Ski-in/Ski-out holiday rentals in Barrie

4.87 out of 5 average rating, 128 reviews

An A-frame house featuring a white exterior and a steep roof stands beside a serene lake. A gravel driveway leads to the entrance, surrounded by greenery. Large windows allow ample natural light, providing views of the lake and trees in the background.

Home in Little Lake

Lakefront detached house on the little lake

♥️an unique, lovely elf house in front of the little lake. Here you’ll find a unique hideaway in the middle of the city Barrie with gorgeous lake views as far as the eye can see. ♥️ Only one hour drive from Toronto. Walking distance to everywhere (shoppers,restaurants, cinemas….) ♥️This home including new furniture, microwave, coffee maker, washing machine and all other appliances ! Walk out the back door and be greeted by our updated dock where you can fish for pike, perch, pickerel and bass.

4.83 out of 5 average rating, 113 reviews

A spacious living area features a comfortable tan sofa and modern black dining chairs surrounding a circular table. A gas fireplace and television are positioned against a light stone wall, while large windows allow natural light to fill the room. Decorative elements include a floor plant and a wine display.

Townhouse in Shanty Bay

Ravine Backyard, King Bed, Jacuzzi, Pool, Hot Tub

Forget your worries in this spacious and serene space at Highland Estates. You get a full designer suite perfect for couples, equipped with a King Sized Bed, and a Jacuzzi for romantics. Prepare your own meals in the fully equipped kitchen with Microwave and Electric Stove. Access your favorite Streaming-TV accounts like Netflix, Prime, and Disney+ Close to Vetta Spa and major Ski Hills; literally the Best Retreat in Oro-Medonte. Book with Us Today! Please note the Fireplace isn't working.

4.99 out of 5 average rating, 114 reviews

An open concept living area features rustic wood beams and sliding barn doors. Comfortable wicker chairs are paired with a wooden coffee table, while a cozy sofa adds to the inviting space. The modern kitchen is visible in the background, creating a seamless flow.

Guest house in Mansfield

Brookside Cottage - Charming Rural Getaway Mulmur

Our cozy guest house, situated in the Headwaters region, has it all! Close to hiking,golfing,biking,skiing. XCski/snowshoe from your door! Big skies for astronomers and astrophotography! We offer 32 acres of forest and fields for walking and taking in the magnificent views. The area boasts fine restaurants, boutiques, markets and artisans. Minutes to Mono Cliffs, Boyne, Mansfield Ski Club and easy driving to Blue Mountain and Wasaga Beach. Ideal for couples, solo adventurers or a small family.

4.95 out of 5 average rating, 128 reviews

Home in Collingwood

Driftwood on 6th Heritage Downtown Collingwood

Welcome to Driftwood on 6th. A pet friendly unique & tranquil space like none other, nestled in the heart of famous heritage downtown Collingwood. Fully renovated boutique hotel inspired century home with all the modern amenities.4bedrooms.1 king,2 queen,1 double.Each bedroom has a unique decor. Fully equipped kitchen with upgraded appliances.Vintage & modern art through out.Large outdoor space, for lounging.Discover unique shops,restaurants & bars walking distance from this historic property.

5 out of 5 average rating, 11 reviews

A welcoming living area is highlighted by comfortable seating arrangements, including a sofa and two armchairs. A round coffee table sits in the center, surrounded by a soft area rug. A mounted television is above a modern fireplace, with natural light filtering through the windows.

Home in Barrie

Luxurious and Beautiful, Barrie

Welcome to our cozy retreat in Barrie, Ontario, just a short walk from the beautiful waterfront and popular beaches. Our home is perfect for a relaxing getaway or an adventurous weekend, offering modern amenities, a fully equipped kitchen, and a spacious outdoor patio in a quiet, family-friendly neighborhood. Our retreat offers year-round appeal, with activities like beach days in summer and skiing in winter. With free parking and easy access, we’re excited to host your unforgettable stay!

