Simcoe Area Rentals
From $2234 per night (USD)VRBO
Stunning Chalet in the heart of Collingwood! 6 Bed, 5 Bath! 2-Acre Property!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
WINTERBROOK CHALET AREA Winterbrook Chalet offers amazing proximity to local activities and amenities, including Blue Mo ...
From $2234 per night (USD)VRBO
From $304 per night (USD)Expedia
6 Bedroom Executive Cottage near Lake Simcoe & Innisfil Beach Park
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 20
Gorgeous 6 Bedroom Executive Cottage. Only 0.5 km short walk to Lake Simcoe, Innisfil Beach Park, Public Beach, Fishing ...
From $304 per night (USD)Expedia
From $2083 per night (USD)VRBO
Luxury & Secluded Cottage 10 Mins from Downtown Barrie
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
**THE ULTIMATE LUXURY EXPERIENCE ON LAKE SIMCOE** NEW LISTING PRICE & NO CLEANING FEE. Extremely secluded location but m ...
From $2083 per night (USD)VRBO
From $353 per night (USD)VRBO
Beautiful & Private Mid Century Modern Country-House on 10 Acres near Caledon!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Welcome to our country house! We rent it for several weeks a year when we can't be there ourselves. Only 45minutes to an ...
From $353 per night (USD)VRBO
From $262 per night (USD)VRBO
Beautiful Lakefront Cottage with Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Lake front Cottage, snuggled by Lake Couchiching. You can spend your days on the dock and your nights sitting on our lar ...
From $262 per night (USD)VRBO
From $254 per night (USD)VRBO
Country House, sleeps 8. Kitchen, BBQ, campfire. Self contained, Event Friendly!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Three bedroom / three bathroom country house on quiet private acreage. Full kitchen, lounge area, outdoor fireplace and ...
From $254 per night (USD)VRBO
From $275 per night (USD)VRBO
Exquisite Log Cabin Retreat- Perfect Couple’s Getaway! Tranquility at its best❤️
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Very private custom crafted log cabin nestled on scenic surroundings overlooking a beautiful spring fed pond and picture ...
From $275 per night (USD)VRBO
From $364 per night (USD)VRBO
4BR Cottage-Private Sandy Beach across the street - amazing sunsets
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Basic 4 BR cottage nestled in the woods. 2 BR are on the upper floor and 2 in basement (with walkout). There's a large ...
From $364 per night (USD)VRBO
From $306 per night (USD)VRBO
Family Ski Season Opportunity/Summer Fun in the sun\n
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Our home is a private, comfortable, clean farmhouse nestled in the heart of Nottawa ON. (Nottawa General, D&L's Variety ...
From $306 per night (USD)VRBO
From $1076 per night (USD)Expedia
Private Wasaga Retreat Just 1.5min Walk To Beach!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 19
Two full cottages with shared & private outdoor patio area! Perfect for summer grilling & entertaining your friends and ...
From $1076 per night (USD)Expedia
From $332 per night (USD)VRBO
Beautiful 3 Bedroom Basement Apartment
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome Beautiful, private (separate entrance), bright and spacious 3 bedroom basement apartment on a quiet/peaceful dea ...
From $332 per night (USD)VRBO
From $125 per night (USD)VRBO
10% Flash Sale! Bright & Airy Apartment: Lovely Backyard & Off Street Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This bright and airy suite is located on the second floor and overlooks a tree-lined street. It has windows on 3 sides f ...
From $125 per night (USD)VRBO
From $156 per night (USD)VRBO
Essence Suites Modern Condo *Collingwood *King Bed *Lake *Beach *Mountains *Spa
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Essence Suites Lodging - Truly Tastefully Renovated, Furnished and Fully Equipped Accommodations with European Touch of ...
From $156 per night (USD)VRBO
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Nautical Cozy camper trailer on Lake Simcoe
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Happy Camper Adventures offers affordable, STRESS-FREE camping adventures in unique, one-of-a-kind themed campers. Each ...
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From $600 per night (USD)VRBO
Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Stunning! Luxurious spacious retreat with unobstructed breathtaking unobstructed lake views from every living space. Re ...
From $600 per night (USD)VRBO
From $106 per night (USD)VRBO
STUNNING LAKEFRONT VIEWS. Beautiful, ground floor unit. Lighthouse Point.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Beautiful lake views from all directions from covered patio and main living spaces. We are booked solid except for the ...
