Women In Travel - Vacation Rentals in Chaplin Estates

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

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10.0 (8 Reviews)
Apartment
  • Air Conditioner
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  • Pool
Oak House Residence From US $124
         

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9.0 (2 Reviews)
Apartment
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Gorgeous Downtown Property, Private Yard From US $152
         

10.0 (2 Reviews)
House
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  • Pet Friendly
  • TV
Beautiful Apt. in Heart of Yorkville From US $148
         

10.0 (2 Reviews)
Apartment
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  • Parking
  • TV
Executive two bedroom condo in Toronto’s prized Yorkville From US $369
         

10.0 (1 Review)
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Charming 5-Bedroom Forest Hill Home From US $299
         

10.0 (1 Review)
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  • Parking
  • Pet Friendly

Luxury Places to Stay in Chaplin Estates

Over 1154+ 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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Luxury Home 5bed5bath Rosedale Pool|Sauna|Parking From US $1,556
         

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Stylish 3BR Home with Office Deck & Parking From US $1,537
         

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Spacious Newly Built home in the heart of Toronto From US $1,463
         

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Stunning 8000sf North York home! From US $1,436
         

Four Seasons Hotel Toronto From US $1,188
         

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9.2 (229 Reviews)
Hotel
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  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Chaplin Estates

Over 159+ Top-Rated Vacation Rentals with a Pool in or Near Chaplin Estates
Victorian Gem - Midtown Toronto From US $373
         

10.0 (1 Review)
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The Omnia Yorkville Toronto From US $364
         

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10.0 (1 Review)
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Park Regent Toronto Yorkville From US $1,077
         

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9.9 (10 Reviews)
Apartment
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The Hazelton Hotel Toronto From US $485
         

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9.8 (987 Reviews)
Hotel
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Traveller home in centre Toronto From US $441
         

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9.7 (4 Reviews)
Apartment
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  • Pool
  • View
The Splendid - Luxury 1BR Uptown Toronto From US $136
         

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9.7 (3 Reviews)
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Four Seasons Hotel Toronto From US $650
         

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9.6 (942 Reviews)
Hotel
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  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Chaplin Estates

Over 318+ 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
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  • Pet Friendly
Luxury Yorkville 2bed 2bath 5 guests Parking From US $201
         

10.0 (1 Review)
Apartment
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  • Pet Friendly
Kimpton Saint George by IHG From US $212
         

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9.2 (1007 Reviews)
Hotel
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  • Pet Friendly
Yorkville Plaza From US $87
         

8.8 (5 Reviews)
Apartment
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  • Parking
  • Pet Friendly
2 Bedroom/2 Bathroom Suite From US $139
         

8.0 (1 Review)
Apartment
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  • Pet Friendly
  • Pool

Large Vacation Homes & Villas in Chaplin Estates

Over 75+ Large Vacation Homes & Villas in or Near Chaplin Estates
Toronto Midtown Home Suites From US $88
         

9.6 (68 Reviews)
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CENTRAL TORONTO From US $293
         

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Premium new-build 3 BD,3 bath Apartment From US $262
         

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Wheelchair Accessible Vacation Homes in Chaplin Estates

Over 213+ Wheelchair Accessible Vacation Homes in or Near Chaplin Estates
Instant Suites -Stunning Designer Studio Yorkville From US $98
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
The Yorkville Royal Sonesta Hotel Toronto From US $258
         

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9.4 (1799 Reviews)
Hotel
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Elegant One-Bedroom in the Heart of Yorkville From US $86
         

Instant Suites Junior Suite at Yorkville ☆ From US $104
         

8.0 (15 Reviews)
Apartment
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  • TV
  • Wheelchair Accessible

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

Over 661+ Chaplin Estates Vacation Rentals and Airbnb Places to Stay Under $200
Downtown Pvt Rm w Desk-Ensuite Bathroom-Near TTC From US $133
         

Charming 2-bedroom, 1 bath apartment in historic Cabbagetown From US $151
         

10.0 (1 Review)
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Kaisar Guest House From US $85
         

8.0 (629 Reviews)
House
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Yorkville Magic. n Toronto's Finest Neighbourhood From US $102
         

Tranquil 2-bedroom house in Central Toronto with 1 Parking From US $99
         

10.0 (1 Review)
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Stylish Condo in Yorkville From US $91
         

10.0 (1 Review)
Condo
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  • TV
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Beautiful Spacious 4 bedroom 4 bathroom family home From US $129
         

2.0 (1 Review)
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Instantly Bookable Vacation Homes in Chaplin Estates

Over 533+ Instantly Bookable Vacation Homes in or Near Chaplin Estates
Elegant, large 2 bedroom main floor apartment From US $230
         

10.0 (1 Review)
Apartment
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  • TV
Luxury Home in Lytton Park From US $479
         

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Orange room From US $34
         

2.0 (1 Review)
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Spacious Loft w/Victorian Charm & Balcony! From US $648
         

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Prestigious Rosedale Neighbourhood 4 BR Home From US $581
         

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About Chaplin Estates Vacation Rentals

With more than 1163 Chaplin Estates vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Womenintravel 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 Womenintravel 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 457.35 ft² on average, with prices averaging US $300 a night.

Womenintravel 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 500
Vacation Homes 369
Hotels 75
B&B 7
Others 5
Villas 4
Hostels 3

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

Pro Tip: Womenintravel makes it easy to compare the best listings on Womenintravel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Womenintravel 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 1163 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.