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Holiday houses in Windsor

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Top-rated holiday rentals in Windsor

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
An outdoor patio area is shown, featuring a table and four chairs arranged on a concrete surface. Two windows flank a door, allowing natural light to enter the space. Green grass surrounds the patio, contributing to the peaceful ambiance.
Cabin in Mattoon
5 out of 5 average rating, 43 reviews

Country Living in Mattoon

Guest house located on personal property offering quiet country living. 800 square feet of living space with a front porch to enjoy nature. Located just outside of Mattoon, IL north of Lake Paradise. Just 10 minutes from Emerald Acres, 10 minutes from Lake Mattoon and 20 minutes from Lake Shelbyville. Only 16 miles from EIU and a perfect place to stay for local sporting events. Other small towns nearby worth visiting include Arthur, IL and Casey, IL. We have ample parking for cars and trailers.

Top Guest favourite
Cottage in Sullivan
5 out of 5 average rating, 263 reviews

3-Acre Country Escape | Wildlife | Total Serenity

A freshly updated cottage, nestled in the country of Sullivan, just minutes from boating, camping, golf, theatre style shows, Amish country, and more. If you are looking for peaceful nights, this place is for you! Surrounded by mature trees and nature, where many days you will catch deer roaming the yard. Plenty of yard space for games, a fire table to converse around, and chairs on the porch to sit back, relax, and take in the tranquil sounds that surround you here at Lakewood Cottage #1.

Top Guest favourite
Cabin in Shelbyville
5 out of 5 average rating, 22 reviews

A Novel Stay

Enjoy peace and nature in this 3 bd 2 bath log cabin located on 3.5 acres of wooded property just a few minutes from Lithia Marina at Lake Shelbyville, IL. This home features a fully stocked kitchen, Blackstone, 6 person hot tub and large solo fire pit. It comfortably sleeps 8 and can flex up to 11, if needed. There are 3 Roku Tv's, bluetooth speakers and many family friendly games for your use. Come stay at a Novel Stay "Into the forest I go, to lose my mind and find my soul".- John Muir

Guest favourite
A cozy tiny house is nestled among trees, featuring a welcoming front porch with a swing. Two bear sculptures stand at the entrance. A fire pit surrounded by chairs is visible in the gravel yard, inviting outdoor relaxation.
Tiny home in Mulberry Grove
4.88 out of 5 average rating, 128 reviews

Cozy Tiny Home in Woods w/ Firepit & Porch Swing

Need a break? Some time to relax and breathe? Come get away from it all at this TINY HOME in the woods. Roast s'mores around the fire pit, go kayaking on nearby Carlyle Lake, stargaze on the porch swing with a cozy blanket...or just cuddle up and binge watch your favorite shows in front of the fireplace. Fully updated with everything you need: full size washer/dryer, stocked kitchen, smart TVs, wifi, outdoor grill, 2 RV hookups, space to park a boat - conveniently right off of I-70!

Top Guest favourite
A welcoming living area features a comfortable sofa and armchair, paired with a decorative area rug. A flat-screen TV is mounted near a stone fireplace, surrounded by natural light from the windows. Indoor plants add a touch of greenery to the space.
Cottage in Effingham
4.94 out of 5 average rating, 583 reviews

Waterfront Cabin•Boat Dock, Fireplace&Beach Access

The cabin sits in the trees along beautiful Lake Sara. The cabin offers a quiet place to relax and unwind. You can bring your kayaks, paddle boards or trailer your family boat along for some fun tubing and skiing on the lake. The dock allows for the boat to be left in the water till the end of your stay. The Marina, Pinky’s (waterfront restaurant), Rusty Reel (bar below Pinky’s ), Cardinal Golf Course, Lake Sara Campground and Lake Sara Beach are all a short walk from the cabin!

Top Guest favourite
Farm stay in Shelbyville Township
5 out of 5 average rating, 75 reviews

The Bin at No Bad Days farm

The Bin at No Bad Days farm is a newly constructed grain bin. As you walk in checkout the beautiful craftsmanship on the ceiling! There is a loft upstairs where you will find a king size bed. There is also an oversized chair that converts to a small bed as well. Main floor has a sofa sleeper for two. There is a kitchenette and full bath. We know you will enjoy the rustic look of this unique property. We are 5 minutes from Lithia Springs Marina and we have room to park a boat!