From $106 per night (USD)VRBO
From $328 per night (USD)VRBO
Marina House with Hot Tub & Sauna
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This beautiful cottage is situated just minutes from the town of Penetanguishene. This cottage is perfect for anyone loo ...
From $328 per night (USD)VRBO
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Family friendly cottage 2 min from the beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
“Enjoy world’s longest freshwater beach with your beloved ones! You will love the unique experience of staying in an am ...
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From $645 per night (USD)VRBO
Lake Simcoe Water Front Cottage
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
The lake Simcoe region is a favourite year round holiday destination with any area events and attraction. This is family ...
From $645 per night (USD)VRBO
From $445 per night (USD)Expedia
Cottage with Private Beach Access and Newly-Built Indoor Sauna #STRTT-2025-092
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Sandals Georgian Bay Cottage! Follow the hidden path from the backyard and a private beach paradise is only 1 ...
From $445 per night (USD)Expedia
From $125 per night (USD)VRBO
10% Flash Sale! Premium Apartment: Kitchen, Garden View & Off Street Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Make yourself at home in our premium suite, Number 2. Almost identical to Suite 1 except it overlooks our backyard Engl ...
From $125 per night (USD)VRBO
From $1660 per night (USD)Expedia
Waterfront Paradise | Sauna • Hot Tub • Sleeps 20
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 20
Luxury lakefront living just 2 hrs from Toronto! Welcome to Waterfront Paradise, a spacious 4-bedroom, 3.5-bath retreat ...
From $1660 per night (USD)Expedia
From $116 per night (USD)VRBO
10% Off Flash Sale! Cozy & Bright Suite: Heated Floors, Fireplace, and Backyard!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
For the more budget-conscious guest, Suite #6 is the perfect fit. Relax in this spacious, bright one-bedroom suite featu ...
From $116 per night (USD)VRBO
From $116 per night (USD)VRBO
10% Off Flash Sale! Luxury Garden Suite: Soaker Tub, Backyard & Off St Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is our luxury Garden Suite. Take time to relax in the large soaker tub while watching your favorite TV program. Per ...
From $116 per night (USD)VRBO
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Forest Cottage- Explore, Discover & Experience the Idyllic Blue Mountains
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
CHOICE LOCATION! Forest Cottage invites you to explore, discover and experience Collingwood & The Blue Mountains. 3 min ...
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From $785 per night (USD)Expedia
Luxury Modern Waterfront Cottage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this luxury, gorgeous newly renovated, spacious all year-round cottage overlooking Lake Simcoe. This beautif ...
From $785 per night (USD)Expedia
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Beautiful & Cozy cottage with amazing lakeviews
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Explore, discover and experience any of the four seasons at this lovely cottage with incredible lake views! A cottage re ...
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From $100 per night (USD)Expedia
3 Bdrm Luxury Condo at Mountain House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Mountain House Living at its finest! This top floor fully furnished penthouse style unit offers three bedrooms two bath ...
From $100 per night (USD)Expedia
From $48 per night (USD)VRBO
Suites of Wasaga Beach Area 2 - mins walk Beach 1
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Beach Area 2, just a 1 minute walk over to beach, with provincial park just in front with trails to walk towards beach a ...
From $48 per night (USD)VRBO
From $48 per night (USD)VRBO
Suites of Wasaga Beach Area 2- mins walk Beach 1
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Wasaga Beach Area 2 - one unit has two bedrooms, full kitchen with full size fridge/stove w oven/microwave; all cooking ...
From $48 per night (USD)VRBO
From $48 per night (USD)VRBO
Wasaga Beach Area 2 - Unit #2- mins walk Beach 1
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Beach Area 2 - One minute walk over to beach, with also the provincial park just in front, with walking trail towards Be ...
From $48 per night (USD)VRBO
From $52 per night (USD)VRBO
Suites of Wasaga Beach Area 1 Unit #4
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Beach Area 1, main strip. just a 3 minute walk over to main strip; two bedrooms, full kitchen with full size fridge/stov ...
From $52 per night (USD)VRBO
From $48 per night (USD)VRBO
Wasaga Beach Area 2 - Unit #2- mins walk Beach 1
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Wasaga Beach Area 2 - Each unit accommodates up to 6 people, two units side by side would accommodate up to 12-14 people ...
From $48 per night (USD)VRBO
From $54 per night (USD)VRBO
Suites of Wasaga Beach Area 1
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Located at Beach Area 1, just a 3 minute walk over to the main strip, two bedrooms, kitchenette with full size fridge/st ...
