My Maple Ridge - Vacation Rentals in Windsor

Another Sunset by the Bay: Waterfront - 2-Bedroom From US $163
         

Windsor Airport Accommodation From US $48
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Omstead's On Erie From US $138
         

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10.0 (73 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Bunker by the Bay - Perfect Couples Getaway From US $99
         

10.0 (61 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
'PELEE SHORES' Point Pelee Lakefront Vacation Cottage From US $278
         

Sunsets by the Bay - Your Waterfront Oasis From US $226
         

10.0 (48 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Beachfront, Hot tub, Sunsets, Moonlight, Romance, From US $294
         

10.0 (38 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Windsor

Over 587+ Luxury Places to Stay in or Near Windsor
South Windsor VILLA Great for parties and events From US $2,519
         

Villa Ibiza From US $1,583
         

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New
Villa
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The Glasswater Lake Estate From US $1,079
         

New
House
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The Julia Kennedy Beach House with Hot tub From US $520
         

9.6 (26 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Hot Tub, Sunsets and Moon lit Lakehouse! From US $489
         

9.8 (22 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV

Top-Rated Vacation Rentals with a Pool in Windsor

Over 46+ Top-Rated Vacation Rentals with a Pool in or Near Windsor
Main Unit luxury South WindsorOasis From US $406
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Main Unit Luxury South Windsor Oasis From US $235
         

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10.0 (1 Review)
House
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  • Pet Friendly
Alluring Private Bachelor Unit From US $63
         

10.0 (1 Review)
House
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  • Parking
  • Pet Friendly
Hyatt Place Windsor From US $126
         

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9.4 (492 Reviews)
Hotel
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  • Parking
  • Pool
Towneplace Suites By Marriott Tecumseh Windsor From US $125
         

9.4 (13 Reviews)
Hotel
  • Parking
  • Pool
  • Wheelchair Accessible
DoubleTree by Hilton Windsor Hotel & Suites From US $139
         

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9.2 (1068 Reviews)
Hotel
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  • Parking
  • Pool
Hampton Inn & Suites by Hilton Windsor From US $136
         

8.8 (1008 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hyatt Place Windsor From US $152
         

8.7 (122 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Windsor

Over 157+ Pet-Friendly Vacation Rentals in or Near Windsor
Cozy waterfront cottage From US $197
         

10.0 (14 Reviews)
House
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  • Parking
  • Pet Friendly
Self contained 2 level apartment with 4 bdrms & 2 bathroom From US $163
         

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10.0 (2 Reviews)
Apartment
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  • Pet Friendly
3 Bedroom basement unit with free parking and wifi From US $152
         

6.8 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Sunrise Retreat - Lakefront Cottage w/Hot Tub From US $224
         

10.0 (12 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern 2BR with Remote Workspace, Patio, BBQ & Gym From US $158
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy & Pet Friendly 2BR w/parking, mins from highway. From US $147
         

10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
See More Pet-Friendly Vacation Rentals in Windsor on PetFriendly.io

Large Vacation Homes & Villas in Windsor

Over 62+ Large Vacation Homes & Villas in or Near Windsor
Luxurious and Fashionable Home | Sleeps 8 From US $366
         

9.8 (17 Reviews)
House
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  • TV
  • Security/Safety
Cozy 9 beds 15 persons house with Tesla Charger From US $188
         

New
House
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  • Child Friendly
Lakeside home with 4 bedrooms and 2 baths! From US $349
         

9.8 (6 Reviews)
House
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  • TV
80 Feet of Private Lakefront House From US $244
         

9.2 (5 Reviews)
Cottage
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  • TV
Luxury getaway with pool and hot tub - family retreat From US $291
         

Wheelchair Accessible Vacation Homes in Windsor

Over 24+ Wheelchair Accessible Vacation Homes in or Near Windsor
Access to the beach and riverside trail. From US $85
         

9.6 (15 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
TownePlace Suites by Marriott Windsor From US $161
         

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8.9 (208 Reviews)
Hotel
  • Air Conditioner
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  • Pet Friendly
Residence & Conference Centre - Windsor From US $159
         

8.2 (400 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
DoubleTree by Hilton Windsor, ON From US $124
         

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8.6 (586 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
TownePlace Suites by Marriott Windsor From US $149
         

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9.2 (713 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Holiday Inn Express Windsor Waterfront by IHG From US $131
         

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8.5 (1017 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Windsor Varoom and Airbnb Places to Stay Under $200

Over 392+ Windsor Varoom and Airbnb Places to Stay Under $200
Cozy 3 bedroom home From US $176
         

New
Apartment
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  • Child Friendly
Ye Olde Walkerville Bed & Breakfast From US $111
         

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9.6 (378 Reviews)
Bed & Breakfast
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  • Parking
  • TV
Beautifully renovated home in historic Walkerville. From US $145
         

10.0 (28 Reviews)
Apartment
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  • TV
Luxury Escape for Professionals with high speed WiFi. From US $126
         

10.0 (11 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Two Bedroom Luxury apartment in Walkerville. From US $120
         

10.0 (3 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Windsor

Over 290+ Instantly Bookable Vacation Homes in or Near Windsor
OASIS ON THE LAKE From US $259
         

10.0 (25 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Erie Shores Lakehouse! · Sunsets N Hot Tub From US $530
         

9.8 (40 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Pelee View Lakehouse From US $326
         

10.0 (22 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Your Perfect Retreat From US $201
         

9.8 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Casa Azul - Cozy Lakefront Cottage near Point Pelee From US $205
         

Tree Top Lakehouse - Breathtaking Views & Sunsets From US $326
         

10.0 (14 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
PhoNest Lake House is Simple Serenity From US $273
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Windsor Vacation Rentals

With more than 596 Windsor vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Mymapleridge and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Windsor.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Mymapleridge Windsor, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Windsor. Places to stay near Windsor are 402.13 ft² on average, with prices averaging $181 a night.

Mymapleridge makes it easy and safe to find and compare vacation rentals in Windsor with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Windsor

Type Count
Vacation Homes 252
Holiday Apartments 182
Cottages 73
Hotels with Suites 52
B&B 12
Cabin Rentals 5
Villas 4
Others 2

Use these Quick Filters to Find a Vacation Rental in Windsor

Pro Tip: Mymapleridge makes it easy to compare the best listings on Mymapleridge homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Mymapleridge homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Windsor.

Weather in Windsor

View the weather forecast for Windsor before booking your Windsor Vacation Rentals to confirm your best time to go.

December - February
High 23°F       Low 2°F
March - May
High 65°F       Low 12°F
June - August
High 76°F       Low 49°F
September - November
High 65°F       Low 8°F