Apartment holiday rentals in Grey Highlands

4.96 out of 5 average rating, 470 reviews

A cozy seating area features two rattan swivel chairs with a view of Georgian Bay through large windows. The hardwood floor is complemented by a small round side table, while a potted plant adds a touch of greenery to the inviting space.

Flat in Meaford

Sunrise and Bayview with Kayaks & Bikes

🌊 Bright and inviting waterfront/view ground level apartment in the heart of Meaford. 👋Entire apartment to yourself 👥Ideal for a romantic getaway 🏔20 minute drive to Blue Mountain attractions. 2 hours from Bruce Peninsula National Park 🏖 5 minute stroll to the Harbour and Sandy Beach or a pebble beach right across the road ! 🚶‍♂️Walking distance to Meaford Hall 🍽Dining options a block away:) Kayaks, Bikes, Floaties, snowshoes and snorkels are complimentary. Come and discover our gem of a town

4.96 out of 5 average rating, 343 reviews

A private wooden deck is shown with an umbrella-covered table and four chairs, surrounded by lush greenery. Windows on the building's façade allow natural light, while potted plants add a touch of color, enhancing the outdoor space for relaxation.

Flat in Horning's Mills

Beautiful Riverside Country Apartment

Bright, warm and newly renovated, this 900sqft apartment, a private floor of a charming country home with separate entrance and garden patio, awaits you in Melancthon. SmartHDTV, Wifi, tranquil surroundings, and the Bruce Trail. Close to Shelburne, Mansfield, Creemore, Pine River Institue and many excellent restaurants (The Globe and Mrs Mitchels). Only 40 minutes to the Scandinave Spa, Collingwood, Blue Mountain, Wasaga Beach. Golf Courses are close by. A perfect retreat just north of Toronto.

4.98 out of 5 average rating, 130 reviews

A spacious living area features a comfortable gray sectional sofa and a decorative accent chair. A modern television is mounted on the wall, while a coffee table sits atop a patterned rug. Large windows allow natural light to illuminate the room, providing views of the greenery outside.

Flat in Minesing

The Loft at Bryn Mawr House

Welcome to your ideal Ontario getaway! Our full luxury suite offers a king-size bed, living room with a pull-out , fully-equipped kitchen, and ample parking . Enjoy our 11 acres, a fire pit, pond, and horseshoe area. Explore numerous provincial snowmobile trails, hiking, kayaking and canoeing in the Minesing Wetlands We're central to Blue Mountain, Horseshoe Valley and Snow Valley ski resorts. And Wasaga Beach is just around the corner! Your unforgettable Ontario adventure awaits – book now!

A cozy sleeping area is highlighted by a black wooden bed frame with a crisp white bedding set. Decorative pillows are arranged on the bed, while a framed image of a bear adorns the wall. Soft bedside lighting is provided by sconces, complementing the mirror opposite.

4.91 out of 5 average rating, 208 reviews

Blue Mountain Studio Retreat

Our cozy studio is located at the base of Blue Mountain at the North chair lift, with ski in / ski out access. Perfect for 2 or a couple with small children, this newly renovated Studio has 1 bedroom, 1 bathroom and sofa bed; fully stocked kitchen, electric fireplace and flat screen T.V. Only 1 km from the Village with many restaurants, shopping and activities. Enjoy a short trip to the Scandinavia Spa or many close by beaches. Blue Mountain is a great place for the whole family to enjoy.

The living area features an inviting seating arrangement with a dark couch, complemented by a light coffee table. A round dining table with black chairs is positioned nearby. A fireplace and large glass doors that lead to a patio add warmth and natural light to the space.

4.94 out of 5 average rating, 186 reviews

8min-BlueMtn:15min-Beach:A/C:FastWifi:FreeParking

Welcome to your cozy retreat in Collingwood. Nestled in Cranberry Village, this 2-bedroom condo offers a private entrance and all the comforts of home. Enjoy the convenience of being within walking distance to a bars, restaurants, and cafés, while also being a short drive from Blue Mountain, Scandinavian Spa, and the charming shops and restaurants of Downtown Collingwood. Whether you're planning a family vacation, a romantic getaway, or a business trip, this space is perfect for all occasions.