From $54 per night (USD)VRBO
From $260 per night (USD)VRBO
Luxury Family Friendly 2 Bedroom Condo at Friday Harbour
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
At Canada's most sought-after all-seasons resort, you, your family, and your friends can unwind to the peaceful serenity ...
From $260 per night (USD)VRBO
From $199 per night (USD)VRBO
walk to private beach across the street -2BR Cozy Forest Cabin -amazing sunsets
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
With a private beach across the street, , Doctor's house is a basic, rustic, 2-bedroom cabin with a queen bed in one r ...
From $199 per night (USD)VRBO
From $392 per night (USD)VRBO
Cheerful 4-bedroom cottage in nature setting
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Relax with the whole family at this peaceful place to stay just minutes off the Highway400 North in Waubaushene, Ontario ...
From $392 per night (USD)VRBO
From $98 per night (USD)VRBO
3 Bed, Attached Garage, Main fl. Lighthouse Point. 10 min to ski. 2 min to lake!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Beautiful Lighthouse Point! 3 bed with peaceful nature surrounding. Walk out from the bedroom and main living space in ...
From $98 per night (USD)VRBO
From $52 per night (USD)VRBO
Beach Area 1 Suites Of Wasaga
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Wasaga Beach Area 1- Unit accommodates 8 people; Featuring stone built; Full kitchen includes full size fridge/stove, m ...
From $52 per night (USD)VRBO
From $324 per night (USD)VRBO
Woods & Water • 4BR Severn Riverfront Cottage
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to a beautiful stretch of the Severn River, just west of Sparrow Lake. This 4-bedroom, 1.5-bath cottage is the pe ...
From $324 per night (USD)VRBO
From $304 per night (USD)VRBO
Schoolhouse Loft near hiking, biking, beach, golf and more
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Spacious private apartment loft above garage at the newly rebuilt Batteaux Schoolhouse. Close to Blue Mountain, Wasaga B ...
From $304 per night (USD)VRBO
From $305 per night (USD)Expedia
Winter & Fall Getaway - Pvt 120’Shoreline w/direct Lake Access - Snowmobiling
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
1.5hr from Toronto. Sandy, Shallow & Quiet Beach on Dead End Street - High Speed Internet included - Amazon & ...
From $305 per night (USD)Expedia
From $103 per night (USD)VRBO
Dock Life Beach 1 - Cottage 6, Riverside Property, 2 Bdrm, 3 min walk to Beach 1
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Great location. River access. Streetview, but use our huge common riverside grassed area and patio to watch the boats fl ...
From $103 per night (USD)VRBO
From $234 per night (USD)Expedia
Dock Life Beach 1 - Walkout River 13, 5 bdrm Sleeps 14, 3 min walk to Beach 1
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 14
Great location! Private Sauna! Riverview and access. From your walkout into the riverside yard, watch the boats float by ...
From $234 per night (USD)Expedia
From $113 per night (USD)VRBO
Dock Life Beach 1 - Cottage 12, Riverview, 1 Bedroom, 3 min walk to Beach 1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Great location! Riverview and access. Simple cottage with a deck. Enjoy our huge common riverside grassed area and patio ...
From $113 per night (USD)VRBO
From $142 per night (USD)Expedia
Dock Life Beach 1 - Cottage 11, Riverside 2 bedroom, 3 min walk to Beach 1
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Great location. Great view! Riverview and access. From your private deck 10ft away from the river's edge, watch the boat ...
From $142 per night (USD)Expedia
From $106 per night (USD)VRBO
Dock Life Beach 1 - Cottage 7, Riverside Property, Studio, 3 min walk to Beach 1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Great location. River access. Streetview, but use our huge common riverside grassed area and patio to watch the boats fl ...
From $106 per night (USD)VRBO
From $169 per night (USD)Expedia
Dock Life Beach 1 - Cottage 1, Riverside 3 bedroom, 3 min walk to Beach 1
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Great location!! Riverview and access. From our riverside yard, watch the boats float by on the beautiful Nottawasaga ri ...
From $169 per night (USD)Expedia
From $112 per night (USD)VRBO
Dock Life Beach 1 - Cottage 9, Riverside Property, Studio, 3 min walk to Beach 1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Great location. River access. Streetview, but use our huge common riverside grassed area and patio to watch the boats fl ...
