Vacation rentals in Simcoe County

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Top-rated vacation rentals in Simcoe County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite
Dome in Bradford West Gwillimbury
Four season glamping dome under the stars
Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...
Nov 27 – Dec 4
$106 per night
4.98 out of 5 average rating, 192 reviews
Guest favorite
Farm stay in Essa
The Schoolhouse
Kick back and relax in this calm, stylish space. This school portable turned into a modern guest home is situated on acreage boasting with gorgeous views of forests, fields, grazing animals and sunsets. In warmer months, cool off in the stock tank pool, play on the volleyball court, and enjoy meals on the deck accessed from the bedroom and main entry. Relax by the campfire, walk nearby trails, visit restaurants, markets and shops. Planning your wedding? Ask about our wedding package!
Aug 21 – 28
$165 per night
5.0 out of 5 average rating, 114 reviews
Guest favorite
Apartment in Wasaga Beach
The Upper Deck
The upper deck is an amazing one bedroom studio with a full newly renovated bathroom, a sweet kitchenette, an amazing king size bed, a 65 “ inch HD smart Samsung TV with a live edge counter- a great workspace or eating area. One wall is floor to ceiling windows -lots of great natural light!!! Outdoors has an amazing hot tub , rustic firepit area , a beautiful covered outdoor eating area with Bbq and you can hear the lake!! Note- the studio is a separate but is part of a house.
Sep 30 – Oct 7
$115 per night
4.94 out of 5 average rating, 324 reviews

Popular amenities for Simcoe County vacation rentals

Other great vacation rentals in Simcoe County

Guest favorite
Condo in Innisfil
Lovely Open Concept Friday Harbor Resort Condo
Apr 17 – 24
$99 per night
4.95 out of 5 average rating, 304 reviews
Guest favorite
Guest suite in Barrie
Cozy and Close to Everything!
Apr 2 – 9
$63 per night
4.97 out of 5 average rating, 130 reviews
Guest favorite
Place to stay in Wasaga Beach
Newly Built Woodsy Loft Retreat
Aug 10 – 17
$170 per night
5.0 out of 5 average rating, 178 reviews
Guest favorite
Tiny home in Waubaushene
Unique Tiny Home
Apr 8 – 15
$93 per night
4.97 out of 5 average rating, 276 reviews
Guest favorite
Cottage in Innisfil
Stunning Lakefront Cottage Hot Tub & Sauna
May 16 – 23
$369 per night
4.9 out of 5 average rating, 126 reviews
Guest favorite
Condo in Innisfil
Lake Simcoe Resort Retreat
Oct 2 – 9
$110 per night
4.93 out of 5 average rating, 105 reviews
Guest favorite
Loft in Barrie
The Penthouse | Luxury at the Lake
May 17 – 24
$136 per night
4.95 out of 5 average rating, 176 reviews
Guest favorite
Guesthouse in Collingwood
The Little House on the Creek
Dec 19 – 26
$129 per night
4.93 out of 5 average rating, 111 reviews
Guest favorite
Apartment in Orillia
Your Downtown *Hot Tub* Getaway!
Feb 1 – 8
$101 per night
4.96 out of 5 average rating, 131 reviews
Guest favorite
Dome in East Gwillimbury
Deerleap Glamping Dome
Dec 6 – 11
$162 per night
4.92 out of 5 average rating, 129 reviews
Guest favorite
Cottage in Innisfil
Lakefront Luxury 5-Bedroom with Private Dock
May 1 – 8
$491 per night
4.94 out of 5 average rating, 17 reviews
Guest favorite
Guesthouse in Innisfil
The Refuge Guesthouse - 1 bedroom w/fireplace
Jun 1 – 8
$55 per night
4.85 out of 5 average rating, 47 reviews

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Simcoe County