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Simcoe Island Vacation Rentals

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Simcoe Island vacation rentals

A modern kitchen with white cabinets, a stainless steel refrigerator, a gas stove, and a stone wall.

1. Dwell Aparthotels

Dwell Aparthotels
4.0 star property
Downtown Kingston
9.6 out of 10, Exceptional, (50 reviews)
"Absolutely incredible spot in Kingston - so comfortable, modern and truly enjoyable - thank you so much to everyone at Dwell!!"
Canada
Aubrie
$246 nightly
The price is $292
Sep 1 - Sep 2
Total with taxes and fees
Dwell Aparthotels
A living room with a television, a wooden coffee table, a chair, and a sofa.

2. Cozy downtown one bedroom free parking

Cozy downtown one bedroom free parking
Sunnyside
6.2 out of 10, (14 reviews)
"A nice cozy place perfectly situated in Kingston"
Canada
Brad G.
$137 nightly
The price is $155
Sep 1 - Sep 2
Total with taxes and fees
Cozy downtown one bedroom free parking
A bedroom with a bed, two bedside lamps, a bench, and a window with blinds.

3. The Neighbourhood: Expansive loft | free parking

The Neighbourhood: Expansive loft | free parking
Downtown Kingston
10.0 out of 10, Exceptional, (1 review)
"Beautiful apartment decorated by an artist, I’m sure. Walking distance to downtown. Lovely and warm even though it was snowing. Host are super friendly and helpful. "
United Kingdom
Elspeth C.
$185 nightly
The price is $215
Sep 1 - Sep 2
Total with taxes and fees
The Neighbourhood: Expansive loft | free parking
A modern living room with a flat-screen TV, a dark-colored sofa, a glass coffee table, and a patterned rug.

4. Prime Location Duo Nest & Rest

Prime Location Duo Nest & Rest
Rideau Heights
7.6 out of 10, Good, (35 reviews)
"Very nice and convenient stay"
Canada
Terry
$157 nightly
The price is $183
Sep 7 - Sep 8
Total with taxes and fees
Prime Location Duo Nest & Rest
A bedroom with a bed, a nightstand, a lamp, and two framed leaf decorations on the wall.

5. Cozy Home Away from Home

Cozy Home Away from Home
Kingston
9.0 out of 10, Wonderful, (27 reviews)
"Close to everything, clean, comfortable, accommodating host, very good value, would stay again "
Canada
David
$121 nightly
The price is $136
Sep 8 - Sep 9
Total with taxes and fees
Cozy Home Away from Home
A modern living room with a dark gray wall, a flat-screen TV, a wooden coffee table, a gray sofa, and a wooden dining table with benches.

6. Spacious 1 bedroom basement suite with free parking near CFB, RMC & Downtown.

Spacious 1 bedroom basement suite with free parking near CFB, RMC & Downtown.
Greenwood Park
10.0 out of 10, Exceptional, (3 reviews)
"Enjoyed our stay. A very nice community / neighborhood. Some nice extra treats and very well laid out information book ."
Canada
Bernie M.
$165 nightly
The price is $186
Sep 9 - Sep 10
Total with taxes and fees
Spacious 1 bedroom basement suite with free parking near CFB, RMC & Downtown.
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.

7. Charming historic 2-bedroom coachhouse in Kingston

Charming historic 2-bedroom coachhouse in Kingston
Downtown Kingston
10.0 out of 10, Exceptional, (32 reviews)
"We were in town for one night for an event- this was the perfect spot - great location, beautiful view of the lake and a stones throw from Richardson Beach, MacDonald Memorial Park, downtown, and Queens U. Lovely stay - Couldn’t really have asked for more."
United States
Danielle H.
$313 nightly
The price is $353
Sep 13 - Sep 14
Total with taxes and fees
Charming historic 2-bedroom coachhouse in Kingston
A compact kitchen with white cabinets, a black countertop, a white refrigerator, and a ceiling fan.

8. Cozy downtown two bedrooms free parking

Cozy downtown two bedrooms free parking
Sunnyside
6.0 out of 10, (9 reviews)
"The title of the review explains it all. Very few amenities. Plan to eat out. Shared home. Nice back yard. Good parking"
Canada
Andre B.
$188 nightly
The price is $213
Sep 1 - Sep 2
Total with taxes and fees
Cozy downtown two bedrooms free parking
A modern kitchen with white cabinetry, a wooden countertop, a built-in washing machine, and a stainless steel refrigerator.

9. Beautiful house right by Portsmouth Olympic Harbour.

Beautiful house right by Portsmouth Olympic Harbour.
Portsmouth
9.4 out of 10, Exceptional, (3 reviews)
"It is a great house with all possible necessities..I would definitely here again!"
United States
margaryta y.
$246 nightly
The price is $278
Sep 1 - Sep 2
Total with taxes and fees
Beautiful house right by Portsmouth Olympic Harbour.

