Windsor Vacation Rentals

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Vacation Rentals in Windsor

Fish, boat, grill, chill, pets, relax
Fridge, microwave, oven, stovetop
Fish, boat, grill, chill, pets, relax
9.4 out of 10, Exceptional, (37)
"We boat on Lake Shelbyville and the property is very close to a ramp. House was nice. Kitchen was very well stocked! Several extra amenities! The garage was an A+ with the extra fridge, grill and utensils. The only thing that I could pick at was the lawn desperately needed to be cut and the firepit was in a weird location on the side of the driveway. Nothing to not want to stay again! I would definitely return!!"
Fish, boat, grill, chill, pets, relax
Oasis on the Prairie - Hot Tub Sunsets - Sleeps 8
Outdoor dining
Oasis on the Prairie - Hot Tub Sunsets - Sleeps 8
10.0 out of 10, Exceptional, (11)
"Another great stay at the Oasis! We look forward to it every year. Rose is a fabulous host and close by if needed."
The price is ￥25,971
per night
Jun 24 - Jun 25
Oasis on the Prairie - Hot Tub Sunsets - Sleeps 8
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY
Pool
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY
10.0 out of 10, Exceptional, (17)
"Stayed at this wonderful place for two nights while in town for a wedding. Enjoyed every minute!!!"
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY
Lake Mattoon Lakehouse
Marina
Lake Mattoon Lakehouse
10.0 out of 10, Exceptional, (4)
"House is beautiful!! Very clean and well stocked. The view from the backyard balcony is amazing!! My Mom and I sat out there for hours every morning drinking our coffee and taking it all in, even in the rain. Erin and Ryan were easy to contact and very accommodating!!! Highly recommend!!!"
Lake Mattoon Lakehouse
LAKE SHELBYVILLE COTTAGE MINUTES FROM BOATING, HUNTING, AND FISHING, Sleeps 2
Property grounds
LAKE SHELBYVILLE COTTAGE MINUTES FROM BOATING, HUNTING, AND FISHING, Sleeps 2
10.0 out of 10, Exceptional, (93)
"We weeee there for a fishing trip but would have enjoyed staying for a getaway trip. The cottage is decorated perfect and includes everything but food and clothes cozy patio with fire pit. Firewood included. The grounds were beautiful I enjoyed sitting on the patio and watching the wildlife. There are also two fishing ponds on the property. Highly recommend!"
LAKE SHELBYVILLE COTTAGE MINUTES FROM BOATING, HUNTING, AND FISHING, Sleeps 2
Historic 1850's downtown home, located downtown, very close to Lake Shelbyville.
Interior
Historic 1850's downtown home, located downtown, very close to Lake Shelbyville.
9.8 out of 10, Exceptional, (37)
"We had a great experience. Thank you!"
Historic 1850's downtown home, located downtown, very close to Lake Shelbyville.
Brickway Retreat
Fridge, microwave, oven, stovetop
Brickway Retreat
9.4 out of 10, Exceptional, (12)
"WOW! Great place! Nice little home that has been totally re-done. Still smells like new! Has everything you would want as they make a great effort to supply what is needed for a comfortable stay. Absolutely NO reason to stay in a hotel in Charleston/Mattoon area with this gem! Will return! "
The price is ￥18,258
per night
Jul 2 - Jul 3
Brickway Retreat
Lake Shelbyville Country Cottage w/ Hot Tub - 5 minutes from Lake
Terrace/patio
Lake Shelbyville Country Cottage w/ Hot Tub - 5 minutes from Lake
10.0 out of 10, Exceptional, (10)
"House was great! We really enjoyed everything about the place! Very peaceful, clean and all around great place to stay!"
Lake Shelbyville Country Cottage w/ Hot Tub - 5 minutes from Lake
Binion Lodge at Beaver Lake - newly renovated
Exterior
Binion Lodge at Beaver Lake - newly renovated
10.0 out of 10, Exceptional, (2)
"We enjoyed our stay at this beautiful and spacious home! Loved sitting on the porch and the swing while listening to the many birds sing! 😊"
The price is ￥37,568
per night
Jul 8 - Jul 9
Binion Lodge at Beaver Lake - newly renovated
Ultimate Country Home with a 4800 sq.ft shed- pickle ball, corn hole, and more!!
Game room
Ultimate Country Home with a 4800 sq.ft shed- pickle ball, corn hole, and more!!
10.0 out of 10, Exceptional, (7)
"This property was amazing!! We were in town for my son's wedding and this was perfect for us and our adult kids/spouses etc. The furnishings are beautiful and this well appointed space had everything we needed. The shed/game space was so much fun!! I have only good things to say!!! Beautiful view off the living area...just wow! The owner was so kind helpful!!!!"
Ultimate Country Home with a 4800 sq.ft shed- pickle ball, corn hole, and more!!
Newly updated and cozy home! Located near downtown!
Private kitchen
Newly updated and cozy home! Located near downtown!
9.0 out of 10, Wonderful, (4)
"Clean,cool, just what we wanted and what we expected. The host was responsive, and had a local contact, t"
The price is ￥15,740
per night
Jun 17 - Jun 18
Newly updated and cozy home! Located near downtown!
Woodsy Home w/ View, 1 Mi to Lake Shelbyville
Fridge, microwave, stovetop, dishwasher
Woodsy Home w/ View, 1 Mi to Lake Shelbyville
9.0 out of 10, Wonderful, (23)
"Stayed there last year we really appreciated the updates to the property. Looks like it’s heading in the right direction."
Woodsy Home w/ View, 1 Mi to Lake Shelbyville
Moose Cabin
TV, fireplace, DVD player
Moose Cabin
10.0 out of 10, Exceptional, (30)
"Very nice spot with privacy"
Moose Cabin
Updated spacious 2 br Flat
Interior
Updated spacious 2 br Flat
9.0 out of 10, Wonderful, (2)
"Was great location for my stay. House had everything I needed. Great communication w the host. Highly recommend"
The price is ￥17,314
per night
Jun 18 - Jun 19
Updated spacious 2 br Flat
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY sleeps 4
Fridge, microwave, oven, stovetop
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY sleeps 4
10.0 out of 10, Exceptional, (35)
"House was nice and Vicky communicated w/ me all the time. Mark was a pleasure to meet and chat with. Already re-booked for next year's fishing trip."
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY sleeps 4
Woodsy Home w/ View, 1 Mi to Lake Shelbyville
Interior
Woodsy Home w/ View, 1 Mi to Lake Shelbyville
3.0 star property
Woodsy Home w/ View, 1 Mi to Lake Shelbyville
Cozy, and private apartment near Lake Shelbyville
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils
Cozy, and private apartment near Lake Shelbyville
9.8 out of 10, Exceptional, (13)
"5 stars!"
Cozy, and private apartment near Lake Shelbyville
LAKE SHELBYVILLE KIMBLE'S FARMHOUSE. SLEEPS 9
LAKE SHELBYVILLE KIMBLE'S FARMHOUSE. SLEEPS 9
10.0 out of 10, Exceptional, (18)
"The property was very quaint and quiet. Loved watching the deer in the morning and evening."
LAKE SHELBYVILLE KIMBLE'S FARMHOUSE. SLEEPS 9
Welcome to "Slice of Paradise"
Smart TV
Welcome to "Slice of Paradise"
Welcome to "Slice of Paradise"
Escape to Paradise New Listing
Private kitchen
Escape to Paradise New Listing
2.0 star property
Escape to Paradise New Listing
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Windsor you may be interested in

