Apartment holiday rentals in Midland

4.96 out of 5 average rating, 324 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.

Flat in Blue Mountain Resort Area

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, 221 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 (Scheduled to open Fri May 8 2026- Tues Oct 13 2026) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

4.98 out of 5 average rating, 112 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!

4.89 out of 5 average rating, 530 reviews

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.

Flat in Penetanguishene

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.

4.91 out of 5 average rating, 138 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.

Flat 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.

4.95 out of 5 average rating, 420 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

Lovely suite with its own 3 piece bathroom, living room with flat screen TV and kitchenette. Has its own deck, barbecue and entranceway overlooking the sandy shores of Georgian Bay. Steps to go swimming, kayaking or a sunset stroll. Parking available. No pets. Between June 30th - September 1st the apartment can only be rented by the week (check in & check out on Saturdays only). Outside of these dates, we are happy to host visitors with a minimum 1 night stay, check in/out any day of the week.

4.99 out of 5 average rating, 102 reviews

A charming two-story house is captured against a clear blue sky. The exterior features horizontal grey siding, wooden accents, and a balcony above the entrance. A stone facade frames the lower part of the structure, while a garage door adds to the home's appeal.

Flat in Penetanguishene

By The Bay spacious one bedroom

This unique place has a style all its own and only steps away from , beaches , water front dining and theater! With all the amenities of home you'll be comfortable to stay for the weekend or extended stays. Fully equipped kitchen with convection oven , dishwasher , microwave, keurig coffee maker and built in washer/ dryer . Spacious bathroom with an over sized walk in shower . And to end the day enjoy the full sized bed room and closet to unpack luggage with a queen size Endy foam mattress .

4.95 out of 5 average rating, 489 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.

4.94 out of 5 average rating, 109 reviews

Muskoka Get Away-Romance & Adventure Awaits !!!

Newly renovated KING SIZE Cozy, Romantic & Stylish. Ideal for long term stays. Grab a book and curl up into the big comfy swing chair by the fireside of the chiminea on your private patio. Start your day off with a Nespresso in the outdoor lounge area surrounded by lush forest and all the nature your eyes & ears can behold. Grab a snack or whip up a gourmet meal in your fully equipped kitchen. And then at days end stretch out onto your very own King size sleigh bed!

Flat in Blue Mountain Resort Area

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, 371 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 (Scheduled to open Fri May 8 2026- Tues Oct 13 2026) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

A hot tub is positioned on a wooden deck, surrounded by natural greenery. Nearby, a fire pit emits a warm glow, creating a cozy atmosphere. Soft outdoor lighting complements the setting, with views of the landscape visible in the background.

4.98 out of 5 average rating, 413 reviews

The Muskoka River Chalet - The King's Den

Welcome to Muskoka River Chalet! **Please read full listing description before booking.** Relax in your fully private one-bedroom walkout apartment with private kitchen, cozy living room, featuring smart TVs and toasty fireplaces. Explore our shared outdoor spaces along 60' of waterfront. Indulge in the hot tub for relaxation. Just minutes walking to town for shopping, dining, and nightlife. Book now for a perfect blend of comfort and convenience!

A modern living area features a gray sectional sofa adorned with yellow cushions. A light wood coffee table is positioned in front. The kitchen bar area with high stools is visible, complemented by sleek cabinetry. Large glass doors provide access to the outdoor patio.

4.87 out of 5 average rating, 123 reviews

Aquarius bldg @ Friday Harbour 1st fl 2 bdr/2 bath

Main floor 2 bdr 2 bath condo in Aquarius building 825 sq. ft of indoor space. With a seasonal pool available . Enjoy a luxurious stay at an all season resort at Friday Harbour. We are Steps away from marina, beach, boardwalk, trails and more. Plenty of outdoor activities to enjoy all year round. Our fully furnished condo is ready for you and your guests to enjoy. Outdoor patio to catch fresh air & a cozy, stylish indoor space to unwind and enjoy.

Popular amenities for Midland apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

An open-plan living space features a modern kitchen island with a sleek countertop. Natural light brightens the area through large windows, illuminating the stylish seating arrangement, which includes wooden chairs and a patterned rug. A flat-screen television is positioned against a wall.

