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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Guest favorite

A welcoming living area features a comfortable sofa and armchair, paired with a decorative area rug. A flat-screen TV is mounted near a stone fireplace, surrounded by natural light from the windows. Indoor plants add a touch of greenery to the space.

Cottage in Effingham

4.94 out of 5 average rating, 515 reviews

Centrally located, Peaceful Cabin by the Beach

KoreyRating, 5 stars1 week ago

We really enjoyed our stay here- it was clean, cozy, and surprisingly quiet. The beds were very comfortable as well. It’s right on the water- the surroundings are just beautiful. My only complaint is that we didn’t get to stay for longer than one night, as we were only passing through. I’d definitely go back for a longer visit!

Guest favorite

Cottage in Decatur

4.9 out of 5 average rating, 115 reviews

Private Dock, Kayaks, Paddleboard - Relax & Play!

Germaid S.Rating, 5 stars1 week ago

Lovely house on the lake. The house is on three levels, so lots of space to spread out. The host was very communicative, supplied us with lots of recommendations, and was responsive. Overall a 5-star experience. Loved the deck to hang out on.

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.

Cottage in Sullivan

5 out of 5 average rating, 212 reviews

Lakewood Cottage #1 @ Lake Shelbyville

RachelRating, 5 stars2 weeks ago

Loved our stay! We’ve stayed at lots of AirBnBs and this was hands-down the cleanest. The large yard was great for my boys. The amenities- from towels to bedding to games - were all clean and well-thought-out. This is a cozy little space for some time to get away. Convenient location for reaching Aikman Wildlife Adventure and Yoder’s restaurant.

Top guest favorite

Cabin in Mattoon

4.94 out of 5 average rating, 157 reviews

Cottage on Lake Paradise,

KatieRating, 5 stars1 week ago

An amazing retreat. The lake was so peaceful and beautiful. The home was extremely well stocked and very well cared for/clean. The hosted provided great pre-check in instructions and check out was a breeze. The location was secluded but less than a 30 minute drive from wineries and restaurants. Would absolutely stay again!!

Top guest favorite

A modern kitchen features a farmhouse-style sink with a sleek stainless steel finish, surrounded by white cabinetry and granite countertops. A compact turquoise toaster sits on the counter, and a large window provides natural light and a view of the outdoor space.

Home in Vandalia

5 out of 5 average rating, 140 reviews

Modern family friendly home in Historic Vandalia

AmberRating, 5 stars3 weeks ago

We had a wonderful stay at Mary’s place. Her home was exactly as described and pictured. She thoughtfully stocked it and made it feel like a pampered resort. My family couldn’t have been more comfortable or at home. Mary was awesome and her home beautiful. If we’re ever traveling through again - we’d stop and stay just for the enjoyment. Highly recommend!

Top guest favorite

Home in Shelbyville

4.94 out of 5 average rating, 17 reviews

The Hub- 4 min to lake ramp/boat parking/Hot Tub

JakeRating, 5 stars7 months ago

Great house with plenty of room for the whole group. Bathrooms and kitchen were very nice and there is plenty of room to hang out as a group both inside and out on the patio. Lots of parking. Renee was easy to get ahold of and check in/out was simple.

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What guests are saying

Modern Farmhouse Upstairs Only

5 out of 5 average rating, 3 reviews13 months ago

I used to live on Vandalia Lake, so I knew what to expect from the location - but the house is much nicer than pretty much anything else you'll find in Vandalia. It was the perfect place to spend the weekend while celebrating my granny's 82nd, and it's very likely we'll rent it again in the future, assuming it remains available for that purpose. The main living/kitchen/dining area is wide open and great for hanging out without feeling cramped, and the screened balcony/patio is a lovely place to enjoy the outdoors without being forced to "enjoy" the bugs. Everything is light, airy, modern, and well-maintained. This isn't one of those listings where the photos look great and the reality is worn and dirty - what you see is what you get.

Home in Vandalia

What guests are saying

Haven on the Lake-Swim/Fishing Dock-8 Beds-2 Baths

4.98 out of 5 average rating, 83 reviews3 weeks ago

My family rented the house for a couple of days for a quick family reunion. The house was great, had plenty of space for all of us. It had everything you could need and was well equipped. We are hoping to make this an annual event and this is our house of choice.

