Guest house holiday rentals in York

4.94 out of 5 average rating, 18 reviews

Guest house in Brampton

Fireside 3BR by Canterra Stays · Sleeps 6

✨ The retreat with a fireplace at its heart. A spacious 3-bedroom suite with 10-foot ceilings, warm lighting, and the kind of cozy that makes you cancel the evening plans. Three real beds sleep 6, the large dining area hosts the shared meals guests write about, and your own private entrance keeps it all effortlessly yours. Twenty-odd minutes from Pearson, quick access to Hwy 410 — visiting family, working nearby, or in town for a celebration at a nearby venue: land here, light the fire, exhale.

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4.94 out of 5 average rating, 112 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.

Guest house 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

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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.

5.0 out of 5 average rating, 101 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. *****

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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.

4.9 out of 5 average rating, 115 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.

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5.0 out of 5 average rating, 18 reviews

Guest house in Newmarket

Chic 2BR Spacious Home Near Yonge St

Welcome to your bright and modern 2-bedroom guest home in Newmarket, just a short walk to Yonge St and close to shopping, restaurants, and Main Street. This private basement suite offers a comfortable, well-appointed stay in a quiet neighbourhood, with a separate entrance, driveway parking, fast Wi‑Fi, in-suite laundry, and a brand-new modern kitchen. Ideal for families, couples, business travellers, and longer stays, the home combines comfort, convenience, and privacy in a peaceful setting.

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Guest house in Richmond Hill

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.

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

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4.93 out of 5 average rating, 196 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.

5.0 out of 5 average rating, 314 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.

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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

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 Gas Fireplace 🛋Super comfy couch Bean bag ✅💯Cool Games features: 🎱Pool Table 🎰Craps Table,Blackjack 🎲Backgammon 🎯♟Dart,Chess,Jenga 📺 TV,AppleTV,chrmcast 🅿️ 1 Drive way Parking License#BL2026-00210

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4.83 out of 5 average rating, 245 reviews

4.96 out of 5 average rating, 81 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 Innisfil

A Greyt Escape

**Our nightly rates now include service fees! The price you see is the price you pay- no surprise service fees added at checkout.** A Greyt Escape is a private, self-contained 4-season guesthouse located on the back half of over 1 acre of land. Aptly named after our beloved retired racing Greyhounds, it is 1 km from Innisfil Beach Park, walking distance to convenience stores and restaurants, a 5-minute drive to shops, pharmacies, gas stations and dining, and 15 minutes to Friday Harbour.

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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.

4.98 out of 5 average rating, 105 reviews

Warm rustic luxury chalet near lake and trails

Barrie's comfortable and friendly chalet, with a rustic ambience that has had a documentary filmed in it! Warm and luxurious privacy with heated floors, gas fireplace, gourmet kitchen and covered porch. Short walk to trails, park, beach and playground on Lake Simcoe. Perfect for work or relaxing with fast WiFi and lots of channels on large TV. A welcoming, fully equipped home away from home for families, couples, friends and travelers in a beautiful and quiet mature neighbourhood.

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Guest house in Richmond Hill

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.

Detached Coach House | 1 Bdrm 1 Bath| Private HVAC

Luxury Detached 1-Bedroom Residence in prestigious Observatory Hill. Unlike nearby studios, this is a true 1-bedroom suite with a separate closing door for quiet and privacy. 100% independent building—no shared walls, no shared air (private HVAC), No Footsteps Above You! Features a condo-style layout with full kitchen, living room, and in-suite laundry. Includes 3Gbps Wi-Fi, 50” Smart TV & Nespresso. Perfect for executives/couples needing space. Parking included.

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4.94 out of 5 average rating, 161 reviews