Guest favourite
The exterior of a historic Folk Victorian home is showcased, featuring a red brick façade and a metal roof. The front porch, adorned with gingerbread trim, is flanked by two blue chairs. Lush green grass surrounds the home, and mature trees provide shade.
Home in Teutopolis
4.9 out of 5 average rating, 271 reviews

Wooden Shoe Haus Folk Victorian Families Breakfast

Free Continental breakfast. This 1880 Wooden Shoe Haus was built by owner & Wooden Shoe Maker Gerhard Deymann. It is a historic Folk Victorian home, fully furnished while keeping much of its historic charm. It has bikes, antique furniture, front porch, swing, grill, back patio, & yard. Private side & back parking. Includes all appliances, 10' ceilings, & 1' thick walls. 6 minutes to interstates 57, 70, Effingham, & dozens of restaurants. 1 block to downtown Teutopolis.

Guest favourite
A spacious deck features a wooden railing, offering views of a landscaped area with tall trees and lush greenery. The scene captures a peaceful blend of woods and open fields, inviting relaxation in a tranquil, natural setting.
Cabin in Strasburg
4.93 out of 5 average rating, 95 reviews

Peaceful Cabin Retreat

Located on 40 acres of secluded tranquility. It's rustic but it's not roughing it. Enjoy the view from the spacious deck overlooking rolling hills of timber, native grasslands and a large creek. Abundant wildlife (deer, turkeys, coyotes, foxes, squirrels, etc.) for viewing and hiking trails to experience the unspoiled habitat. The property is located at the end of an all-season road. You're likely to see absolutely no one except for your family/friends for the entire stay.

Top Guest favourite
A tree-lined street is visible, showcasing a yellow house with a light-colored roof. The grassy yard is bordered by shrubs, leading to a sidewalk. Nearby buildings and a well-maintained road add to the neighborhood's residential character, with open space extending in the distance.
Home in Findlay
5 out of 5 average rating, 13 reviews

Charming Yellow House

This home is just 5 minutes from Lake Shelbyville and Findlay Marina! Whether you’re here to fish, boat, hunt, explore, or unwind, this adorable yellow house is your spot. 🍽️ Walk to the café, park, bait/gas station 1+ block 🥩 Dinner or drinks at the local steakhouse or the winery just 4 blocks 🛶 Boat-friendly with side street parking parking on East and South road **unfortunately we do not allow pets anymore **Jack and Jill bathroom shared between bedrooms

Top Guest favourite
The cabin features a covered porch with rocking chairs, offering a shaded area surrounded by lush greenery. A sloped metal roof and large windows enhance the natural light. The setting is serene, framed by tall trees and a stone chimney, creating a tranquil outdoor space.
Cabin in Strasburg
4.98 out of 5 average rating, 60 reviews

Rocky Springs Cabin: A Secluded Cabin On 40 Acres

Rocky Springs Cabin became a home away from home for many beginning in 2013. We have now just joined Airbnb! You can also find us on Google. The cabin is just 10 minutes from Lake Shelbyville and is surrounded by the Hidden Springs State Forest! This cabin rental sets on 40 acres with a pond right outside the front door. It is surrounded by trees and walking trails. The pond has a variety of fish, including, Catfish, Bluegill, and Bass.

Top Guest favourite
The exterior of Paradise Cottage features vibrant red wood paneling, with a stone path leading to a welcoming front door. Large windows allow natural light and views of the surrounding trees, enhancing the cottage's connection to its lakeside environment.
Cabin in Mattoon
4.95 out of 5 average rating, 187 reviews

Cottage on Lake Paradise,

Welcome to Paradise Cottage nestled on Lake Paradise! Cozy and warm with wood finishes throughout. Includes three-tiered deck/patio, with the lowest level sitting over the water. Perfect for fishing (this lake hosts an annual fishing tournament), canoeing/kayaking, or just relaxing. Great for bird watching, with great blue herons, egrets, ducks, bald eagles, plovers, cormorants, woodpeckers and other species seen daily.

Guest favourite
Home in Shelbyville
5 out of 5 average rating, 5 reviews

The Boho Loft | Lake Shelbyville

The Boho Loft 🌿 Walk in and feel the difference. Unwind in a private library with two massage chairs, surrounded by living plants and warm, calming spaces. Sleep deep, wake slow, and enjoy views over a brick road. Just 1 mile from Lake Shelbyville and a short walk to downtown. Fire pit, full kitchen, WiFi, Smart TVs, and boat parking. Superhost stay for girls weekends, couples, or time to yourself.

Popular amenities for Windsor holiday rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Shelby County
  5. Windsor