Pet-friendly holiday rentals in Collingwood

A charming century home features a blend of red brick and light siding. The entryway is highlighted by a covered porch and decorative star. Lush greenery surrounds the property, adding to its inviting appeal under clear blue skies.

4.97 out of 5 average rating, 174 reviews

Beach & Hiking Nearby • Large Private Fenced Yard

Whether you’re looking to rest and recharge or head out on an adventure in the hills, this cozy century home is the perfect base. Located in the heart of Meaford, you’re walking distance to shops, restaurants, and the waterfront. Enjoy a large fenced backyard, fire pit, patios, two living rooms, laundry, and a fully stocked kitchen. Recently updated while keeping its original charm, it’s a great spot for families, groups, kids, and pets to relax and unwind. Perfect for making lasting memories :)

4.95 out of 5 average rating, 131 reviews

Farm stay in Kimberley

Valley View Farm Retreat ~ Family, Pets, Hiking

Enjoy this unique 4 bedroom Farm House as a gorgeous space to gather with family or friends. -Ideal location to come together, relax, & connect. -Central heat & AC. -Take in the spectacular views of the Beaver Valley. -Explore the Niagara Escarpment and lookouts of the Bruce Trail. -Relax and read by the fireplace. -5 min walk to our swimming pond with dock & beach -Convenient drive to groceries and local villages. -25 min drive to the Blue Mountains. -Reliable, consistent high speed internet.

4.95 out of 5 average rating, 151 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, 3 queen beds. 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.

An open-concept living area features a spacious beige couch facing a wall-mounted television. A modern kitchen includes bar seating with two metal stools and a sleek countertop. Pendant lights with a golden hue hang above a white dining table surrounded by four wicker chairs, complemented by natural light from large windows.

4.9 out of 5 average rating, 175 reviews

Jewel of Blue Mountain- steps 2 village- sleeps 10

Welcome to the Jewel of Blue Mountain, a luxury retreat steps from Village nightlife, slopes, and restaurants. This spacious 4 bd 4 bth house is perfect for families, ski groups, and long weekends enjoying the full Blue Mountain experience. The modern open-concept main floor is ideal for gatherings—cozy up by the fireplace after a day on the slopes, relax on the large sectional, or enjoy a great meal at the huge dining table ONLY TWO PARKING SPACES ARE AVAILABLE LICENSE NO. LCSTR20230000046

4.94 out of 5 average rating, 298 reviews

A circular stone fire pit is surrounded by wooden Adirondack chairs, offering a cozy gathering space. A vibrant fire burns in the center, with lush greenery and a serene riverside view in the background under a colorful sky.

Cottage in Wasaga Beach

Charming riverside cottage, B&B license

Charming riverside cottage available on Wasaga Beach. Just a 4-minute stroll from a pristine sand beach. Immerse yourself in nature's beauty while enjoying modern amenities, including a private hot tub for relaxation. Unwind with a friendly round of mini-golf or gather around the fire pit for cozy evenings under the stars.Create lasting memories at this perfect oasis that combines riverside tranquility, mini-golf fun, hot tub relaxation, and the warmth of a fire pit. Your dream getaway awaits!

4.94 out of 5 average rating, 187 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.

Apartment in Collingwood

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 game room is featured with a classic pool table, blue felt top, and wooden frame. Overhead lighting highlights the area, while adjacent walls are adorned with natural wood paneling and stone accents. A vintage arcade game is also visible in the background.

4.8 out of 5 average rating, 194 reviews

Ski in/out Chalet Hot Tubs Sauna Fireplace

This Ski in/out chalet is only 13 min walk to the nearest Ski Lift. We have an outdoor Hot Tubs, an indoor Sauna, and Entertainment such as a Pool Table, video games and a large 75 inch HD TV for your movie nights. Surround your friends/families around our renovated Kitchen, large Centre Island and large Dining Room Table. Seat in our covered Sunroom to have a morning coffee or enjoy your BBQ food all year round. Worry free and leave your cars at our home: Only 7 min walk to the Village

4.97 out of 5 average rating, 135 reviews

A spacious living area is highlighted by a stunning gallery wall featuring scenic photography. A comfortable gray sectional sofa and a cozy chair are positioned near a window, allowing natural light to illuminate the space. A gas fireplace adds warmth to the inviting setting.

Townhouse in Collingwood

Blue Mountain Gallery Getaway

Welcome to a cozy family escape featuring a stunning gallery wall showcasing scenic photography of South Georgian Bay. This peaceful retreat is just minutes from Blue Mountain Village or downtown Collingwood. Listen to the soothing sounds of the Cranberry Marsh Wetland, or walk to nearby Georgian Bay. Whether you’re hitting the slopes, the spas or the shops, unwind in a space that’s as inspiring as it is relaxing. Send us a message if you have any questions — we're always happy to help!

