Pet-friendly holiday rentals in Collingwood

4.85 out of 5 average rating, 279 reviews

A spacious living area features a comfortable brown sofa positioned near a glass coffee table. Natural light pours in through large windows with blinds, illuminating a dining area with seating for four. A modern kitchen is visible in the background, equipped with sleek appliances.

Guest suite in Moonstone

RELAX @ our HOT TUB and SAUNA in the woods

PLEASE READ! Mt. St. Louis & Horseshoe Valley at doorstep! This is a bright, large and private walk-out GUEST SUITE (basement apartment). Hot tub, patio, fire pit & secluded path in the woods to enjoy nature. Kitchen is equipped with an induction cooktop and all things necessary, even wine bottle opener:) Open concept living room/kitchen/dining room with TV & Roku. Bedroom is a work of Art: dark, mysterious and romantic! Custom Queen bed made from weathered barn wood salvaged from our property.

Condo in Blue Mountain Resort Area

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, 466 reviews

Base of Blue Mountain, Modern Studio

This updated studio ski chalet is absolutely perfect for two, or a couple with small children! Our studio is newly renovated with a custom kitchen and fireplace. Located right at the base of the ski hill, our clean, cozy chalet is a lovely fully furnished 1 bedroom, 1 bath. Blue Mountain Village only 1Km away, as well as the Scandinavia Spa , Northwinds Beach and restaurants. Our chalet is ski in ski out and located right at the North Chair. Come and enjoy all that Blue Mountain has to offer!

Townhouse in Blue Mountain Resort Area

A dining area features a wooden table set with a red-striped runner and natural decorations. In the background, the kitchen is visible, showcasing modern appliances and cabinetry. The living space is bright and welcoming, adorned with comfortable seating, including a grey couch and decorative accents.

4.96 out of 5 average rating, 342 reviews

Great kitchen, comfy beds, games, walk 2 village +

You will love our fully renovated, condo with quality mattresses, well stocked kitchen, beautiful bathrooms, private ski locker, free parking & the comforts of home. You can trust our 300+ reviews telling stories of amazing getaways & cherished memories made! Our ideal location, only a 5 minute stroll to the village is something you will be sure to enjoy. NETFLIX, cable & unlimited wifi, a cozy gas fireplace, quality towels/ linens + games/duplo...message us with any questions or to book now.

4.95 out of 5 average rating, 128 reviews

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.

Chalet in Blue Mountain Resort Area

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, 177 reviews

King’s Escape at Blue Mountain

Welcome to our cozy, ground-level, two-bedroom condo in Historic Snowbridge, just a short walk from Blue Mountain Village-your perfect year-round escape! Backing onto Monterra Golf Course, you’ll enjoy stunning views and endless outdoor activities. Ski in winter or hike and bike in summer. Relax at our *seasonal* outdoor pool and take advantage of free rides to the village. Amenities include comfortable sleeping for families, a fully equipped kitchen, and a cozy living space LCSTR20210000165

Farm stay in Township Of Southgate

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.

4.86 out of 5 average rating, 174 reviews

Loft Where City Meets Country With Hot Tub

This unique place has a style all its own, while situated on a very private 39 acres where city style meets country living. The industrial apartment has been designed inside of a driving shed and offers all the luxuries of real glamping. Comfort and style throughout, complete with hotel quality mattress and linnens. The forested trails and beautiful property are a nature lovers paradise. You will find everything needed for a perfect getaway rather walking the trails or relaxing by the pond!

4.85 out of 5 average rating, 389 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.

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.

4.91 out of 5 average rating, 223 reviews

JJ’s Collingwood bar & games house.

welcome to beautiful 4 season collingwood! This house offers a 3 bedroom 2 bathroom fully detached house on a large mature lot in collingwood. Less than 10minute walk to sunset point beach and a 10 minute walk to downtown collingwood. House is in a prime location approximately 10 minute drive to blue mountain, 20 minutes to Thornbury and 15 minute drive to Wasaga beach. Big fenced in backyard for fires, horse shoes or whatever you would like, plenty of parking ( 4 car maxim)

Apartment in Blue Mountain Resort Area

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.

4.83 out of 5 average rating, 243 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

4.93 out of 5 average rating, 595 reviews

A straight road stretches into the distance, framed by green trees and vibrant grass on either side. A clear blue sky is dotted with fluffy white clouds, creating an inviting atmosphere that emphasizes the natural surroundings.

Guest suite in Stayner

Cozy & Private Guest Suite in Stayner, Ontario.

