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Vacation Homes in Cookstown

Interior
Lake Simcoe 4-Bedroom Home 5 Minutes to Beach Park

Lake Simcoe 4-Bedroom Home 5 Minutes to Beach Park

Innisfil
10.0 out of 10, Exceptional, (22)
"Homey with ample space. "
United States
Daphne
Lake Simcoe 4-Bedroom Home 5 Minutes to Beach Park
Fridge, microwave, oven, stovetop
Modern 4 Bedroom Townhouse in Barrie South

Modern 4 Bedroom Townhouse in Barrie South

Barrie
9.2 out of 10, Wonderful, (17)
"6 of my friends and I stayed here for a festival nearby and we had a good experience. Overall the house was very nice and comfortable to sleep in. Would recommend to anyone looking for a place to stay for a couple days. "
Canada
Haylee R.
$215 nightly
The price is $243
Dec 4 - Dec 5
Total with taxes and fees
Modern 4 Bedroom Townhouse in Barrie South
Fridge, microwave, oven, stovetop
3-Bedroom Home – Perfect for Beach & City Getaways

3-Bedroom Home – Perfect for Beach & City Getaways

Barrie
8.0 out of 10, Very Good, (3)
"Fantastic place, nice and clean. Easy access to food and bar. Very quite. Highly recommend. (only one suggestion, maybe provide slippers. Wooden floor is a bit to walk around bare foot) "
Canada
Joe
$188 nightly
The price is $212
Dec 4 - Dec 5
Total with taxes and fees
3-Bedroom Home – Perfect for Beach & City Getaways
Fridge, microwave, oven, stovetop
Central & Cozy 2BR Townhome—Steps to Plaza, 5 Min Drive to Innisfil Beach Park!

Central & Cozy 2BR Townhome—Steps to Plaza, 5 Min Drive to Innisfil Beach Park!

Innisfil
8.8 out of 10, Excellent, (3)
"We had a great trip! The place was very clean and the host was easy to contact. It was also right next to a plaza with a No Frills and many other places to eat."
Canada
Isabella S.
$245 nightly
The price is $277
Dec 10 - Dec 11
Total with taxes and fees
Central & Cozy 2BR Townhome—Steps to Plaza, 5 Min Drive to Innisfil Beach Park!
Fridge, microwave, oven, stovetop
Cozy house at south end Barrie

Cozy house at south end Barrie

Barrie
9.8 out of 10, Exceptional, (10)
"Excellent, clean property with all the necessary amenities. "
Canada
John
$228 nightly
The price is $258
Dec 4 - Dec 5
Total with taxes and fees
Cozy house at south end Barrie
Terrace/patio
Luxurious Spacious Dream Home with Parking!

Luxurious Spacious Dream Home with Parking!

Richmond Hill
9.0 out of 10, Wonderful, (12)
"Had a great time - thank you!"
Canada
Curtis B.
$214 nightly
The price is $242
Dec 5 - Dec 6
Total with taxes and fees
Luxurious Spacious Dream Home with Parking!
4 bedrooms, desk, iron/ironing board, WiFi
Spacious 4 Bedroom House in Angus

Spacious 4 Bedroom House in Angus

Angus
9.4 out of 10, Exceptional, (3)
"Like i mentioned to our host it was on our top 3 list of places we stayed . The beds, livingroom and location was great. I commented to our host a few suggestion that could help in future guests. Iwould definitely recommend this location to friends and family."
Canada
Mary W.
$221 nightly
The price is $250
Dec 11 - Dec 12
Total with taxes and fees
Spacious 4 Bedroom House in Angus
Private kitchen
The Allandale Residence

The Allandale Residence

Barrie
10.0 out of 10, Exceptional, (2)
"Clean pet friendly would be pleased to stay again "
Canada
Michael P.
$238 nightly
The price is $269
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Allandale Residence
Exterior
Luxury 2BR/2BA Retreat + Netflix + Free Parking –Lake Wilcox-Richmond Hill-VRBO

Luxury 2BR/2BA Retreat + Netflix + Free Parking –Lake Wilcox-Richmond Hill-VRBO

Richmond Hill
10.0 out of 10, Exceptional, (2)
"This was our first time in a VRBO and what a fabulous experience! From booking to check out the communication with the owner was fantastic. They were pleasant, friendly and very accommodating! We highly recommend this property to stay at for yourself or a family! "
Canada
Lisa T.
$203 nightly
The price is $229
Dec 7 - Dec 8
Total with taxes and fees
Luxury 2BR/2BA Retreat + Netflix + Free Parking –Lake Wilcox-Richmond Hill-VRBO
Exterior
Wonderful place of Lake Simkoe

Wonderful place of Lake Simkoe

Innisfil
8.8 out of 10, Excellent, (8)
"Nice clean interior with full kitchen and living room space. Very close to Lake Simcoe. Perfect for our brief weekend stay. "
Canada
Jeremy O.
$229 nightly
The price is $259
Dec 31 - Jan 1, 2026
Total with taxes and fees
Wonderful place of Lake Simkoe
Interior
Cedar Suite At The Taiga Animal Sanctuary

Cedar Suite At The Taiga Animal Sanctuary

2.0 star property
East Gwillimbury
$183 nightly
The price is $206
Dec 16 - Dec 17
Total with taxes and fees
Cedar Suite At The Taiga Animal Sanctuary
Private kitchen
Modern comfy brand new basement apartment in a convenient place, pet friendly.