4.87 out of 5 average rating, 451 reviews

An aerial view of the tiny house surrounded by lush greenery and trees. The rustic wooden structure features a slanted red roof and an inviting porch area with seating. A clear view of the grassy land leads to the house, emphasizing its quaint and natural setting.

Tiny home in Meaford

Tiny Home Nestled between Thornbury & Meaford

Tinyhome situated 10 min to Thornbury and Meaford, and 20 min from Blue Mountain Village, nestled a country/residential area so it is quiet and dark at night. Has all the basic comforts including spacious 3 piece bathroom. Close drive to beaches and many hikes and cross country ski trails in the area. It is also a 15 minute drive from Beaver Valley Ski Club and a number of different cideries. Shared heated pool available for the summer months. Window Aircon/pool opens end of May or June.

4.97 out of 5 average rating, 137 reviews

Chalet in Meaford

Sundance of Blantyre Lodge +Hot Tub +Sauna +Pond

Welcome to Sundance of Blantyre! Step back in time in this historic yet modernized Lodge! This 3600 sq. ft retreat on the Bruce Trail has Breathtaking Valley Views from your own Private Hot Tub & Fire Pit all the Way to Georgian Bay. We invite you to enjoy our truly unique and tranquil getaway with 6 bedrooms + Private Sauna House! With 3 firepits, swimmable/fishing pond, hiking, cross country skiing and snow shoeing + snowmobile/ ATV trail access at your door, Your adventure awaits!

Outdoor spacesViewQuiet

A spacious bedroom is showcased with a large bed dressed in neutral linens and accented by decorative pillows. Natural light enters through a window, illuminating the room's soft gray walls. A contemporary art piece adorns one wall, while a doorway leads to a bathroom.

4.91 out of 5 average rating, 141 reviews

Upgraded 3-Bed Chalet in Blue Mtn Village

Licensed with Town of Blue Mountain # LCSTR20220000176 Exquisite and modern three bedroom chalet at Mountain Walk. Right at Blue Mountain Village, ALL LINENS AND TOWELS INCLUDED. Ski hills and golf course. Accommodate up to 7 people and features beautiful kitchen, two and half baths and wood fireplace. Beautifully decorated with tons of upgrades and perfect location this condo offers best of both worlds. kitchen fully equipped! Perfect vacation getaway with all amenities of modern living.

An open game room features a polished wooden pool table at its center, surrounded by exposed timber beams and vibrant green walls. Large windows provide natural light, while a television is mounted nearby. Additional seating is available, enhancing the space's social atmosphere.

4.98 out of 5 average rating, 116 reviews

Birdsong, the perfect Blue Mountains getaway

Welcome to Birdsong: a lavishly comfortable, highly unique, year-round space designed with an eye for the eclectic and enjoyable. This enchanting vacation property boasts an enormous hot tub that doubles as a heated indoor pool; as well as a sauna, well-equipped boutique gym, pool table, dedicated conference room/business center, outdoor fire pit and treehouse for kids. Surrounded by the gorgeous Blue Mountains, Birdsong is the perfect ski season rental; as well as summer family getaway.

HikingPoolHot tub

Popular amenities for Collingwood pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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.

Serene mountainside home with View/Shuttle Bus

4.93 out of 5 average rating, 247 reviews

4.97 out of 5 average rating, 114 reviews

Stonefox Retreat: Acerage, Pond, Hot Tub & Sauna

4.85 out of 5 average rating, 336 reviews

Home in Collingwood

Bright & Spacious Family Home Close to Ski Hill

4.97 out of 5 average rating, 113 reviews

A spacious dining area features a large wooden table surrounded by black chairs. A clock with a white face is mounted on the wall, and natural light fills the room through large windows. A view into the living area is visible in the background.

Home in Bond Head

3BR Spacious Home - KING BED

4.91 out of 5 average rating, 279 reviews

A vibrant bar and games room is featured, with a pool table occupying the center space. An air hockey table and foosball table are visible in the foreground. Colorful decor, including flags and artwork, adds to the lively atmosphere, while red lighting enhances the playful environment.

Home in Collingwood

JJ’s Collingwood bar & games house.

The entrance of a charming house features a welcoming porch with a red front door. Flanking the entrance, bright orange lilies bloom alongside well-maintained greenery. Sunlight filters through the surrounding trees, casting a warm glow on the home's exterior.

4.94 out of 5 average rating, 221 reviews

The Meaford Retreat! Beautiful Home on Wooded Lot.