4.82 out of 5 average rating, 22 reviews

Home in Angus

The Angus Nest

Enjoy this bright and open space that features a master suite with a jacuzzi, cozy family room with a fireplace, and a fully equipped kitchen with modern appliances, and laundry room. Stay entertained with high-speed internet and a smart TV, and take advantage of the spacious deck. Four parking spots available extra spot if needed. Whether you're planning a family vacation, a ski trip, or a peaceful retreat, our home is the perfect place to relax and unwind. Book your stay today!

4.83 out of 5 average rating, 64 reviews

A row of charming units features gabled roofs and inviting porches, framed by colorful trees and well-maintained landscaping. The path leads towards the units, which are complemented by lush lawns and seasonal foliage.

Flat in Shanty Bay

Gym+Pool+PetFriendly+KingBeds

Located just about 1.5 hours North of Toronto, this is the place you'll want to be. In an area where most units are similar, what makes this property unique is all the extra things we add to ensure you'll taken care of. Whether you aim to ski, hit golf at one of eighteen golf courses, mountain bike or hike in several landscape trails, soak in the healing experience of Vetta Nordic spa, or simply relax at the tranquility of the area, this place is simply yours to enjoy!

The marina at twilight features calm waters reflecting the vibrant colors of the sunset. Multiple boats are docked along the well-lit marina, with modern buildings lining the shore, creating a serene and inviting atmosphere.

4.94 out of 5 average rating, 88 reviews

Luxury Getaway @ Friday Harbour Condo at Marina

Book your accommodations with us & enjoy the prestigious FH Resort. FH wasn’t designed to be a place. It was designed to be a destination. Were you can unwind, disconnect & reconnect all your senses with the healing powers of the forest & beautiful sunsets, truly feel relaxed. Whether you come to take in the peaceful serenity of the lake, spend hours in the Nature Preserve or mingle with friends over a gourmet meal, there’s no shortage of ways to enjoy your days."

Place to stay in Oro Station

A serene winter landscape is depicted with the sun shining through bare trees. Snow blankets the ground, creating a tranquil atmosphere, while long shadows from the trees stretch across the snow-covered forest floor.

4.96 out of 5 average rating, 105 reviews

The Bunkie- A Cozy Modern Escape

Our cozy, modern Bunkie is nestled in a secluded forest setting with access to local trails and attractions. Whether you are seeking relaxation, adventure or exploration - this beautiful, four season destination will not disappoint. The bunkie has ski in ski out/ ride in ride out access to the Trails at Hardwood Ski and Bike for those who are interested. Trail passes are required, and available at a discount when staying at the bunkie. Contact us for more info.

5 out of 5 average rating, 12 reviews

The exterior of a spacious cottage is displayed, surrounded by lush green grass and trees. Large windows provide ample natural light to the interior, while a stone pathway leads to the entrance. The multi-level structure features a red roof and earthy stone accents.

Cottage in Utopia

Simcoe Cottage + Hot Tub + Sauna + Private Retreat

Welcome to your own private cottage situated on 3 acres of beautiful woodlands, where comfort and relaxation awaits! This massive custom-built cottage is the perfect setting for large families or travelling friends. Our tastefully furnished oasis boasts one of a kind décor, with plenty of room for indoor and outdoor activities. All accompanied with private access to the Nottawasaga River. Only 1hr from Greater Toronto Area.

4.93 out of 5 average rating, 184 reviews

A cozy living area features an orange L-shaped sofa adorned with decorative pillows, paired with a round coffee table. A 55" smart TV sits on a sleek black stand against the wall, surrounded by neutral decor and natural light from the nearby window.

Home in Barrie

4 Bedroom Fully Private Townhouse in Barrie

This spacious four-bedroom, four-bath townhouse is in Barrie South. It is a fully private and independent house, so you will have full privacy in and out. Enjoy the beautiful lake, which is five minutes away. Guests will have access to a fully stocked kitchen, washer/dryer, free high-speed internet (1500mbps), and a 55" smart TV with popular streaming services. All popular stores and amenities are nearby, within five minutes.

