Hot Tub Homes - Vacation Rentals in Chaplin Estates

Charming 5-Bedroom Forest Hill Home From US $284
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Stylish 2BR Downtown Sanctuary - Free Parking From US $804
         

|
10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Four Seasons Hotel Toronto From US $738
         

|
9.6 (958 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Beautiful Spacious 4 bedroom 4 bathroom family home From US $128
         

2.0 (1 Review)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Orange room From US $33
         

2.0 (1 Review)
House
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
Forest living in Toronto From US $325
         

New
House
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Chaplin Estates

Over 1193+ Luxury Places to Stay in or Near Chaplin Estates
Lux 1BR Yorkville Condo Fast WiFi and Work Desk From US $1,691
         

|
New
House
  • Air Conditioner
  • Accessibility
  • Security/Safety
Luxury Home 5bed5bath Rosedale Pool|Sauna|Parking From US $1,653
         

New
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Stylish 3BR Home with Office Deck & Parking From US $1,537
         

|
New
House
  • Air Conditioner
  • View
  • Security/Safety
Spacious Newly Built home in the heart of Toronto From US $1,463
         

New
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Stunning 8000sf North York home! From US $1,409
         

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

New
House
  • Air Conditioner
  • Security/Safety
  • Fireplace/Heating

Top-Rated Vacation Rentals with a Pool in Chaplin Estates

Over 153+ Top-Rated Vacation Rentals with a Pool in or Near Chaplin Estates
Victorian Gem - Midtown Toronto From US $365
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pool
The Hazelton Hotel Toronto From US $515
         

|
9.8 (1001 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
The Splendid - Luxury 1BR Uptown Toronto From US $136
         

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

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

|
9.6 (7 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • Private Pool
The Hazelton Hotel From US $836
         

|
9.5 (183 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
The Yorkville Royal Sonesta Hotel Toronto From US $321
         

|
9.4 (1918 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Chaplin Estates

Over 326+ Pet-Friendly Vacation Rentals in or Near Chaplin Estates
Sapphire Suite Modern 1BR and Sofa Bed Apartment From US $193
         

|
10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Kimpton Saint George by IHG From US $283
         

|
9.2 (1001 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Yorkville 2bed 2bath 5 guests Parking From US $230
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
2 Bedroom/2 Bathroom Suite From US $167
         

8.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Urban Elegance Home in Yorkville | 3bed3baths From US $949
         

New
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

Large Vacation Homes & Villas in Chaplin Estates

Over 79+ Large Vacation Homes & Villas in or Near Chaplin Estates
Luxury Toronto Villa | Pool, Sauna & Rooftop Deck From US $879
         

New
Villa
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
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
Premium new-build 3 BD,3 bath Apartment From US $279
         

New
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Wheelchair Accessible Vacation Homes in Chaplin Estates

Over 214+ Wheelchair Accessible Vacation Homes in or Near Chaplin Estates
Parkside Student Residence Downtown Toronto From US $75
         

The Anndore House, part of JdV by Hyatt From US $259
         

|
9.4 (1149 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Instant Suites -Stunning Designer Studio Yorkville From US $135
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Instant Suites Junior Suite at Yorkville ☆ From US $139
         

8.0 (15 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
YORKVILLE LUXURY CORNER SUITE! From US $334
         

New
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

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

Over 682+ 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
Oak House Residence From US $160
         

|
9.0 (33 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
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
Yorkville Magic. Toronto's Finest Neighbourhood From US $111
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV
Stylish Condo in Yorkville From US $86
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • TV
  • Security/Safety
New 2 bedroom apartment in Toronto 782 St. Clair ave.west From US $198
         

New
Apartment
  • Air Conditioner
  • Security/Safety
  • Fireplace/Heating

Instantly Bookable Vacation Homes in Chaplin Estates

Over 481+ Instantly Bookable Vacation Homes in or Near Chaplin Estates
Luxury Home in Lytton Park From US $479
         

New
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
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
Prestigious Rosedale Neighbourhood 4 BR Home From US $585
         

New
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Spacious Loft w/Victorian Charm & Balcony! From US $579
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

About Chaplin Estates Vacation Rentals

With more than 97 Chaplin Estates vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Hottubhomes 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 Hottubhomes 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 628.11 ft² on average, with prices averaging US $394 a night.

Hottubhomes 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 31
Vacation Homes 31
Hotels 7
Villas 1

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

Pro Tip: Hottubhomes makes it easy to compare the best listings on Hottubhomes homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Hottubhomes 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 97 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.