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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
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

Cabin in nature Close to trails and Thermea 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 ducks and chickens! If you are feeling adventurous, enjoy a hike or bike ride on one of the many local trails within walking distance in the Trail Capital of Canada! Later cozy up to the indoor Woodstove or outdoor Firepit. Catch up on your fav programs w/Roku TV or play Super Nintendo. Enjoy the newly renovated therapeutic rainfall shower.

4.93 out of 5 average rating, 193 reviews
Top 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

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.

4.96 out of 5 average rating, 404 reviews
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

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. 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. You must have a minimum of 2 reviews and a 4.7 rating to book a stay

4.97 out of 5 average rating, 309 reviews
Guest favorite
A dining area is featured with a modern table set for four, including a wooden table and bench, complemented by upholstered chairs. The backdrop consists of vertical wooden panels, and a wall clock is mounted nearby, enhancing the functional and stylish design.
Guesthouse in Barrie

The Barrie Nook | Coffee Bar & Backyard Grill

Cozy and comfortable, this two-bedroom lower-level apartment tucked away in the heart of Barrie offers the perfect locally inspired retreat. Located just minutes from downtown, the waterfront, and local shops. The space features a custom coffee bar, fully equipped kitchen, cozy living area, WIFI, parking, private entrance and backyard making it ideal for small groups, families, or business professionals. Enjoy all the comforts of home while you relax and unwind in this charming, private space.

4.89 out of 5 average rating, 114 reviews
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

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.

5.0 out of 5 average rating, 307 reviews
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

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 free parking

4.93 out of 5 average rating, 192 reviews
Superhost
A cozy sleeping area features a king size bed with decorative pillows and textured bedding. A small table with metal legs sits in front, adorned with a vase of colorful flowers. Two comfortable chairs are positioned on either side, with desk lamps providing soft illumination.
Guesthouse in Beaverton

Cozy getaway, with beautiful property and firepit

A cozy spot, nicknamed 'The Snug', has a king size bed, kitchenette, fireplace, a TV and 3 piece bathroom for you to enjoy some time away from the city. Wake up to natural light with a window overlooking a natural pond. The snug, STRICTLY NON-SMOKING, located on our 1.5 acre property, surrounded by trees and flower gardens, next to our log cabin. Wooded trails are accessible at the back of the lot. The large fire pit and gazebo with BBQ and comfy patio furniture. Quiet time after 10 pm.

4.9 out of 5 average rating, 133 reviews
Top guest favorite
A serene view of Gull Lake is captured, featuring calm blue waters bordered by lush greenery. Rocky shores are visible, providing a natural transition from the grassy area in the foreground to the tranquil lake expanse beyond.
Guesthouse in Gravenhurst

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.

4.96 out of 5 average rating, 135 reviews
Top guest favorite
An aerial view of the rustic chalet reveals a warm wooden exterior complemented by brick accents. A fenced-in yard features a heated, welcoming saltwater pool. Two cars are parked in the driveway, and greenery from surrounding trees enhances the serene atmosphere.
Guesthouse in Barrie

Chalet w/ yard & pool, walk to beach & playground

Barrie's most comfortable and friendly chalet, with a rustic ambience that has had a documentary filmed in it! Warm and luxurious with A/C, gas fireplace and gourmet kitchen, with park. beach and playground on Lake Simcoe a two minute walk away. A welcoming, fully equipped home away from home for families, couples, friends and travellers in a beautiful, mature neighbourhood featuring nearby walking and biking trails. For longer stays we are happy to offer discounts, just inquire!