Home in Blue Mountain Resort Area

The exterior of the town-home is showcased, featuring a combination of stone and blue siding. Neatly manicured lawns surround the property, and several large windows allow natural light to illuminate the interior. A small tree is planted in the foreground, adding a touch of greenery.

Blue Mountain Village Townhome 4 Bedroom w Shuttle

WalkabilityLocationCleanliness

4.82 out of 5 average rating, 128 reviews

4.94 out of 5 average rating, 109 reviews

A well-maintained front yard features lush green grass, framed by trees. The entrance of the home is highlighted by a gray facade and a distinctive yellow accent above the doorway. Well-kept shrubs are positioned on either side of the path leading to the entrance.

Home in Wasaga Beach

2 minute walk to the beach / games room

FamilyLocationIndoor spaces

Pet-friendly home rentals with a pool

A spacious living area is highlighted by modern furnishings, including two dark sofas and a wooden coffee table. A kitchen island with bar seating offers additional space, while dining chairs surround a large table in the background. Bright lights illuminate the well-equipped kitchen and open layout.

4.97 out of 5 average rating, 208 reviews

King’s Escape at Blue Mountain

4.96 out of 5 average rating, 177 reviews

A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.

Cottage in Tiny

Ultimate Georgian Bay Vacation Getaway

A clear, inviting outdoor pool is surrounded by landscaped greenery and stone seating areas. The pool features a curved shape with steps leading in, and two poolside lounge chairs are visible. Mature trees provide shade in the background, enhancing the serene environment.

4.96 out of 5 average rating, 372 reviews

Walk 2 Village, Great Kitchen & Beds, Summer Pool!

A modern living space features a stone fireplace and large windows that invite natural light. Comfortable seating is arranged around a dark coffee table, and a dining area with a long table is visible. The decor highlights a blend of contemporary style and a cozy atmosphere.

4.89 out of 5 average rating, 186 reviews

The Snowbridge Lookout on Monterra Golf Course

Condo in Blue Mountain Resort Area

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

4.87 out of 5 average rating, 325 reviews

4.91 out of 5 average rating, 288 reviews

Cottage in Innisfil

Utopia villa and spa

4.91 out of 5 average rating, 140 reviews

Cottage in Meaford

Cottage on 5 Private Acres, Heated Pool & Hot Tub

A private outdoor pool surrounded by a spacious patio is showcased, featuring colorful lounge chairs in shades of pink. Lush trees and greenery border the area, contributing to a serene setting under clear blue skies.

4.84 out of 5 average rating, 103 reviews

7BR Chalet | Hot Tub + Seasonal Heated Pool

Private, pet-friendly home rentals

4.98 out of 5 average rating, 153 reviews

A tranquil lakeside view displays a spacious cottage with large windows, reflecting on the calm water. Surrounding trees and a clear blue sky add to the serene atmosphere, inviting relaxation and enjoyment of the natural beauty.

Cottage in Georgian Bay

Muskoka Stunning Cottage On Little Lake

An open concept living space features a pool table at the center, surrounded by a sectional couch and a small dining table. Large windows provide natural light, while a 70-inch TV is mounted on the wall. A gas fireplace is visible in the background.

4.97 out of 5 average rating, 211 reviews

Entire Rustic Chalet - Hot Tub, Sauna, Large Yard!

Cottage in Grey Highlands

A charming cottage exterior is surrounded by vibrant flower beds and lush greenery. The entrance features a set of stairs leading to a spacious deck, where colorful furniture is positioned. A garage with a dark door complements the inviting atmosphere of the property.

Hilltop garden cottage

Hospitality

4.93 out of 5 average rating, 194 reviews

4.86 out of 5 average rating, 227 reviews

An industrial-style apartment features a spacious open living area with a dark leather couch and a wooden coffee table. A staircase leads to an upper sleeping area, while concrete walls provide a modern backdrop. Natural light enters from nearby windows, enhancing the interior space.

Farm stay in Southgate

Loft Where City Meets Country With Hot Tub

4.95 out of 5 average rating, 159 reviews

Cottage in Flesherton

All-Season Cottage on the Lake

4.97 out of 5 average rating, 100 reviews

The rustic exterior of High Pines Cottage is highlighted by large, floor-to-ceiling windows that allow natural light to fill the interior. Surrounding the cottage, a well-tended garden features a variety of plants, stones, and landscaping elements, adding to the inviting allure of the property.

Chalet in Flesherton

Cozy cottage in the woods near trails & waterfalls

4.99 out of 5 average rating, 154 reviews

A log cabin exterior showcases a blend of rustic charm and natural surroundings. The structure features various window styles, allowing light to enter, while green grass and garden elements enhance the peaceful ambiance. Surrounding trees create a serene and private setting.

Cabin in Holstein

Kettle Creek Cabin