Simcoe Island Vacation Rentals

Dates

November 2026

December 2026

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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

Downtown Kingston

Karen

CA $380 total

includes taxes & fees

Nov 8 - Nov 9

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.

2. Charming historic 2-bedroom coachhouse in Kingston

Downtown Kingston

Bryn B.

CA $324 total

includes taxes & fees

Nov 8 - Nov 9

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

3. Historic Portsmouth Village - Modern Comfort

Portsmouth

CA $192 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with white cabinetry, a wooden countertop, a built-in washing machine, and a stainless steel refrigerator.

4. Beautiful house right by Portsmouth Olympic Harbour.

Portsmouth

margaryta y.

CA $303 total

includes taxes & fees

Nov 10 - Nov 11

A modern kitchen with white cabinets, stainless steel appliances, and a wooden bar stool.

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

Kingston

Marco

CA $375 total

includes taxes & fees

Nov 8 - Nov 9

A bedroom with a bed, a nightstand, a lamp, and two framed leaf decorations on the wall.

6. Cozy Home Away from Home

Kingston

David

CA $167 total

includes taxes & fees

Nov 9 - Nov 10

A brick building with a sign reading "Mermaid Avenue Sandwich Factory" at the entrance.

7. Spacious Historic Downtown Stableman`s House Loft

Downtown Kingston

Michael D.

CA $326 total

includes taxes & fees

Nov 15 - Nov 16

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

Rideau Heights

CA $536 total

includes taxes & fees

Nov 9 - Nov 10

A bedroom with a bed, two bedside lamps, a bench, and a window with blinds.

9. The Neighbourhood: Expansive loft | free parking

Downtown Kingston

Jennifer K.

CA $254 total

includes taxes & fees

Nov 16 - Nov 17

A modern living room with a flat-screen TV, a dark-colored sofa, a glass coffee table, and a patterned rug.

10. Prime Location Duo Nest & Rest

Rideau Heights

Terry

CA $242 total

includes taxes & fees

Nov 8 - Nov 9

A stone building with a dark door, two Adirondack chairs, a small table, and a pink umbrella.

11. Historic & Spacious Two-Bedroom Luxury Suite

KIngston

CA $292 total

includes taxes & fees

Nov 10 - Nov 11

A living room with a television, a wooden coffee table, a chair, and a sofa.

12. Cozy downtown one bedroom free parking

Sunnyside

Brad G.

CA $203 total

includes taxes & fees

Nov 16 - Nov 17

A living room with a glass coffee table, a yellow chair, a black cabinet, and a TV on the wall.

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

Rideau Heights

Olivia C.

CA $343 total

includes taxes & fees

Nov 8 - Nov 9

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

Bayridge West

Joe W.

CA $240 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with white cabinets, stainless steel appliances, a black countertop, and a wooden floor.

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

Kingston

Eric

CA $902 total

includes taxes & fees

Nov 8 - Nov 9

A spacious living area with a fireplace, a sofa, a coffee table, and a dining area in the background.

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

Calvin Park

Fiona

CA $381 total

includes taxes & fees

Nov 15 - Nov 16

A porch with three yellow chairs and a wooden table, white siding walls, and a window with a view of trees.

17. Happy House | Free Parking | Downtown

Downtown Kingston

Julia B.

CA $381 total

includes taxes & fees

Dec 3 - Dec 4

A modern kitchen with stainless steel appliances, wooden cabinets, and a central island with stools.

18. Full House - Thousand Islands Getaway

Rideau Heights

CA $324 total

includes taxes & fees

Nov 9 - Nov 10

A dining area with a chandelier, a potted plant, and a dining table with chairs.

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

Kingston

young k.

CA $324 total

includes taxes & fees

Nov 8 - Nov 9

A staircase leading to a second floor, a purple ottoman, and a door with a decorative glass panel.

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

Kingston

Judy

CA $521 total

includes taxes & fees

Nov 8 - Nov 9

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Find vacation rentals that suit your style

Top Simcoe Island Hotel Reviews

A modern indoor swimming pool with clear blue water, glass doors, and a seating area with a sofa and chairs.

Hampton Inn by Hilton Kingston

St. Lawrence South

10/10 Excellent

We have stayed a few times at this hotel and found it VERY clean, and friendly service from the staff. The only thing we didn't appreciate was a tween hockey team staying in the hotel and the children were running up and down the halls to the point where we had to open the door and ask them to quiet down, and when that didn't work called the front desk and they handled it. This is a posted policy in their elevator, we would appreciate the parents of these kids to be more attentive and respect...