4.98 out of 5 average rating, 104 reviews
Top guest favorite
An open living area features a cozy seating arrangement with a blue couch and a rustic wooden island. A spiral staircase ascends to the loft above. Large windows provide natural light, while a wall-mounted TV and a pellet stove enhance the space.
Guesthouse in Port Perry

Port Perry Island Krazee Acres Hobby Farm

Krazee Acres! Private 8-acre hobby farm a short walk to Lake Scugog, with Farm Fresh smells! Rustic Boho accents, Relaxing Soaker tub, walk-in shower, fully equipped kitchen, pellet stove, and air conditioning. Enjoy outdoor wood fires, sunsets and stars year-round. Free Parking for cars, trailers, boats. Large patio. BBQ provided. 3KM to the Great Blue Heron Casino, minutes to Historic Downtown Port Perry. Close to trails and Marina/Restaurant, (Seasonal). Relax

4.95 out of 5 average rating, 133 reviews
Top guest favorite
Two wooden Adirondack chairs are positioned on a lush green lawn facing the water, framed by overhanging tree branches. The sunset creates a colorful display on the horizon, reflecting on the calm surface of the lake, while a small table holds a wine bottle and glasses.
Guesthouse in Victoria Harbour

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

4.96 out of 5 average rating, 303 reviews
Top guest favorite
The image captures a serene lake at sunset, reflecting vibrant hues of orange and purple in the sky and water. A wooden dock extends into the calm water, providing a tranquil setting for evening activities.
Guesthouse in Port Perry

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. 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.

4.99 out of 5 average rating, 166 reviews

Popular amenities for Lake Simcoe guesthouse rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly guest house rentals

Superhost
Guesthouse in Shanty Bay

Charming tinyhome Experience

4.83 out of 5 average rating, 127 reviews
Top guest favorite
A cozy sitting area is presented with a blue checkered sofa and a striped armchair, adorned with nautical-themed cushions. Light is provided by two lamps on either side, illuminating the artwork and rustic wooden beams above.
Guesthouse in Erin

The Captain's Cottage at Willow Pond

4.96 out of 5 average rating, 153 reviews
Guest favorite
A rustic cabin is nestled in a vast field, surrounded by vibrant autumn foliage. The warm-toned structure contrasts with the lush greenery and colorful trees, while the expansive sky adds depth to the serene landscape.
Guesthouse in Newcastle

Bee Keeper's Cabin - a very private retreat

4.89 out of 5 average rating, 250 reviews
Guest favorite
A bright sleeping area features a light-colored bed and soft linens, with two large windows allowing natural light to illuminate the space. A ceiling fan provides airflow, and a small area rug adds comfort to the wood floor. An outdoor view is visible through the door.
Guesthouse in Bobcaygeon

Casita Luna Bobcaygeon

4.9 out of 5 average rating, 233 reviews
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

Cozy Seldom Scene Cottage

4.87 out of 5 average rating, 260 reviews
Guest favorite
A cozy bedroom features a double bed adorned with a light quilt and accent pillows. A decorative wall art piece is displayed above the bed. Bedside tables hold minimalist lamps, while a clothing rack stands to one side, adding functionality to the serene space.
Guesthouse in Collingwood

Cozy Collingwood Retreat | Walk to Beach & Cafés

4.92 out of 5 average rating, 155 reviews
Superhost
A pool table is prominently featured in the foreground, showcasing a neatly arranged set of colored billiard balls. In the background, a stylish bar area is visible, lined with glassware and illuminated by soft lighting.
Guesthouse in Newmarket

Private cozy stylish fun Chill Basement pool table

4.83 out of 5 average rating, 244 reviews
Top guest favorite
A modern living space is highlighted by a spacious bed and an entertainment area featuring a large wall-mounted TV. A cozy seating arrangement includes a soft couch and a stylish armchair. Ambient lighting is provided by a chandelier above, complemented by a decorative fire feature.
Guesthouse in Pickering

Luxury Ground-Level "Suite Escape"

4.95 out of 5 average rating, 131 reviews

Guest house rentals with a patio

Guest favorite
A private hot tub is situated on a wooden deck, its water gently bubbling. A tray displays a bottle of rosé and two glasses with lemon slices, alongside fresh flowers. Snow can be seen in the background, suggesting a cozy winter setting.
Guesthouse in Port Perry

Hakuna-matata

4.86 out of 5 average rating, 149 reviews
Guest favorite
A spacious living area is furnished with a modern gray sofa and a white TV unit, which holds a flat-screen TV. Natural light enters through sliding glass doors leading to a balcony. In the background, a kitchen with white cabinetry and a dining area is visible.
Guesthouse in Richmond Hill