From $112 per night (USD)VRBO
From $111 per night (USD)Expedia
Dock Life Beach 1 - Unit 16, Riverside Property, 2 Bdrm, 3 min walk to Beach 1
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Great location. River access. Streetview, but use our huge common riverside grassed area and patio to watch the boats fl ...
From $111 per night (USD)Expedia
From $142 per night (USD)VRBO
Dock Life Beach 1 - Cottage 8, Riverside, 2 bdrm and Loft, 3 min walk to Beach 1
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Great location! River access. Streetview, but use our huge common riverside grassed area and patio to watch the boats fl ...
From $142 per night (USD)VRBO
From $102 per night (USD)Expedia
Dock Life Beach 1 - Cottage 5, Riverside Property, 2 Bdrm, 3 min walk to Beach 1
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Great location! River access. Streetview, but use our huge common riverside grassed area and patio to watch the boats fl ...
From $102 per night (USD)Expedia
From $142 per night (USD)VRBO
Dock Life Beach 1 - Cottage 10, Riverside 2 bedroom, 3 min walk to Beach 1
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Great location. Great view! Riverview and Access. From the windows, watch the boats float by on the beautiful Nottawasag ...
From $142 per night (USD)VRBO
From $113 per night (USD)Expedia
Dock Life Beach 1 - Cottage 3, Riverside 2 bedroom, 3 min walk to Beach 1
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Great location!! Riverview from your deck and river access. Partial lake views. Watch the boats float by on the beautifu ...
From $113 per night (USD)Expedia
From $169 per night (USD)VRBO
Dock Life Beach 1 - Cottage 2, Riverside 3 bedroom, 3 min walk to Beach 1
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Great location!! Riverview and access. From our riverside yard, watch the boats float by on the beautiful Nottawasaga ri ...
From $169 per night (USD)VRBO
From $558 per night (USD)VRBO
Georgian Bay waterfront cottage in a quiet cove w/HOT TUB
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
** During July and August, we only do weekly rentals from Friday-to-Friday. 🔥 Hot Tub 🔥 👉4 Bedrooms & 3 bathrooms ...
From $558 per night (USD)VRBO
From $441 per night (USD)VRBO
Family-friendly, relaxing retreat in Wasaga Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our special home in Wasaga Beach, Ontario. This super clean, renovated and family-owned cottage is located ...
From $441 per night (USD)VRBO
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2 bedroom luxury private Cabin located in the Lakes of Wasaga Resort
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This family oriented air conditioned 2 Bedroom, 1 Bathroom fully furnished Cabin (Max # of renters 6) Master bedroom has ...
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From $493 per night (USD)VRBO
Big Beautiful Georgian Bay Family Cottage
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 14
*Full refund, in case your booking gets cancelled due Ontario Covid Restrictions * Find the luxury and rest you've bee ...
From $493 per night (USD)VRBO
From $414 per night (USD)Expedia
Sandy beach getaway
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 12
Modern cottage with gorgeous private Cuba-like sandy beach (one of the most beautiful sandy beaches in Ontario). Private ...
From $414 per night (USD)Expedia
From $243 per night (USD)VRBO
Amazing fully upgraded 3 bedroom+ new furniture, 1 full bath lake property
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Totally renovated house - new paint - all new furnishing-3 bedroom 4-piece bathroom, full kitchen & laundry on beautifu ...
From $243 per night (USD)VRBO
From $156 per night (USD)VRBO
Friday Harbor - Ontario Luxury resort open all year round
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Views of Lake Simcoe and underground parking included. Ideal for up to 4 people. All season resort with events at the pi ...
From $156 per night (USD)VRBO
From $130 per night (USD)VRBO
The North Shore Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The North Shore Suite Largely accommodating longer stays for Corporate Clients, Professionals, and Clients of RVH and ...
From $130 per night (USD)VRBO
From $51 per night (USD)VRBO
quiet studio in Cranberry resort .
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nice quiet ground floor studio apartement with private entrance and parking near by . Large room airy and light with two ...
From $51 per night (USD)VRBO
From $400 per night (USD)VRBO
Nature's Cottage Washago - Beautiful Private Waterfront property with Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Nature's Cottage Washago. This beautiful waterfront property is a one of a kind. Spend time with family or ...
From $400 per night (USD)VRBO
From $218 per night (USD)Expedia
Beautiful 3-Bdrm Cottage close to Ski Resorts w/ Hot Tub, Game Room, & more!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Our cottage has everything you need from a 7-person hot tub to full kitchen (oven, stove, microwave, coffee maker, keuri ...
