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

A modern kitchen is presented, featuring sleek white cabinetry and a textured backsplash. Stainless steel appliances, including a refrigerator and oven, are prominently displayed. A countertop offers space for meal preparation, while a coffee maker and microwave add to the kitchen's functionality.

Guesthouse in Whitby

4.96 out of 5 average rating, 206 reviews

One bedroom apartment/guesthouse.

Welcome to your peaceful private getaway located north of the 401 in Whitby. Guest will have the entire apartment with separate entrance to themselves. This newly constructed apartment is equipped with a fully functional kitchen, bathroom, living room and bedroom. Apartment comes with Wifi, 43” television with Amazon Prime TV services. Guest will have a designated parking space on the driveway. Please refrain from smoking inside the unit, smoke alarm are interconnected, and are highly sensitive.

Guest favorite

An outdoor pool area features a surrounding deck with wooden steps leading up to it. Bright blue water reflects the sky, and vibrant green grass borders the patio. Two red Adirondack chairs are placed nearby, complemented by lush trees and a distant green landscape.

Guesthouse 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.

Top guest favorite

A studio room features a spacious bed with crisp linens and a decorative throw. Comfortable seating areas include armchairs and a small table. Natural light filters in through the windows, enhanced by a ceiling fan overhead. The kitchen and dining area are visible in the background.

Guesthouse in Orangeville

4.96 out of 5 average rating, 139 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 :)

Guest favorite

The inviting living area features warm wood accents and a cozy seating arrangement. A brick fireplace stands as a focal point, complemented by large windows that flood the space with natural light. Ferns add a touch of greenery, enhancing the relaxing atmosphere.

Guesthouse in Uxbridge

4.94 out of 5 average rating, 157 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 spacious sleeping area features a queen bed with crisp white linens, a sleek dresser, and a work desk with a chair. A decorative vase of roses adds a touch of color. Natural light enters through the glass doors leading to the patio.

Guesthouse in Richmond Hill

4.97 out of 5 average rating, 155 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 favorite

A cozy sleeping area features a spacious bed adorned with soft linens. A neutral color palette is complemented by light streaming from a nearby window. A modern TV and comfortable seating area are visible in the background, providing a relaxed space for entertainment.

Guesthouse in Angus

4.98 out of 5 average rating, 241 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 favorite

A comfortable living area is furnished with two beige couches, a glass-topped coffee table, and a wooden side table. A television is mounted on the wall, and window treatments consist of yellow curtains. Artwork and indoor plants add subtle details to the space.

Guesthouse in Cavan

4.87 out of 5 average rating, 230 reviews

Cozy Seldom Scene Cottage

Note-when submitting your booking request, please acknowledge you have read and agree to all of our house rules. Romantic get away or family fun. Wooded, setting minutes from Peterborough and Millbrook. We are approx 3 min off the 115 highway, 15 min off the 407 hwy, <2 hours from Toronto. Our Bunkie is perfect for anyone looking for a furnished getaway in the Kawarthas nestled in a natural setting that includes wifi-STARLINK Our log home is approx 150 ft directly located from the Bunkie.

Top guest favorite

The exterior of the studio mini-cottage is showcased, featuring tall windows with decorative trim. Dark wood complements the vibrant greenery surrounding the property. Outdoor seating, including two Adirondack chairs and additional patio furniture, is positioned nearby, providing a welcoming space for guests to relax.

Guesthouse in Algonquin Highlands

4.92 out of 5 average rating, 168 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

The open-concept living area features a comfortable sofa set against wooden accents and a rustic coffee table. The kitchen is visible in the background, equipped with modern appliances. Large windows allow natural light to fill the space, complementing the warm tones of the wood flooring.

Guesthouse in Barrie

5 out of 5 average rating, 202 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

An open-concept living space features a cozy seating area with black leather sofas, a dining table, and a fully equipped kitchen. A spacious bed is positioned against the wall, with large windows providing natural light and views of the peaceful surroundings.

Guesthouse in Schomberg

4.93 out of 5 average rating, 458 reviews

Country Cabin Escape | King Bed | Pet Friendly

Tucked away on our peaceful family farm, this private cabin offers tranquility and comfort—while not secluded in the woods, it provides a true countryside experience. The cabin is located on the same property as our farmhouse, Country Suite, and Event Barn. Blinds are provided to enhance your privacy during your stay. The Cabin includes a full kitchen, king sized bed, propane BBQ and many other amenities, for a full list please review the "What this place offers" section of our listing.

Superhost

The inviting interior features wooden walls with large windows allowing natural light to illuminate the space. A compact kitchenette is visible with appliances, while stylish stools complement a natural wood countertop. A cozy seating area with a futon sits adjacent to a wooden staircase leading to the loft.

Guesthouse in Shanty Bay

4.86 out of 5 average rating, 112 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.

Superhost

A peaceful dock stretches over calm waters, featuring two classic Adirondack chairs positioned to face serene natural surroundings. The still surface of the lake reflects the clear blue sky and lush greenery along the shore, creating a tranquil setting for relaxation.

Guesthouse in Gravenhurst

4.91 out of 5 average rating, 174 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.