Chris

A hotel with a modern design, featuring a large entrance, multiple floors, and a prominent hotel name on the facade.

Holiday Inn Express Kingston West by IHG

Cataraqui North

10/10 Excellent

Roger

A modern cafe with seating areas, a coffee station, and a large TV screen.

Holiday Inn Express & Suites Kingston Central by IHG

Rideau Heights

10/10 Excellent

Allison

A modern café with a counter displaying breakfast items, a refrigerated display case, and a menu board above.

Courtyard by Marriott Kingston Highway 401/Division Street

Novelis

10/10 Excellent

Lynne

A hotel room with two beds, a desk, a chair, and a large window with curtains.

Comfort Inn and Suites

Kingston

10/10 Excellent

Danny

A room with a television mounted on a cave-like wall, a sofa, and a staircase with illuminated steps.

Best Western Fireside Inn

Strathcona Park

10/10 Excellent

Welcome to the wild west—well, sort of! This joint looks like a classic western hotel that time forgot, complete with vintage decor straight out of a 1960s postcard. If you're into that retro vibe, you're going to love it here—think of it as a theme park for nostalgia! Each room is like a treasure chest filled with antique books and doodads that scream 'history lesson!' But wait, there's more! They’ve tossed in a modern TV and a fireplace too, blending the comforts of today with the fabulous...

Andre

A marina with boats docked, surrounded by modern buildings and a calm body of water reflecting the structures.

Delta Hotels by Marriott Kingston Waterfront

Downtown Kingston

10/10 Excellent

Danyang

A modern building with large windows and a well-maintained garden with colorful flowers.

Donald Gordon Hotel and Conference Centre

Kingston

10/10 Excellent

Elizabeth

A large, historic building with a prominent tower, a grand entrance with steps, and a stone facade.

The Rosemount Inn

Downtown Kingston

10/10 Excellent

Honeymooners

A reception desk with a wooden panel design, potted plants, framed welcome signs, and pendant lighting.

Confederation Place - Hotel

Downtown Kingston

10/10 Excellent

Denise

A modern hotel lobby with a reception desk, seating area, and large windows offering a view of the outdoors.

DoubleTree by Hilton Kingston

Kingston

10/10 Excellent

Elizabeth

A spacious entryway with hardwood floors, a chandelier, and a bookshelf filled with books and decorative items.

The Secret Garden B&B Inn

Downtown Kingston

10/10 Excellent

Siobhan

A gazebo with a white lattice roof surrounded by lush green foliage.

Green Acres Inn

Cataraqui North

10/10 Excellent

We stayed at the Green Acres Inn last week on the long weekend. It was a charming place to stay - very clean. The outdoor pool was great, the gardens were beautiful and I especially enjoyed having my morning tea in the lovely gazebo. The room was small, but very well organized. We had a kettle, coffee pot, fridge and all the essentials for our morning coffee and tea. It was a very quiet place to stay and I would recommend it to anyone. The staff was very polite and helpful supplying...

Ruth

Transparent geodesic domes with seating inside, connected by string lights, on a paved surface.

Holiday Inn Kingston Waterfront by IHG

Downtown Kingston

10/10 Excellent

Danuta

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simcoe Island vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simcoe Island vacation rentals we have selected for you start as low as CA $100 per night. Entering your travel dates in the search wizard 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.

Simcoe Island Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Simcoe Island vacation rentals

1. Dwell Aparthotels

2. Charming historic 2-bedroom coachhouse in Kingston

3. Historic Portsmouth Village - Modern Comfort

4. Beautiful house right by Portsmouth Olympic Harbour.

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

6. Cozy Home Away from Home

7. Spacious Historic Downtown Stableman`s House Loft

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

9. The Neighbourhood: Expansive loft | free parking

10. Prime Location Duo Nest & Rest

11. Historic & Spacious Two-Bedroom Luxury Suite

12. Cozy downtown one bedroom free parking

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

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

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

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

17. Happy House | Free Parking | Downtown

18. Full House - Thousand Islands Getaway

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

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

Find vacation rentals that suit your style

Top Simcoe Island Hotel Reviews

Hampton Inn by Hilton Kingston

10/10 Excellent

Find out more about Simcoe Island

Simcoe Island vacation rentals: An excellent choice for every season

How to find incredible deals on Simcoe Island rentals

Explore a world of travel with Expedia