From $218 per night (USD)Expedia
From $547 per night (USD)VRBO
Sandy Beach/Boating/Swimming/Hot Tub/Marina/Trails
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Welcome to the Georgian Bay Retreat in beautiful Port McNicoll. Relax and enjoy this oasis like setting with stunning vi ...
From $547 per night (USD)VRBO
From $258 per night (USD)VRBO
House on the Lake, Orillia
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Township of Ramara Approved Short Term Rental Accommodation. License Number: 2024.043 A beautiful Lake Couchiching lo ...
From $258 per night (USD)VRBO
From $371 per night (USD)VRBO
Waterfront!! Beautiful. New Hot tub. On Trent-Severn Waterway. Muskoka.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Entire cottage to you and your guests, Spacious areas. Three fireplaces, Fire Pit, NEW HOT TUB, Nice deck to have fun in ...
From $371 per night (USD)VRBO
From $202 per night (USD)Expedia
The Loon Muskoka Cabin - TeaLakeCottages
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Tea Lake Cottage (TLC), a serene and secluded retreat that's just 90 minutes away from Toronto and Pearson In ...
From $202 per night (USD)Expedia
From $362 per night (USD)VRBO
Driftwood on 6th in Historic Downtown Collingwood/Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Come stay @ Driftwood on 6th in the heart of Heritage Collingwood downtown. Pet friendly historic home, fully fenced, an ...
From $362 per night (USD)VRBO
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Rustic country chic
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Just over 1hr. North of Toronto. Enjoy the open fields and fresh gardens at sweetfields farm . Outdoor fun ,50 acres o ...
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From $256 per night (USD)VRBO
3 bedroom, 2 bathroom chalet; 3 minute walk to pristine beach; dog friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
1 & 3/4 hours from Toronto, this charming chalet style 3 bedroom cottage is nestled on a beautiful treed lot. A 3 minute ...
From $256 per night (USD)VRBO
From $820 per night (USD)VRBO
Luxurious All-season Simcoe Lakefront Cottage
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
A luxurious all-season family lakefront cottage with 100'+ of private shoreline on Lake Simcoe. An open-concept, gourmet ...
From $820 per night (USD)VRBO
From $169 per night (USD)VRBO
A very special getaway in a private Coach House in the Purple Hills of Creemore
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The coach house is in a very private setting in the Purple Hills of Creemore in the Niagara Escarpment on 50 acres just ...
From $169 per night (USD)VRBO
From $1571 per night (USD)Expedia
The Mansion, Wasaga beach, Blue mountain
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 25
Welcome to The Mansion , the luxury Cottage A spacious 6000 sqft Mansion and country Estate . Conveniently located n ...
From $1571 per night (USD)Expedia
From $491 per night (USD)VRBO
Beach Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our beach cottage :) Our beautifully cottage with a vintage feel and all modern amenities will be your perfec ...
From $491 per night (USD)VRBO
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19th century school house, modernized to a family home. Mins from Blue Mountain
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
This century old school house has been curated and restored throughout its life from artist studio to present day as a s ...
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Large family home, minutes from base of Blue Mountain and Osler.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Return home to this modern chalet after a day on the slopes to a large open communal kitchen and dining space perfect fo ...
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From $146 per night (USD)VRBO
Georgian Bay Cottage - 3 bedrooms - 1.5 hrs from Toronto
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
WELCOME TO APPLETON COTTAGE- My Summer Place by the lake located along the shores of Southern Georgian Bay only 1.5 hour ...
From $146 per night (USD)VRBO
From $274 per night (USD)VRBO
Lakefront Cedar Haven- Free use Canoe and Kayak, 1 hr from Toronto, All Seasons
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Waterfront all seasons cottage just 1 hr north of Toronto. Situated on Orr Lake, shallow water. You get the entire house ...
From $274 per night (USD)VRBO
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Rustic Tiny Home on Paradise Acres
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Rustic Tiny Home with deck and patios on a private trail nestled in the woods. Has loft bedroom, living area, dining are ...
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From $442 per night (USD)VRBO
Luxury Waterfront Cottage with Hot Tub in Downtown Washago, Ontario
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to The Cottage Living Co., your dreamy escape nestled in the heart of Severn, Washago — north of Lake Simcoe. S ...
From $442 per night (USD)VRBO
From $263 per night (USD)VRBO
Bright rennovated 5 Bedroom home backing onto Golf Course
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This 5 bedroom home is a jewel in a quiet neighborhood, looking out onto the Cranberry golf course. The main level incl ...
