Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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

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Top guest favorite

The entrance features a welcoming front porch with cedar pillars and a stamped concrete surface. A white door with a black handle and number displays offers access to the home, while large windows on either side allow natural light to brighten the space.

Home in Mattoon

4.94 out of 5 average rating, 204 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

Guest favorite

A modern seating area features a round wooden table and two black chairs. A wall-mounted TV displays a serene image, while an electric fireplace below adds warmth to the space. A circular mirror reflects light from the cozy interior.

Apartment in Teutopolis

4.95 out of 5 average rating, 572 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

A wooden deck extends over a serene pond, framed by greenery. Two black Adirondack chairs are positioned for relaxation, overlooking the water. The surrounding area is graced with a mix of trees and open space, under a bright blue sky dotted with clouds.

Home in Sullivan

4.97 out of 5 average rating, 116 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 friendly Golden Retriever is seated beside a gravel road, surrounded by lush green grass. The background features open fields extending toward a distant tree line, under a cloudy sky. The dog's golden fur contrasts with the earthy tones of the path.

Cottage in Sullivan

4.95 out of 5 average rating, 188 reviews

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.

Top guest favorite

The exterior of The Candy Kitchen features a classic storefront with large windows that display decorative signage. The structure retains historic architectural details, including a decorative cornice and a welcoming entrance. A small flowerbed can be seen in front, adding a touch of greenery.

Place to stay in Greenup

5 out of 5 average rating, 184 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

A bright and airy sleeping area features two twin beds with white metal frames, adorned with black and white checkered bedding. Natural light enters through two windows, covered with checkered valances. Wall decor includes round signs with welcoming phrases, enhancing the cozy ambiance.

Home in Sullivan

5 out of 5 average rating, 221 reviews

3Acres | CircleDrive | 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.

Guest favorite

A historical photograph captures six individuals posed in front of a brick factory structure. Three men and a boy stand beside wheelbarrows, showcasing the brickwork of the factory. One man is positioned near a doorway, and another is positioned on a ledge, highlighting a rustic setting.

Home in Teutopolis

4.96 out of 5 average rating, 228 reviews

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.

Guest favorite

An open living area features exposed wooden beams and warm wood paneling. A comfortable seating arrangement includes a sofa and armchair, while a dining table with chairs stands nearby. A staircase leads to upper rooms, and a soft light illuminates the space.

Cabin in Ashmore

4.89 out of 5 average rating, 229 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 covered outdoor seating area is shown, featuring a picnic table and several chairs beneath a wooden ceiling. A grill stands nearby, and the space is surrounded by lush greenery and a well-maintained yard.

Cottage in Arthur

4.98 out of 5 average rating, 275 reviews

Sisters Cottage

A recently renovated Cottage, nestled in the heart of the small, quaint town of Arthur. Located next to the Arthur Park. Enjoy the clip clop of the horse & buggies going by as you relax out front on a swing, or enjoy the back porch with table & seating as you enjoy the perennial garden out back. Plenty of back yard for playing games. A fire pit is located close to porch for roasting marshmallows at night. Arthur is a very innovative town with lots of shops to explore.

Top guest favorite

An evening scene captures a wooden deck adorned with string lights, providing a warm glow. A fire pit is centrally located, surrounded by outdoor seating. The cottage's pink exterior contrasts with the darkening sky, while a grassy area extends beyond the deck.

Guesthouse in Effingham

4.92 out of 5 average rating, 386 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.

Guest favorite

The cabin is set alongside a tranquil pond, surrounded by trees that reflect in the water. The exterior features a porch and is nestled within the forest, offering a serene view of the natural landscape.

Cabin in Strasburg

5 out of 5 average rating, 41 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 favorite

A stone fire pit with a square opening is surrounded by six black metal chairs on a paved patio. The area is bordered by manicured grass and landscaping, creating an inviting space for relaxation.

Apartment in Arthur

4.98 out of 5 average rating, 254 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.