Find Cabins in Winchester for Rent

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Check prices for these dates

Next weekend
Apr 25 - Apr 27
In two weeks
May 2 - May 4
In one month
May 16 - May 18
In two months
Jun 13 - Jun 15

Browse Select Winchester Cabin Rentals

Serenity Log Inn -Log out and Log Inn to Serenity
TV, fireplace, DVD player

Serenity Log Inn -Log out and Log Inn to Serenity

10.0 out of 10, Exceptional, (24)
"Beautiful place will recommend to others"
Serenity Log Inn -Log out and Log Inn to Serenity
Cozy 1-Bedroom Cabin Retreat
Property grounds

Cozy 1-Bedroom Cabin Retreat

2.0 star property
Cozy 1-Bedroom Cabin Retreat
Hillside Cabin on 43 Acres w/ Private Lake & View!
Interior

Hillside Cabin on 43 Acres w/ Private Lake & View!

10.0 out of 10, Exceptional, (52)
"Stay was amazing for our family. Did have to shelter in the owners house during a bad storm. Owners and family were supper friendly to our family and friends that stopped by and walked the property. The cabin is really comfortable and homey. Would or planning to stay again in the future .Ken Moeser"
Hillside Cabin on 43 Acres w/ Private Lake & View!
‘The Reubling House’ - Modern-Rustic Cabin!
Fridge, microwave, stovetop, dishwasher

‘The Reubling House’ - Modern-Rustic Cabin!

9.6 out of 10, Exceptional, (20)
"First let me say the property manager was amazing! When we first arrived we ran into some issues with a large amount of dead Asian Beetles in the house after a brief warm front blew through. This is an old building so totally normal (it happens). We made the property manager aware and they were immediately responsive with the offer to use a different property but we decided to allow them to clean it as we didn’t figure any more bugs would show due to the current cold temps now. They showed in...
‘The Reubling House’ - Modern-Rustic Cabin!
‘Bross Brother's Cabin’ w/ Wraparound Porch!
Property grounds

‘Bross Brother's Cabin’ w/ Wraparound Porch!

10.0 out of 10, Exceptional, (27)
"A beautiful historic cabin in a beautiful town. Exceeded expectations! "
‘Bross Brother's Cabin’ w/ Wraparound Porch!
4 Bedroom Cabin Retreat
Interior

4 Bedroom Cabin Retreat

10.0 out of 10, Exceptional, (1)
"Came in for a wedding but had a partial day to enjoy the place. Good walking and activities. "
4 Bedroom Cabin Retreat
4 Bedroom Cabin Retreat
Interior

4 Bedroom Cabin Retreat

2.0 star property
10.0 out of 10, Exceptional, (3)
"This is a great location if visiting St. Louis! It’s peaceful and the scenery is amazing. We saw tons of deer and turkey, along with other birds and small animals. The entire place is clean and very tastefully decorated. The entire layout is well thought of and I don’t know if we’ve stayed anywhere as technologically advanced. This isn’t just a “cabin in the woods”, it’s truly a beautiful place with a very luxurious feel. The owner, Chris, is super responsive to messages and we would absolutely...
4 Bedroom Cabin Retreat
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 Winchester

Studio, sleeps 4, patio, short drive to Ski Resort, Six Flags & concert venues
Interior

Studio, sleeps 4, patio, short drive to Ski Resort, Six Flags & concert venues

2.0 star property
8.4 out of 10, Very good, (9)
"It was a great place! The backyard was very cute and my boys enjoyed running around and playing while we were there. We were so close to using the firepit, but alas, we did not have time. It was awesome of Debbie to get that set up for us before we arrived! Overall, it was a cute little vibe for the space. The upstairs neighbor was relatively quiet, so that was a plus as well! The only thing that went weong was the fault of Google Maps bronging me to the wrong location, but it was literally just...
The price is CA $104
CA $201 total
includes taxes & fees
Apr 24 - Apr 25
Studio, sleeps 4, patio, short drive to Ski Resort, Six Flags & concert venues
White House at Grand Central
Comfort Apartment

White House at Grand Central

4.0 star property
8.6 out of 10, Excellent, (103)
"Our stay was very home-like, safe, and comfortable."
The price is CA $142
CA $256 total
includes taxes & fees
Apr 22 - Apr 23
White House at Grand Central
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
Outdoor dining

1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!

10.0 out of 10, Exceptional, (199)
"My husband and I stayed two nights at this cottage and loved it so much. It’s super cute and cozy, perfect for just the two of us. And you can’t beat the location! Within walking distance to everything on Main Street. My husband said he wanted to stay here again!"
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
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 Winchester?
Ranging from small and quaint to spacious and luxurious, there are 82 cabins to choose from in and around Winchester. Some great options include King Studio, 1 Bath Log Cabin With Fireplace Near St Louis And Scott Afb and Authentic Log Cabin With Something For Everyone.
Are there cheap cabins near Winchester?
For a budget-friendly vacation in nature, you can’t top our cheap cabins near Winchester. Wake each morning to the sounds of birds and wildlife from one of our cozy cabins priced from to per night.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 family cabins near Winchester?
Stay at a family cabin in or near Winchester and fill up the family photo album with more precious memories. Cabin - The Magic Tipi Retreat is a great choice. In addition to the promise of adventure and fun, it comes with lots of handy amenities like on-site watersports and children’s activities. Also check out Authentic Log Cabin With Something For Everyone. Children’s activities and on-site watersports will help keep your entourage happy and comfortable.