The bedroom displays a king-sized bed adorned with soft linens and multiple decorative pillows. Next to the bed, a stylish lamp provides warm light, while three framed nature photos hang above the headboard. A cozy seating area features a plush sofa with decorative cushions and a small table, enhancing comfort.

4.96 out of 5 average rating, 24 reviews

Serenity 1Bed+Sauna+HotTub+Indoor/OutdoorPool

Welcome to our modern zen retreat in Horseshoe Valley—perfect for families or friends looking to relax, explore, and make lasting memories. Just 2 hours from Toronto, our condo offers a prime location to experience it all. Minutes away from the Vettä Nordic spa, skiing, mountain biking, golf, tree-top trekking and more. Created with tranquility in mind, our space is the perfect place to return to after a day of adventure.

Popular amenities for Barrie ski-in/out rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/out house rentals

A spacious outdoor deck provides a comfortable lounge area, featuring a sectional sofa, colorful accent chairs, and a dining table. A large yellow umbrella offers shade, while views of the private dock and calm waters create a serene setting for relaxation.

Home in Innisfil

4.73 out of 5 average rating, 70 reviews

Luxurious Lake front Island Townhome, Innisfil, ON

A stunning view features a bright sunset behind an industrial building along a tranquil body of water. The vibrant orange and golden hues reflect on the surface, creating a serene atmosphere. Silhouettes of trees and distant structures outline the scene, enhancing the natural beauty.

Home in Collingwood

Dream vacation in Georgian Bay Collingwood, ON (2)

4.54 out of 5 average rating, 52 reviews

Home in Gilford

Beautiful House by Lake Simcoe

4.75 out of 5 average rating, 12 reviews

An open living area features a high wooden ceiling with large angled windows allowing natural light to fill the space. A stone fireplace serves as a focal point, complemented by a dark leather sectional sofa and a coffee table. A plush armchair adds extra seating.

Home in Collingwood

Charming Chalet in Collingwood

4.92 out of 5 average rating, 25 reviews

An aerial view of Olive & Willow Lodge reveals a spacious green lawn surrounded by trees. The white house is centrally located, with a driveway leading to the entrance. Scenic highways are visible along the property's edge, enhancing the natural tranquility of the setting.

Home in Uxbridge

Cozy 3-Bdrm Lodge beside Dagmar & Lakeridge Resort

The entrance of the home features a wide staircase leading to double front doors, framed by elegant columns. Two black chairs are positioned on the porch, accompanied by warm outdoor lighting. A garage is visible on the left, showcasing brick detailing along the facade.

Home in Springwater

4.75 out of 5 average rating, 8 reviews

3 bedroom 4 bathroom escape

A dark-clad chalet features large windows that provide natural light. In the foreground, three red Adirondack chairs are arranged on a grassy area, surrounded by a stone pathway and a small shrub, creating a relaxed outdoor space.

Home in Mansfield

4.55 out of 5 average rating, 20 reviews

Peace and Quiet at our Vacation home

An exterior view of the modern farmhouse showcases a sloped roof and a prominent red door. Sturdy wooden steps lead up to a private deck, surrounded by trees and greenery, creating a connection to the natural surroundings.

Home in Mansfield

The Sheds: 2 BR Coach House Apmt

Family-friendly, ski-in/out home rentals

Home in Blue Mountain Resort Area

4.88 out of 5 average rating, 250 reviews

Large 4 Br - 4.5 Bathroom: 2 King beds/Sauna/games

Townhouse in Blue Mountain Resort Area

An open concept living and dining area features a comfortable grey sectional sofa and two circular coffee tables on a textured area rug. The kitchen bar is equipped with four high-backed chairs. Large windows allow natural light to illuminate the space, with views of lush greenery outside.

