Find Cabins in Winchester for Rent

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Check prices for these dates

Next weekend
Apr 4 - Apr 6
In two weeks
Apr 11 - Apr 13
In one month
Apr 25 - Apr 27
In two months
May 23 - May 25

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, (51)
"Very quiet, beautiful and amazing place to stay. Loved watching the birds at the feeder right outside the front porch. Enjoyed seeing and petting the horses. Great view from the front porch. Hosts were great and took care of any needs that we had. Highly recommend!!"
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, (26)
"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

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
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
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
8.0 out of 10, Very good, (6)
"We enjoyed it! Debbie was amazing, brought firewood for us to enjoy a fire. Communication was great! The place was perfect for our family. Thank you for everything Debbie!"
The price is CA $107
CA $207 total
includes taxes & fees
Mar 30 - Mar 31
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, (100)
"clean and comfortable"
White House at Grand Central
Funky mini loft in fox park! Pet friendly!!
Private kitchen

Funky mini loft in fox park! Pet friendly!!

7.8 out of 10, Good, (49)
"This place is INCREDIBLE!!! We have little kids, a teenager, a senior and two adults in the family and EVERYONE absolutely LOVED it! We can't wait to go back! This will definitely be our go to spot when visiting St Louis. The host was extremely communicative. There was plenty of space for everyone. It is decorated incredibly, everyone got a kick out of it! "
The price is CA $79
CA $190 total
includes taxes & fees
Apr 6 - Apr 7
Funky mini loft in fox park! Pet friendly!!
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?
Lock in one of our 76 cabins in Winchester and you’ll be rewarded with striking scenery, outdoor adventure and memories you’ll never forget. King Studio, 1 Bath Log Cabin With Fireplace Near St Louis And Scott Afb is where life seems to slow down. Authentic Log Cabin With Something For Everyone is another top pick if you’d love to spend time in Mother Nature.
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?
If you’re on the lookout for an escape your little ones won’t stop raving about, a family cabin rental in or near Winchester is an awesome choice. Take the gang to Cabin - The Magic Tipi Retreat. It offers on-site watersports and children’s activities along with plenty of outdoor adventure. Authentic Log Cabin With Something For Everyone also rolls out the red carpet for small groups and families and comes with children’s activities and on-site watersports.
What are the best river cabins near Winchester?
If you’re searching for a homely getaway near the water, a Winchester river cabin is hard to beat. Spend your break at Angela Custom Log Houseon 7 acres. Pets Not Allowed. No Smoking. and let all your stresses disappear downstream. Handy amenities here include a firepit and a queen bed. Another awesome riverside retreat is “Exclusive” River Cabin on Stilts. It offers outdoor furniture, a firepit and more.
What are the best cabins with pools near Winchester?
Slip on your board shorts or bikini and go for a dip whenever your heart desires when you choose one of our cabin rentals with a pool. Cabin - The Magic Tipi Retreat is a standout. On-site watersports and a patio are some of the other amenities you can make use of here. Or you can escape to Firefly Inn lakefront family/pet friendly retreat. Book early!. As well as a nice pool, this cabin comes with on-site watersports and a swimming pool.
Can I find beach cabins near Winchester?
Wake up and wander down to sparkling blue waters when you escape to a Winchester beach cabin rental. Sun, fun and family time should be the main things on your mind at Secluded Garden Cabin Located on the Bourbeuse River. It comes with parking facilities and air conditioning. Alternatively, unpack your suitcase and cozy up at Cabin 1 at the Pallet Factory. Conveniences here include clothes washing facilities and children’s activities.
What are the best weekend cabin rentals in Winchester?
Nothing tops a weekend cabin getaway after a tiring week at work. Swap your cramped office for a couple of days in the outdoors at Cabin - The Magic Tipi Retreat. On-site watersports and a patio are some of the conveniences it comes with. Alternatively, forget all about work at Authentic Log Cabin With Something For Everyone. Get cozy here and enjoy access to on-site watersports and a patio.
What are the best cabin prices near Winchester?
With prices starting at just per night for a cabin rental near Winchester, there’s no reason to wrangle with that hard-to-pitch tent.
Can I find log cabins in Winchester?
Begin your day with a cup of coffee in your cute log cabin and then spend the rest of your time rock climbing and caving. Sound heavenly? Then check out Authentic Log Cabin With Something For Everyone. Another escape that comes with ample charm and warmth is Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis. Close-by activities like cycling and fishing will add to your memorable experience here.
What are the highest-rated cabins in Winchester?
Travelers just keep coming back to Angela Custom Log Houseon 7 acres. Pets Not Allowed. No Smoking.. This top-notch option features a host of handy amenities including a patio and a firepit. It won’t take you very long to understand why Cozy Cottage, we’re told it’s heavenly! is also popular with vacationers. Conveniences like a patio and a firepit will help make your stay even more memorable.
Why should I book a cabin near Winchester?
Affordability, outdoor activities, rustic charm — there are countless reasons to choose a Winchester cabin. Get away from the cacophony of the city and rise with the sound of songbirds and wildlife. There’s tons of adventure just a stone’s throw away too. Whether you’re on vacation with friends, relatives or your honey, you’ll locate the perfect rental cabin on Expedia.
What are the top nature cabins in Winchester?
If you can bear to step away from the comforts of Angela Custom Log Houseon 7 acres. Pets Not Allowed. No Smoking., you’re in for a treat. One of our most sought-after nature cabins in Winchester, it offers fantastic access to the outdoors and amenities such as a fireplace and a patio. “Exclusive” River Cabin on Stilts should also be on your list. Location, a firepit, a patio … They’re just a few things to love about this place.