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, 208 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)

4.97 out of 5 average rating, 104 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.

4.9 out of 5 average rating, 130 reviews

A modern kitchen features natural wood cabinetry and a large marble countertop island with seating. Stainless steel appliances, including an electric stove and refrigerator, are visible. The space is well-lit with recessed lighting, and decorative plants add a touch of warmth.

Apartment in Midland

Loft By The Bay

Welcome to our charming second storey apartment in downtown Midland, Ontario. This cozy space features a bedroom, office with futon, full kitchen, bathroom, laundry, and a bright open concept living area. Enjoy easy access to local shops, restaurants, and attractions. Explore the picturesque waterfront and nearby hiking trails. Retreat to this comfortable and inviting apartment after a day of work or play. Book your stay today for a convenient, comfortable, and memorable experience in Midland.

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, 178 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.

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, 254 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, 128 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.

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.

4.84 out of 5 average rating, 271 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

4.98 out of 5 average rating, 274 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.

Apartment 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.

The living area features a sectional couch positioned near a small white coffee table, creating a comfortable gathering space. A doorway leads to a staircase, while a kitchenette is visible in the background. Natural light enters through a nearby window, enhancing the neutral decor.

4.77 out of 5 average rating, 394 reviews

Hotel Style Freshly painted;1 Bdrm; Pull-out coach

Come stay at this all-season built 2019, private & modern guest suite close to all Innisfil has to offer! 1 km on 6th line away from Lake Simcoe , Big Cedar Golf Course, Ic finshing & minutes away from all major Ski hills in Barrie! Enjoy summer activities such as multiple beaches, boating/marinas, golfing & fishing- all within walking range. Enjoy winter activities such as skiing, snowboarding and very special ice fishing spot at the end of the road.

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, 148 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

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, 509 reviews

Hidden Gem Escape at Blue Mtn @Great Rates@

4.95 out of 5 average rating, 22 reviews

Apartment in Dundalk

Cozy Dundalk Stay |Basement Suite w/ Side Entrance

4.92 out of 5 average rating, 115 reviews

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.

Apartment in Collingwood

Private, spacious 3 bedroom flat.

4.89 out of 5 average rating, 38 reviews

SerraVista - Outdoor Pool / Walk to Village

4.95 out of 5 average rating, 88 reviews

A sleek bathroom features a modern vanity with a vessel sink and polished faucet. Clean white tiles adorn the walls, complemented by a spacious walk-in shower. Minimalist accents include a framed decorative piece and neatly arranged white towels on shelves.

Apartment in Orangeville

A bright & modern urban studio

5 out of 5 average rating, 4 reviews

Apartment in Flesherton

Cozy Retreat Near Eugenia Falls

5 out of 5 average rating, 43 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

4.77 out of 5 average rating, 56 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.

Apartment in Hanover

A home away from home

Private apartment rentals

A light-filled living area is furnished with a plush sofa adorned with decorative cushions. A round coffee table sits in the center, accompanied by stylish accent chairs. Natural elements are present, such as a potted plant and woven decorative items, enhancing the serene ambiance.

4.83 out of 5 average rating, 35 reviews

Oasis of luxury: 1 bdrm retreat w/Hot Tub Access

4.95 out of 5 average rating, 21 reviews

Apartment in Barrie

Modern apartment in Barrie, Ontario

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

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.

4.93 out of 5 average rating, 14 reviews

1BR Friday Harbour Retreat | Balcony + Pool Access

4.91 out of 5 average rating, 32 reviews

A modern kitchen is displayed, featuring sleek white cabinets and dark granite countertops. Illuminated by pendant lights, the space includes a double sink and an island with seating. Stainless steel appliances and a mosaic backsplash add to the contemporary design while maintaining an organized feel.

Apartment in Barrie

Clean, bright and cozy walkout basement

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, 67 reviews

Gorgeous Two Bedroom Condo Overlooking Ski Hill

4.94 out of 5 average rating, 72 reviews

A modern kitchen and dining area are depicted, featuring stainless steel appliances, a wooden dining table with six chairs, and a cozy red couch. A white coffee table lays in front of the couch, and light streams in from an adjacent space.

Apartment in Harriston

Lovely 1 bedroom apartment in Harriston

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, 32 reviews

Guest suite near the lake

Apartment rentals with a hot tub

4.79 out of 5 average rating, 38 reviews

PS5 * Pool * Hot Tub * Fire Pit

4.86 out of 5 average rating, 59 reviews

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.

Apartment in Oro

Large Resort Studio Suite Near Horseshoe

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, 383 reviews

The Perfect Getaway in Renovated Corner Unit

4.91 out of 5 average rating, 23 reviews

A spacious living area is presented with a comfortable sectional sofa facing a wall-mounted television. Natural light enters through the window, enhancing the neutral color palette. A dining table is visible in the foreground, complemented by a cozy fireplace and decorative elements.

Apartment in Shanty Bay

Stylish 1 bedroom Pet friendly Condo by Sage Homes

An outdoor seating area is furnished with a large sectional sofa and a table, providing a comfortable space for relaxation. The balcony overlooks a pool surrounded by greenery and modern buildings, offering a serene view of the outdoor amenities.

4.98 out of 5 average rating, 40 reviews

Modern Luxury Delight with a Pool and Hot Tub

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.

4.93 out of 5 average rating, 55 reviews

Trendy 1 Bdrm w/Pool & Hot Tub View

4.97 out of 5 average rating, 58 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

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.