Holiday houses in Winchester

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Popular amenities for Winchester holiday rentals

Other great holiday rentals in Winchester

Townhouse in Grafton
4.87 out of 5 average rating, 109 reviews

Heaven's Gate

JenniferRating, 5 stars1 week ago
We LOVE this place. Perfect for our girls weekends!!! We will be back!!
Top Guest favourite
Home in Payson
4.96 out of 5 average rating, 48 reviews

15 minutes to Quincy! - 3 bedroom/2 Full Bath

NatalieRating, 5 stars2 weeks ago
Great place to stay! The bed was so comfortable! There were little touches/ upgrades all around the house, that are very thoughtful and accommodating! Would recommend.
Superhost
Home in Quincy
4.86 out of 5 average rating, 43 reviews

Gramke Guest House w Country Setting

ErnestRating, 5 stars1 month ago
We stayed for 5 days to see my sister and let me tell you way worth it. We really enjoyed ourselves. Will definitely be back. Stephen was very responsive and teneded to all our needs. 5 star for sure
Cottage in Havana
4.83 out of 5 average rating, 89 reviews

Lakeside Charm | Cozy Cottage + Golden Hour Magic

PhillipRating, 5 stars2 days ago
Great communication, helpful, understanding! Will definitely revisit, and highly recommend!
Top Guest favourite
Cabin in Rushville
5 out of 5 average rating, 49 reviews

Whispering Oaks Cabin

LoganRating, 5 stars5 months ago
This was an excellent cabin with an excellent host! Spotless clean. Great location and amenities. Will be using it again. A+ rating
Guest favourite
Home in Fowler
4.71 out of 5 average rating, 76 reviews

Unplug and relax

MyraRating, 5 stars2 months ago
Sure! Here’s a polished Airbnb review based on your experience: 5 Stars - Perfect Girls’ Getaway! This Airbnb was exactly what we needed for our Best Friend weekend getaway! The location is about 20 minutes from the heart of Quincy, making it convenient for shopping and dining while still offering a peaceful and secluded retreat. The home itself was incredibly spacious, and we especially loved the enclosed front porch and back patio—perfect spots to relax and unwind. One of the best parts was the tranquility; with no close neighbors and only a handful of cars passing by all day, it felt like a true escape from the hustle and bustle of daily life. If you’re looking for a quiet, comfortable, and private place to recharge, this is it. Highly recommend, and we’d absolutely stay here again!
Superhost
Home in Mount Olive
4.87 out of 5 average rating, 47 reviews

Lake House off Route 66

AutumnRating, 5 stars2 days ago
Very peaceful stay! There was a fire waiting for us in the firepit. Plenty of space inside and out. There is plenty of outdoor space to walk or just sit and relax. There is a doggie door that makes it so easy to let my pups out. I wish I could have stayed longer!
Top Guest favourite
Cabin in Winchester
4.96 out of 5 average rating, 157 reviews

Container Home GREAT Countryside Views COZY Stay

SabrinaRating, 5 stars1 month ago
We needed a peaceful evening away and this was perfect. Wonderful porch to sit on and soak in the fresh air and places to walk and unwind.

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Scott County
  5. Winchester