Suite Dreams Hotel
2 bars/lounges
Suite Dreams Hotel
2.5 star property
7.2 out of 10, Good, (337)
"Great shower water pressure, room size was good - plenty of room - I would stay again as a stopover on a road trip."
The price is ￥14,796
per night
Jun 25 - Jun 26
Suite Dreams Hotel
Comfort Suites Mattoon
Lobby
Comfort Suites Mattoon
2.5 star property
8.8 out of 10, Excellent, (568)
"Hotel and rooms were clean. Staff were extremely friendly and helpful. Breakfast and dining area were very good. And the pool area was great for the kids to swim in. Only thing that would have made this hotel even better would be if their elevator (which has been out for over 9 months), had been fixed."
The price is ￥13,883
per night
Jul 7 - Jul 8
Comfort Suites Mattoon
Best Western Heartland Inn
Exterior
Best Western Heartland Inn
2.5 star property
8.2 out of 10, Very Good, (470)
"Front desk staff was amazing. Very helpful guiding us to a great place to eat dinner. Not as happy about the pool being closed."
The price is ￥15,581
per night
Jun 26 - Jun 27
Best Western Heartland Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Are there vacation rentals in Windsor?

Yes, we have vacation rentals close to the most popular sights in Windsor, or you can choose a more remote option if you're looking for relaxation. Windsor is known for its restaurants and shopping.

What are some of the best vacation home rentals in Windsor?

Fish, boat, grill, chill, pets, relax: This vacation home near Windsor is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the arcade game room in this rental home to help you unwind.

What can I see and do in Windsor?

While you're exploring the area, Wolf Creek State Park and Lake Shelbyville are a couple of picturesque spots to get outside and enjoy nature. Lake Shelbyville Beach and Mattoon Peterson Park are a couple of places you'll find in the larger area.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned properties you can book for a couple days or more in Windsor. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for small groups.

Recent reviews of Windsor properties
Expedia verified reviews

Super 8 by Wyndham Mattoon

Super 8 by Wyndham Mattoon

5/5 Excellent
"Easy access off the interstate."
A verified traveler stayed at Super 8 by Wyndham Mattoon
Posted 4 hours ago
Super 8 by Wyndham Mattoon