PLEASE READ THE DESCRIPTION In "The Space" BEFORE BOOKING. The space DOES NOT HAVE A SHOWER. We are a proud Superhost destination close to Wasaga Beach (15-20 mins), Collingwood (20-25 mins) and Blue Mountain Village (30-35 mins.) The place is super cozy. You'll love the location, the privacy, the amenities, the hosts and the value. This place is fabulous for couples, solo adventurers, business travellers, and canine companions. Also… THERE IS NO SHOWER

4.98 out of 5 average rating, 105 reviews

The striking facade of the modern lake house is framed by lush greenery, showcasing large windows and a unique architectural design. A custom pickleball court is visible in the foreground, bordered by flower planters, enhancing the outdoor environment.

Cottage in Meaford

Bayview Oasis: Luxe Lakeside Escape w/ Pickleball

Welcome to Bayview Oasis, our luxurious lake house on Georgian Bay. Enjoy breathtaking water views, a modern kitchen with high-end appliances, a cozy basement with a pool table and bar, and a master suite with top-notch amenities. Outdoors, relax in the cabana with a pizza oven, fireplace, picnic tables, spacious patio, hot tub, and our new custom pickleball court. Whether it's a romantic getaway or family vacation, Bayview Oasis is the perfect retreat.

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.

4.93 out of 5 average rating, 215 reviews

Serene mountainside home with View/Shuttle Bus

Welcome to this peaceful haven within the mountains. We have decorated our spacious and cozy home with comfortable beds, ample living amenities, and high-quality furniture to welcome you, your family and friends. Enjoy the carefully curated art pieces collected from around the world and look upon a stunning view of the snow-capped mountains from the master bedroom. Heated outdoor pool is seasonal! Walkable to the Village. Free Shuttle Bus

Popular amenities for Collingwood pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.89 out of 5 average rating, 132 reviews

A cozy living area features warm wooden paneling and a rustic brick wall. A dark purple couch and a wooden coffee table create a welcoming setting. A wood stove is positioned near the entrance, adding a touch of warmth to the space.

Home in Wasaga Beach

Relax & enjoy fall- 20 min drive to Blue Mnt

Home in Blue Mountain Resort Area

The living area features a modern design with a stone fireplace and a mounted TV. Large windows allow natural light, while a spacious coffee table sits between a sectional couch and a sleek armchair. A neutral color palette is complemented by decorative plants.

4.97 out of 5 average rating, 399 reviews

Mountain Cedar Chalet! Across from The Village

5 out of 5 average rating, 48 reviews

A historic stone cottage is nestled among lush greenery, surrounded by well-maintained gardens. The structure showcases characteristic architectural features, with a gentle slope of the roof and multiple windows reflecting the warm glow of the sunset. The expansive lawn offers a serene outdoor space.

Home in Meaford

Stonefox Retreat: secluded cottage on 100 acres

4.97 out of 5 average rating, 144 reviews

A charming farmhouse is set amidst a lush green lawn, surrounded by mature trees. A white fence complements the landscape. The building features a red door and light grey siding. Two dogs can be seen on the grass, adding a warm touch to the serene country setting.

Home in Grey Highlands

Newly Renovated! Charming Beaver Valley Farmhouse

4.88 out of 5 average rating, 207 reviews

The kitchen features an open layout with warm wood flooring and a large dining table set for twelve. Natural light enters through two windows beside the door. Stainless steel appliances and a well-equipped countertop complete the functional space.

Home in Kimberley

Heart of Kimberley - with views and a hot tub

An open-concept main floor is displayed, featuring a modern kitchen with stainless steel appliances and a central island. A comfortable seating area with a light gray sofa is positioned near a coffee table, accented by a decorative bowl. A dining area with a circular clock is visible in the background.

4.93 out of 5 average rating, 55 reviews

Elegant Home in Collingwood -15 min from Village

A private outdoor patio area features a table surrounded by chairs, an umbrella for shade, and lounge chairs. A BBQ grill sits nearby, set against a backdrop of green trees and a spacious lawn, creating an inviting space for relaxation.

4.86 out of 5 average rating, 35 reviews

Happy Valley Ski Golf Spa Relax

Home in Blue Mountain Resort Area

4.82 out of 5 average rating, 34 reviews

Mountain View Townhouse near Blue w/ Free Shuttle

Pet-friendly home rentals with a pool

4.92 out of 5 average rating, 116 reviews

A swimming pool is surrounded by a spacious patio, featuring lounge chairs for relaxation. The sleek water reflects sunlight, creating a serene atmosphere. Lush greenery and trees provide a natural backdrop, while a shed sits nearby, offering additional outdoor storage.

