Search by Location
Bedrooms
Min Price
Max Price
Updating Results
186 Listings Match Your Search

Lake Simcoe - Simcoe County Cottage Rentals

 Vacation Rentals

Lake Simcoe - Simcoe County Vacations

Vacation Rentals in Lake Simcoe - Simcoe County, Ontario

Located in south central Ontario, Simcoe County cottage rentals are scattered along the shores of Georgian Bay and Lake Simcoe among picturesque meadows, marshes, and forests.

Lake Simcoe and Georgian Bay are two of Ontario’s top kitesurfing and windsurfing destinations and Wasaga Beach, which, at 14 kilometres long, is the longest freshwater beach in the world, is a swimming and sunbathing paradise. Anglers will be well served with catches of bass, pike, and walleye and with over 50 golf courses, there is no shortage of opportunities for visitors to hit the links. 

At the region’s national and provincial parks, popular activities include hiking, cycling, mountain biking, and horseback riding in the summer, and cross-country skiing, snowshoeing, and snowmobiling come winter. Further, nearby Blue Mountain provides Ontario’s best downhill skiing and snowboarding and a range of après-ski activities for adults and kids.

With plenty of restaurants, cafés, pubs, and spas in the region, there’s no shortage of places to retire to after a day on the water, trails, or slopes. Sample a hoppy beer or two at Flying Monkey Craft Brewery, or take a drive along the Apple Pie Trail, a scenic route that stops at orchards, vineyards, and eateries. 

Just 90 minutes north of Toronto, Simcoe County is a very popular place to rent a cottage in Ontario.

What to Do

Activites in Lake Simcoe - Simcoe County, Ontario

Snowmobiling
Skiing & Snowboarding
National & Provincial Parks
Lake Country
Hiking & Biking
Fishing
Cross-country Skiing
Beach
Snowshoeing
Sailing & Yachting
Food & Wine
Golf
Kayaking & Canoeing
Arts & Culture

Articles

Lake Simcoe - Simcoe County Cottage Rentals & Cottages For Rent

Li'L Cottage Down The Twisted Road

Cottage Rentals in Sutton, Ontario

4
Beds

2
Baths

$2,500
Week

LITTLE COTTAGE IS A COZY INVITING COTTAGE OPEN YEAR ROUND ON THE SOUTH SANDY SHORE OF LAKE SIMCOE JUST 1 HOUR NORTH OF TORONTO . BEAUTIFUL GARDENS SURROUND THIS… More →

CanadaStays Secure Payments

Luxury Lake Simcoe Lake House

Cottage Rentals in Orillia, Ontario

3
Beds

1
Baths

$1,995
Week

5 Star 4 Season Luxury Lake House truly has a city feeling in a country setting with all the amenities of home. Located in Joyland Beach, only 10 minutes from … More →

CanadaStays Secure PaymentsCanadaStays Refund Protection

Bass Lake Cottage-Amazing Property

Cottage Rentals in Orillia, Ontario

4
Beds

3
Baths

$1,750
Week

Bass Lake Cottage is rated as a 5* VACATION PROPERTY on Trip Advisor and is one of Canada Stays most popular locations - Summer of 2015 from June 26th to … More →

CanadaStays Secure Payments

517 Lake Couchiching

Cottage Rentals in Orillia, Ontario

6
Beds

4+
Baths

$1,650
Week

This year round cottage/home is located on Lake Couchiching approx. 15 min. from Orillia by car or 10 min. by boat. You can boat right into town for all your … More →

CanadaStays Secure Payments

Summer Cottage - Week Long Rental

Cottage Rentals in Gamebridge, Ontario

4
Beds

1
Baths

$1,600
Week

Two-storey rustic cedar cottage with all the charm yet fully functional is available on a weekly rental basis only. It is in immaculate dry condition with level… More →

CanadaStays Secure PaymentsCanadaStays Refund Protection

Lake Simcoe Luxury Cottage

Cottage Rentals in Brechin, Ontario

3
Beds

2
Baths

$1,500
Week

1200 sq ft WATERFRONT cottage direct on Lake Simcoe. Lagoon City. Brechin. ON RATES from MAY 05th TO SEPT 9th Weekly rental $1550. Weekly rental MON TO SUNDAY … More →

CanadaStays Secure PaymentsCanadaStays Refund Protection

Waterfront Cottage On Lake St. John

Cottage Rentals in Rama, Ontario

4
Beds

1
Baths

$200
Night

Large, beautiful, quiet cottage on the 4km wide Lake St. John. Great fishing, boating, swimming. 1.5 hours from Toronto, just next to Lake Couchiching and Lake … More →