4.94 out of 5 average rating, 535 reviews

3BR Sierra Scandi Chic - Closest to Village

Loft in Blue Mountain Resort Area

A cozy living area features a comfortable grey sectional sofa facing a modern television. A wooden coffee table rests in the center, accompanied by a soft decorative pillow. Natural light enters through large windows with dark curtains, offering views of the snowy outdoor landscape.

4.81 out of 5 average rating, 135 reviews

Sunshine Summit – Ski-In/Out • Pool • Shuttle

A cozy family room features a spacious gray sectional sofa and a wooden coffee table. Light-colored walls and a patterned rug create a welcoming atmosphere. In the background, a kitchen area is visible, equipped with modern appliances and seating for two.

4.93 out of 5 average rating, 310 reviews

Cozy Studio Mountainside stay in Blue Mountains

4.87 out of 5 average rating, 273 reviews

Stylish & Spacious 2 Bdrm/2 bths/2 balc Condo Loft

Home in Blue Mountain Resort Area

A master bedroom features a spacious bed adorned with a blue and white comforter. Light wooden flooring is complemented by a decorative nightstand and a stylish chandelier. Large windows allow natural light to fill the room, offering views of the greenery outside.

4.94 out of 5 average rating, 216 reviews

Serene mountainside home with View/Shuttle Bus

A modern kitchen area features blue cabinetry with open shelves displaying neatly arranged dishes. A central island with seating for two is complemented by sleek bar stools. Stainless steel appliances are integrated into the kitchen layout, providing a functional and inviting cooking space.

4.87 out of 5 average rating, 467 reviews

Base of Blue Mountain, Modern Studio

A modern living area features a cozy brown leather sofa complemented by black accent pillows. A large flat-screen TV is mounted above a fireplace, and a wooden coffee table displays a decorative tray. Natural light streams through sliding glass doors leading to a patio area.

4.88 out of 5 average rating, 266 reviews

Northern Peaks – Ski In/Out • Hot Tub • Shuttle Ac

Ski-in/out apartment rentals

5 out of 5 average rating, 4 reviews

King Suite – heated Pool, Sauna & Kitchen

An aerial view captures the expansive layout of Friday Harbour, showcasing various buildings along the marina and natural surroundings. A peaceful golf course is visible with a distinctive lighthouse, all framed by serene water reflections under a twilight sky.

4.9 out of 5 average rating, 90 reviews

Family-friendly luxury getaway at Friday Harbour

5 out of 5 average rating, 15 reviews

A cozy bedroom is presented with a spacious bed adorned in crisp white linens and a dark throw blanket. Flanking the bed are two bedside lamps, adding soft illumination. A plant adds a touch of greenery, while a living area is visible through an open doorway.

Apartment in Oro-Medonte

NEW Ski-In Ski-Out 1-BED Condo - Pool, Gym, Sauna

The living area is furnished with a light sofa and an accent chair, accompanied by a circular coffee table on a patterned rug. Large windows provide natural light and views of the outdoors. A modern kitchenette showcases sleek cabinetry and an island with seating.

4.45 out of 5 average rating, 71 reviews

Romantic stay at Friday Harbour

A sandy beach area features several wooden picnic tables shaded by blue umbrellas, overlooking a calm body of water. In the background, a modern building with a blue roof houses outdoor seating along the waterfront, surrounded by a vibrant landscape.

4.77 out of 5 average rating, 31 reviews

Luxury 2 BR Condo at FH All Season Resort

A spacious studio features a king-size bed with premium bedding, adjacent to a stylish sectional couch. Natural light pours in through large windows, illuminating the open floor plan. A dining table is positioned nearby, providing a comfortable area for meals.

4.67 out of 5 average rating, 57 reviews

Lux Studio in Horseshoe Valley

A serene swimming pool is framed by a modern building with large glass windows. Surrounding trees exhibit vibrant autumn colors, enhancing the tranquil outdoor setting. A small diving board is visible at the shallow end, while a ladder provides access to the pool.