Cottage in Meaford

Woodski Retreat w/Heated Pool on 3+ Private Acres

4.83 out of 5 average rating, 143 reviews

Guest suite in Minesing

Farmhouse Guest Suite; Year round hot tub

Condo in Blue Mountain Resort Area

A spacious living area features a dark leather sofa complemented by blue accent pillows. A wooden coffee table holds magazines, while a decorative rug covers the floor. The open layout connects to a modern kitchen with white cabinetry, bar seating, and large windows allowing natural light.

4.92 out of 5 average rating, 158 reviews

Large 3BR Modern Luxury Escape | Walk to Blue

Chalet in Blue Mountain Resort Area

An outdoor heated swimming pool is surrounded by a spacious patio. Red and blue lounge chairs are placed around the pool area, with tall green trees providing shade in the background. A safety fence encloses the pool, creating a private atmosphere for guests.

4.76 out of 5 average rating, 132 reviews

*Haven on Blue*- Hot Tub, Heated Pool & Sauna

5 out of 5 average rating, 106 reviews

A cozy balcony space is adorned with soft lighting and potted plants, creating a serene atmosphere. Comfortable seating is arranged around a glass table, inviting relaxation while overlooking lush greenery and a sunset sky in the background.

Condo in Innisfil

Oasis Spa w/ Private Sauna!

Guesthouse in Orangeville

An outdoor pool area features a surrounding deck with wooden steps leading up to it. Bright blue water reflects the sky, and vibrant green grass borders the patio. Two red Adirondack chairs are placed nearby, complemented by lush trees and a distant green landscape.

4.95 out of 5 average rating, 375 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

4.92 out of 5 average rating, 130 reviews

A modern living area features a large wall-mounted TV and a stylish black accent wall. Two small coffee tables in front of a comfortable sofa are complemented by decorative items. Natural light streams in through the sliding glass doors, which lead to the balcony.

Apartment in Innisfil

Modern Condo at Friday harbour/Pet Friendly

Townhouse in Blue Mountain Resort Area

A spacious dining area is showcased, featuring a large wooden table surrounded by black chairs. The kitchen area blends seamlessly with the space, equipped with stainless steel appliances and wooden cabinetry. A decorative plant sits at the center of the table, adding a touch of greenery.

4.98 out of 5 average rating, 207 reviews

Hidden gem! Amazing, Corner-unit

Private, pet-friendly home rentals

4.89 out of 5 average rating, 419 reviews

A cozy cottage is nestled among vibrant autumn foliage. The front features large windows and a welcoming deck, with outdoor seating visible. Surrounding trees display various shades of yellow and orange, contributing to a serene nature setting.

Cabin in Innisfil

Kempenhaus- Lake Simcoe Cottage & Spa

4.98 out of 5 average rating, 66 reviews

A spacious outdoor deck features lounge chairs arranged for relaxation, with an adjacent gazebo providing shade. A barbecue grill and outdoor bar area are visible, complemented by a pathway leading through the lush greenery towards a distant view of the water.

Cottage in Wasaga Beach

Charming cottage on the Beach

4.98 out of 5 average rating, 81 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

5 out of 5 average rating, 14 reviews

A charming two-story structure is set amidst lush greenery, featuring a wooden deck that extends from the upper level. Large windows provide natural light, while the building's rustic exterior blends harmoniously with the surrounding landscape.

Home in Meaford

Weather Hill - carriage house on acreage

4.95 out of 5 average rating, 38 reviews

A charming lodge is surrounded by lush trees, featuring gray wooden siding and a stone pathway leading to the entrance. The structure includes a distinct chimney and a small utility shed beside it, creating a cozy, inviting outdoor setting.

Home in Singhampton

Blue Mountain Riverside Lodge | Hottub & Sauna

4.82 out of 5 average rating, 441 reviews

A rustic log cabin is nestled in a lush forest, featuring a welcoming porch with rocking chairs. The structure combines a traditional log design with a modern metal roof. A grassy area surrounds the cabin, providing a serene space for relaxation.

Cabin in Maxwell

Charming Pioneer Cabin in the Woods

5 out of 5 average rating, 12 reviews

A spacious common area features a large, light-colored sectional sofa arranged around a warm fireplace built into a stone wall. Large glass doors provide access to a serene outdoor space, while natural light enhances the wood-beamed ceiling. Decorative elements include woven wall art and a wooden side table.

Cabin in Tiny

The Beach House, Georgian Bay, Beach View w/ Sauna