Home in Effingham

What guests are saying

909 & Vine Photo Worthy Home With Pool & Hot Tub

4.95 out of 5 average rating, 43 reviews1 week ago

Renee was a great host with quick response time and provided added resources for what shelbyville had to offer. The house exceeded our expectations and we appreciated all the amenities that the house had to offer- will be recommending to other organizations to use for retreats!

Home in Shelbyville

What guests are saying

Lake Shelbyville Home with a View

4.9 out of 5 average rating, 49 reviews8 months ago

This is our second time staying here as a family. There are several reasons we came back: check in and out is very easy; the space accommodates our extended family very well; there is direct lake access though you have to be aware the path is “natural“ and as Doug has said in other reviews, they do not have control over improving the path; the space was very clean and all the essentials are provided; Doug is very responsive and got back to us very quickly when we had minor questions! We would highly recommend staying here, as long as it doesn’t interfere with the time we want to come back😁

Guest suite in Shelbyville

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Popular amenities for Windsor vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Windsor

Guest favorite

A historic brick building features classic architectural details, including large front windows and a decorative entrance. A wide concrete walkway with gradual steps leads to the door, while nearby trees provide shade. Streetlamps enhance the welcoming exterior along the sidewalk.

Loft in Moweaqua

4.9 out of 5 average rating, 29 reviews

Hidden Gem

NicoleRating, 5 starstoday

My stay here was great and it was just what I needed during my work contract. It’s in a quiet neighborhood which gave me an extra level of comfort. I felt right at home and the apartment looks just like the photos. The hosts were very responsive and made sure I was comfortable. Highly recommend!

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, 32 reviews

Rocky Springs Cabin: A Secluded Cabin On 40 Acres

AnnieRating, 5 stars1 month ago

We had a great stay! The place was clean and the surroundings were very peaceful. We enjoyed exploring the trails around the property. There was also easy access to trails on the adjacent park which were very private.

Guest favorite

A bright red mailbox is mounted on a wooden post in a grassy area. Surrounding pine trees and a large tree with a spreading canopy provide shade. The scene suggests a tranquil country setting, ideal for relaxation.

Home in Decatur

5 out of 5 average rating, 13 reviews

City/Country Home NW edge of Decatur IL

PaulRating, 5 stars4 months ago

Lovely home, semi-rural setting but only 10 minutes from downtown. Perfect for our family of five. There is a paved bike path to town just about two blocks away.

Guest favorite

A stylish room features exposed brick walls, three full-length mirrors with black frames, and two elegant seating areas. A light-colored rug creates a soft contrast with the dark flooring. A kitchenette can be seen in the background, complemented by modern cabinetry.

Apartment in Greenup

4.92 out of 5 average rating, 13 reviews

Village Vacation

RodneyRating, 5 stars1 week ago

We needed it just overnight traveling through. Nice and spacious. Our needs were taken care of! A quaint little place being a former store. But it was well fixed up and furnished.

Superhost

A child is seen standing on a rocky path beside a shallow creek, with gentle water flowing over smooth stones. Lush greenery surrounds the area, and a grassy slope rises in the background, creating a natural and peaceful setting.

Campsite in Dalton City

4.75 out of 5 average rating, 12 reviews

Camp at Serenity Fields Farm!

TeriRating, 5 stars5 months ago

I'm not an advide camper. I took my sister with me to get a weekend away from family. Julie was on top of all my concerns and questions. I may have been too annoying. so I'm sorry if I was. However, if she'll have me I'd love to bring my family back for next spring. perfect for light camping.

Superhost

A white squirrel rests on the edge of a wooden feeder, preparing to access seeds inside a glass container. The background features a fenced grassy yard, with a large tree providing shade.

Home in Decatur

4.9 out of 5 average rating, 63 reviews

Discover Decatur in this 3 BR 2 BA Getaway

JessicaRating, 5 stars1 month ago

Was a great stay. The house was spacious and comfortable. Having six people in our group it was nice to all be together but not feel overcrowded. We centrally located to what we needed. Will definitely stay again if we are in the area in the future.

Guest favorite

The covered front porch features seating for up to six, including a sofa adorned with colorful cushions and a patterned area rug. A small glass table is positioned in front of the seating, enhancing the inviting setting under the home’s awning.

Home in Taylorville

5 out of 5 average rating, 13 reviews

Newly rebuilt cozy cottage

JodyRating, 5 stars4 months ago

The house was decorated very nice. It was clean and it had everything you’d need for a short term or long-term stay. Very convenient location. David was very helpful and friendly. I would definitely stay there again!

Top guest favorite