Villa Kanaya - Vacation Rentals in Chaplin Estates

Stylish 2BR Downtown Sanctuary - Free Parking From US $804
         

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10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
The Yorkville Royal Sonesta Hotel Toronto From US $320
         

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9.4 (1913 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
2 Bedroom/2 Bathroom Suite From US $142
         

8.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Orange room From US $33
         

2.0 (1 Review)
House
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
Spacious 3 Bedroom with stunning city view From US $310
         

Luxury Places to Stay in Chaplin Estates

Over 1195+ Luxury Places to Stay in or Near Chaplin Estates
Lux 1BR Yorkville Condo Fast WiFi and Work Desk From US $1,691
         

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New
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Spacious 4BR Toronto Stay Near U of T & Downtown From US $1,218
         

New
House
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Four Seasons Hotel Toronto From US $1,188
         

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9.2 (229 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Toronto Bloor Crown Residence From US $1,160
         

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5.5 (2 Reviews)
Apartment
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  • Parking
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The Modern Stay From US $1,102
         

New
House
  • Parking
  • Security/Safety
  • Internet
FIFA FEVER FLAT-Proximity to Matches,Transit & Free Wifi From US $1,047
         

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3.5 (2 Reviews)
House
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Designer Bay Street Condo Sleep 6 From US $851
         

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Apartment
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Top-Rated Vacation Rentals with a Pool in Chaplin Estates

Over 156+ Top-Rated Vacation Rentals with a Pool in or Near Chaplin Estates
DT Apt great view whit garden From US $218
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
The Splendid - Luxury 1BR Uptown Toronto From US $136
         

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9.8 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Traveller home in centre Toronto From US $441
         

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9.7 (4 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • View
DT Cozy 1B1B with Den near UofT and Bay St From US $163
         

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9.6 (7 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • Private Pool
Cozy Condo in Centre of Downtown Toronto From US $187
         

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9.4 (16 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Luxury Condo on Bay Street From US $555
         

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9.4 (12 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Stylish Downtown Toronto Residential Hotel From US $465
         

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9.3 (77 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • TV
The Nobleton Suites - Yorkville From US $359
         

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9.3 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Chaplin Estates

Over 327+ Pet-Friendly Vacation Rentals in or Near Chaplin Estates
Sapphire Suite Modern 1BR and Sofa Bed Apartment From US $193
         

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10.0 (3 Reviews)
Apartment
  • Air Conditioner
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  • Pet Friendly
Luxury Home in Lytton Park From US $479
         

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House
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  • Pet Friendly
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1 Bedroom/1 Bathroom Suite From US $125
         

New
Apartment
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  • Pet Friendly
  • Pool
Light Filled Little Italy Suite w/Private Garden From US $94
         

6.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Vintage Little Italy 2 Bedroom From US $249
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Fire It Up In Little Italy 3 Bedrooms And Fireplace From US $207
         

Chic 2BR Oasis with Skyline Views near Berczy Park From US $154
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool

Large Vacation Homes & Villas in Chaplin Estates

Over 81+ Large Vacation Homes & Villas in or Near Chaplin Estates
The Jade Hostel From US $129
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • TV
  • View
CENTRAL TORONTO From US $293
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
A cozy home minutes walk from Eaton Centre From US $125
         

Resort Style Living in Lawrence Park From US $5,763
         

New
House
  • TV
  • Security/Safety
  • Child Friendly

Wheelchair Accessible Vacation Homes in Chaplin Estates

Over 216+ Wheelchair Accessible Vacation Homes in or Near Chaplin Estates
Parkside Student Residence Downtown Toronto From US $75
         

just 5 minute walk to U of T From US $117
         

8.0 (8 Reviews)
Condo
  • Air Conditioner
  • Designated Smoking Area
  • TV
Amazing Toronto downtown view. From US $229
         

Luxury Yorkville 2bed 2bath 5 guests Parking From US $230
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Instant Suites -Stunning Designer Studio Yorkville From US $135
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Luxury Executive Condo in Yorkville From US $121
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • Pet Friendly
  • Pool

Chaplin Estates Vacation Rentals and Airbnb Places to Stay Under $200

Over 675+ Chaplin Estates Vacation Rentals and Airbnb Places to Stay Under $200
Toronto Midtown Home Suites From US $88
         

9.6 (68 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Town Inn Suites Hotel From US $163
         

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8.6 (3830 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Spacious 1BR Basement Apt with King Size Bed! From US $104
         

Spacious 1BR Penthouse Suite with Amazing Terrace! From US $118
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Spacious 1BR w/King Bed and Amazing Terrace! From US $129
         

Spacious 1BR Executive Style Suite - King Bed From US $121
         

New
Apartment
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  • TV
  • Balcony/Terrace
1000 sq. ft. Stunning 2.5 storey loft in the Heart of the City From US $108
         

Instantly Bookable Vacation Homes in Chaplin Estates

Over 492+ Instantly Bookable Vacation Homes in or Near Chaplin Estates
Spacious 3-bdrm in leafy Hillcrest Village From US $161
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety
Luxury Downtown Condo, Prime Location! From US $96
         

New
Condo
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Executive Stay - Gym - Pool From US $219
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Executive two bedroom condo in Toronto’s prized Yorkville From US $362
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Elegant, large 2 bedroom main floor apartment From US $230
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV
Tranquil 2-bedroom house in Central Toronto with 1 Parking From US $196
         

10.0 (1 Review)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Charming 2-bedroom, 1 bath apartment in historic Cabbagetown From US $148
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

About Chaplin Estates Vacation Rentals

With more than 1204 Chaplin Estates vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Villakanaya 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 Chaplin Estates.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Villakanaya Chaplin Estates, 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 Chaplin Estates. Places to stay near Chaplin Estates are 480.01 ft² on average, with prices averaging US $300 a night.

Villakanaya makes it easy and safe to find and compare vacation rentals in Chaplin Estates 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 Chaplin Estates

Type Count
Holiday Apartments 529
Vacation Homes 376
Hotels 77
B&B 7
Villas 6
Others 4
Hostels 3

Use these Quick Filters to Find a Vacation Rental in Chaplin Estates

Pro Tip: Villakanaya makes it easy to compare the best listings on Villakanaya homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Villakanaya 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 Chaplin Estates.

Weather in Chaplin Estates

View the weather forecast for Chaplin Estates before booking your Chaplin Estates 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

Complexes around Chaplin Estates, ON


Chaplin Estates Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Chaplin Estates?
How many vacation rentals are available in Chaplin Estates?

Currently, the total number of properties listed in 2026 is over 1204 in the Chaplin Estates area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chaplin Estates.