Guest house holiday rentals in Simcoe County

Find and book unique guest house rentals on Airbnb

Top-rated guest house rentals in Simcoe County

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

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Top guest favourite

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.

Guest house in Orangeville

4.95 out of 5 average rating, 395 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

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

4.93 out of 5 average rating, 188 reviews

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.

Top guest favourite

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

4.99 out of 5 average rating, 119 reviews

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.

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.

Guest house in Newmarket

4.82 out of 5 average rating, 237 reviews

Private cozy stylish fun Chill Basement pool table

🔆Cozy Bright Spacious stylish Furnished Separate Entrance On The Ground basement: 🧖W/New 3 pc Bathroom 🛏 Super comfy Queen bed Exquisite Bar/Kitchenette 🔸Air fryer , Ice maker 🔹Mini Fridge,Counter top Burner 🔸Microwave,Coffee Maker,Toaster ☕️🍵Complimentary coffee and Tea 🔥Nice New Gas Fireplace 🛋Super comfy couch Bean bag ✅💯Super Cool Games and features: 🎱Pool Table 🎰Craps Table,Blackjack,Poker Chips 🎲Backgammon 🎯♟Dart,Chess,Jenga 📺 TV,AppleTV,chrmcast 🅿️ 1 Drive way Parking

Guest favourite

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.

Guest house in Barrie

4.9 out of 5 average rating, 102 reviews

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.

Guest favourite

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

4.97 out of 5 average rating, 300 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

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.

Guest house in Barrie

5.0 out of 5 average rating, 284 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

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.

Guest house in Beaverton

4.9 out of 5 average rating, 124 reviews

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.

Guest favourite

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.

Guest house in Shanty Bay

4.85 out of 5 average rating, 124 reviews

Charming tinyhome Experience

🌞 Summer Escape in Our Cozy Hideaway! 🌿 Step into your private retreat! Hike trails, climb treetop lookouts, or explore dirt bike & cycling paths. Paddle rivers, relax by waterways, or soak up the sun. 🚴‍♂️ Adventure Awaits: Mountain biking, forest trails, and nearby lakes make every day an adventure. 💆‍♀️ Relax & Recharge: Minutes from the Vetta Spa—or disconnect and enjoy quiet moments with loved ones. 🌳 Nature, Comfort & Fun: Adventure, peace, or both—your cozy hideaway has it all.

Top guest favourite

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.

Guest house in Gravenhurst

4.95 out of 5 average rating, 129 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.

Guest favourite

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.

Guest house in Gravenhurst

4.92 out of 5 average rating, 195 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

Guest house in Barrie

4.92 out of 5 average rating, 127 reviews

Quiet 2BR Suite • Kitchen, Workspace + Parking

A comfortable, no-stress place to unwind, work, and feel at home. Enjoy a cozy, quiet 2-bedroom retreat designed for comfort and convenience. Located in a safe, peaceful neighbourhood, it’s perfect for professionals, couples, or small families. The space features a full kitchen, dining area, and dedicated workspace. Minutes to downtown with quick highway access, free parking, and nearby trails. Ideal for short or extended stays. Please note: not wheelchair accessible.