Guest house holiday rentals in Oro-Medonte

4.92 out of 5 average rating, 48 reviews

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.

Guest house in Mono

Mono Countryside Home & Farm

If you’re looking for a quiet place to get away, Mono Countryside Home and Farm is the place for you. This charming guest home in Mono, is set back from the road and surrounded by towering pines with lots of room to roam in the forest and nearby Mono Cliffs Provincial Park. This open concept guest home with stunning views includes a warm fireplace, full kitchen and high speed internet. Complimentary biscotti and fresh farm eggs + you can order Italian cuisine from your host at Connie's Kitchen.

The chalet showcases a rustic wooden exterior with large windows and a sloped roof, surrounded by a snow-covered landscape. A fenced yard provides privacy, and an outdoor staircase leads to the upper level, enhancing the chalet's two-story design.

4.98 out of 5 average rating, 92 reviews

Warm rustic luxury chalet near lake & skiing

Barrie's most comfortable and friendly chalet, with a rustic ambience that has had a documentary filmed in it! Warm and luxurious with in-floor heat, 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!

4.99 out of 5 average rating, 114 reviews

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.

Guest house in Mansfield

Brookside Cottage - Charming Rural Getaway Mulmur

Our cozy guest house, situated in the Headwaters region, has it all! Close to hiking,golfing,biking,skiing. XCski/snowshoe from your door! Big skies for astronomers and astrophotography! We offer 32 acres of forest and fields for walking and taking in the magnificent views. The area boasts fine restaurants, boutiques, markets and artisans. Minutes to Mono Cliffs, Boyne, Mansfield Ski Club and easy driving to Blue Mountain and Wasaga Beach. Ideal for couples, solo adventurers or a small family.

4.98 out of 5 average rating, 266 reviews

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.

Guest house 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. 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.

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.

5 out of 5 average rating, 84 reviews

Centrally Located 2 bedroom Hidden Gem

Enjoy your stay in Barrie at the Willoughby Guesthouse! Bright, newly constructed, fully detached from main residence & private. The Willoughby is well equipped for all your needs. Wifi & parking included. This modern, 850 sq ft., sun-drenched apartment offers a tranquil residential vibe, as well as quick & easy access to downtown & many local beaches. Sit back & admire the peaceful view overlooking Willoughby greenspace. ***** For Video Tour - click on the first photo in our listing. *****

4.98 out of 5 average rating, 49 reviews

Guest house in Innisfil

2 bedrooms, 3+1 beds in Pines Guest House

Welcome to our Pines Guest House located in Innisfil, Sandy Cove and walking distance from private Lake Simcoe beach. Your place has 2 bedrooms with balcony, a fully equipped kitchen, spacious living room and patio with BBQ. Explore several ski resorts with cross country, downhill skiing, tubing , snowmobile trails just a short drive away during winter time. Hiking, kayaking, canoeing in Simcoe County. Paddle boarding or boating can be arranged for you. This place is family and pets friendly.

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.

5 out of 5 average rating, 225 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 house in Gravenhurst

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.

4.95 out of 5 average rating, 126 reviews

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.

4.95 out of 5 average rating, 21 reviews

The Hideout

Welcome to The Hideout – Your Cozy Garden Escape 🌿✨ The Hideout is a stylish one-bedroom, one-bathroom garden suite designed for comfort and relaxation. Thoughtfully decorated in calming blue and warm brown tones, with elegant gold accents, this inviting retreat blends modern sophistication with a warm, homey atmosphere. Whether you’re here for a weekend getaway or a short stay, The Hideout is perfectly situated just minutes from Barrie’s downtown, waterfront, and local attractions.

4.97 out of 5 average rating, 63 reviews

A modern living area features a wall-mounted television above a sleek fireplace. A circular glass coffee table sits on a black and white striped rug. Two black chairs and a light-colored sofa provide comfortable seating. Soft natural light filters through sheer curtains.

Guest house in Georgina

Bright & Modern Lower Level Apt in Keswick

Enjoy our brand new apartment in a quiet, non-smoking home. Few minutes walk to Lake Simcoe, perfect place to relax and a retreat for those who appreciate fishing, hiking; Ice fishing, snowboarding during the winter months. Close to Shops & Restaurants, The Roc, Imagine Cinema, The Ice Palace and Stephen Leacock Theatre. The Space Modern comfort and decor. Your luxury stay includes access to high-speed internet, Smart TV with access to Netflix. Full Kitchen and Laundry in suite.

5 out of 5 average rating, 25 reviews

Hillside Studio: Midland + Winter Escape

Welcome to the Hillside Studio — a bright 900 sq.ft. 1-bedroom guesthouse in the heart of Midland. Perched on a hill, the Studio offers a modern, clean, airy retreat for 1–2 guests. It’s the ideal home base for your winter adventures around Southern Georgian Bay: • 10-min walk to Midland’s Downtown and the Curling Club • 10-min drive to Mountainview Ski Centre • 20-min drive to Awenda Provincial Park • 30-min drive to Moonstone, Horseshoe, Vetta Spa, and Quayle’s Brewery

Guest house in Victoria Harbour

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.