From $263 per night (USD)VRBO
From $113 per night (USD)VRBO
Bright, Cozy, and Spacious Family Home less than 10 minutes from the Village
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
***Note: Families Only*** Spacious, Cozy, and Bright 1,470 sq ft home perfectly situated in the heart of Collingwood. ...
From $113 per night (USD)VRBO
From $201 per night (USD)VRBO
walk to private beach across the street - 2 BR Cabin - amazing sunsets
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
With a private beah across the street, RnR is a basic, cabin with a double and twin bed in one bedroom and a queen bed ...
From $201 per night (USD)VRBO
From $441 per night (USD)VRBO
Muskoka - The Eagle's Nest
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Looking for a luxurious and private getaway? Look no further than Tea Lake Cottage (TLC)! Our stunning property is locat ...
From $441 per night (USD)VRBO
From $155 per night (USD)VRBO
Your Perfect Get Away Retreat Awaits You
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our Collingwood retreat for 5, located in the Cranberry community. This 2 bedroom condo is only a short drive ...
From $155 per night (USD)VRBO
From $187 per night (USD)VRBO
Washago Waterfront : Hot Tub, Sauna, ATV/Snowmobile Access, Fishing Paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Charming 2-Bedroom Waterfront Retreat – Perfect for Family Getaways & Outdoor Adventure. With Hot tub and a sauna! 🔥HO ...
From $187 per night (USD)VRBO
From $166 per night (USD)VRBO
Home On A Golf Course
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Collingwood is a beautiful part of Canada, two and half hours from Toronto and two and half hours from Niagara Falls and ...
From $166 per night (USD)VRBO
From $214 per night (USD)VRBO
PRIVATE PRESIDENTIAL SUITE 1 BEDROOM
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Beautiful one bedroom that comes with two TVs, jacuzzi ted, glass stand-up showers, large breakfast island, full kitchen ...
From $214 per night (USD)VRBO
From $305 per night (USD)Expedia
Friday Harbour Resort on Lake Simcoe
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Super host rated! Premium All Season Resort available Brand new 805 sq foot 2 bedroom 2 bathroom condo located in the ...
From $305 per night (USD)Expedia
From $150 per night (USD)VRBO
1 BEDROOM STUDIO RESORT APARTMENT (4 PERSON) ORO-MEDONTE
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A GORGEOUS! 4-star resort apartment located a bit North of Barrie; in Oro-Medonte, a magnificent resort town. Amenities ...
From $150 per night (USD)VRBO
From $1236 per night (USD)Expedia
Clearview Manor (Wasaga Beach)(Blue Mountain)
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 30
THE PROPERTY: This Ranch style Estate located in the beautiful Ontario countryside comfortably lodges 30+ guests, a full ...
From $1236 per night (USD)Expedia
From $139 per night (USD)VRBO
COZY COTTAGE WALKING DISTANCE TO LAKE SIMCOE & FRIDAY HARBOUR
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Fully insulated cottage with 2 bedrooms with 1 bath comfortably sleeps 5. Short walks to a private resident beach on L ...
From $139 per night (USD)VRBO
From $269 per night (USD)Expedia
Georgian Bay Cottage-\nHot Tub/Sauna/Trail/Run/Bike/Swim//Marina!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
*** MIN 3 NIGHTS STAY DURING LONG WEEKENDS HOLIDAYS, AND IN THE SUMMER*** There is nothing like packing up the car and ...
From $269 per night (USD)Expedia
From $182 per night (USD)VRBO
2 bedroom Waterfront Cottage in Wasaga - Ash Lane Cottages
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled between the lazy waters of the Nottawasaga River and the sparkling beaches of Georgian Bay, this cottage is in ...
From $182 per night (USD)VRBO
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Cottage tiny heaven.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 18
Enjoy the Caribbean Sunset, Extraordinary View, Long shoreline, Blue Water (On a clear day) from this 6000 SQF Four Seas ...
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Very private 40 Acres Property - Cozy 2 Bedroom Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in a large wooded land, the two bedroom cabin by a scenic pond provides complete privacy yet it is close to the ...
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From $332 per night (USD)Expedia
BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 7
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 12
CHECK-IN: AFTER 3 PM CHECK-OUT: 9:00 AM 5 BEDROOM COTTAGE MAXIMUM CAPACITY FOR THIS COTTAGE IS 12 PEOPLE. PARKING - 2 ...
From $332 per night (USD)Expedia