Holiday rentals in Windsor

Brickway Retreat

Newly Remodeled 2 Bed, 1.5 Bath home in quiet neighborhood. This modernized house features a large fully furnished kitchen that is open to the dining area. The large living room with 10 ft ceilings has a pull-out sofa. Big screen TVs equipped with Roku streaming service in the master bedroom and living room. Wi Fi throughout the house is included. Enjoy your mornings on the cozy front porch featuring cedar pillars and stamped concrete and enjoy your evenings on the back patio around the fire pit

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

Game Room | Hot Tub | Fire Pit @ Lake Shelbyville

Sitting just a mile outside city limits and minutes to Lake Shelbyville is this beautifully appointed home waiting for guests to enjoy all of its amenities; pool table, fire pit, grilling area, corn hole set, and hot tub. Inside, nothing was held back when it came to decorating this home for a truly relaxing experience. All the amenities of home are here just waiting for you to arrive, relax, and enjoy. We are sure you will rest easy in this boutique style home located at Lake Shelbyville.

Lake Shelbyville-Lakeside Villas

Lake Shelbyville is the perfect place to spend your next vacation, reunion, weekend away you name it! Our property offers amenities shared among the villas; fully stocked pond, half basketball court, fire pits, playground, & backs up to a local popular camping ground, just minutes from the lake and marina! Inside our villas are fully equipped kitchens, washer and dryer, free WiFi, smart TVs, fully stocked with starter amenities to get your vacation started without rushing to the store!

Prairieview Cottage Retreat - Hot Tub Sunsets

REST, RELAX, RETREAT... Escape to tranquility at this picturesque, pet-friendly cottage, nestled in the serene countryside. Whether you're coming for a romantic retreat, family getaway, or a solo sanctuary, this charming haven offers a wonderful blend of comfort and serenity. Enjoy stunning sunsets from the hot tub, cozy up by the firepit on the patio, or simply unwind indoors in comfort. This retreat is ideally located in the heart of Illinois Amish country and near Lake Shelbyville.

The Candy Kitchen

Take a step back in time as you enter this authentic 1930's Soda Fountain located in downtown Greenup Village of the Porches situated on the Historic National Road. The Loomis Family immigrated from Greece and operated the Soda Fountain and Confectionary until the 1960's. It has since been transformed into a spacious and comfortable living area with the original Soda Fountain still intact, beautiful tin ceiling, and also includes a large kitchen, a separate shower room & powder room.

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!

Modern Loft in Historic Downtown

Lincoln’s Loft is close to everything making it easy to plan your visit to downtown Vandalia. This loft offers a bedroom, full kitchen and bath, dining room, living room with a pull out sofa, and large smart TV. This loft also offers beautiful views of the oldest State Capitol in IL and is within walking distance to many restaurants, bars, and local shops. It is located on the 3rd level and will require you to climb 2 flight of stairs. For events please contact the host!

Wooden Shoe Factory, Historic, w/ Bar & Breakfast

Historic 1880 Wooden Shoe Factory by Wooden Shoe Maker Gerhard Deymann. A great getaway Tiny House from the past with a Bar & Books. Please take some & leave some :-) Fully furnished. Tons of charm. It has a loft, luggage lift, exposed brick/beams, fireplace, bikes, antiques, front sitting area, swing, grill, back patio, yard, private parking, appliances, vaulted ceilings. 6 minutes to I57, I70, Effingham, & dozens of restaurants. 1 block to 7 Teutopolis Bars, & diners.

Sweet Dreams Cabin. Peaceful & Relaxing

Get some quality family time at this newly remodeled cabin near the beautiful Embarrass river. You are surrounded by beautiful woods and a small creek. Lush wildlife is all around you so you can be one with nature. The cabin has all the luxury's to allow for a long term stay as well. Beautiful Lake Charleston is not far away. The large circle drive offers plenty of parking for your boat and guest. The large deck on the rear gives a beautiful view to be enjoyed by all.

The Hideaway - Charming apartment in Arthur IL

Enjoy exploring Illinois' largest Amish settlement while relaxing in this one-bedroom apartment one block from downtown Arthur, a village of 2200. Country charm abounds in this gem which sleeps three (full bed plus fold-out love seat). There is a private entrance, access to laundry facilities, and private parking off the street. We are 9 miles west of I-57 on Route 133 (take exit 203 at Arcola) and 40 miles from Champaign.

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.