Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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Guest favorite
The exterior of the Elk Ridge cabin is showcased from across the pond, surrounded by lush greenery. A spacious deck is visible, offering seating options and access to the waterfront. Two water buffalo are seen grazing nearby, highlighting the natural wildlife setting.
Cabin in Arcola
4.97 out of 5 average rating, 113 reviews

Elk Ridge

Come and enjoy yourself at Elk Ridge, the first B&B of Wildlife Manor! Located within Aikman Wildlife Adventure, we are home to over 240 animals. This retreat offers the scenery of wildlife inside or outdoors. You have the chance to see zebras, bison, camels, and much more! Elk and water buffalo love to take a swim in the pond that Elk Ridge overlooks as well. Enjoy the natural scenery in the evening around a firepit on the waterfront deck. This will be an overnight adventure you won't forget!

Guest favorite
A cozy sleeping area features a spacious bed with multiple pillows in neutral tones. Wall sconces provide gentle lighting on either side. A decorative sign with the word 'welcome' is displayed above the headboard, adding a personal touch to the inviting space.
Apartment in Teutopolis
4.95 out of 5 average rating, 657 reviews

The Shoe Inn, a modern apt in downtown Teutopolis

Welcome to The Shoe Inn! You'll be at the center of town within walking distance to all the places you need to be: banquet halls, five bars, restaurants, Wessel's grocery store, ice cream shop, church, hardware store, and community parks. Smart lock, contactless entry is available for a convenient & safe stay. Enjoy the full size washer & dryer (no detergent provided) , fireplace, kitchenette (no stove), free parking, Samsung 50" smart TV w/ 100's of cable channels, Alexa device, & free WiFi

Top guest favorite
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 favorite
Home in Sullivan
4.99 out of 5 average rating, 78 reviews

Asa Creek Cottage

This open concept cottage offers the perfect blend of nature and modern comfort for families and small group gatherings. Enjoy the creek side deck, and listen to the gentle sound of the little waterfall nearby. On cooler evenings, gather around the fire to warm up. The interior boasts a spacious design, close to The Little Theatre on the Square, walking trails, and Lake Shelbyville with boating, fishing and swimming. Relax with a modern kitchen, 3 bedrooms, 2 bathrooms and a rainfall shower.

Top guest favorite
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

Superhost
A spacious living area features two comfortable leather sofas with decorative pillows, arranged around a central coffee table. Large mirrors adorn the wall above the table. Light wood cabinetry and modern appliances are visible in the open kitchen area, enhancing the inviting atmosphere.
Home in Sullivan
4.83 out of 5 average rating, 89 reviews

Shelbyville- Fish, boat, grill, chill, pets, relax

Welcome to REST ASHORED where you can be as restful or as active as you please! Boat around Lake Shelbyville in the morning and return home to play a 9-hole round of golf on the Timberlake course in the afternoon. The boat launch is only a mile away so you won't need much leeway to make your tee time. Or to restock the cooler, for that matter. Enjoy dinner in a full kitchen and watch TV on your large screen TV. Wind-down watching the sunset over the golf course from your back deck.

Top guest favorite
A charming lake house is set among lush trees, featuring a large shaded area with a fabric canopy. Red shutters adorn the windows, while a gravel path leads to the entrance. Colorful floats are arranged in front of the house, enhancing the outdoor space.
Cottage in Effingham
4.97 out of 5 average rating, 303 reviews

Lakefront Cottage • Dock, Kayaks, Fire Pit & Beach

Welcome! Imagine waking up ten steps from the water, kayak paddles already calling your name. The Lake House on Lake Sara puts you right at the edge of the lake — with four kayaks, a crackling fire pit, and a sunlit enclosed porch to come home to. The Lake House is located just a short walk to the Beach, Pinky’s , The Rusty Reel Bar (below Pinky’s) and The Marina. The beach offers a beautiful playground, pavilions, exercise equipment, pickleball courts and a frisbee golf course!

Top guest favorite
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 favorite
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.

Guest favorite
A white, single-story cottage is set amidst greenery, with a shaded porch featuring a wooden bench. Large windows allow natural light in, while landscaped areas with shrubs enhance the outdoor space. The surrounding trees create a peaceful, natural environment.
Tiny home in Arcola
4.87 out of 5 average rating, 78 reviews

The Little Homestead Haven

Welcome to the Little Homestead Haven! Whether you are looking for an anniversary getaway or if you are traveling through the area and looking for a relaxing spot to rest, you will thoroughly enjoy your stay here. Relax and take a soak in the hot tub, while the soothing jets work the tension out of your muscles. It is located less than 2 miles east of Arcola and just off Interstate 57 on Rt. 133, 30 minutes to Champaign airport and right outside of Amish country.

Top guest favorite
A spacious living area features a large sectional sofa with decorative pillows and a patterned area rug. Natural light filters through window blinds, illuminating the wood flooring. A lamp and a small table complement the seating space, while a dining area is visible in the background.
Home in Findlay
5 out of 5 average rating, 43 reviews

The Findlay House

5 to 15 mins from boating, fishing, the beach and golfing. Findlay offers a great park /playground. The Findlay Fast Stop has bait/beer/snacks and gas. Tailwinds Steak House, & Rosie & Irl's BBQ offer good food/drink. The Dollar General is also at the edge of town. We are now able to accommodate boats and vehicles across the street in a fully rocked pull thru parking lot.Electric available across the street at house with extention cord...

Top guest favorite
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.

Popular amenities for Windsor vacation rentals

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