Default HTG hotel image

Holiday Homes in Simcoe Island

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Simcoe Island holiday homes

A modern interior with a wooden staircase, a glass console table, a mirror, and a vase with flowers.

1. Historic Portsmouth Village - Modern Comfort

Historic Portsmouth Village - Modern Comfort
Portsmouth
The price is €95
includes taxes & fees
23 Nov - 24 Nov
Historic Portsmouth Village - Modern Comfort
A modern kitchen with white cabinets, stainless steel appliances, and a wooden bar stool.

2. Cozy, Quiet Home in Kingston. Short drive to Queen's University. Pet Friendly!

Cozy, Quiet Home in Kingston. Short drive to Queen's University. Pet Friendly!
Kingston
9.4 out of 10, Exceptional, (6 reviews)
"The instructions were simple but clear. Everything was clean, nice place."
Canada
Marco
The price is €237
includes taxes & fees
8 Nov - 9 Nov
Cozy, Quiet Home in Kingston. Short drive to Queen's University. Pet Friendly!
A living room with a glass coffee table, a yellow chair, a black cabinet, and a TV on the wall.

3. Cozy home on a quiet street minutes to downtown Kingston!

Cozy home on a quiet street minutes to downtown Kingston!
Rideau Heights
10.0 out of 10, Exceptional, (10 reviews)
"It clean Well maintained Owner alway available to respect your questions."
Canada
Olivia C.
The price is €227
includes taxes & fees
3 Nov - 4 Nov
Cozy home on a quiet street minutes to downtown Kingston!
A spacious living area with a fireplace, a sofa, a coffee table, and a dining area in the background.

4. Charming Kingston Home w/Private Yard & Peaceful Vibes — Family Friendly!

Charming Kingston Home w/Private Yard & Peaceful Vibes — Family Friendly!
Calvin Park
5.6 out of 10, (12 reviews)
"Very great!"
Canada
Fiona
The price is €230
includes taxes & fees
7 Nov - 8 Nov
Charming Kingston Home w/Private Yard & Peaceful Vibes — Family Friendly!
A living room with a TV, a dining area with a table and chairs, a kitchen with cabinets and appliances, and a large window with a view of the outdoors.

5. Charming historic 2-bedroom coachhouse in Kingston

Charming historic 2-bedroom coachhouse in Kingston
Downtown Kingston
10.0 out of 10, Exceptional, (37 reviews)
"Cute property in a great location!"
United States
Bryn B.
The price is €209
includes taxes & fees
3 Nov - 4 Nov
Charming historic 2-bedroom coachhouse in Kingston
A dining area with a chandelier, a potted plant, and a dining table with chairs.

6. Home Away from Home - Relax and unwind in this beautifully decorated 3-bedroom

Home Away from Home - Relax and unwind in this beautifully decorated 3-bedroom
Kingston
9.2 out of 10, Wonderful, (7 reviews)
"Good location and easy check in"
United States
young k.
The price is €236
includes taxes & fees
8 Nov - 9 Nov
Home Away from Home - Relax and unwind in this beautifully decorated 3-bedroom
A modern kitchen with white cabinetry, a wooden countertop, a built-in washing machine, and a stainless steel refrigerator.

7. Beautiful house right by Portsmouth Olympic Harbour.

Beautiful house right by Portsmouth Olympic Harbour.
Portsmouth
9.8 out of 10, Exceptional, (6 reviews)
"It is a great house with all possible necessities..I would definitely here again!"
United States
margaryta y.
The price is €196
includes taxes & fees
3 Nov - 4 Nov
Beautiful house right by Portsmouth Olympic Harbour.
A round wooden table with a black metal chair, a green plate with three bowls, and a potted plant with lights.

8. Beautiful 3-bedroom bed & breakfast in wonderful Kingston location

Beautiful 3-bedroom bed & breakfast in wonderful Kingston location
Rideau Heights
The price is €349
includes taxes & fees
4 Nov - 5 Nov
Beautiful 3-bedroom bed & breakfast in wonderful Kingston location
A modern kitchen with a white countertop, a dining area with a table and chairs, and a view of the outdoors.

9. Kingston Lodge: Comfy & Cozy w/ Natural Scenery

Kingston Lodge: Comfy & Cozy w/ Natural Scenery
Bayridge West
8.8 out of 10, Excellent, (6 reviews)
"Great space. A perfect layout."
United States
Joe W.
The price is €156
includes taxes & fees
3 Nov - 4 Nov
Kingston Lodge: Comfy & Cozy w/ Natural Scenery
A kitchen cabinet with stainless steel pots and pans.

10. Happy House | Free Parking | Downtown

Happy House | Free Parking | Downtown
Downtown Kingston
10.0 out of 10, Exceptional, (11 reviews)
"We loved this house and had a great stay - very cosy house with great amenities "
Canada
Julia B.
The price is €263
includes taxes & fees
8 Nov - 9 Nov
Happy House | Free Parking | Downtown
A corner with a light green wall, a framed picture, a small table with a vase and a stone, and a red door.

11. Full House - Thousand Islands Getaway

Full House - Thousand Islands Getaway
Rideau Heights
The price is €210
includes taxes & fees
3 Nov - 4 Nov
Full House - Thousand Islands Getaway
A staircase leading to a second floor, a purple ottoman, and a door with a decorative glass panel.

12. Big & Charming Bungalow Getaway (nearby Walmart, LCBO, Beer Store, Mall, etc.)

Big & Charming Bungalow Getaway (nearby Walmart, LCBO, Beer Store, Mall, etc.)
Kingston
8.4 out of 10, Very good, (9 reviews)
"Family friendly, we were a family of 8 and it met all our needs."
Canada
Judy
The price is €331
includes taxes & fees
8 Nov - 9 Nov
Big & Charming Bungalow Getaway (nearby Walmart, LCBO, Beer Store, Mall, etc.)
A modern kitchen with white cabinets, stainless steel appliances, a black countertop, and a wooden floor.

13. Arbour Ridge Vacation Home - Trail View! 5 bedrooms, 7 beds

Arbour Ridge Vacation Home - Trail View! 5 bedrooms, 7 beds
Kingston
9.6 out of 10, Exceptional, (25 reviews)
"Was a really pleasant stay :)"
Canada
Eric
Arbour Ridge Vacation Home - Trail View! 5 bedrooms, 7 beds
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Simcoe Island Hotel Reviews

Hampton Inn by Hilton Kingston

Hampton Inn by Hilton Kingston

10/10 Excellent
"Quiet hotel , clean , good breakfast, staff was polite and friendly."
Hendry 1-night trip
Posted 4 hours ago
Hampton Inn by Hilton Kingston

Find out more about Simcoe Island

Simcoe Island Holiday Homes information

Number of reviews
116
Accommodation
38 Holiday Homes
Lowest Price
€95
Highest Price
€349

Explore a world of travel with Expedia