Holiday Rentals in Windsor

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Holiday Rentals in Windsor

Exterior
LAKE SHELBYVILLE COTTAGE MINUTES FROM BOATING, HUNTING, AND FISHING, Sleeps 2
10.0 out of 10, Exceptional, (90)
"2nd time staying here. Host makes everything easy for check-in and when leaving. Very clean and organized."
LAKE SHELBYVILLE COTTAGE MINUTES FROM BOATING, HUNTING, AND FISHING, Sleeps 2
Pool
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY
10.0 out of 10, Exceptional, (15)
"2 employees stayed while working a few days near by. They liked and want to go back when they return. Vickie was easy to deal with"
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY
Marina
Lake Mattoon Lakehouse
10.0 out of 10, Exceptional, (2)
"The house was beautiful. Amazing location with beautiful views. Comfortable beds. Everything we needed for our family."
Lake Mattoon Lakehouse
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Games 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!!
TV, fireplace, DVD player
Moose Cabin
10.0 out of 10, Exceptional, (28)
"Great space, peaceful country setting."
Moose Cabin
Terrace/patio
Lake Shelbyville Country Cottage w/ Hot Tub - 5 minutes from Lake
10.0 out of 10, Exceptional, (9)
"Wonderful quiet place to stay with everything you need. Highly recommended."
Lake Shelbyville Country Cottage w/ Hot Tub - 5 minutes from Lake
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
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
Outdoor dining
Oasis on the Prairie - Hot Tub Sunsets - Sleeps 8
9.8 out of 10, Exceptional, (10)
"Perfect place for a gal's getaway !"
The price is €258
includes taxes & fees
20 May - 21 May
Oasis on the Prairie - Hot Tub Sunsets - Sleeps 8
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.
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
Fridge, microwave, oven, stovetop
Fish, boat, grill, chill, pets, relax
9.4 out of 10, Exceptional, (30)
"We traveled from St Louis to have family Christmas. The house was perfect for what we needed. It sits on a golf course so looking for a great away weekend of golf you should rent this house."
The price is €302
includes taxes & fees
22 May - 23 May
Fish, boat, grill, chill, pets, relax
Fridge, microwave, oven, stovetop
Brickway Retreat
9.4 out of 10, Exceptional, (11)
"This place was amazing! Friendly neighbors, safe neighborhood, and very quiet! We felt like royalty during our entire stay. THe place was so spacious and clean, and even though it was just the two of us, we really enjoyed the convenience of having a second bathroom. The kitchen was probably the best equipped of all our rentals to day and we have stayed in over 20 of them. There was tons of counter space and the island in the kitchen made it easy to spread out. The coffee bar and my favorite...
The price is €161
includes taxes & fees
27 May - 28 May
Brickway Retreat
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 €140
includes taxes & fees
27 May - 28 May
Updated spacious 2 br Flat
Iron/ironing board, WiFi, bed sheets
Newly updated and cozy home! Located near downtown!
8.8 out of 10, Excellent, (3)
"Great!"
Newly updated and cozy home! Located near downtown!
Fridge, microwave, stovetop, dishwasher
Woodsy Home w/ View, 1 Mi to Lake Shelbyville
8.8 out of 10, Excellent, (21)
"Overall the place was just fine, we can see the property is a working process. More seating on the useable deck would have been nice, but we made due for the time we were there. It worked out perfect for our weekend plans. Thank you!"
Woodsy Home w/ View, 1 Mi to Lake Shelbyville
Exterior
Binion Lodge at Beaver Lake - newly renovated
The price is €392
includes taxes & fees
21 May - 22 May
Binion Lodge at Beaver Lake - newly renovated
Interior
Woodsy Home w/ View, 1 Mi to Lake Shelbyville
3.0 star property
Woodsy Home w/ View, 1 Mi to Lake Shelbyville
Smart TV
Welcome to "Slice of Paradise"
Welcome to "Slice of Paradise"
Interior
Family Friendly Home in Cowden
Family Friendly Home in Cowden
Don't see what you're looking for?
See all available properties in Windsor
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

Lobby
Comfort Suites Mattoon
2.5 star property
8.8 out of 10, Excellent, (552)
"Staff was wonderful the elevator is under construction but they were thoughtful and called me ahead of time to let me know! Breakfast was good very clean!"
The price is €90
includes taxes & fees
2 Jun - 3 Jun
Comfort Suites Mattoon
Exterior
Holiday Inn Express & Suites Mattoon, an IHG Hotel
2.5 star property
8.4 out of 10, Very good, (651)
"The bed was very comfortable and I liked how the soft and firm pillows were marked. "
The price is €120
includes taxes & fees
19 May - 20 May
Holiday Inn Express & Suites Mattoon, an IHG Hotel
Exterior
Best Western Heartland Inn
2.5 star property
8.2 out of 10, Very good, (456)
"Clean sheets and towels"
The price is €102
includes taxes & fees
27 May - 28 May
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.

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as €140 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay. Windsor is known for its restaurants and shopping.

What are some of the best holiday rentals that Windsor has to offer?

Fish, boat, grill, chill, pets, relax: This holiday home rental outside of Windsor is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with an arcade/games room and 1 hot tub.

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 wider area.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for family trips.

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