Holiday rentals with a pool in Collingwood

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.

4.96 out of 5 average rating, 241 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 15 2026- Tues Oct 13 2026) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

4.95 out of 5 average rating, 343 reviews

A charming two-story cabin is nestled among lush greenery, with a pathway leading to the entrance. Tall trees and well-maintained hedges surround the home, creating a sense of privacy. Soft sunlight illuminates the cabin, enhancing its rustic appeal.

Cabin in Mono

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!

4.86 out of 5 average rating, 435 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.

An open-concept living area showcases a modern kitchen with stainless steel appliances and a large island. A cozy seating area features a dark sofa and an armchair, positioned near a stone fireplace. Natural light fills the space through multiple windows.

4.92 out of 5 average rating, 194 reviews

Blue Mountain condo in Historic Snowbridge

Newly renovated 2BR/2BA ground-level condo in Historic Snowbridge! Backs onto the 15th hole of Monterra Golf and is minutes from Blue Mountain Village. With shuttle available for pick up and drop off at the front door. Features open-concept living, beer fridge, cable TV, WiFi, board games, & workspace. Sleeps 6 with 2 queen beds & sofa bed. Incl. ensuite, 2nd bath, washer/dryer, fully stocked kitchen & year-round BBQ on private patio, perfect for a golf, ski or friends or family getaway!

An open-concept living area features a spacious bed with a dark headboard and matching bedside lamps. A modern kitchen is visible, highlighted by stainless steel appliances and a breakfast bar with three stools. A soft gray couch with decorative pillows is placed in the foreground.

4.89 out of 5 average rating, 114 reviews

Studio Condo @ North Creek|Pool/Hot Tub/Crave TV

Come and relax by the mountain and enjoy our renovated open concept living space. Our clean & comfortable studio condo has everything you need for a memorable getaway. We want you to have a fantastic time and have stocked our condo with all the things we expect when we travel. You'll find all the extras that make a place special: 40 inch flat screen T.V., fresh linens, well stocked kitchen, newer furnishings & decor, napoleon fireplace, deep jetted tub & free WiFi, NETFLIX and cable.

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, 572 reviews

3BR Sierra Scandi Chic - Closest to Village

CONSTRUCTION ALERT Please see property details below Treat yourself to a getaway at our uncluttered, spacious, and fully-equipped 3 bedroom end-unit stacked townhouse at 110 Fairway Court. Just a 5 minute walk from the village and facing the Monterra golf course 1st hole, you’ll enjoy beautiful views of the mountain and easy access to village activities. With over 1,600 square feet of living space and all the comforts of home, our place has everything you need for a relaxing stay.

4.96 out of 5 average rating, 171 reviews

Apartment in Innisfil

Upscale Spa Getaway w/ Private Sauna

Welcome to our most Dramatic & Romantic Penthouse Spa Getaway Suite! Reconnect with your loved one or celebrate that special milestone in our professionally designed to play with all your senses spa suite, this escape will leave you feeling refreshed and rejuvenated! Cozy up to any of 3 fire elements and then cleanse and detox in your own private in-suite Infrared Sauna! Cook up a gourmet meal in our fully equipped chef's dream kitchen and year round Weber BBQ for grilling!

The studio features a spacious living area with a comfortable sofa and a modern armchair. A king bed adorned with blue and yellow linens is positioned in the background. Natural light filters through the window treatments, enhancing the serene ambiance.

4.84 out of 5 average rating, 462 reviews

Ski in/out @ North Creek W King bed! New Hot Tub

Welcome to our beautiful studio at the foot of Blue Mountain ski hills. Fully renovated from top to bottom in 2021 and ready for visitors! 'Cascade Cabin' is a modern studio which sleeps 3 and features a King bed with a queen sofa bed in the living area. Unit features a fully equipped kitchen with seating for 3, full bathroom with shower & new soaker tub. The condo is located within minutes from Blue Mountain Village and within walking distance to the north ski lift.

A cozy living area features a plush sectional couch and a wooden coffee table. Large windows provide views of the golf course, allowing natural light to brighten the space. A modern fireplace adds a welcoming touch, complemented by soft curtains and decorative wall accents.

4.94 out of 5 average rating, 638 reviews

*Blue Mountain Village* Pool, Hot Tub, WalkToBlue

SHUTTLE, HOT TUB & SEASONAL POOL 360 degree views! We are a 3-5 minute walk to the Village with stunning views of the golf course and mountain! Perfect place to relax on the balcony or couch after a busy day of soaking up all Blue has to offer! ★Self-Check In ★Equipped kitchen, towels & linens ★ SMART TV, WIFI & CABLE ★ Games, high chair, PackNPlay ★ Resort hot tub with indoor changeroom and washrooms ★ Pool projected to open Monday June 15th 2026

Flat in Blue Mountain Resort Area

4.97 out of 5 average rating, 194 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 (Scheduled to open Fri May 15 2026- Tues Oct 13 2026) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)!

The living area is designed with a cozy sectional and an armchair, accompanied by a coffee table. A television is mounted above a stone fireplace. Large windows provide ample natural light and views of the surrounding hills and golf course.

4.95 out of 5 average rating, 999 reviews

Stunning Mountain View- Pool, Hot Tub, WalkToBlue

SHUTTLE, HOT TUB, SEASONAL POOL 5-7 minute walk to the Blue Mountain Village. This cozy 2 bedroom condo gives you immediate access to the action or a quiet place to relax by the fireplace while looking out at the mountain views. ★ SMART TVs in living room (WIFI and Cable) and bedrooms (WIFI) ★ Family Ready! Games, booster seat, packnplay etc ★ Resort hot tub with indoor changeroom and washrooms ★ Pool projected to open Monday June 15th 2026

The living room is designed with a cozy sectional sofa and a coffee table placed centrally. A mounted flat-screen TV is positioned above a white-brick fireplace. Natural light filters through sheer curtains, enhancing the welcoming feel of the space.

