Guesthouse holiday rentals in Lake Simcoe

Find and book unique guesthouse rentals on Airbnb

Top-rated Guesthouses in Lake Simcoe

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Guesthouse in Aurora

4.91 out of 5 average rating, 146 reviews

Adorable Guesthouse Apartment With Free Parking

This beautiful brand new suite offers, Separate private guesthouse with vaulted ceilings & heated floors throughout. Private bathroom with standing shower. Queen loft bed & pull out couch. Flat screen smart TV. Kitchenette which includes: Fridge, cooktop & cookware, toaster oven, kettle, coffee maker. Live edge walnut table with 2 stools. Free wifi. 1 Free parking space. Close to Go Train. Fresh bed sheets & towels are provided. Phone charger and blue tooth speaker. Instagram @blueheronloft

Guest favourite

Guesthouse in Uxbridge

4.95 out of 5 average rating, 131 reviews

Guesthouse in nature mins to Ski hills and Spa!

Relax and unwind at this peaceful and private guesthouse situated on 25 acres of forest. We are family friendly and invite you to roam the land and visit our resident ducks! If you are feeling more adventurous, enjoy a hike on our private onsite trail or on one of the many local trails within walking distance in the Trail Capital of Canada! Later we'll get the Woodstove lit for you (Dec - Feb). Catch up on your fav programs with Roku TV. Enjoy the therapeutic rainfall shower guests rave about!

Guest favourite

Guesthouse in Mansfield

4.99 out of 5 average rating, 104 reviews

Brookside Cottage - Charming Rural Getaway Mulmur

Our cozy guest house, situated in the Headwaters region, has it all! Close to hiking,golfing,biking,skiing. XCski/snowshoe from your door! Big skies for astronomers and astrophotography! We offer 32 acres of forest and fields for walking and taking in the magnificent views. The area boasts fine restaurants, boutiques, markets and artisans. Minutes to Mono Cliffs, Boyne, Mansfield Ski Club and easy driving to Blue Mountain and Wasaga Beach. Ideal for couples, solo adventurers or a small family.

Guest favourite

Guesthouse in Angus

4.98 out of 5 average rating, 206 reviews

Serene Comfort. Hot Tub, Full Suite with Kitchen

Welcome to Centre Street Studio! Our 600 sq/ft bachelor suite offers a private, clean and cozy retreat. Enjoy access to a beautiful private 2 person hot tub and/or explore our local trail system on foot or by bikes available on site. Looking for R&R? Discover Scandinavia Spa or Vetta Nordic Spa, both within 40-min. Barrie, Creemore, & Wasaga Beach are all within 30-mins, while Collingwood & Blue Mountain are just 40 min. A 2-min drive to town amenities. Book now for your ultimate getaway!

Guest favourite

Guesthouse in Algonquin Highlands

4.93 out of 5 average rating, 152 reviews

Charming mini-cottage, footsteps to water's edge

**No extra fees other than airbnb fees** Relax in a quaint, studio mini-cottage surrounded by water on 3 sides! Enjoy the freshness of spring, summer water activities & gorgeous autumn colours in cottage country. Perfect for 1 or 2 guests; peninsula location & tall windows give 270 degree lakeviews. Wifi, 1 parking space, kitchenette, 3pce bthrm, Queen bed, futon bed, satelliteTV. Private for guests: shoreline, island, dock, barbeQ, mountain bikes, hammock, firepit, canoes, kayaks, tubes.

Superhost

Guesthouse in Wasaga Beach

4.86 out of 5 average rating, 107 reviews

2 -Sun Angel Court Couples Cabin 2

We are a group of ten unique and pretty cottages, located directly In front of Beach 2. We back onto the Nottawasaga River(excellent for fishing). We are extremely clean and have a separate washroom facility for our cottages. There is a common picnic area , overlooking the river with 2 full Bbq's available for guest use. We have a fire pit for late night hotdogs, smores and marshmallow roasting. We are a 5 min walk from the waterfront square- this is where all the special events take place.

Guest favourite

Guesthouse in Schomberg

4.93 out of 5 average rating, 411 reviews

Country Cabin for Long and Short Stays King bed

Escape to a relaxing retreat at our Country Cabin—perfect for both short and long stays. The cabin is located on our family farm, offering a private and peaceful experience, but not secluded. Enjoy a full kitchen, wood fire pit, and propane BBQ Stay connected with WiFi, a 40" Smart TV, and a cozy 3-piece bathroom. Laundry facilities and walking trails are available. The cabin is in view of our farmhouse, Suite and Event Barn but remains private with blinds. We look forward to hosting you!

Guest favourite

Guesthouse in Gravenhurst

4.96 out of 5 average rating, 115 reviews

Take a few steps and enjoy the sand and water

Welcome to the Guest House. Located in Gravenhurst, Ont. on Gull Lake. Private beach, boat launch & docking available. There is one canoe and one paddle boat available for guest to use. Lifejackets are provided. 2 minute car ride or boat ride into Gravenhurst. BBQ on your deck or roast marshmallows around the fire pit. Two bedrooms with queen beds. Full kitchen with new stainless steel appliances microwave, fridge and stove. Bathroom with walk in shower. Satellite TV, Wi Fi, and Parking.

Superhost

Guesthouse in Pickering

4.83 out of 5 average rating, 139 reviews

Hotel 65. Our Spacious 2-Bedrm Basement w/Parking

Stunning, spacious, cozy basement apartment . Open concept living/dining room with kitchen. The larger room offers a queen bed and a futon for additional sleeps. The second has two twins that can be setup as an optional king. A TV in each room with Netflix, Prime, Disney+ and IPTV with multiple sports, North American and International channels. Many kitchen amenities. Mins to 401, Grocery, Resturants, Malls, Casinos, National Park, Toronto Zoo and only 5 minutes to GO Train. Book & Enjoy!

Guest favourite

Guesthouse in Newcastle

4.87 out of 5 average rating, 183 reviews

Bee Keeper's Cabin - a very private retreat

91 acres, trails, total privacy, spring fed lake, solar power/propane heated, gas stove top, propane fridge, out-house, firepit, wi-fi ; canoe/paddleboat (seasonally) Self check in and self cleaning For those who leave a "light foot print" Basic kitchen utensils, pots, pans, and dishes are provided, BUT guests must bring their own drinking water, pillows and bedding. We ask our guests to leave the cabin better than you found it and to take all garbage and recycling home with you."

Guest favourite

Guesthouse in Shanty Bay

4.99 out of 5 average rating, 156 reviews

The Guest House, Maplewood Hills

The Guest House is set in the midst of our beautiful hardwood forest and is only minutes from Horseshoe Resort and Vetta Spa. Being separated from the main house by a 4 car garage ensures you have full privacy. You will enjoy the full kitchen, dining area and cozy living room. 2 bedrooms & 2 bathrooms provide a comfortable oasis after a day of hiking the trails or skiing & tubing the hills. Prepare your favourite dish on the BBQ and end the day with a hot drink around the campfire.

Guest favourite

Guesthouse in Oro Station

4.94 out of 5 average rating, 159 reviews

Horseshoe Valley Carriage House/6 Guests/Fast Wifi

Welcome to our private coachhouse in the heart of Horseshoe Valley. Situated on beautiful 12 acres, we are minutes from Copeland forest trails. Located 5 minutes from Horseshoe Valley Ski Resort + VETTA SPA, Mount St. Louis Moonstone and Hardwood Hills! 10 minutes from BOOTS, Quales Brewery A wonderful retreat for you! Relax in the cozy living room by the gas stove or enjoy sitting on the private deck. You can also relax around an outside gas fireplace to enjoy the country view!