5.0 out of 5 average rating, 118 reviews

An open-concept living room and kitchen area is highlighted by a cozy gas fireplace and a cathedral ceiling. Light-colored walls complement the stylish green cabinetry. Two barstools are positioned at the kitchen island, with natural light streaming through the window.

Flat in Nottawa

The Nottawa Nest

Spacious loft apartment, nestled in the heart of Nottawa, a quiet and friendly village just 5min. south of downtown Collingwood and 15min. from Blue Mountain and Wasaga Beach. Enjoy next door the local pub restaurant, cafe, bookstore & LCBO variety store. This beautifully finished getaway has two comfortable bedrooms, laundry room with daybed, dedicated work space, open concept living room & kitchen with cathedral ceiling & gas fireplace. Perfect for two couples, small family or group.

4.98 out of 5 average rating, 146 reviews

Private Suite • Near Bruce Trail • Modern & Bright

License: STR2025-9250261010 Welcome to our bright, private one-bedroom suite — a perfect basecamp for exploring the Bruce Peninsula. Minutes from the Bruce Trail, this clean and modern space is ideal for couples seeking a quiet, comfortable getaway with easy access to hiking, beaches, and Tobermory. Relax after a day outdoors with a comfortable queen bed, quality linens, a fully equipped kitchen, modern bathroom, and high-speed internet with streaming. Free parking & self check-in.

4.93 out of 5 average rating, 161 reviews

A modern living area is presented with two light grey sofas facing a glass coffee table, which rests on a decorative rug featuring shades of blue and neutral tones. Natural light enters through two windows, highlighting the stylish wall decor.

Flat in Shelburne

L&S Comfy Suite

Beautiful inviting space for families as well as individuals. Brand New Fully renovated area with lots of amenities for the whole family. 2 Great size bedroom with queen size beds. Jack And Jill full washroom with an amazing shower that boast body jets. Comes with all the bells and whistles. Open concept with Living room, Dining room, Full Kitchen, Washer and Dryer, free parking, work area ideal for remote work, and lots more…. NO UNREGISTERED GUESTS ARE ALLOWED AS PER HOUSE RULES.

4.95 out of 5 average rating, 512 reviews

The spacious bedroom features a king-sized bed adorned with decorative pillows, complemented by a wooden bedside tray. An armchair occupies one corner, with a desk and paddles adorning the wall. Floor-to-ceiling windows illuminate the room, while exposed wooden accents add a rustic touch.

Flat in Wasaga Beach

The Upper Deck

The upper deck is an amazing one bedroom studio with a full newly renovated bathroom, a sweet kitchenette, an amazing king size bed, a 65 “ inch HD smart Samsung TV with a live edge counter- a great workspace or eating area. One wall is floor to ceiling windows -lots of great natural light!!! Outdoors has an amazing hot tub , rustic firepit area , a beautiful covered outdoor eating area with Bbq and you can hear the lake!! Note- the studio is a separate but is part of a house.

An open layout of the studio unit is displayed, featuring a modern kitchen with a breakfast bar and sleek cabinetry. The cozy living area contains a pullout sofa with decorative cushions, and a spacious king bed is situated in the corner, complemented by subtle green accent walls.

4.96 out of 5 average rating, 255 reviews

Evergreen Studio | King Bed/Pool/Hot Tub/Shuttle

Welcome to Evergreen Studio, a cozy mountain retreat at North Creek Resort featuring a stone fireplace. *King bed *Pull-out sofa *Stone fireplace *SMART TV, Rogers Ignite TV & high-speed Wi-Fi *Equipped kitchen *No traditional oven; stovetop + microwave/convection oven Resort Amenities: *Shuttle Service *Year-round hot tub *Pool (scheduled to close Tues Oct 13, 2026) *Tennis Courts *Ski or hike in/out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

The airy studio unit features a spacious king bed framed by green accent walls. A cozy sectional sofa is positioned in front of a coffee table. Natural light filters through window shutters, highlighting the adjacent balcony with Muskoka chairs.