Modern comfy brand new basement apartment in a convenient place, pet friendly.

East Gwillimbury
10.0 out of 10, Exceptional, (1)
"The location was perfect for me. The unit was really nice, reminded me of a hotel I stayed at once in NYC. Hostess is supper friendly, quick to respond and was able to accommodate a little request I had. Would stay again. "
Canada
Ashley O.
$156 nightly
The price is $176
Dec 31 - Jan 1, 2026
Total with taxes and fees
Modern comfy brand new basement apartment in a convenient place, pet friendly.
Fridge, microwave, oven, stovetop
Barrie house close to all amenities

Barrie house close to all amenities

Barrie
9.0 out of 10, Wonderful, (29)
"Came for a kids sporting event, house was exactly as shown in listing and covered all we needed. Def would stay again."
Canada
Scotty M.
$267 nightly
The price is $302
Dec 15 - Dec 16
Total with taxes and fees
Barrie house close to all amenities
Smart TV, books
All-Season Chalet Retreat | Sleeps 14 | Ski & Spa

All-Season Chalet Retreat | Sleeps 14 | Ski & Spa

Minesing
9.2 out of 10, Wonderful, (5)
"Place was really great for a big group Not to far from places "
Canada
Tia C.
$377 nightly
The price is $426
Dec 9 - Dec 10
Total with taxes and fees
All-Season Chalet Retreat | Sleeps 14 | Ski & Spa
Exterior
Newly built and perfect for vacations. In the middle of both hwy 400&40

Newly built and perfect for vacations. In the middle of both hwy 400&40

2.0 star property
Bradford West Gwillimbury
10.0 out of 10, Exceptional, (1)
"amazing all around "
Canada
Leshaun W.
$350 nightly
The price is $395
Dec 5 - Dec 6
Total with taxes and fees
Newly built and perfect for vacations. In the middle of both hwy 400&40
Exterior detail
Woodspring Vacation Home

Woodspring Vacation Home

Newmarket
9.4 out of 10, Exceptional, (12)
"Nice spacious space with basic essentials, well appreciated."
Canada
Jessica L.
$348 nightly
The price is $393
Dec 5 - Dec 6
Total with taxes and fees
Woodspring Vacation Home
Exterior detail
5br 3.5bth home w Free Parkings+Ensuite laundry Barrie,ON

5br 3.5bth home w Free Parkings+Ensuite laundry Barrie,ON

Barrie
9.8 out of 10, Exceptional, (6)
"Nice and clean place for a group"
Canada
Emily R.
$563 nightly
The price is $636
Dec 6 - Dec 7
Total with taxes and fees
5br 3.5bth home w Free Parkings+Ensuite laundry Barrie,ON
Terrace/patio
4 Bedroom Spacious Enclave near Lake Wilcox

4 Bedroom Spacious Enclave near Lake Wilcox

Richmond Hill
$433 nightly
The price is $489
Dec 5 - Dec 6
Total with taxes and fees
4 Bedroom Spacious Enclave near Lake Wilcox
Terrace/patio
Large Estate with Luxury Collection of Amenities

Large Estate with Luxury Collection of Amenities

Schomberg
9.8 out of 10, Exceptional, (48)
"Everything that we needed for a great getaway was available! The house was clean, spacious and the host was very accommodating. We spent most of our time on site in the pool and hot tub. And our group of 14 enjoyed every moment!"
United States
Bonnie S.
$2,284 nightly
The price is $2,581
Dec 22 - Dec 23
Total with taxes and fees
Large Estate with Luxury Collection of Amenities
1 bedroom, WiFi, bed sheets
Escape to Nature, Sleep Under The Stars

Escape to Nature, Sleep Under The Stars

Zephyr
$245 nightly
The price is $277
Dec 15 - Dec 16
Total with taxes and fees
Escape to Nature, Sleep Under The Stars
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 Cookstown Hotel Reviews

Comfort Inn & Suites Barrie

Comfort Inn & Suites Barrie

10/10 Excellent
"Yes"
Michael 2-night trip
Posted 3 days ago
Comfort Inn & Suites Barrie

Find out more about Cookstown

Cookstown Vacation Homes information

Number of reviews
174
Accommodation
205 Vacation Homes
Lowest Price
$176
Highest Price
$2,581

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