Holiday Rentals in Simcoe County

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Top Cities in Simcoe County

Collingwood featuring heritage architecture
Holiday RentalsHoliday Rentals

Collingwood

Collingwood

Featured Holiday Rentals in Simcoe County

Our top choices for Simcoe County holiday rentals

SUMMERHILL
Classic Cottage, Resort View | Private kitchen

SUMMERHILL

2.0 star property
8.0 out of 10, Very good, (2)
"We liked the property a lot"
The price is €229
includes taxes & fees
24 Aug - 25 Aug
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 €210
includes taxes & fees
25 Aug - 26 Aug
Alton Lodges
Downtown Collingwood Condos
Family Condo | In-room dining

Downtown Collingwood Condos

3.0 star property
9.6 out of 10, Exceptional, (13)
"Very spacious, newly renovated. Wonderful fireplace and tv. Comfortable bed"
The price is €201
includes taxes & fees
2 Sept - 3 Sept
Downtown Collingwood Condos
Exquisite Log Cabin Retreat- Perfect Couple’s Getaway! Tranquility at its best❤️
Fridge, microwave, oven, stovetop

Exquisite Log Cabin Retreat- Perfect Couple’s Getaway! Tranquility at its best❤️

10.0 out of 10, Exceptional, (306)
"A very relaxing and comfortable stay set with the beautiful backdrop of the Blue Mountains."
Exquisite Log Cabin Retreat- Perfect Couple’s Getaway! Tranquility at its best❤️
The Nordic -Central Collingwood Condo
Coffee/tea maker, electric kettle

The Nordic -Central Collingwood Condo

3.0 star property
4.0 out of 10, (1)
"It is a shame that third party companies are offering properties with no sole, renting someones home should be an adventure"
The price is €187
includes taxes & fees
18 Sept - 19 Sept
The Nordic -Central Collingwood Condo
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!

2.0 out of 10, (1)
The price is €150
includes taxes & fees
4 Sept - 5 Sept
Modern Tiny Wood Cottage #3 Camping style Cottages 5 minutes to the beach!
Traditional Tiny Wood Cottage #17 Camping style Cottages 5 minutes to the beach!
Outdoor dining

Traditional Tiny Wood Cottage #17 Camping style Cottages 5 minutes to the beach!

The price is €147
includes taxes & fees
24 Aug - 25 Aug
Traditional Tiny Wood Cottage #17 Camping style Cottages 5 minutes to the beach!
Hidden Gem!!!
Exterior

Hidden Gem!!!

7.8 out of 10, Good, (20)
"Really disappointed absolutely spider infested inside ceilings was like a horror movie, back door was broken wouldn’t open “backyard private beach” wasn’t maintained spoke to the property owner who said he would send someone over to fix the property and clean it while we were there nothing got done. It’s an amazing view poorly ran I would not stay here again I had hoped with the communication I had with the owner things would get done they were not also it had many child hazards broken...
The price is €376
includes taxes & fees
24 Aug - 25 Aug
Hidden Gem!!!
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, (19)
"I had a wonderful vacation and i will return next year. If you are looking for beachfront this is the place. The small cottage had everything we needed. Thank you..."
The price is €388
includes taxes & fees
25 Aug - 26 Aug
BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 9
Traditional Tiny Wood Cottage #14 Camping style Cottages 5 minutes to the beach!
Outdoor dining

Traditional Tiny Wood Cottage #14 Camping style Cottages 5 minutes to the beach!

The price is €212
includes taxes & fees
24 Aug - 25 Aug
Traditional Tiny Wood Cottage #14 Camping style Cottages 5 minutes to the beach!
Carriage Studio Retreat
Property grounds

Carriage Studio Retreat

The price is €143
includes taxes & fees
1 Sept - 2 Sept
Carriage Studio Retreat
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
Muskoka - The Eagle's Nest
Smart TV, fireplace

Muskoka - The Eagle's Nest

9.6 out of 10, Exceptional, (58)
"Spent a cozy 2 days here, the sunroom grills were amazing!"
Muskoka - The Eagle's Nest
The Georgian Bay Cottage - Hot Tub + Sauna + Fire-pit + More!
Exterior detail

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

10.0 out of 10, Exceptional, (1)
"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!
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
Property grounds

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

9.8 out of 10, Exceptional, (6)
"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 €270
includes taxes & fees
23 Sept - 24 Sept
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
Chic Staycation Condo at FH
Private kitchen

Chic Staycation Condo at FH

7.6 out of 10, Good, (9)
"Such an amazing experience, me and my boyfriend spent the weekend there and the host was amazing. Host was extremely friendly and provided us with amazing instructions, we had no trouble finding where we needed to go. The place itself was absolutely beautiful and host provided local areas where we could dine. Overall an amazing experience we hope to be able to spend time there next summer! "
The price is €188
includes taxes & fees
23 Sept - 24 Sept
Chic Staycation Condo at FH
Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!
Fridge, microwave, oven, stovetop

Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!

9.4 out of 10, Exceptional, (78)
"Great stay. Excellent location and beautiful outdoor area."
Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!
Cozy Waterfront Cottage with Pool/Sauna/BBQ/Wifi
Terrace/patio

Cozy Waterfront Cottage with Pool/Sauna/BBQ/Wifi

10.0 out of 10, Exceptional, (1)
"Great get away for our family, our host was great. Beautiful property located close to everything you would need. Check in was quick and easy. I would highly recommend."
Cozy Waterfront Cottage with Pool/Sauna/BBQ/Wifi
Cozy 2BR Highpoint located at the Friday Harbour
Marina

Cozy 2BR Highpoint located at the Friday Harbour

9.4 out of 10, Exceptional, (15)
"Wonderful area and host was very helpful "
Cozy 2BR Highpoint located at the Friday Harbour
The Family Escape Townhome
Outdoor dining

The Family Escape Townhome

9.0 out of 10, Wonderful, (32)
"This property is well maintained and the perfect location. It is 5 minutes from the heart of Collingwood and 10 minutes from Blue Mountain. Would highly recommend. "
The price is €220
includes taxes & fees
22 Sept - 23 Sept
The Family Escape Townhome
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

Holiday Inn Express & Suites Collingwood by IHG

Holiday Inn Express & Suites Collingwood by IHG

10/10 Excellent
"Safe "
Pratisha 2-night trip
Posted 2 days ago
Holiday Inn Express & Suites Collingwood by IHG