Vacation Rentals in Simcoe County

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Top Vacation Rentals in Simcoe County

Margarita Vacation Getaway
Property amenity

Margarita Vacation Getaway

3.5 star property
9.6 out of 10, Exceptional, (9)
"Great location and amenities. "
Margarita Vacation Getaway
Downtown Collingwood Condos
Family Condo | In-room dining

Downtown Collingwood Condos

3.0 star property
9.2 out of 10, Wonderful, (16)
"Beautiful property "
The price is ￥15,670
￥34,702 total
includes taxes & fees
Sep 30 - Oct 1
Downtown Collingwood Condos
SUMMERHILL
Classic Cottage, Resort View | Private kitchen

SUMMERHILL

2.0 star property
6.6 out of 10, (4)
"We liked the property a lot"
The price is ￥15,999
￥39,591 total
includes taxes & fees
Sep 19 - Sep 20
SUMMERHILL
Alton Lodges
Exterior

Alton Lodges

2.0 star property
7.8 out of 10, Good, (8)
"I love the place ❤️❤️❤️.And the owner is very friendly and easy to communicate. Definitely we will come back again ❤️❤️❤️."
The price is ￥64,795
￥84,065 total
includes taxes & fees
Sep 19 - Sep 20
Alton Lodges
Chic Staycation Condo at FH
Private kitchen

Chic Staycation Condo at FH

7.8 out of 10, Good, (10)
"Amazing stay! It was very beautiful and the place was kept very clean. Had a balcony with seating. Really close walking distance to the boardwalk. Just bring your own shower amenities (ex; body wash)"
The price is ￥13,866
￥31,698 total
includes taxes & fees
Oct 17 - Oct 18
Chic Staycation Condo at FH
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
Property grounds

Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage

9.4 out of 10, Exceptional, (8)
"This rental was very affordable with lots of beds. We enjoyed our stay and had plenty of room for a larger group."
The price is ￥13,528
￥44,317 total
includes taxes & fees
Sep 30 - Oct 1
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
Modern Tiny Wood Cottage #3 Camping style Cottages 5 minutes to the beach!
Outdoor dining

Modern Tiny Wood Cottage #3 Camping style Cottages 5 minutes to the beach!

7.4 out of 10, Good, (3)
"A fantastic stay. Thank you "
Modern Tiny Wood Cottage #3 Camping style Cottages 5 minutes to the beach!
BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 9
Outdoor dining

BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 9

9.2 out of 10, Wonderful, (20)
"Great little get away"
The price is ￥23,998
￥58,334 total
includes taxes & fees
Sep 21 - Sep 22
BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 9
Horseshoe Valley Suites - The Glade
Indoor pool, outdoor pool

Horseshoe Valley Suites - The Glade

4.0 star property
9.0 out of 10, Wonderful, (9)
"Great place to stay"
Horseshoe Valley Suites - The Glade
The Family Escape Townhome
Outdoor dining

The Family Escape Townhome

9.0 out of 10, Wonderful, (34)
"It is a great place. Just could use a few comfy blankets for cold nights"
The price is ￥15,350
￥37,113 total
includes taxes & fees
Sep 30 - Oct 1
The Family Escape Townhome
Muskoka - The Eagle's Nest
Smart TV, fireplace

Muskoka - The Eagle's Nest

9.6 out of 10, Exceptional, (62)
"Spent a cozy 2 days here, the sunroom grills were amazing!"
Muskoka - The Eagle's Nest
COZY COTTAGE WALKING DISTANCE TO LAKE SIMCOE & FRIDAY HARBOUR
Beach

COZY COTTAGE WALKING DISTANCE TO LAKE SIMCOE & FRIDAY HARBOUR

9.2 out of 10, Wonderful, (49)
"We had a great time. Place was nice and the host was great. Would definetly consider returning if we visit the area again"
COZY COTTAGE WALKING DISTANCE TO LAKE SIMCOE & FRIDAY HARBOUR
Modern Tiny Wood Cottage #0 Camping style Cottages 5 minutes to the beach!
Outdoor dining

Modern Tiny Wood Cottage #0 Camping style Cottages 5 minutes to the beach!

