Apartment holiday rentals in Grey Highlands

4.98 out of 5 average rating, 104 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!

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.

4.95 out of 5 average rating, 130 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.

A welcoming exterior view features a large, charming house with yellow siding and a brown roof. The entrance is adorned with colorful flower pots filled with vibrant plants, and a well-maintained pathway leads to the front door. Lush greenery surrounds the property.

4.93 out of 5 average rating, 111 reviews

Private, spacious 3 bedroom flat.

Also available for seasonal winter ski rental, private 1300sff flat, with very comfortable beds and linens. Living area has lazy boy sofas for comfort. Parking for 2 vehicles max during evening hours, with a large, private mudroom to store skis or bikes safely. Located above our residence and flower studio. Minutes from skiing, golfing, and the longest freshwater beach in the world. Walk into Collingwood downtown for fantastic shopping, restaurants, brew houses, pubs, entertainment and more.

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.

4.9 out of 5 average rating, 163 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.

4.79 out of 5 average rating, 245 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

Spend the day exploring and come home to this fully equipped space to relax. Located steps from the beach and trails, and close to the centre of town, great restaurants, Meaford Hall, Bruce Trail and skiing. We love dogs! There's a fenced in dog park and a leash free beach steps from our place . That same park and its trails are leash free from November - April. For peace of mind and convenience, we provide a universal EV car charger. Public charging stations are not available in Meaford.

4.96 out of 5 average rating, 313 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 next to the Bruce Trail. Close to Shelburne, Mansfield, Creemore, and many excellent restaurants (like The Globe and Mrs Mitchels). Only 40 minutes to the Scandinave Spa, Collingwood, Blue Mountain, and Wasaga Beach. Golf Courses are close by. A perfect retreat just north of Toronto.

4.93 out of 5 average rating, 109 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, 464 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.

4.98 out of 5 average rating, 259 reviews

A modern living area features a sleek gray sofa flanked by decorative pillows. A glass coffee table sits atop a circular patterned rug, with decorative items placed on it. Natural light enters through two windows dressed with sheer curtains, while a door leads to another room.

Flat in Shelburne

A&M Cozy Home Away From Home

Bring the whole family to this great place with lots of room for fun. Guests can enjoy this beautiful modern 2 bdrms with queen size beds, legal/separate entrance apartment equipped with kitchen appliances, microwave, stove, dishwasher, fridge, toaster, coffee maker, pots, plates, utensils, separate laundry. Equipped with your comfort in mind. It offers shampoo, conditioner, body wash, towels, keyless entry. Ignite TV premier PKG, Netflix, free 500 mbps Wifi.

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.

4.99 out of 5 average rating, 179 reviews

Evergreen Studio-KingBed/Pool/HotTub/Shuttle

Renovated studio unit at the North Creek Resort featuring: * King Bed * SMART TV, High-Speed Rogers Ignite WIFI and TV * New Pull Out Sofa * Stone Fireplace * Modern, Stylish Decor *please note there is not a traditional oven- there is a microwave/convectional oven combo along with a stove top *Shuttle Service *2 Year Round Hot Tubs *Pool *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

4.95 out of 5 average rating, 161 reviews

A cozy living room features a teal sofa, a brown armchair, and a wooden television stand. A flat-screen TV is mounted on the wall. A patterned area rug covers the hardwood floor, while a coffee table with a geometric design sits in the center. Natural light enters through a window.

Flat in Owen Sound

Suite on the Creek

Keep it simple at this peaceful and centrally located walkout apartment. The suite backs onto the Niagara escarpment and sections of the Bruce Trail. Though you’ll feel secluded in nature, head out front and you can walk downtown in less than 15 minutes. Rest well in the king-sized bed that looks out onto the walking bridge in the back yard. Enjoy cozy evenings in with a movie and a fire, or relax with a book in your private backyard sitting area.

The bedroom features a queen size bed with light blue and white bedding, complemented by a decorative pillow. Natural light enters through windows, illuminating the space. A mirror and coastal-themed artwork enhance the calming decor, while a doorway leads to a separate living area.

4.87 out of 5 average rating, 231 reviews

1BR Boutique Suite #4 - 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. No parties or events

Popular amenities for Grey Highlands apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

5 out of 5 average rating, 96 reviews

The kitchen area features modern appliances including a stainless steel refrigerator and oven. A marble island is complemented by two metal bar stools. A woven wall hanging adds texture, and various kitchen items are neatly arranged, providing a functional and inviting space.

Flat in Alcona

Spacious Apartment 5 Minute Walk to Innisfil Beach

A bright living area features a brown leather sofa and a dark coffee table on a patterned rug. An adjacent dining space includes a small table and chairs. Natural light enters through a door leading to an outdoor deck, enhancing the welcoming ambiance.

4.97 out of 5 average rating, 37 reviews

Stylish Private Suite

5 out of 5 average rating, 58 reviews

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.