4.96 out of 5 average rating, 403 reviews

Sage & Stone | King Bed/Pool/Hot Tub/Shuttle

Welcome to Sage & Stone, a warm and stylish studio retreat at mountainside North Creek Resort. *King bed *Double sofa bed with memory foam mattress *SMART TV, Rogers Ignite TV & high-speed Wi-Fi *Equipped kitchen with cookware, utensils & Keurig *Updated bathroom Resort Amenities: *Shuttle Service *Year-round hot tub *Pool (scheduled to close Tues Oct 13, 2026) *Tennis Courts *Ski or hike in/out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

A serene bedroom features a queen bed adorned with soft blue and white linens. Natural light floods the space through a nearby window, illuminating the beach-themed artwork above the headboard. Sleek wooden beams contrast with the light-colored walls, enhancing the open feel of the suite.

4.82 out of 5 average rating, 299 reviews

1BR Boutique Suite #6 - The Lake at Blue Mountains

Experience The Comforts of Home While You're Away & we are pet friendly! All rental check-ins are “non contact/digital” and every suite has it’s own heating and cooling system (no shared air)! All our suites are fully contained and separated with concrete walls & outside access only (no shared hallways or doors). Your safety is our priority! Just drive-up and check yourself in safely. Located in a quiet community, we ask that there are no parties or events

Popular amenities for Grey Highlands apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.95 out of 5 average rating, 433 reviews

The exterior of the house is showcased with a large, angled roof and expansive glass windows reflecting the evening light. A spacious deck presents colorful chairs in pink and yellow, surrounded by sandy beach and foliage, enhancing the inviting outdoor space.

Flat in Wasaga Beach

2 bedroom beachfront apartment

A cozy sleeping area features a spacious bed adorned with soft linens and decorative pillows. Bedside lamps provide gentle illumination, while framed artwork adds a touch of color to the wall. A dresser and mirror complement the room's design.

4.88 out of 5 average rating, 830 reviews

Brookside Studio at Blue Mountain - King Bed

4.92 out of 5 average rating, 156 reviews

A panoramic view captures the stylish interior featuring a blended living space and kitchen. Rock-themed decor adorns the walls, while a cozy dining area is visible. A guitar hangs next to a bookshelf stocked with various items, and a modern stainless steel refrigerator adds to the inviting atmosphere.

Flat in Minto

Harriston Hideout

The entrance to the townhome features a covered porch with a stone facade. A pair of large windows flank the front door, allowing natural light to enter. Neatly arranged flower beds reflect well-maintained landscaping. A driveway is visible on the left, leading to a garage.

4.9 out of 5 average rating, 343 reviews

Cozy Hideaway

4.79 out of 5 average rating, 271 reviews

A well-lit living area features a light-colored sofa and a patterned accent chair. A wooden coffee table sits in front of the sofa, alongside a small lamp. A small window brings in natural light, highlighting the simple decor and neutral tones of the space.

Flat in Meaford

Birch & Bannock UNIT 2

A comfortable living area features a light-colored sofa with throw pillows, a wooden coffee table, and a plush armchair. A brick fireplace is positioned against a textured wall, while artwork adorns the space. Soft natural light illuminates the room through a large window.

4.94 out of 5 average rating, 339 reviews

East Side Serenity Apartment

4.95 out of 5 average rating, 109 reviews

A stone fireplace is set into a rustic wall made of various sized natural stones, providing a textured and earthy backdrop. A flat-screen TV is mounted above, and a wooden cabinet is positioned to the left, adding warmth to the living space.

Flat in Caledon

Separate apartment with pool, on golf course.