Detached Coach House | 1 Bdrm 1 Bath| Private HVAC

4.94 out of 5 average rating, 160 reviews
Superhost
A charming boathouse is depicted with a wooden exterior surrounded by greenery. A spacious deck offers seating and overlooks the lake. A private dock extends into the water, providing access. Steps lead from the deck to the lush landscape and entrance.
Guesthouse in Barrie

Cozy Waterfront Boathouse with Lake Simcoe Views

4.69 out of 5 average rating, 61 reviews
Top guest favorite
An outdoor seating area is shown with a black canopy sheltering a glass-topped table surrounded by two comfortable chairs. A vibrant flower arrangement sits at the center, providing a welcoming touch. Tall trees in the background add shade and privacy to the peaceful setting.
Guesthouse in Innisfil

PinesGuestHouse walk to lake 2bdrms

4.99 out of 5 average rating, 82 reviews
Top guest favorite
Guesthouse in Leskard

Private guest house, romantic spa-sauna hot tub

4.97 out of 5 average rating, 61 reviews
Top guest favorite
An outdoor seating area features a gazebo with comfortable seating and a decorative rug. The surrounding garden showcases various plants and flowers, alongside a pathway leading to the guest home. The structure is nestled among trees, contributing to a serene setting.
Guesthouse in Mono

Mono Countryside Home & Farm

4.93 out of 5 average rating, 70 reviews
Top guest favorite
The modern kitchen and living area feature light wood flooring and ample natural light. A central island with two bar stools acts as a divider. Stainless steel appliances, including a microwave, are neatly arranged in the kitchen, while a comfortable sofa is positioned nearby.
Guesthouse in Barrie

Centrally Located 2 bedroom Hidden Gem

5.0 out of 5 average rating, 99 reviews
Top guest favorite
A charming entrance pathway is flanked by tall greenery leading to a welcoming door with a light fixture. The stone path is bordered by well-maintained landscaping, and a potted plant adds a touch of color beside the entrance.
Guesthouse in Innisfil

A Greyt Escape

4.96 out of 5 average rating, 79 reviews

Guest house rentals with a washer and dryer

Top guest favorite
The exterior of a newly constructed coach house is showcased, featuring a modern design with stone and brick elements. Two garage doors are visible, along with a front porch and balcony above. A well-maintained lawn and a young tree add greenery to the inviting entrance.
Guesthouse in Richmond Hill

Entire 1 Bedroom Detached Coach House

4.94 out of 5 average rating, 111 reviews
Top guest favorite
An open concept living area features rustic wood beams and sliding barn doors. Comfortable wicker chairs are paired with a wooden coffee table, while a cozy sofa adds to the inviting space. The modern kitchen is visible in the background, creating a seamless flow.
Guesthouse in Mansfield

Brookside Cottage - Charming Rural Getaway Mulmur

4.99 out of 5 average rating, 122 reviews
Guest favorite
Guesthouse in Barrie

Quiet 2BR Suite • Kitchen, Workspace + Parking

4.87 out of 5 average rating, 136 reviews
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

Country Cabin Retreat | King Bed | Pet Friendly

4.93 out of 5 average rating, 513 reviews
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

A bright & stylish urban studio

4.94 out of 5 average rating, 151 reviews
Superhost
A spacious living area features a comfortable dark sectional sofa adorned with accent pillows. A coffee table with a decorative vase sits in front. Opposite, a flat-screen TV is positioned on a wooden stand, while a dining table with green chairs is visible in the background.
Guesthouse in Markham

2 bedroom Guest house in North of Toronto

4.87 out of 5 average rating, 104 reviews
Top guest favorite
Guesthouse in Georgina

Modern Cozy Lower Level Getaway | Near Lake Simcoe

4.95 out of 5 average rating, 88 reviews
Top guest favorite
Guesthouse in Midland

Hillside Studio • Midland • Cozy Fall Escape

5.0 out of 5 average rating, 41 reviews

Destinations to explore