Holiday rentals in Windsor

4.94 out of 5 average rating, 204 reviews

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, 570 reviews

Flat 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

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, 187 reviews

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.

5 out of 5 average rating, 182 reviews

Place to stay in Greenup

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.

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.

4.89 out of 5 average rating, 226 reviews

Cabin in Ashmore

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.

4.98 out of 5 average rating, 275 reviews

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

Guest house 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.

4.98 out of 5 average rating, 254 reviews

Flat 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, 160 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.

4.92 out of 5 average rating, 90 reviews

Loft in Strasburg

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.

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Windsor holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Windsor

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

Home in Findlay

Ultimate Country Home!

JoyceRating, 5 stars1 week 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!

5 out of 5 average rating, 6 reviews

Asa Creek Cottage

JoshRating, 5 stars2 days ago

We had such an amazing time! The house was absolutely perfect…we only booked one night but wish we had more time! When you drive up it doesn’t seem like much out of the ordinary, but once you step inside it’s so dreamy and gets better when you step out on the back patio. This was by far the cleanest Airbnb we’ve stayed in!!!

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

Home in Neoga

Tranquil Lakefront Home on Lake Mattoon

CaleyRating, 5 stars5 days 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

Home in Mattoon

Charming Lumpkin Heights Historic District Retreat

SandiRating, 5 stars3 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.

5 out of 5 average rating, 14 reviews

Kas Villa Lake Side Getaway

TheresaRating, 5 stars5 days ago

Our annual summer lake vacation with our kids and grandkids was a big success thanks to Shelby and Dan’s wonderful accommodations. The house is beautiful, had everything we needed for a comfortable stay, and was the cleanest lake house rental we’ve ever stayed in (and we’ve stayed in many). They live close enough to be super helpful but without being intrusive. Our entire family gives this place an A+ and we would definitely book again.