Flat in Owen Sound

The Roamin' Donkey

4.91 out of 5 average rating, 54 reviews

A spacious dining area features a wooden table surrounded by upholstered chairs. Natural light fills the room through large windows, highlighting the modern décor and vaulted ceiling. A comfortable seating area with a couch and armchair sits adjacent, creating an inviting open-plan layout.

Flat in Orangeville

A bright & chic 2 bedroom urban apartment

4.97 out of 5 average rating, 94 reviews

The exterior of a green-grey one-story apartment is visible, featuring a private entrance and wooden steps. Large windows allow natural light to illuminate the space, while fallen leaves frame the walkway. A small shrub is positioned beside the entrance, enhancing the inviting appearance.

Flat in Owen Sound

Private with Self Check-in Bright & Modern Comfort

5 out of 5 average rating, 69 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

5 out of 5 average rating, 50 reviews

A bright bedroom features a spacious, inviting bed adorned with soft white linens. A tray holding a book, a candle, and glasses of wine rests on the bed. Framed photographs of coastal scenes hang above the headboard, complemented by a lamp casting a gentle glow.

Flat in Midland

Hidden Gem

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 out of 5 average rating, 31 reviews

Grandpa Jake's

Private apartment rentals

5 out of 5 average rating, 15 reviews

A view along a gravel path is captured from the perspective of a horse. Lush green grass lines the pathway, leading towards a distant barn framed by trees. The sky is dotted with fluffy white clouds, creating a serene backdrop for the countryside setting.

Flat in Orangeville

Charming 1 bdrm + den on a beautiful horse farm.

Skiers are seen on a ski lift ascending a snowy slope, surrounded by frosted trees glistening in sunlight. The lift chairs are black, suspended above a white winter landscape, with snow covering the ground and branches of surrounding trees.

4.6 out of 5 average rating, 380 reviews

The Perfect Getaway in Renovated Corner Unit

4.93 out of 5 average rating, 30 reviews

A wooden deck area is featured, with a dark door framed by large windows. The brick wall displays a warm texture, and decorative elements can be seen near the door. Sunlight reflects off the glass, providing a bright ambiance.

Flat in Paisley

Walnut Grove Guest Suite

4.86 out of 5 average rating, 28 reviews

A spacious outdoor deck is illuminated by soft lights, featuring a wooden seating area and a small round table. Surrounding greenery provides a natural backdrop, enhancing the serene environment. The deck invites relaxation and outdoor gatherings.

Flat in Penetanguishene

Guest suite near the lake

A modern living area is presented with a light-colored sofa and a cozy blue armchair. A coffee table adorned with flowers centers the space, while built-in shelves display decorative items and a television is mounted on the wall. Soft light filters through the windows, enhancing the serene atmosphere.

4.95 out of 5 average rating, 20 reviews

Perfect 2 bedrm resort style unit Getaway-Top Host

4.83 out of 5 average rating, 30 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 Apartment

4.78 out of 5 average rating, 55 reviews

A small kitchen area features a table with two chairs and a potted plant. Cupboards and a countertop provide space for food preparation. A microwave and sink are visible, contributing to the functional design of the space.

Flat in Hanover

A home away from home

4.95 out of 5 average rating, 96 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.

Apartment rentals with a hot tub

A cozy living area features a comfortable sofa facing a mounted flat-screen TV, complemented by a fireplace beneath. Large windows with sheer curtains provide natural light and an outdoor view. A small dining table is visible on the patio, enhancing the space.

4.64 out of 5 average rating, 496 reviews

Hidden Gem Escape at Blue Mtn @Great Rates@

4.88 out of 5 average rating, 34 reviews

SerraVista - Outdoor Pool / Walk to Village

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 out of 5 average rating, 55 reviews

Gorgeous Two Bedroom Condo Overlooking Ski Hill

A modern living area features a gray sofa adorned with decorative pillows, accompanied by a glass coffee table and a patterned area rug. Wall shelves display decorative items and potted plants, adding a fresh touch to the muted backdrop.

4.98 out of 5 average rating, 44 reviews

Trendy 1 Bdrm w/Pool & Hot Tub View

4.96 out of 5 average rating, 47 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.

Flat in Mono

Guest Suite in Hockley Valley

A modern living area features a large wall-mounted TV and a stylish black accent wall. Two small coffee tables in front of a comfortable sofa are complemented by decorative items. Natural light streams in through the sliding glass doors, which lead to the balcony.

4.92 out of 5 average rating, 131 reviews

Modern Condo at Friday harbour/Pet Friendly

A modern living space features a sleek television mounted above a stylish wooden media console with drawers. A comfortable chair with a cushion is positioned nearby, complemented by a small potted tree. Natural light fills the area through large windows.

4.92 out of 5 average rating, 50 reviews

Beautiful 2 Bed/2 Bath Condo, Private Balcony

A spacious bed is centered within the room, adorned with patterned throw pillows and a soft blanket. Nightstands with lamps flank the bed, providing balanced lighting. A peaceful artwork featuring a cow hangs above the headboard, complemented by a plant on the side.