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Search the Best Cabins in Winchester

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Winchester cabin rentals

Exterior

1. Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Jacksonville
10.0 out of 10, Exceptional, (26 reviews)
"Really enjoyed our stay. The place was very clean and bed really comfortable "
United States
David W.
$119 nightly
The price is $126
Sep 23 - Sep 24
Total with taxes and fees
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Exterior

2. Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Jacksonville
10.0 out of 10, Exceptional, (17 reviews)
"The place was really neat and the host was incredibly friendly"
United States
Dylan
$149 nightly
The price is $158
Sep 23 - Sep 24
Total with taxes and fees
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Exterior

3. Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee

Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee
Murrayville
9.8 out of 10, Exceptional, (69 reviews)
"Kevin was a great host. Responsive when I had issues with the lock. Great homemade cookies. "
United States
Anonymous traveler
$131 nightly
The price is $139
Sep 24 - Sep 25
Total with taxes and fees
Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee
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 Winchester Hotel Reviews

William Watson Hotel

William Watson Hotel

8/10 Good
"We enjoyed our weekend stay at the unique and historical hotel. Will warn if you have difficulty with stairs to make sure and book a room on the main floor. The breakfast is very minimal. Love the charm of the hotel. And views of courthouse."
Roy 3-night trip
Posted 1 day ago
William Watson Hotel

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
2,775
Accommodation
29 Cabin Rentals
Lowest Price
$63
Highest Price
$144

Frequently asked questions

What are the best cabins near Winchester?
Vacation in one of our 24 cabins in Winchester and be rewarded with striking scenery, outdoor adventure and long-lasting memories. Cabin - Spacious Riverfront Perch/easy Access To St. Charles Less Than 1 Hr To St. Louis offers a more leisurely pace of life. Cabin - Family - Friendly And Perfect For Large Groups And Family Reunions is also perfect if you need time out in nature.
Are there cheap cabins in Winchester?
Priced from $63 to $144 per night, getting away with the family is easy and affordable. Rent one of our cheap cabins in Winchester and enjoy some outdoorsy fun without breaking 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 family cabins near Winchester?
Stay at a family cabin in or near Winchester and top up the family photo album with some joyful new memories. Cabin - Luxurious Otter Pointe is an enticing option. Along with the promise of fun and adventure, it comes with handy amenities like a toaster and children's activities. Also check out Cabin - Family - Friendly And Perfect For Large Groups And Family Reunions. Children's activities and on-site watersports will help keep the troops nice and comfy.
What are the best river cabins near Winchester?
If you're seeking a peaceful place to stay overlooking the water, a Winchester river cabin is hard to go past. Stay at Exclusive" River Cabin On Stilts and let any stresses drift downstream. Handy amenities here include outdoor furniture and a firepit. Another riverside escape is Little Red Cabin By The Spoon River. Its conveniences include outdoor furniture, a queen bed and more.
What are the best romantic cabins near Winchester?
Treat your honey to a few dreamy nights at a romantic cabin rental. You and your other half will fall head over heels for Cabin - Spacious Riverfront Perch/easy Access To St. Charles Less Than 1 Hr To St. Louis. With a beautiful setting, a king-sized bed and a patio, it has everything you need for an idyllic escape. Peaceful Cozy Cabin, With Fireplace is another place to curl up together. A king-sized bed and winery tours are waiting for you here.
What are some great Winchester cabins?
When you want to spend some time out in nature but aren't fond of wrestling with tent poles, a cabin is the ideal solution. Book a few nights or longer at Little Red Cabin By The Spoon River. This property comes with an electric car charging station, a fireplace and more. Alternatively, experience outdoor fun and comfort at the same time at Cabin - Family - Friendly And Perfect For Large Groups And Family Reunions. A firepit and a nearby waterfront are among the amenities here.
What are the best weekend cabin rentals in Winchester?
It doesn't get better than a weekend cabin getaway after a tiring week at work. Swap the office cubicle for a few days or so in the great outdoors at Cabin - Luxurious Otter Pointe. A patio and a fireplace are among the amenities it offers. Work will also be the furthest thing from your mind at Cabin - Family - Friendly And Perfect For Large Groups And Family Reunions. Put your bags down here and make the most of on-site watersports and a firepit.
What are the best cabin prices in Winchester?
If you want to save on your stay, Expedia has some great deals on Winchester cabins that won't put a dent in your budget. Like the sound of $63 per night?
What are the highest-rated cabins in Winchester?
With an impressive rating, it's no surprise why Cabin - Family - Friendly And Perfect For Large Groups And Family Reunions is such a favorite with Expedia travelers. Some amenities here include on-site watersports and a firepit. Cabin - Luxurious Otter Pointe is another fantastic option. Conveniences such as a patio and a fireplace will help make your stay a comfy one.
Why should I book a cabin in Winchester?
Affordability, nature-filled surroundings, rustic charm — there are countless reasons to opt for a Winchester cabin. Get away from the noisy concrete jungle and wake up to the sweet sound of birdsong. There's tons of adventure within striking distance too. Whether you're taking a break with friends, family or your special someone, you'll find the ideal cabin on Expedia.
What are the top nature cabins in Winchester?
If you can drag yourself away from the coziness of Exclusive" River Cabin On Stilts, adventure is everywhere. One of our premier nature cabins in Winchester, it offers superb access to the great outdoors and amenities such as a firepit and a barbecue grill. Little Red Cabin By The Spoon River should also be on your short list. Rustic charm, location, a patio, a barbecue grill ... This escape has it all.

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