Guesthouse vacation 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.

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Top guest favourite

Guesthouse in Orangeville

4.95 out of 5 average rating, 373 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.

Guest favourite

Guesthouse in Uxbridge

4.93 out of 5 average rating, 162 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 favourite

Guesthouse in Richmond Hill

4.94 out of 5 average rating, 161 reviews

Balcony House with Separate Entrance，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 parking

Top guest favourite

Guesthouse in Angus

4.98 out of 5 average rating, 246 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 new to AirBNB or who have no previous reviews attached to their profile.

Guest favourite

Guesthouse in Algonquin Highlands

4.92 out of 5 average rating, 171 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 favourite

Guesthouse in Barrie

5 out of 5 average rating, 205 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 favourite

Guesthouse in Shanty Bay

4.86 out of 5 average rating, 115 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.

Guest favourite

Guesthouse in Halton Hills

4.92 out of 5 average rating, 142 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? On The Bruce Trail and minutes from Silvercreek & Terra Cotta Cons. areas, the Credit River, the villages of Glen Williams &Terra Cotta, &the town of Georgetown. Spend your day hiking, cycling, antique hunting, tubing, or site seeing, then order in or grab take-out and come relax by a roaring fire. Firewood is included, adding great value to your stay. You WILL hear wildlife and farm animals here.

Guest favourite

Guesthouse in Newcastle

4.89 out of 5 average rating, 214 reviews

Beaverlodge Cabin

Small spring fed lake, 91 acres, privacy, wood/electric heat, electric cook-top & wi-fi. Pets welcome! To keep your costs low; No Cleaning Fee! However, you must clean up ALL mess and take your garbage/recycling home with you. No indoor washroom or running water. Clean private outhouse. Basic utensils, cutlery/bowls/plates, pots, and pans provided. This is and independent stay. Bring your own bedding, blanket, pillow, drinking water. Please leave the cabin better than you found it

Guest favourite

Guesthouse in Gravenhurst

4.91 out of 5 average rating, 175 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.

Top guest favourite

Guesthouse in Port Perry

5 out of 5 average rating, 120 reviews

Lakeside Guest Suite, on Lake Scugog, Port Perry

WATERFRONT PROPERTY….Enjoy stunning sunsets from the basement walkout guest suite. Take in views from the living room, bedroom (queen bed), or large 34 foot long private patio! The backyard leads directly to the lake including a fire pit for your use. Please note that the natural slope of the yard (40 stairs) may not be suitable for those with mobility issues. While the suite doesn't feature a kitchen, Port Perry is only an 8 min drive and offers many culinary options.

Top guest favourite

Guesthouse in Kawartha Lakes

4.9 out of 5 average rating, 186 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, or with a baby. Located only 20 minutes walking distance from downtown Bobcaygeon, it offers the perfect combination of nature, dining out and shopping. Our casita is new and has a kitchen to prepare small meals. Enjoy our beautiful outside area with a bbq and the day by the lake.