CanadaStays Secure PaymentsCanadaStays Refund Protection

Whispering Pines-Summer Available

Cottage Resorts in Orillia, Ontario

$1,500
Week

We have just had a change of plans for the summer and our amazing 4 season cottage is available for rent. In spring of 2015, Whispering Pines was one of Canada… More →

CanadaStays Secure Payments

Lake Dalrymple Family Retreat

Cottage Rentals in Barrie, Ontario

3
Beds

2
Baths

$1,400
Week

UNIQUE SANDY BEACH AT Kawartha Lakes, GREAT FOR CHILDREN AND ADULTS, ENJOY Unique sandy beach at Kawartha Lakes, great for children and adults, enjoy cottage … More →

CanadaStays Secure PaymentsCanadaStays Refund Protection

New Sunset Charmer On Lake Simcoe

Cottage Rentals in Beaverton, Ontario

3
Beds

1
Baths

$1,400
Week

RECENT REBUILD. ELEGANCE BY THE LAKE. NO AUGUST DATES REMAINING THIS SUMMER Barely an hour’s drive from Toronto, this charming waterfront cottage feels like a… More →


Sunport Beach Resort And Motel

Hotel Resorts in Balm Beach, Ontario

$1,285
Week

Our beach is perfect… sand and more sand! Safe family swimming, breath taking sunsets, lovely shade tree, lit beach at night, no rocks, ooze or gooze. Jet ski… More →

CanadaStays Secure PaymentsCanadaStays Refund Protection

Riverside Cottage

Cottage Rentals in Pefferlaw, Ontario

3
Beds

2
Baths

$1,250
Week

Nestled on the Pefferlaw River, with just a 2-minute Boat Ride to Lake Simcoe. Watch Magnificent Boats as they Pass by your Backyard on their Way to the Lake! … More →

CanadaStays Secure PaymentsCanadaStays Refund Protection

The Beach House

Cottage Rentals in Innisfil, Ontario

1
Beds

1
Baths

$1,250
Week

NO Bedrooms.Open Concept 600 square feet This open concept Bachelor 4 season cottage is located 45 mins from Toronto. It has a queen pillow top mattress with … More →

CanadaStays Secure PaymentsCanadaStays Refund Protection

Primrose Cottage 14

Cottage Rentals in Balm Beach, Ontario

2
Beds

1
Baths

$1,200
Week

Newly renovated and winterized cottage located on one acre. 20 steps from popular Balm Beach which has arcades, restaurants, convenience store, and tavern. Town… More →

CanadaStays Secure PaymentsCanadaStays Refund Protection

Simcoe Cottage

Cottage Rentals in Georgina, Ontario

3
Beds

1.5
Baths

$1,200
Week

Simcoe Cottage is situated in Georgina town, Sutton, south part of Simcoe Lake, and just 2-3 minutes walk to the public beach. The beach is equipped with desks… More →

CanadaStays Secure PaymentsCanadaStays Refund Protection

A Lake Simcoe Waterfront 4 Bdrm Yr

Cottage Rentals in Sutton, Ontario

4
Beds

1
Baths

$1,100
Week

Virginia Cedars Cottage, a year round waterfront cottage is located in Virginia, Ontario and is less than one hour north of Toronto. This family style … More →

CanadaStays Secure PaymentsCanadaStays Refund Protection

Beach-Front Private Paradise

Cottage Rentals in Beaverton, Ontario

4
Beds

1
Baths

$1,000
Week

1930's Cottage with municiple water & sewers. Located on a gorgeous street with large mature trees. Wood Floors throughout. Electronics include: Satellite TV… More →

CanadaStays Secure PaymentsCanadaStays Refund Protection

The Briars Resort & Spa

Hotel Resorts in Jacksons Point, Ontario

$143
Night

A whole new take on cottaging. All the comforts of a modern resort, including all meals, resort facilities and programming for all ages, with all the adventures… More →

CanadaStays Secure Payments

Cottage 11a

Cottage Rentals in Balm Beach, Ontario

2
Beds

1
Baths

$950
Week

Fully winterized cottage located on one acre. 20 steps from popular Balm Beach which has arcades, restaurants, convenience store, and tavern. Town tennis courts… More →

CanadaStays Secure PaymentsCanadaStays Refund Protection

Primrose Cottage 11

Cottage Rentals in Balm Beach, Ontario

2
Beds

1
Baths

$950
Week

Newly renovated and winterized cottage located on one acre. 20 steps from popular Balm Beach which has arcades, restaurants, convenience store, and tavern. Town… More →

CanadaStays Secure PaymentsCanadaStays Refund Protection

1 - 20 of 186 Rentals

Sort

Trending Rentals in Lake Simcoe - Simcoe County

Travel Deals in Lake Simcoe - Simcoe County

Marketplace

Your One Stop Shop for Cottage Essentials

View More Items →