Stay If You Dare - Vacation Rentals in Whitby

Cozy Whitby Retreat (Private 2 Bedroom Townhouse) From US $174
         

9.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Two bedroom basement apartment From US $108
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Fabulous 3 bedroom in Whitby From US $201
         

New
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Fabulous 3 bedroom in Whitby. Main level. From US $201
         

6.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
One bedroom apartment/suite From US $91
         

10.0 (21 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Luxury Places to Stay in Whitby

Over 192+ Luxury Places to Stay in or Near Whitby
Stylish 3 BR Apt with Free Parking, Wifi and Patio From US $480
         

|
2.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Beautiful 3 bedroom Entire detached home From US $430
         

|
9.5 (9 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Largest ensuite bedroom in a guest house From US $370
         

5.9 (7 Reviews)
House
  • Parking
  • Pet Friendly
  • Child Friendly
Luxe 4BR Retreat w Heated Pool Hot Tub and BBQ From US $317
         

|
New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Residence Inn by Marriott Whitby From US $239
         

|
8.0 (365 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury home 4BR, Pool, & 5 Mins to 401 From US $211
         

|
8.4 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express Whitby Oshawa by IHG From US $181
         

|
8.8 (530 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Whitby

Over 8+ Top-Rated Vacation Rentals with a Pool in or Near Whitby
Poolside entire lower level apt From US $96
         

|
9.3 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express Whitby by IHG From US $136
         

9.2 (1110 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Residence Inn by Marriott Whitby From US $143
         

|
8.4 (1002 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Whitby·Vacation home with heated pool From US $170
         

6.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Luxe 4BR Retreat w/Heated Pool, Hot Tub & BBQ From US $164
         

6.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury home 4BR, Pool, & 5 Mins to 401 From US $371
         

Pet-Friendly Vacation Rentals in Whitby

Over 30+ Pet-Friendly Vacation Rentals in or Near Whitby
Stylish 3 BR Apt w/Free Parking, Wifi & Patio From US $203
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Rita's Kunjo - 2BR, 3BD, 2WR, Full Ktchn, Living From US $109
         

|
9.1 (37 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Willow Nest - 5 Beds, 2.5 Baths, 3 Park, Backyard, Thermea Spa From US $350
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
4BR 2.5WR Townhouse Downtown Whtiby From US $171
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy Retreat Great for Short/Long Term Stays. From US $103
         

8.8 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Stunning & Bright - My home is close to the highway & Thermea Spa From US $507
         

Spacious 2 beds Apartment in Downtown Whitby From US $151
         

5.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Laundry
See More Pet-Friendly Vacation Rentals in Whitby on PetFriendly.io

Large Vacation Homes & Villas in Whitby

Over 20+ Large Vacation Homes & Villas in or Near Whitby
Modern Whitby Railway Home From US $134
         

New
Villa
  • Air Conditioner
  • Parking
  • Security/Safety
Cozy 4-Bedroom Home with Large Yard in Whitby From US $305
         

Quaint 4-bedroom house with AC in charming Whitby on From US $562
         

Luxury 6BR House in Whitby From US $443
         

New
House
  • Security/Safety
  • Child Friendly
Nature's Paradise in the city From US $186
         

New
House
  • Air Conditioner
  • Designated Smoking Area
  • Child Friendly
Comfy Basement Suite in Quiet Neighbourhood From US $116
         

New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Whitby

Over 4+ Wheelchair Accessible Vacation Homes in or Near Whitby
Quality Suites From US $130
         

|
7.8 (663 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Quality Suites Whitby From US $106
         

8.2 (1114 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Motel 6-Whitby, ON - Toronto East From US $87
         

5.6 (532 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Motel 6 Whitby, ON - Toronto East From US $100
         

6.2 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV

Whitby Vacation Rentals and Airbnb Places to Stay Under $200

Over 99+ Whitby Vacation Rentals and Airbnb Places to Stay Under $200
Beautiful 2 bedroom with free parking space From US $130
         

10.0 (2 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace
LOVE and Relax at Dream Catcher Retreat From US $98
         

|
9.8 (24 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Luxurious Waterfront Residence From US $155
         

|
2.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Beautiful & Spacious 1 Bedroom Apartment From US $66
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Basement apartment in Whitby. From US $135
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Fabulous 2-bedroom apartment with AC in charming Whitby From US $99
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV
Clean and Modern Guest Suite in Whitby From US $127
         

9.8 (26 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Whitby

Over 58+ Instantly Bookable Vacation Homes in or Near Whitby
Charming Townhouse Retreat Near Nordic Spa From US $238
         

9.2 (22 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Brand new 3 Bedroom House, Thermea Spa Village From US $206
         

9.0 (10 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Whitby Gateway - 2BR 3BD 2WR Kitchen Laundry From US $191
         

9.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Home of Sweet Dream From US $119
         

8.6 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Newly Renovated 3BR in Whitby | Family-Friendly From US $148
         

8.4 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Whitby Vacation Rentals

With more than 201 Whitby vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Stayifyoudare 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 Whitby.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Stayifyoudare Whitby, 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 Whitby. Places to stay near Whitby are 799.15 ft² on average, with prices averaging US $201 a night.

Stayifyoudare makes it easy and safe to find and compare vacation rentals in Whitby 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 Whitby

Type Count
Vacation Homes 132
Holiday Apartments 53
Hotels 9
Villas 3
Cottages 2

Use these Quick Filters to Find a Vacation Rental in Whitby

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

Weather in Whitby

View the weather forecast for Whitby before booking your Whitby 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

Whitby Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Whitby?
How many vacation rentals are available in Whitby?

Currently, the total number of properties listed in 2026 is over 201 in the Whitby area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Whitby.