help make your stay even more memorable.
Why should I book a cabin near Winsted?
For an escape that’s big on character, affordability and comfort, a cabin is the best choice. Leave your city blues behind and explore the greenery of the wilderness. From action-packed days to peaceful evenings cuddled up with your special someone, cabins offer both relaxation and excitement. Check out the great Winsted options on Expedia.
What are the top nature cabins in Winsted?
With ample charm and creature comforts, Charming, Quiet, River Front is among our leading nature cabins in Winsted. But with loads of things to see and do nearby, don’t spend too much time relaxing indoors. Activities such as ice skating nearby and nearby hiking and biking trails are waiting here. ROMANTIC LAKE RETREAT is another getaway where you can get back to nature. Mountain climbing and nearby basketball are a couple of enjoyable ways to do it.