4.88 out of 5 average rating, 40 reviews

Friday Harbour - Aquarius Penthouse Escape (2B/2B)

4.92 out of 5 average rating, 12 reviews

Cozy Private Basement Suite in quite neighbourhood

Superhost

4.76 out of 5 average rating, 21 reviews

Cozy 2BR Barrie Suite | Fire Pit + Lake Nearby

5 out of 5 average rating, 21 reviews

Wynwood Suites Unit 3, located on Lake Muskoka

A modern kitchen is visible, featuring stainless steel appliances and light gray cabinetry. A dining table with wooden chairs is positioned in the foreground, surrounded by a cozy sofa adorned with patterned cushions. Natural light pours in from a nearby window, enhancing the space's welcoming feel.

4.95 out of 5 average rating, 43 reviews

Cosy Apartment Downtown Barrie

4.96 out of 5 average rating, 24 reviews

A cozy bedroom features a spacious bed adorned with patterned bedding. A wooden dresser is positioned nearby, and a lamp provides soft lighting. Natural light filters through the window, which is dressed with dark curtains, and rustic wooden walls contribute to the cabin's charm.

Flat in Tiny

Cabin A in Wymbolwood Lodge

5 out of 5 average rating, 38 reviews

A serene lakeside view is presented at dusk, showcasing a calm water surface reflecting moonlight. Stone pathways wind through the lawn, leading to seating areas by the water. Surrounding trees and distant lights from across the lake create a peaceful atmosphere.

Flat in Washago

Little slice of heaven!

4.9 out of 5 average rating, 67 reviews

A verdant outdoor space highlights a fire pit surrounded by rustic benches, set against a backdrop of lush greenery. A pathway leads towards a serene lake, partially obscured by water lilies, with a private dock extending into the water.

Flat in Coldwater

Sanctuary in the Woods

Private apartment rentals

4.94 out of 5 average rating, 160 reviews

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.

Flat in Collingwood

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

5 out of 5 average rating, 31 reviews

Tranquil Forest Oasis

4.97 out of 5 average rating, 58 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.

Flat in Collingwood

Stylish Private Suite

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.

4.93 out of 5 average rating, 83 reviews

Myra's Cozy Place in Barrie

A cozy sleeping area is featured, with a spacious queen bed centered against the wall. Nightstands with modern lamps flank the bed, and a decorative wall piece adds a touch of character. Soft, ambient lighting enhances the serene atmosphere of the room.

5 out of 5 average rating, 22 reviews

Queen Bed Suite-Private Entrance

Superhost

4.67 out of 5 average rating, 9 reviews

Sunseeker Friday Harbour • Luxury 2BR Ground Floor

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.

Flat in Collingwood

Grandpa Jake's

A comfortable seating area is arranged with a large sectional sofa and an armchair. A coffee table sits in the center, and a TV is placed on a low stand. Natural light enters through a window, complemented by a wall art piece and a decorative shelf.

4.99 out of 5 average rating, 99 reviews

Dog Friendly Bracebridge Suite

Apartment rentals with a hot tub

5 out of 5 average rating, 23 reviews

Flat in Oro-Medonte

On the Fifth - Basement Apartment in the Country.

A cozy seating area features a sofa and two matching armchairs, all with a multicolored tribal pattern. A small wooden coffee table is centrally placed on a textured area rug. Natural light enters through a window set in a triangular wall, highlighting the wooden accents.

4.97 out of 5 average rating, 29 reviews

Muskoka Loft

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, 17 reviews

1BR Friday Harbour Retreat | Balcony + Pool Access

Flat in Blue Mountain Resort Area

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, 76 reviews

Gorgeous Two Bedroom Condo Overlooking Ski Hill

A modern kitchen features sleek cabinetry and stainless steel appliances, including an oven and refrigerator. A large island with seating for four is present, complemented by a minimalist design. Soft lighting illuminates the space, enhancing the clean lines and organized layout.

4.97 out of 5 average rating, 39 reviews

Fantastic 1 Bdrm With A View.

4.95 out of 5 average rating, 87 reviews

A wooden deck features two lounge chairs positioned under a white pergola. Lush greenery surrounds the area, providing a sense of privacy. The entrance to the apartment is visible in the background, alongside a short staircase leading up to the entryway.

Flat in Orillia

Cedar-View Studio with Hot Tub+ PlayStation Gaming

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.