4.96 out of 5 average rating, 104 reviews

The open-concept living area is furnished with a spacious sofa and patterned armchairs. A circular coffee table is centered on a soft area rug, while a flat-screen television is mounted on a dark media console. Natural light enters from a window, complemented by modern decor.

Flat in Alliston

The Oake Room: Modern Suite

Private apartment rentals

4.98 out of 5 average rating, 41 reviews

Flat in Dundalk

Cozy Dundalk Stay |Basement Suite w/ Side Entrance

4.88 out of 5 average rating, 60 reviews

Blue Mountain Studio, 2 Queen Beds, Lake Huron

5.0 out of 5 average rating, 88 reviews

A tranquil pond is surrounded by lush greenery and features fountains that gently spray water into the air. The area is well-maintained, providing a serene landscape for relaxation and contemplation.

Flat in Erin

Country Getaway in Erin

4.97 out of 5 average rating, 70 reviews

Renovated 2BR Suite, Walk to Downtown Collingwood

4.91 out of 5 average rating, 77 reviews

A modern kitchen is equipped with stainless steel appliances including a refrigerator and stove. A wooden dining table with four chairs sits in the center, complemented by a decorative vase filled with sunflowers. Ample storage is provided by the white cabinetry and countertop space.

Flat in Orangeville

The Bee Hive - Lower Level Raised Bungalow

Two lively donkeys are featured against a snowy backdrop. One donkey, wearing a halter, stands prominently, showcasing its expressive eyes, while the other donkey is positioned to the side, partially visible. The snow-covered ground suggests a crisp and serene outdoor setting.

5.0 out of 5 average rating, 92 reviews

The Roamin' Donkey

4.92 out of 5 average rating, 12 reviews

Cozy getaway in the heart of the Blue Mountains

An aerial view of a spacious brick home surrounded by lush greenery and vibrant autumn foliage. The property features a circular above-ground pool, a fenced garden area, and several trees scattered throughout the yard, creating an inviting outdoor atmosphere.

5.0 out of 5 average rating, 55 reviews

Grandpa Jake's

Apartment rentals with a hot tub

A cozy seating area is presented with a soft beige couch featuring two textured white throw pillows. The backdrop is adorned with a vibrant tapestry depicting intricate patterns in blue, red, and black colors, adding a decorative touch to the space.

4.86 out of 5 average rating, 144 reviews

One bedroom apartment on the river, with hot tub

Superhost

The spacious living area features a comfortable couch and an additional patterned armchair. Two side tables with lamps are present, providing soft lighting. Large windows with sheer curtains allow natural light to fill the room, while a flat-screen TV is mounted on the wall.

Flat in Horseshoe Valley

4.84 out of 5 average rating, 125 reviews

Spacious Hideaway in Nature

Superhost

The exterior showcases a multi-level brick structure with large windows. A spacious rooftop patio can be seen above a side entrance, offering an additional outdoor area. Snow covers the driveway, accentuating the architectural features of the building against a cloudy sky.

Flat in Arthur

4.68 out of 5 average rating, 102 reviews

*HOME FOR NOW - Ground level apartment no stairs!

An open-concept living and dining area features a large wooden table with gray chairs. A comfortable gray sofa and armchairs are arranged around a coffee table. Large windows offer views of the mountains, framed by yellow drapes, and a light fixture hangs above the dining table.

5.0 out of 5 average rating, 88 reviews

Gorgeous Two Bedroom Condo Overlooking Ski Hill

5.0 out of 5 average rating, 40 reviews

Flat in Oro-Medonte

On the Fifth - Basement Apartment in the Country.

4.81 out of 5 average rating, 43 reviews

Nordic Nook - Pool & Shuttle with Patio

4.94 out of 5 average rating, 34 reviews

An aerial view captures the serene waterfront, bordered by a rocky shoreline and lush greenery. Woodland hills rise gently in the background, and a mix of residential homes can be seen along the coast, emphasizing the natural beauty of the location.

Flat in Annan

The Sixth Great Lake Breeze