Compare Windsor Cottage Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Cottages in Windsor

Beautiful, clean cottage, 4 min walk to the beach/playground. Many wineries!

Beautiful, clean cottage, 4 min walk to the beach/playground. Many wineries!

Harrow ON
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Fantastic Lake View! Quiet, Clean w/Deck, BBQ & Fire pit* Walk to 3 Wineries

Fantastic Lake View! Quiet, Clean w/Deck, BBQ & Fire pit* Walk to 3 Wineries

Harrow (Town of Essex) ON
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Lake front escape - a quiet lake front cottage with easy access to the beach

Lake front escape - a quiet lake front cottage with easy access to the beach

Colchester ON
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Colchester cottages a stones throw away from beaches, wineries, marina, parks.

Colchester cottages a stones throw away from beaches, wineries, marina, parks.

Colchester ON
This cottage is a smoke-free cottage.
Kitchen
Air conditioning
MILL Creek COTTAGE - Luxury defined 💝

MILL Creek COTTAGE - Luxury defined 💝

Kingsville ON
Guests staying at this cottage have access to a garden and barbecue grills.
Kitchen
Free WiFi
Colchester cottages a stones throw away from beaches, wineries, marina, parks.

Colchester cottages a stones throw away from beaches, wineries, marina, parks.

Colchester ON
This cottage is a smoke-free cottage.
Kitchen
Air conditioning
Unique Space - Beautiful home on 17th green of golf resort

Unique Space - Beautiful home on 17th green of golf resort

Belle River ON
At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills. Other amenities at this golf cottage include a garden and a water dispenser.
Pool
Kitchen
Erie Breeze Cottage, right on Lake Erie, EPIC wine route!

Erie Breeze Cottage, right on Lake Erie, EPIC wine route!

Essex ON
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Support your nature prescription at The Nest, situated in a conservation area!

Support your nature prescription at The Nest, situated in a conservation area!

Amherstburg ON
At this cottage, guests have access to a gym, laundry facilities, and barbecue grills. Dry cleaning/laundry services make packing light an option. This beach cottage also has a picnic area.
Kitchen
Free WiFi
Don't see what you're looking for?
See all available properties in Windsor
View all properties
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.

Hotel Options in Windsor

    Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

    Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

    377 Riverside Dr E Windsor ON
    $71 nightly
    The price is $85 total per night from Aug 3 to Aug 4
    $85 total
    Aug 3 - Aug 4
    Total with taxes and fees
    8.6/10 Excellent! (3,322 reviews)
    Best Western Plus Waterfront Hotel

    Best Western Plus Waterfront Hotel

    277 Riverside Drive West Windsor ON
    $91 nightly
    The price is $108 total per night from Jul 27 to Jul 28
    $108 total
    Jul 27 - Jul 28
    Total with taxes and fees
    8.2/10 Very Good! (1,133 reviews)
    DoubleTree by Hilton Windsor Hotel & Suites

    DoubleTree by Hilton Windsor Hotel & Suites

    333 Riverside Dr W Windsor ON
    $104 nightly
    The price is $125 total per night from Aug 3 to Aug 4
    $125 total
    Aug 3 - Aug 4
    Total with taxes and fees

Cottages

Book a cottage in Windsor
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Windsor. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Windsor better.

Cottage apartments in Windsor range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Windsor
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Windsor and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Windsor cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Windsor. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Windsor Cottages essential information

Accommodation
44 Cottages
Lowest Price
$85
Highest Price
$125
Popular accommodation
Beautiful, clean cottage, 4 min walk to the beach/playground. Many wineries!, Fantastic Lake View! Quiet, Clean w/Deck, BBQ & Fire pit* Walk to 3 Wineries, Lake front escape - a quiet lake front cottage with easy access to the beach, Colchester cottages a stones throw away from beaches, wineries, marina, parks., MILL Creek COTTAGE - Luxury defined 💝, Colchester cottages a stones throw away from beaches, wineries, marina, parks., Unique Space - Beautiful home on 17th green of golf resort, Erie Breeze Cottage, right on Lake Erie, EPIC wine route!, Support your nature prescription at The Nest, situated in a conservation area!

More to Explore