10. Cozy 2BR – Walk to Downtown & University!

Cozy 2BR – Walk to Downtown & University!
Sunnyside
Cozy 2BR – Walk to Downtown & University!
A dining area with a chandelier, a potted plant, and a dining table with chairs.

11. 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, (5 reviews)
"Beautiful place, very professional host and communication was superb.I will definitely recommend this place and rent again when in the area."
Canada
David S.
$245 nightly
The price is $277
Sep 3 - Sep 4
Total with taxes and fees
Home Away from Home - Relax and unwind in this beautifully decorated 3-bedroom
A spacious living area with a stone wall, wooden beams, a large chandelier, and a blue sofa set.

12. 18th Century Luxury Suite with Rustic Charm

18th Century Luxury Suite with Rustic Charm
KIngston
10.0 out of 10, Exceptional, (1 review)
"Great place. Great location. Lots of room. Clean. Maybe a few more steps than two 77 year olds would normally want. But still worth it!!! "
United States
thomas h.
$245 nightly
The price is $249
Sep 3 - Sep 4
Total with taxes and fees
18th Century Luxury Suite with Rustic Charm
A spacious living area with a fireplace, a sofa, a coffee table, and a dining area in the background.

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

Charming Kingston Home w/Private Yard & Peaceful Vibes — Family Friendly!
Calvin Park
5.4 out of 10, (9 reviews)
"Very great!"
Canada
Fiona
$288 nightly
The price is $325
Sep 14 - Sep 15
Total with taxes and fees
Charming Kingston Home w/Private Yard & Peaceful Vibes — Family Friendly!
A modern kitchen with a white countertop, a dining area with a table and chairs, and a view of the outdoors.

14. 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.
$221 nightly
The price is $224
Sep 13 - Sep 14
Total with taxes and fees
Kingston Lodge: Comfy & Cozy w/ Natural Scenery
A staircase leading to a second floor, a purple ottoman, and a door with a decorative glass panel.

15. 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
$352 nightly
The price is $397
Sep 8 - Sep 9
Total with taxes and fees
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.

16. 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, (23 reviews)
"Was a really pleasant stay :)"
Canada
Eric
$572 nightly
The price is $646
Sep 1 - Sep 2
Total with taxes and fees
Arbour Ridge Vacation Home - Trail View! 5 bedrooms, 7 beds
A small cabin with a deck, surrounded by greenery.

17. Small Cottage Charming 2-Bed Cottage: Your Lakeside Oasis for 4!

Small Cottage Charming 2-Bed Cottage: Your Lakeside Oasis for 4!
Perth Road
6.0 out of 10, (1 review)
"Beach doesn't exist All weeds and seaweed Room dirty Dishes dried food Towels hard and smell Bedding fitted sheet and fleece blanket No sheets Just disappointed"
Canada
Rosslyn
$192 nightly
The price is $217
Sep 28 - Sep 29
Total with taxes and fees
Small Cottage Charming 2-Bed Cottage: Your Lakeside Oasis for 4!
A two-story house with a red door, a covered porch, and a satellite dish.

18. A Cozy Country House - Family Sized w/ Game Room and Large Property!

A Cozy Country House - Family Sized w/ Game Room and Large Property!
Kingston
8.6 out of 10, Excellent, (7 reviews)
"Had a great stay! Would absolutely recommend this house for a vacation stay with a group of friends. And Yvonne was so responsive and a pleasure to deal with. Thanks!"
United States
Emily S.
$513 nightly
The price is $579
Sep 6 - Sep 7
Total with taxes and fees
A Cozy Country House - Family Sized w/ Game Room and Large Property!
A wicker sofa with patterned cushions on a balcony with a white railing, overlooking a green landscape and water.

19. Luxury Penthouse Overlooking the 1000 Islands

Luxury Penthouse Overlooking the 1000 Islands
KIngston
Luxury Penthouse Overlooking the 1000 Islands
A stone building with a dark door, two Adirondack chairs, a small table, and a pink umbrella.

20. Historic & Spacious Two-Bedroom Luxury Suite

Historic & Spacious Two-Bedroom Luxury Suite
KIngston
$276 nightly
The price is $280
Sep 9 - Sep 10
Total with taxes and fees
Historic & Spacious Two-Bedroom Luxury Suite
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.
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Top Simcoe Island Hotel Reviews

Ramada by Wyndham Kingston

Ramada by Wyndham Kingston

10/10 Excellent
"Very clean and totally refurbished. Excellent value and location."
paul 2-night trip
Posted 6 hours ago
Ramada by Wyndham Kingston

Find out more about Simcoe Island

Everything you need to know about Simcoe Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Simcoe Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Simcoe Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Simcoe Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Simcoe Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Simcoe Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $136 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Simcoe Island rentals

At Expedia, we put the best Simcoe Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Simcoe Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Simcoe Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Simcoe Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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