Apartment holiday rentals in Grey Highlands

4.96 out of 5 average rating, 469 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.

Apartment 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

FamilyLocationHiking

Apartment in Horning's Mills

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.

4.96 out of 5 average rating, 341 reviews

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.

ValueFamilySolo travel

Apartment in Wasaga Beach

A stylish bedroom is highlighted by a spacious bed adorned with soft linens. Decorative wall accents and hanging plants create an inviting atmosphere. A dresser and a small table add functionality, while an en-suite bathroom is visible in the background through a glass door.

4.97 out of 5 average rating, 506 reviews

The Boat Bow- an eco friendly studio

Steps to the longest and best fresh water beach in the world and just an hour outside Toronto, The Boat Bow is a absolute must stay! Gorgeous designer studio with everything you could ask for- comfy bed, great coffee maker, big TV and fully equipped kitchen. Imagine the best retreat you ever had - huge hot tub, amazing sauna, cool fire pits, cold plunge pool, Pinterestable Silo Lounge , French country Bbq area and much more . This is place is poetry waiting for you to create your own memories.

LocationValueBackyard

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, 185 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.

FamilyLocationPets

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, 207 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.

LocationValueSkiing

5.0 out of 5 average rating, 116 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.

Apartment 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.

FamilyLocationSkiing

4.98 out of 5 average rating, 142 reviews

Apartment in Owen Sound

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.

ValueLocationCleanliness

4.93 out of 5 average rating, 160 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.

Apartment 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.

FamilyValueSleep quality

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, 254 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)

FamilyValueGetting around

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, 400 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)

LocationValueCondition

The bedroom features a spacious bed with light blue and white bedding, complemented by decorative pillows. A piece of coastal artwork adorns the wall above the bed. Natural light filters in through the window, illuminating the light-colored walls and wooden ceiling beams.

4.88 out of 5 average rating, 221 reviews

1BR Boutique Suite #7 - 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

ValueLocationSleep quality

An open-concept studio unit is shown, featuring a cozy living area with a dark sectional sofa and a wooden coffee table. The king bed is visible in the background, accompanied by modern bedding. The kitchen area includes a bar with stools and is equipped with countertop appliances.

4.97 out of 5 average rating, 206 reviews

Alpine Bliss | King Bed/Pool/Hot Tub/Shuttle

Welcome to Alpine Bliss, a bright and inviting studio at mountainside North Creek Resort with modern, stylish décor. *King bed *Double pull-out sofa *SMART TV, Rogers Ignite TV & high-speed Wi-Fi *Equipped kitchen with 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)

ValueLocationWalkability

Popular amenities for Grey Highlands apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.94 out of 5 average rating, 215 reviews

A modern garage apartment is displayed, featuring a neutral-toned exterior with a large garage door and a side entrance. A spacious driveway is visible, providing ample parking space. The entrance is highlighted by a white door, and trees are partially visible in the background.

Apartment in Midland

Hosted by Nous Midland

LocationValueWalkability

Apartment in Wasaga Beach

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.

4.95 out of 5 average rating, 432 reviews

2 bedroom beachfront apartment

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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, 829 reviews

Brookside Studio at Blue Mountain - King Bed

LocationFamilyView

4.94 out of 5 average rating, 107 reviews

A dining area is presented with a wooden table and six folding chairs, positioned on a light wood floor. A decorative runner is centered on the table, while a view of the kitchen can be seen through a mirrored wall, highlighting the open-concept design.

Apartment in Barrie

Myra's Cozy Place in Barrie

LocationFamilyParking

4.96 out of 5 average rating, 103 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.

Apartment in Alliston

The Oake Room: Modern Suite

LocationFamilyParking

4.9 out of 5 average rating, 339 reviews

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.

Apartment in Owen Sound

Cozy Hideaway

FamilyValueIndoor spaces

4.93 out of 5 average rating, 192 reviews

A comfortable living area features a leather sofa and two watching chairs surrounding a central coffee table. Natural light enters through multiple windows, and a flat-screen television is mounted on the wall. A small dining table for two and a corner desk add functional elements.

Apartment in Barrie

Cozy 2 bedroom Apartment

FamilyValueCheckout

4.86 out of 5 average rating, 138 reviews

A modern living space features a comfortable couch positioned in front of a wall-mounted television. A dining area with sleek white chairs is visible, along with a cozy bed beyond a sliding door. Natural light is softly illuminated by recessed lighting.

Apartment in Barrie

The Chieftain Suite

ValueLocationComfort

Private apartment rentals

4.79 out of 5 average rating, 269 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.

Apartment in Meaford

Birch & Bannock UNIT 2

LocationValueAir conditioning

4.98 out of 5 average rating, 40 reviews

Apartment in Dundalk

Cozy Dundalk Stay |Basement Suite w/ Side Entrance

ValueLocationBathroom

4.97 out of 5 average rating, 69 reviews

Renovated 2BR Suite, Walk to Downtown Collingwood

FamilyValueBathroom

4.67 out of 5 average rating, 15 reviews

Apartment in Flesherton

Cozy Retreat Near Eugenia Falls

LocationComfortGetting around

4.91 out of 5 average rating, 57 reviews

Blue Mountain Studio, 2 Queen Beds, Lake Huron

FamilyValueHospitality

5.0 out of 5 average rating, 84 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.

Apartment in Erin

Country Getaway in Erin

FamilyLocationCheck-in

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, 54 reviews

Grandpa Jake's

FamilyValueOutdoor spaces

5.0 out of 5 average rating, 9 reviews

Apartment in Clifford

Small Town Charm II - Elevated

LocationHospitalityAccuracy

Apartment rentals with a hot tub

4.86 out of 5 average rating, 142 reviews

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.

Apartment in Owen Sound

One bedroom apartment on the river, with hot tub

LocationFamilyBiking

Apartment in Horseshoe Valley

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.

4.84 out of 5 average rating, 123 reviews

Spacious Hideaway in Nature

LocationFamilyLaundry

4.68 out of 5 average rating, 102 reviews

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.

Apartment in Arthur

*HOME FOR NOW - Ground level apartment no stairs!

ValueFamilyIndoor spaces

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

LocationFamilyComfort

5.0 out of 5 average rating, 40 reviews

Apartment in Oro-Medonte

On the Fifth - Basement Apartment in the Country.

ValueFamilyDecor

4.96 out of 5 average rating, 78 reviews

A charming wooden structure is set against a backdrop of lush greenery. A bright red door serves as a focal point, complemented by a large deck with outdoor seating. Flowering plants and trees enhance the serene environment, creating a welcoming arrival space.

Apartment in Mono

Guest Suite in Hockley Valley

LocationFamilyAccuracy

4.8 out of 5 average rating, 40 reviews

Nordic Nook - Pool & Shuttle with Patio

FamilyLocationCleanliness