Vacation rentals in Windsor

4.94 out of 5 average rating, 204 reviews

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

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

4.95 out of 5 average rating, 572 reviews

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

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

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.

4.97 out of 5 average rating, 115 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!

4.95 out of 5 average rating, 188 reviews

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

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.

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.

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.

4.96 out of 5 average rating, 228 reviews

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

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.

4.98 out of 5 average rating, 275 reviews

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

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.

4.92 out of 5 average rating, 386 reviews

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

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.

5 out of 5 average rating, 41 reviews

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

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.

4.98 out of 5 average rating, 254 reviews

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

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.

4.94 out of 5 average rating, 161 reviews

Cabin in Mattoon

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.

4.89 out of 5 average rating, 28 reviews

An integrated charging station is situated on the wooden headboard beside the bed, featuring one USB port and two standard electrical outlets. The design complements the rustic ambiance, with a textured finish visible on the wood, and soft bedding displayed in muted tones.

Home in Mattoon

Mattoon home by sports complex

Cozy home located in a quiet neighborhood about 5min. from the new Emerald Acres sports complex, shopping and food. Only 20 minutes to an Amish shopping community in Arthur. We pride ourself in the small details from a full coffee bar to soaps and shampoo’s in the showers. Roku TV’s in each bedroom and living room. Simply log on to your streaming accounts. Fenced in backyard with patio. No pets.

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Other great vacation rentals in Windsor

A spacious kitchen is equipped with modern appliances, including a black refrigerator and stainless steel microwave. A round wooden dining table is surrounded by six chairs, while light green walls and natural light enhance the open layout. Indoor plants add a touch of greenery to the space.

Home in Neoga

4.7 out of 5 average rating, 27 reviews

Glampers Corner at Lake Mattoon

ColleenRating, 5 stars2 weeks ago

I would definitely stay here again. Walking distance to Lake Mattoon marina and the small beach they have. Yard is a great relaxing area. Plenty of parking. Beds were comfortable, shower had plenty of water pressure and plenty of hot water.

5 out of 5 average rating, 54 reviews

A spacious interior is revealed, featuring a multipurpose area with a high ceiling. Tables for activities are arranged alongside various game setups, including a ping pong table, cornhole boards, and a badminton net. Natural light enters through the large openings, enhancing the open feel.

Home in Findlay

Ultimate Country Home!

JoyceRating, 5 stars2 weeks ago

this house is fabulous! Open floor plan, spacious bedrooms and bathrooms made it the perfect place to host multiple families together. The very amazing "gym" as our grandkids called it is a spectacular treat on its own!

A wooden deck overlooks a gently flowing creek, surrounded by lush greenery. Two metal chairs are positioned on the deck, offering a relaxing view of the natural landscape. The sound of water can be heard, complemented by the presence of nearby trees.

5 out of 5 average rating, 7 reviews

Asa Creek Cottage

JesseRating, 5 stars1 week ago

We had such a great time at Asa Creek Cottage in Sullivan. The house was clean, spacious, and really comfortable—perfect for our group of friends. It had everything we needed to unwind after a long day out on Lake Shelbyville. One of our favorite parts was the back deck overlooking the creek—super peaceful and a great spot to hang out. We also enjoyed using the fire pit in the evenings. It made for a nice, laid-back end to each day. If you’re looking for a quiet place to relax with friends and enjoy nature, this is a great spot. We’d definitely stay here again.

Tiny home in Arcola

4.82 out of 5 average rating, 17 reviews

The Little Homestead Haven

JonathanRating, 5 stars2 weeks ago

She was a great host! east to communicative and very friendly. I also had a special request to have flowers ordered for my wife, she went above and beyond to pick up the flowers and deliver it to the homestead. We hope to stay again soon.

5 out of 5 average rating, 10 reviews

The exterior of a charming lake house is illuminated at dusk, highlighting large glass windows that reflect warm indoor lighting. A wooden deck wraps around the house, and cozy outdoor seating is visible. The peaceful ambiance suggests a welcoming retreat.

Home in Neoga

Tranquil Lakefront Home on Lake Mattoon

CaleyRating, 5 stars1 week ago

This is a must stay! Super beautiful home with a great view of the lake. Lake access via 2 docks/a boat lift. We enjoyed the easter eggs hidden around the house;) and the welcome basket! Beds are very comfortable and they had hair dryers, laundry pods, etc. which you are likely to forget. We will be back!

5 out of 5 average rating, 7 reviews

The kitchen showcases modern cabinetry in two-tone grey, complemented by a patterned tile backsplash. A window allows natural light to illuminate the space, while a dishwasher and coffee maker are conveniently positioned within reach. The countertop offers ample space for food preparation.

Home in Mattoon

Charming Lumpkin Heights Historic District Retreat

SandiRating, 5 stars4 weeks ago

We came to town for a graduation. Natalie's place was in a great location on a beautiful street in a beautiful neighborhood. It was centrally located. This house was beautifully decorated and had a lot of really nice touches. I loved the Mickey Mouse dishes myself. There was plenty of room for our party of 6. Natalie very accommodating with our request. And very quick to respond with my questions. We will be booking this home again this fall.

A dock with a red-roofed shelter is visible, providing space for a boat and seating. The two-story house, located on a grassy lot, features a large deck and exterior steps leading to the upper level, surrounded by lush greenery and trees.

Home in Neoga

4.73 out of 5 average rating, 11 reviews

Lake Mattoon Lakehouse

KristinRating, 5 stars8 months ago

Lovely, peaceful location. Spacious and well furnished home. Comfy beds and bedding, plush bathroom towels. Erin was an accomodating host and replied quickly to our messages. Will definitely stay again.

A bright, four seasons room is showcased, featuring large glass windows that offer expansive views of the lake and surrounding greenery. A small round table with a potted plant occupies one corner, enhancing the serene ambiance of the space.