Guest house holiday rentals in Lake Simcoe

Find and book unique guest house rentals on Airbnb

Top-rated guest house rentals in Lake Simcoe

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

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Top guest favourite

Guest house in Orangeville

4.95 out of 5 average rating, 372 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

Guest house in Uxbridge

4.94 out of 5 average rating, 159 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

Guest house in Richmond Hill

4.94 out of 5 average rating, 158 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

Guest house in Angus

4.98 out of 5 average rating, 245 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.

Top guest favourite

Guest house in Barrie

5 out of 5 average rating, 203 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

Guest house 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.

Top guest favourite

Guest house in Richmond Hill

4.95 out of 5 average rating, 130 reviews

New Entire 1 Bedroom Coach House Apartment

This completely private independent one bedroom coach house apartment is located in the prestigious Observatory Hill neighborhood in south Richmond Hill. Great for couple or small family, sleeps up to 4 people. Close to malls, public transit, restaurants, parks, library and mins to Hwy 404, Hwy 407 and Toronto. This 2nd floor apartment offers 3 Gbps internet, Nespresso coffee machine, 50 Inch Smart TV, independent AC, furnace, laundry, private entrance with lockbox access and free parking.

Guest favourite

Guest house in Newcastle

4.88 out of 5 average rating, 215 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

Guest house 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.

Guest favourite

Guest house in Parry Sound

4.91 out of 5 average rating, 148 reviews

Parry Sound Bunkie |Dock, BBQ, Firepit & Pets

🍁 Escape to Hemlock Cabin, your private fall lakeside retreat. Wake to sunrise views over vibrant foliage, spend crisp autumn days kayaking, hiking, or enjoying the calm lake, then savor BBQ dinners on the covered patio. End evenings by the fire pit under starlit skies 🔥. With cozy interiors, A/C, and space for couples or small families, this rustic-meets-modern gem is perfect for leaf-peeping, relaxation, and making Muskoka memories. Book your fall getaway today! 🍂

Top guest favourite

Guest house in Port Perry

5 out of 5 average rating, 119 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

Guest house in Kawartha Lakes

4.9 out of 5 average rating, 186 reviews

Moon House 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.