Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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Guest favorite

A modern kitchen features sleek cabinetry and a spacious island with a marble-like countertop. Stainless steel appliances include a refrigerator and an oven, while a ceiling fan provides air circulation. A dining area with a wooden table is visible in the background, complemented by rich red curtains.

Home in Mattoon

4.94 out of 5 average rating, 215 reviews

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

Top 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, 599 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

Guest favorite

The exterior of a spacious villa is presented under a clear blue sky. The building features a welcoming entrance with a covered porch and multiple windows. A gravel pathway leads to the front door, surrounded by well-maintained landscaping and green trees in the background.

Home in Sullivan

4.96 out of 5 average rating, 129 reviews

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!

Top guest favorite

A renovated red caboose, TP&W 527, is positioned on railroad tracks surrounded by grass. The structure features white wheels and an elevated cupola, with windows and a yellow emblem. Green trees provide a natural backdrop, and a cobblestone pathway leads to the entrance.

Train in Oreana

4.99 out of 5 average rating, 128 reviews

The Caboose on Mayberry

Welcome to our mid 1900s caboose TP&W 527 and step back in time. Unwind and relax as you settle into your retreat. Enjoy the view from the cupalo as you browse through one of the books on board, or sit at your dinette and enjoy a board game. Sit out back in one of the adirondack chairs around your own private fire pit and enjoy s'mores, or just a peaceful evening. The caboose has been completely renovated and many modern convienences added. You'll love this unique and romantic escape!

Top guest favorite

The exterior of the Candy Kitchen is illuminated by vibrant neon signs, highlighting its historical architecture. A prominent Coca-Cola sign is displayed above the entrance. A clearly marked door and large windows can be seen, inviting guests to explore the vintage charm within.

Place to stay in Greenup

5 out of 5 average rating, 210 reviews

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.

Top guest favorite

An outdoor patio area features a square fire table surrounded by four wooden chairs. Lush green grass stretches out beyond the patio, with trees and open fields visible in the background, creating a serene setting for relaxation.

Home in Sullivan

5 out of 5 average rating, 235 reviews

3 Acres | Fire Table | Wildlife @ Lake Shelbyville

A completely renovated cottage, nestled in the country of Sullivan, just minutes from boating, camping, golf, theatre style shows, and more. If you are looking for peaceful nights, this place is for you! Surrounded by 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.

Top guest favorite

The bedroom features a queen-sized bed, complemented by exposed brick walls and two windows allowing natural light to fill the space. Soft drapes frame the windows, while nightstands with lamps provide gentle illumination, creating a calm and inviting atmosphere.

Loft in Vandalia

4.94 out of 5 average rating, 286 reviews

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!

Top guest favorite

A large tree with a sign reading '9330 The Cabin' is visible in the foreground. A gravel driveway leads to the cabin, framed by lush, green trees that create a serene natural environment.

Cabin in Ashmore

4.9 out of 5 average rating, 255 reviews

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.

Top guest favorite

A cozy cottage is positioned within a spacious yard, surrounded by greenery and a fence. A clear blue sky and open fields are visible in the background, highlighting the rural setting. Nearby features include a small shed and animal enclosures.

Guesthouse in Effingham

4.93 out of 5 average rating, 420 reviews

Country cottage tiny home.

This 240sq ft cottage offers big living in a tiny space. The cottage is on our 2 acre property that is used for a hobby farm and primary residence. The cottage features luxury vinyl flooring, granite counter tops and an updated farm house feel. The queen size bed is sure to provide the right amount of comfort. When you wake up, walk on over and grab a cup of coffee from the keurig. Enjoy a walk around to see the goats and chickens before heading off for the day.

Top guest favorite

The entrance features a white door framed by blue and white siding. A welcome sign is prominently displayed beside the door, complemented by a potted plant at the base of the steps. Sunlight brightens the area, highlighting the welcoming ambiance.

Apartment in Arthur

4.98 out of 5 average rating, 266 reviews

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.

Top guest favorite

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

4.94 out of 5 average rating, 168 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.

Top guest favorite

A spacious gravel parking area is highlighted, accommodating up to two vehicles. The exterior of the apartment is visible, featuring white siding and a brown shingled roof. Surrounding trees provide shade, contributing to a peaceful rural atmosphere.

Loft in Strasburg

4.93 out of 5 average rating, 100 reviews

One bedroom apartment above garage

One bedroom apartment above a garage in a small and quiet town with fast fiber Internet. We are located in the middle of Shelbyville, Effingham, and Mattoon. 10 minutes to Hidden Springs State Forest. 20 minutes to Lake Shelbyville, Lake Sara, and Lake Mattoon. 20 % off per night for stays longer than 7 nights. 30% off per night for stays longer than 28 nights. Ideal for up to 2 traveling workers.