Apartment vacation rentals in Grey Highlands

4.96 out of 5 average rating, 449 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

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.

4.97 out of 5 average rating, 213 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 * Pull Out Sofa * Stone Fireplace * Modern, Stylish Decor *please note there is not a traditional oven- there is a microwave/convection oven combo along with a stove top *Shuttle Service *Year Round Hot Tub *Pool (closed for the winter season- to reopen Spring '26) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

4.98 out of 5 average rating, 110 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.

Apartment 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!

4.97 out of 5 average rating, 106 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.

Apartment in Owen Sound

Private with Self Check-in Bright & Modern Comfort

License: STR2025-9250261010 Welcome to our bright and clean one-bedroom suite ideal for singles, couples, or small families. Walking distance to the Bruce Trail, a short drive to parks, beaches, and lakes; and a good home base to explore the Bruce Peninsula and Tobermory. A comfortable queen size bed in the bedroom with a selection of bedding and pillows. Fully equipped kitchen, modern bathroom, full suite of TV streaming with high-speed internet. Residential area on the west side of town.

Apartment in Penetanguishene

The historic Beck House, a striking Victorian structure, stands with a distinctive red façade and slate roof. A spacious porch with white railings invites guests, while the well-kept lawn adds to its charm. A wooden sign identifies the property, blending history with a warm welcome.

4.89 out of 5 average rating, 525 reviews

The Haunted House Apt 302

As you pull into the driveway this 1885 Victorian towers above you, your mouth drops in awe of the size. Up the porch to enter a small front door, a dimly lit winding staircase creaks as you ascend to 3rd floor. Original architecture painted many times over oozes with history. 70 years ago the house was turned into apartments, unloved for many of those years, time has definately taken its tole, yet to the spirits within, their big old house still stands proud and distinguished in all its glory.

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, 321 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 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.

4.8 out of 5 average rating, 255 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

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 free on-site parking and a universal EV charger for those who may require it.

4.93 out of 5 average rating, 129 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.

Apartment in Wasaga Beach

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.

4.95 out of 5 average rating, 486 reviews

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.

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, 361 reviews

Studio at Blue-KingBed/Pool/HotTub/Shuttle

Welcome to our studio unit in the mountainside North Creek Resort! *King bed *sofa bed-double sized memory foam mattress *SMART TV, High-Speed Rogers Ignite WIFI and TV *Cookware, Utensils and Keurig *freshly painted *remodeled washroom Property Features: *Shuttle Service *Year Round Hot Tub *Pool (closed for the winter season- to reopen Spring '26) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

4.95 out of 5 average rating, 183 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

Small-town charm at its best! Our centrally located apartment is the perfect home base for your small-town adventures. We're minutes from the unique shops and restaurants in downtown Midland and the Midland Harbour. There is plenty to experience; attend a local festival, take in a tourism site, hop onto the Trans Canada Trail System with your bike or snowmobile, attend a show/concert at the Midland Cultural Centre, or snowshoe through the Wye Marsh.

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, 158 reviews

Alpine Bliss: King Bed/Pool/HotTub/Shuttle

Newly renovated studio unit at the mountainside North Creek Resort featuring: * King Bed * SMART TV, High-Speed Rogers Ignite WIFI and TV * Double Pull Out Sofa * Remodeled Washroom *Equipped Kitchen with Keurig * Modern, Stylish Decor *Shuttle Service *Year Round Hot Tub *Pool (closed for the winter season- to reopen Spring '26) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)!

Popular amenities for Grey Highlands apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.99 out of 5 average rating, 111 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.

Apartment in Alcona

Spacious Apartment 5 Minute Walk to Innisfil Beach

4.95 out of 5 average rating, 22 reviews

Apartment in Dundalk

Cozy Dundalk Stay |Basement Suite w/ Side Entrance

5 out of 5 average rating, 64 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.

Apartment in Owen Sound

The Roamin' Donkey

4.86 out of 5 average rating, 7 reviews

Apartment in Flesherton

Cozy Retreat Near Eugenia Falls

5 out of 5 average rating, 45 reviews

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.

Apartment in Collingwood

Grandpa Jake's

4.95 out of 5 average rating, 20 reviews

A cozy living area is furnished with a gray sofa, a wooden coffee table, and a small circular side table. A dining table with black chairs is positioned near large windows, allowing natural light to brighten the space. Decorative plates are displayed on the wall.

Apartment in Meaford

The Olde Hotel Suite 2

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.

4.81 out of 5 average rating, 107 reviews

Gorgeous Studio Condo in Blue Mountains Sleeps 4

5 out of 5 average rating, 22 reviews

Apartment in Southgate

Country Escape in Southgate

Private apartment rentals

5 out of 5 average rating, 26 reviews

Apartment in King City

The King's Rest

5 out of 5 average rating, 55 reviews

A well-furnished living area features a soft gray couch with decorative cushions, flanked by two light-colored armchairs. A wooden coffee table sits at the center, adorned with a decorative piece. Two lamps provide gentle lighting, enhancing the tranquil atmosphere.

Apartment in Coldwater

Cozy in Coldwater

4.96 out of 5 average rating, 54 reviews

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.

Apartment in Collingwood

Stylish Private Suite

4.94 out of 5 average rating, 78 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

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, 72 reviews

Gorgeous Two Bedroom Condo Overlooking Ski Hill

Apartment in Penetanguishene

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.

4.88 out of 5 average rating, 33 reviews

Guest suite near the lake

4.97 out of 5 average rating, 62 reviews

A cozy retreat is partially hidden among snow-covered trees, showcasing a charming wooden structure with expansive balconies. A guest can be seen sitting on a chair, surrounded by the serene winter landscape, with trees blanketed in fresh snow adding to the tranquil atmosphere.

Apartment in Mono

Guest Suite in Hockley Valley

Apartment in Georgian Drive

4.93 out of 5 average rating, 60 reviews

2BR Main-Floor · w/ Parking · Near Hwy 400 & RVH

Apartment rentals with a hot tub

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!

Apartment in Horseshoe Valley

A modern building featuring large glass windows overlooks a refreshing pool. The pool is surrounded by a stone patio, and picnic tables are positioned nearby for comfortable outdoor seating. A life-saving ring is visible on the side of the pool for safety.

4.87 out of 5 average rating, 61 reviews

Large Resort Studio Suite Near Horseshoe

5 out of 5 average rating, 3 reviews

Forest-view retreat with direct patio access

A modern kitchen features sleek appliances, ample counter space, and cabinetry, creating an inviting cooking area. An expansive outdoor pool area is surrounded by lounge chairs, providing a relaxed atmosphere. The marina glows with lights, showcasing boats and waterfront amenities, encapsulating serene evenings by the water.

4.94 out of 5 average rating, 16 reviews

1BR Friday Harbour Retreat | Balcony + Pool Access

4.89 out of 5 average rating, 38 reviews

SerraVista - Outdoor Pool / Walk to Village

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.

4.61 out of 5 average rating, 386 reviews

The Perfect Getaway in Renovated Corner Unit

A contemporary living space features a spacious sofa with cozy blue pillows set against large windows. A round coffee table rests on a patterned rug, and stylish dining chairs surround a kitchen island in the open-concept design.

4.95 out of 5 average rating, 56 reviews

NEW Luxurious Corner Unit at Friday Harbour Resort