Guesthouse vacation rentals in Lake Simcoe

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Lake Simcoe

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

0 of 0 items showing

1 of 3 pages

Guest favorite

A spacious wooden deck is surrounded by tall evergreen trees, creating a secluded outdoor space. Comfortable seating is arranged on the deck, inviting relaxation while taking in the views of the rolling hills and landscape beyond. Sunlight streams down, enhancing the tranquil environment.

Guesthouse in Orangeville

4.95 out of 5 average rating, 353 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

Top guest favorite

The exterior showcases a two-story grey structure featuring three garage doors and a large, shared driveway. The surrounding foliage is highlighted by autumn leaves, while the sky transitions to sunset hues, creating a serene evening ambiance.

Guesthouse in Orangeville

4.96 out of 5 average rating, 130 reviews

A bright & stylish urban studio

Come & relax...in privacy. In the "Carriage House" you will be away from the main house, in your own building! Its a 634 square foot studio-style unit, that is unique & intimate. A nice sized kitchen, complete with gas range. Spacious & bright over-sized bathroom. The Murphy bed has a luxury-firm queen mattress, & stows away in a snap for more room. A diner booth for meals, or working at home! A short hop from Toronto, Dufferin County has all you need for a relaxing getaway! Come & See :)

Top guest favorite

A private outdoor hot tub is nestled under a wooden structure with soft, glowing lights. Surrounding stones and gravel create a path, complemented by an inviting garden area with plants and rocks, enhancing the serene atmosphere.

Guesthouse in Angus

4.98 out of 5 average rating, 221 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 private 2 person hot tub and/or explore our local trail system. Beautiful 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. NOTE: We don't host guests who are new to AirBNB or have no previous stays attached to their profile.

Guest favorite

A modern bathroom sink is set on a wooden countertop, featuring a clean white basin and polished chrome faucets. A large mirror is mounted above, reflecting soft light. A decorative towel rests beside the sink, adding a subtle touch to the serene space.

Guesthouse in Uxbridge

4.96 out of 5 average rating, 140 reviews

Guesthouse in nature mins to Durham trails & 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 favorite

A private balcony is shown featuring two black metal chairs and a small round table on a wooden deck. Double glass doors lead back into the interior space, with sunlight illuminating the area, suggesting a bright and open environment.

Guesthouse in Richmond Hill

4.97 out of 5 average rating, 140 reviews

Balcony House 30% off monthly with free Parking

Enjoy the glamour of this spacious, stylish, worry free, upscale place. It is brand new and located in the Heart of Richmond Hill, walking distance from David Dunlap Observatory Park, Plazas, Malls, Schools, Restaurants and Supermarkets. Close To Highway And Go Station, Viva, Yrt. Separate entrance and all inclusive with 1 queen bed, 1 double Sofabed if more than 2 guests, 65in smart TV, high speed wifi. Micro oven, Fridge, K-cup coffee machine, full bathroom, patio sittings, 1-2 free parkings

Guest favorite

A dining table with a reflective surface is positioned in front of a large window. The view showcases a spacious green lawn, colorful trees, and distant structures under a partly cloudy sky, providing a serene outdoor backdrop.

Guesthouse in Schomberg

4.93 out of 5 average rating, 429 reviews

Country Cabin Escape | King Bed | Pet Friendly

Tucked away on our peaceful family farm, this private retreat offers tranquility and comfort—while not secluded in the woods, it provides a true countryside experience. ✨ Full kitchen 🔥 Wood fire pit & propane BBQ 📶 WiFi + 40” Smart TV 🚿 Cozy 3-piece bathroom 🧺 Laundry access 🌲 Scenic walking trails Located near our farmhouse, Country Suite, and Event Barn, the cabin remains fully private with blinds for added comfort. We look forward to welcoming you for a restful and memorable stay!

Top guest favorite

A stone patio surrounds a firepit, accompanied by four adirondack chairs facing the lake. Tall trees provide shade and outline the peaceful shoreline, while a canoe rests nearby. The scene invites relaxation and connection with nature.

Guesthouse in Algonquin Highlands

4.93 out of 5 average rating, 154 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.

Top guest favorite

An open-concept living space features warm wood accents and a rustic kitchen island made of reclaimed wood. A cozy seating area with a fireplace and a wall-mounted TV is visible. A spiral staircase leads to the upper level, enhancing the room's unique layout.

Guesthouse in Barrie

4.99 out of 5 average rating, 171 reviews

Warnica Coach House

Welcome to the Warnica Coach House! This unique and historic property will not disappoint! Built by George R. Warnica in 1900, this spectacular property was the recipient of the Heritage Barrie award in 2018. The Coach House where you will stay, once housed horses and carriages, has been completely renovated top to bottom in 2023 with the finest touches. We are centrally located with a 30 second drive from the 400, and an 8 minute walk to the waterfront, restaurants, and downtown fun.

Guest favorite

A sandy area features a simple firepit surrounded by a circle of stones. A rustic wooden bench made from a log is positioned nearby. The backdrop includes an old stone wall, partially covered by greenery, creating a natural and serene setting.

Guesthouse in Shanty Bay

4.87 out of 5 average rating, 104 reviews

New Charming tinyhome Experience

Come spend a few days in our warm and cozy hideaway. Enjoy the winter wonderland with some Snow shoeing, cross country skiing or Snowmobiling right from your backyard! OR, perhaps you would like to go to the new Vetta Spa only mins away. Or downhill, snowboard at Horseshoe or Moonstone? OR maybe you just want to disconnect from technology for awhile and reconnect with yourself or loved one. Please inquire if you would like more than 3 guests. The options are plentiful from this location.

Top guest favorite

A spacious deck is shown with two chairs and a purple umbrella, overlooking a green lawn leading to the water. The serene lake is visible in the distance, framed by trees and rocky landscaping, creating a peaceful outdoor setting.

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.

Guest favorite

The exterior of Main St. Market is shown, featuring a dark wood facade with a prominent sign. Colorful flowers in planters adorn the entrance, while outdoor seating arrangements include chairs and a small table. A Canadian flag flutters gently above the entrance.

Guesthouse in Halton Hills

4.94 out of 5 average rating, 108 reviews

The Clayhill Bunkie

Looking for a place to get away that’s semi off-grid or a place that’s kind of like glamping? The Clayhill Bunkie is just the place and minutes from Silvercreek and Terra Cotta Conservation areas, the Credit River, the villages of Glen Williams and Terra Cotta, as well as the town of Georgetown. Spend your day hiking, cycling, antique hunting, tubing, or site seeing in Halton Hills or Caledon, then order in or grab some take-out and come relax by a roaring fire. Firewood is included.

Guest favorite

A secluded cabin is illuminated warmly against a dark skyline, surrounded by lush trees. The solar panel is visible beside the cabin, and a clear view of the starry sky adds to the serene atmosphere. The surrounding grass reflects the soft glow of the cabin's light.

Guesthouse in Newcastle

4.88 out of 5 average rating, 199 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."