Guesthouse holiday rentals in York Region

A modern two-story home with a welcoming front facade features a double garage and a stone pathway leading to the entrance. Lush trees and landscaped shrubs frame the property, while a clear blue sky highlights the structure's architectural details.

4.86 out of 5 average rating, 36 reviews

Spacious & Bright 1Bdr Private Walkout Basement

Relax and enjoy your stay at this bright and newly renovated modern private walkout basement apartment located in the prestigious Bayview Hills in Richmond Hill. Our place is located in a safe and quiet neighborhood, within walking distance to a park with a large and well equipped playground. It is just a few minutes drive to nearby grocery stores and restaurants such as Freshco, Walmart, Shoppers, KFC, McDonalds, etc. It has a quick access to highway 404, which can take you to Downtown Toronto.

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.

4.95 out of 5 average rating, 164 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

4.92 out of 5 average rating, 91 reviews

A spacious living area is presented with a light gray couch, a stylish armchair, and a small round table. A dedicated workspace is visible in the background, featuring a desk and a chair. Neutral-toned walls and flooring create a calm environment.

Guesthouse in Aurora

Cozy 2 Bedroom Guest Suite in Aurora

Welcome to our charming cozy guest suite, nestled in the heart of Aurora, Ontario. Has a separate entrance with 2 bedrooms, full washroom, dedicated work space, spacious living area and kitchenette. Our space is designed for families, couples, business travelers, seeking tranquility, cozy space, proximity to attractions, and a safe family friendly neighborhood. Minutes away from: - Downtown Aurora - Restaurants/Fastfood - Parks Other offers: Complimentary Snacks, Free Parking, Free WiFi

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.

4.95 out of 5 average rating, 135 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 1 parking space.

4.98 out of 5 average rating, 48 reviews

Guesthouse 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.

5 out of 5 average rating, 13 reviews

A modern studio is depicted with a spacious layout. A large wall-mounted TV is positioned against a white wall, while a minimalist floating shelf adds decor. A light area rug complements a gray sofa and a bright yellow chair. A cozy bed is dressed with soft linens.

Guesthouse in Markham

Chic & Cozy: Renovated Studio

Relax in this newly renovated basement studio, complete with a fully stocked kitchen, 55-inch TV, high speed Wi-Fi and washer/dryer. Enjoy the convenience of on-site parking and easy access to nearby parks, public transit, downtown Toronto and amazing restaurants. Whether you're here for business or leisure, this cozy retreat offers the perfect blend of comfort and convenience for your stay. *** As central as it gets in the GTA; close to Person Airport, Hwy 401/404/407, and shopping malls!

5 out of 5 average rating, 222 reviews

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.

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.

Guesthouse in Schomberg

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.

4.95 out of 5 average rating, 21 reviews

Guesthouse in Barrie

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, 61 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.

Guesthouse 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.

A cozy living area is highlighted by two comfortable sofas in red and gray. A wooden coffee table sits at the center, while vibrant artwork adorns the walls. Natural light enters through a large window, framed by red curtains, offering views of greenery outside.

4.89 out of 5 average rating, 47 reviews

Cozy Guest House

Experience the serenity of a charming basement apartment where you can unwind in comfort while still being just a 10-minute stroll away from the vibrant heart of downtown Richmond Hill. Plus, with convenient access to a direct bus route, you can easily reach downtown Toronto. Within a short 10-minute walk, you'll discover an array of conveniences at your fingertips, including supermarkets, boutiques, a cinema, and a delightful selection of bars and restaurants.

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.