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.

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Guest favorite

Guesthouse in Orangeville

4.95 out of 5 average rating, 310 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.

Aug 18 – 25

G$30,960 GYD per night

Guest favorite

Guesthouse in Aurora

4.92 out of 5 average rating, 114 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

Sep 13 – 20

G$18,901 GYD per night

Guest favorite

Guesthouse in Bobcaygeon

4.98 out of 5 average rating, 110 reviews

Rustic forest bunkie at Ravenswood

Enjoy a peaceful, rustic retreat at Ravenswood, our beautiful 15 acres of forest. Glamp in style with a seasonal outdoor hot water shower, compost toilet, and kitchenette with fridge, kettle, Nespresso and toaster oven. Gaze at the famous Bobcaygeon constellations at your fire pit. The energy here is amazing. Your little cabin in the woods is located just up the hill from our main residence, it offers a balance of privacy and convenience with easy access to all that the Kawarthas has to offer.

Jun 29 – Jul 6

G$30,117 GYD per night

Guest favorite

Guesthouse in Algonquin Highlands

4.92 out of 5 average rating, 139 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 singles/couples; 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.

Feb 2 – 9

G$28,778 GYD per night

Guest favorite

Guesthouse in Angus

4.98 out of 5 average rating, 140 reviews

Serene Comfort. Hot Tub, Full Suite with Kitchen

Welcome to your private oasis! Our 600 sq/ft bachelor suite offers a clean and cozy retreat. Relax and unwind in the hot tub or with WIFI, Netflix & Prime TV. Just a 2-min drive to restaurants and groceries. CFB Borden & the North Trillium Trail within 5-min. Looking for more 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. Book now for your ultimate getaway!

Jun 16 – 23

G$17,676 GYD per night

Guest favorite

Guesthouse in Newmarket

4.93 out of 5 average rating, 122 reviews

Stylish 1-Bedroom Home in the heart of Newmarket

This recently renovated unit is located walking distance from Newmarket's GO-Train, public transit, regional hospital, and Historic Main St strip. With its central location you are steps away from nature walks, hiking trails, lovely shops, great restaurants and excellent local craft breweries. Not to mention Upper Canada Mall. Nestled on a quaint street, and sitting on a half acre lot filled with old growth trees this place gives off serious cottage vibes. (But with better Wifi)

Aug 26 – Sep 2

G$28,935 GYD per night

Guest favorite

Guesthouse in Kawartha Lakes

4.92 out of 5 average rating, 247 reviews

The Loft on Sturgeon Lake

Enjoy the lakeside lifestyle on Sturgeon Lake! This beautiful custom loft features one spacious bedroom with a queen bed and large, bright windows. The suite has a private washroom with a large walk-in shower. There is a full kitchen available and living space with a pull out couch. Experience stunning sunsets over Sturgeon Lake from your private balcony or by the lake at the dockside fire pit. There is an outdoor pool that can be used when available and canoes and kayaks.

Sep 15 – 22

G$28,803 GYD per night

Guest favorite

Guesthouse in Gravenhurst

4.92 out of 5 average rating, 121 reviews

Waterfront Guest Cabin in Muskoka

Upscale guest cabin with brand new hot tub and WiFi deep in the heart of Muskoka. Unlimited access to a private hot tub, a dock with deep water diving, and a fireplace with night sky views. Remote cabin in nature with modern amenities and touches, accessible only by private road. Great for unplugging from social media and getting away from the city. Ideal for couples looking to relax, have campfires, and enjoy water activities such as swimming, kayaking, and paddle boating.

May 27 – Jun 3

G$37,972 GYD per night

Guest favorite

Guesthouse in Tiny

5.0 out of 5 average rating, 109 reviews

Welcome to the Wood Road House

This 485 sq ft garage conversion will be sure to make you feel at home. Complete with one queen sized bed, and sofa bed, it suits well to a couple or small family. Open the garage door to have sunsets land on your front step, and oversized patio doors allow you to have the outside come in. Cozy up to a gas fireplace, while catching a movie or enjoying a glass of wine. Enjoy calm and quiet nature in this private space, that allows tranquility in a country setting.

May 6 – 13

G$21,542 GYD per night

Guest favorite

Guesthouse in Victoria Harbour

4.98 out of 5 average rating, 229 reviews

Sunset Beach Cottage

Part log treehouse, part beach house and 100% of what you need to enjoy a peaceful getaway only 1.5 hours from Toronto! Walk up the private staircase and pause to enjoy the spectacular treetop and waterfront views from your own wraparound deck before entering your 900 sq. ft. oasis. Enjoy access to your own lawn, picnic table and beach* area and all that Georgian Bay and the area has to offer. *water levels fluctuate Insta: sunset_beach_cottage_canada

Aug 27 – Sep 3

G$36,565 GYD per night

Superhost

Guesthouse in Newcastle

4.9 out of 5 average rating, 254 reviews

Waterside Nature Cabin - Private & Comfortable

Spring-fed lake, 91 acres, trails, max privacy, solar power, heat, gas stove, cooler, clean out-house, wi-fi, firepit, 2SLGBTQ Pets ok To keep your costs low; No Cleaning Fees! You must clean up ALL personal mess & litter basic kitchen utensils, dishes, pots, pans provided bring bed sheet, pillow, blanket & drinking water Take all Garbage & Recycling back home with you when leaving Try to "leave the cabin, and the property better than you found it"

Jun 22 – 29

G$15,338 GYD per night

Guest favorite

Guesthouse in Kawartha Lakes

4.86 out of 5 average rating, 125 reviews

Casita Luna Bobcaygeon

Enjoy the lake at this peaceful and centrally located casita (little house). Surrounded by trees and right on the water, this casita is perfect for a romantic weekend get away for two. Located only 20 minutes walking distance from downtown Bobcaygeon, it offers the perfect combination of nature, dining out and shopping. Our casita is brand new and has a kitchen to prepare small meals. Enjoy our beautiful outside area with a bbq and the day by the lake.

Jan 18 – 25

G$33,215 GYD per night