4.96 out of 5 average rating, 279 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

Popular amenities for guest house rentals in Oro-Medonte

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

4.93 out of 5 average rating, 170 reviews

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.

Guest house in Uxbridge

Guesthouse w/Woodstove in Nature Near Trails & Spa

4.93 out of 5 average rating, 40 reviews

A heated pool is set within a spacious patio area, featuring inviting blue waters and a bright green inflatable float. Two chairs are positioned alongside the pool, with a tall red umbrella providing shade. Lush greenery and a secure fence surround the area.

Guest house in Uxbridge

Redwood Haven East: Your Dream Getaway in Uxbridge

Guest house in Orangeville

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.

4.96 out of 5 average rating, 378 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

4.93 out of 5 average rating, 475 reviews

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.

Guest house in Schomberg

Country Cabin Escape | King Bed | Pet Friendly

Guest house rentals with a patio

A comfortable sitting area is presented, featuring a light-toned sofa with decorative cushions. A wooden coffee table occupies the center, and a dining table with two chairs is positioned nearby. Natural light enters through two large windows, adorned with patterned curtains.

Guest house in Shanty Bay

Budget Lux Horseshoe Stay XO

A comfortable living area features a dark leather sectional sofa and a matching armchair. A modern coffee table sits in front of the seating, while a sleek television is mounted on a stand. Light wooden flooring adds a relaxed ambiance, and a doorway leads to additional rooms.

4.81 out of 5 average rating, 16 reviews

Guest unit

A welcoming entryway features a wooden pergola above a spacious deck. Comfortable seating is available, with four red chairs arranged on one side. Lush flower beds filled with vibrant blooms line the walkway, creating an inviting atmosphere as guests arrive.

Guest house in Port Severn

Lakehouse Cottage

A light-filled living space is presented, featuring a plush couch accented with decorative cushions and a wooden coffee table. A small dining area with a round table and two chairs is visible. Large windows offer views of the outside, framed by elegant drapes.

Guest house in Shanty Bay

Discount Lux Horseshoe Resort XO- best location

4.97 out of 5 average rating, 58 reviews

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.

Guest house in Alcona

A Greyt Escape

The exterior showcases a contemporary cottage design with dark blue and wooden paneling. A vibrant yellow front door stands prominently, complemented by two side windows. The landscape features various plants and a gravel path leading to the entrance, with the tranquil lake visible in the background.

4.96 out of 5 average rating, 24 reviews

Windfall Cottage On Little Lake

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.

4.7 out of 5 average rating, 44 reviews

Cozy Waterfront Boathouse with Lake Simcoe Views

An aerial view captures a two-bedroom guest house nestled among trees, with sandy beach visible nearby. The surrounding area features a tidy arrangement of similar cottages and pathways leading to the water's edge, showcasing a tranquil coastal setting.

Guest house in Wasaga Beach

4.66 out of 5 average rating, 29 reviews

Adorable 2 Bedroom guest house with fire place.

Guest house rentals with a washing machine and dryer

A spacious room is presented featuring a large bed with white linens, complemented by two bedside lamps. A cozy seating area includes a sofa and a coffee table, while a dining table is positioned nearby. Large windows allow natural light to illuminate the space.

Guest house in Shanty Bay

Luxury Horseshoe resort style- Near Vetta spa

5 out of 5 average rating, 36 reviews

The cottage exterior features a covered porch with wooden paneling, a picnic table, and potted plants at each corner. Sunlight casts a warm glow over the area, highlighting the entrance and surrounding landscape. A gravel path leads to the front of the cottage, set amidst trees.

Guest house in Orillia

Woods Bay Cottage Severn

5 out of 5 average rating, 4 reviews

Garden Suite Getaway

A modern living area showcases a stylish gray sofa and two round wooden coffee tables. A flat-screen TV is mounted above a decorative stone fireplace, while a dining table is visible in the background. Bright lighting enhances the open space, creating an inviting ambiance.

Guest house in Newmarket

5 out of 5 average rating, 4 reviews

Spacious Airy Central Guesthome

5 out of 5 average rating, 15 reviews

2 BR 1.5 BA Lower Level - Comfort with Character

5 out of 5 average rating, 13 reviews

Pete’s bike and stay

An inviting living area features a cozy white couch facing a wall-mounted television. A rustic fireplace with a wooden mantel serves as a focal point. Shelving displays blue glassware, while a patterned area rug adds warmth to the wooden floor.

Guest house in Severn

5 out of 5 average rating, 4 reviews

Charming Lakefront Boathouse & Bunkie

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.