7.0 out of 10, Good, (4)
"Great staff and experience overall! Will definitely be back!! "
Modern Tiny Wood Cottage #0 Camping style Cottages 5 minutes to the beach!
BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 8
On the beach

BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 8

9.4 out of 10, Exceptional, (19)
"Absolutely fantastic location, we had a great time at the beach, the sand is wonderfully fine and confortable. The cottage is well kept and was very clean. BBQ worked great. Communication with host was fast and pleasant. Would definitely come back, thank you!"
The price is ￥23,998
￥58,334 total
includes taxes & fees
Sep 21 - Sep 22
BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 8
Four Season Waterfront Cottage Over-the-Water view
Interior

Four Season Waterfront Cottage Over-the-Water view

9.2 out of 10, Wonderful, (5)
"Great place to stay highly recommend. "
Four Season Waterfront Cottage Over-the-Water view
The Nordic -Central Collingwood Condo
Coffee/tea maker, electric kettle

The Nordic -Central Collingwood Condo

3.0 star property
7.4 out of 10, Good, (3)
"It is a shame that third party companies are offering properties with no sole, renting someones home should be an adventure"
The Nordic -Central Collingwood Condo
Amazing 2BR/2BA Resort Condo w/ Balcony & Parking!
Interior

Amazing 2BR/2BA Resort Condo w/ Balcony & Parking!

10.0 out of 10, Exceptional, (1)
"The unit looked just like as advertised on the photos! Communication was smooth as owner almost always replied in timely manner. Unit was clean overall; kitchen/laundry/washrooms were well equipped so it felt like home without being home! The patio furniture was also nice where you could just sit and enjoy the breeze at the balcony.If you're looking for place where you would just like to relax and do nothing, this is definitely one of those places! "
Amazing 2BR/2BA Resort Condo w/ Balcony & Parking!
New, Modern, Relaxing home in Collingwood. 3 bedroom, Sleeps 6.
Smart TV, fireplace

New, Modern, Relaxing home in Collingwood. 3 bedroom, Sleeps 6.

10.0 out of 10, Exceptional, (13)
"R.S from VA USA Aug. 2025 Stayed 5 Days We had a fantastic stay in this place, definitely we will come back. "
New, Modern, Relaxing home in Collingwood. 3 bedroom, Sleeps 6.
The Georgian Bay Cottage - Hot Tub + Sauna + Fire-pit + More!
Exterior detail

The Georgian Bay Cottage - Hot Tub + Sauna + Fire-pit + More!

7.0 out of 10, Good, (2)
"It was very nice and quiet. Right across the street from a good restaurant which was also nice. "
The Georgian Bay Cottage - Hot Tub + Sauna + Fire-pit + More!
Peaceful Country Escape | Smart Home, Near Wonderland & Lake Simcoe
Smart TV, fireplace, books, stereo

Peaceful Country Escape | Smart Home, Near Wonderland & Lake Simcoe

10.0 out of 10, Exceptional, (2)
"The property was fresh, clean and modern, absolutely beautiful home, with nothing missing.... and with a taste of nature, woke up to a peaceful and beautiful sunrise.... cant wait to go back, it was a wonderful stay for our family ❤️ Thank you David for always writing back and being ready and willing to accompdate us if anything was needed "
Peaceful Country Escape | Smart Home, Near Wonderland & Lake Simcoe
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 County Hotel Reviews

Candlewood Suites Collingwood by IHG

Candlewood Suites Collingwood by IHG

10/10 Excellent
"Felt very new and fresh. Great amenities in the room... very comfortable. Close to local shops, etc."
Marian 1-night trip
Posted 2 days ago
Candlewood Suites Collingwood by IHG

Find out more about Simcoe County

Find out more about Simcoe County

Vacation Apartments in Simcoe County

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