4.93 out of 5 average rating, 392 reviews

Cozy & Charming Retreat at Blue Mountain

***POOL OPENING IS JUNE 19, 2026*** Enjoy a stylish experience at this centrally located retreat! Welcome to Rivergrass Resort with stunning views of beautiful Blue Mountain and backing onto the picturesque 18th hole of the award winning Monterra Golf Course. Our recently upgraded unit includes all the comforts of home with a modern flare. Short Term Accommodation License #LCSTR20210000237

Popular amenities for Collingwood rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious bed is adorned with a textured white bedspread and a decorative 'welcome' pillow. Behind the bed, a scenic mural displays misty mountains and lush forests, enhancing the room's atmosphere. Two sleek reading lights are positioned on either side, adding functionality to the space.

4.84 out of 5 average rating, 117 reviews

Cozy Corner Townhome | Shuttle + Patio + Pool

4.86 out of 5 average rating, 281 reviews

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

4.85 out of 5 average rating, 114 reviews

A modern living area is highlighted by a sleek, electric fireplace beneath a large flat-screen TV. A rustic accent wall features wooden panels and decorative art. A comfortable gray sofa and a table set for dining complete the welcoming space, complemented by blue and natural tones.

Home in Innisfil

2 Bd Boardwalk Condo Patio Oasis

4.85 out of 5 average rating, 117 reviews

A bright and spacious living area features a comfortable white sofa paired with dark blue accent chairs. A stylish dining table is set for meals, while a gas fireplace and mounted television create a cozy atmosphere. Natural light fills the room through large windows.

Home in Horseshoe Valley

King Bed, Pool, Gym, Ravine View, Your Getaway!

The living area features large windows allowing natural light to illuminate the space. A modern sectional sofa with colorful pillows and a decorative throw faces a sleek coffee table. A cozy fireplace is positioned beneath a wall-mounted TV, creating a warm environment.

4.88 out of 5 average rating, 143 reviews

Blue Mtn Retreat w Summer Pool, XBox, Free Shuttle

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, 240 reviews

Serene mountainside home with View/Shuttle Bus

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.

4.85 out of 5 average rating, 119 reviews

Blue Mountain Village Townhome 4 Bedroom w Shuttle

4.88 out of 5 average rating, 209 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

Apartment rentals with a pool

4.86 out of 5 average rating, 533 reviews

Enjoy the Summer Fun at Blue Mountain

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, 327 reviews

Cozy Studio Mountainside stay in Blue Mountains

4.86 out of 5 average rating, 152 reviews

Luxury Blue Mountain Condo-Walk to Village-Pool

An open-concept living area features a large sectional sofa and a coffee table centered on a textured rug. A cozy fireplace is flanked by windows, allowing natural light to fill the space. Decorative wall paddles add a subtle touch of charm.

4.92 out of 5 average rating, 147 reviews

The Fairway Chalet

4.87 out of 5 average rating, 307 reviews

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

A contemporary living area is equipped with a mounted television above a modern fireplace. A wooden table is positioned in the center, surrounded by stylish seating, including an armchair. The adjacent kitchen features blue cabinetry and modern appliances, providing a cohesive and welcoming space.

4.87 out of 5 average rating, 500 reviews

Modern Studio, close to Village

A bright living area features large windows that allow natural light to fill the space. Comfortable seating is arranged around a central coffee table, with a modern fireplace and a wall-mounted TV providing amenities. Soft, neutral tones dominate the décor, creating a relaxed atmosphere.

4.98 out of 5 average rating, 120 reviews

3 Peaks at Blue Mountains, your luxury staycation!

An open-concept living area is showcased, featuring a cozy sectional sofa and a stone fireplace with a modern TV mounted above. Natural light streams through large windows, illuminating the earthy tones of the decor. A circular wooden coffee table with decorative elements completes the inviting space.

4.92 out of 5 average rating, 154 reviews

Highlands Lodge & Loft - Shuttle & Outdoor Pool

Other holiday rentals with a pool

Two comfortable sofas with decorative pillows are positioned around a dark coffee table in a spacious living area. A minimalist art piece adorns one wall, while a staircase leads to the upper level. The modern kitchen is visible in the background.

4.89 out of 5 average rating, 180 reviews

The Snowbridge Lookout on Monterra Golf Course

A spacious living area features tall windows allowing natural light to fill the room. A large screen TV is mounted above a gas fireplace, surrounded by comfortable seating. Decorative pillows enhance the sectional sofa, and an elegant coffee table sits centrally, adding to the inviting atmosphere.

4.97 out of 5 average rating, 261 reviews

Après Blue- 2bed2bath w/Pool 6 min walk to village

Loft in Blue Mountain Resort Area

A well-appointed bedroom features a spacious bed dressed in a white coverlet, flanked by two bedside tables with blue lamps. Neatly arranged towels are stacked on the bed, and warm, muted tones create a calming atmosphere.

4.83 out of 5 average rating, 204 reviews

Home Away From Home at Blue - Renovated Clean Loft

Dome in Bradford West Gwillimbury

Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.

4.97 out of 5 average rating, 490 reviews

Four season glamping dome under the stars

Chalet in Blue Mountain Resort Area

A bright, spacious dining area is illuminated by natural light from large windows. A long, rustic table is accompanied by white, spindle-back chairs. A vase with greenery is centered on the table, enhancing the inviting atmosphere of the space.

4.97 out of 5 average rating, 263 reviews

White Cedar Chalet (Pool & Free Village Shuttle)

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.

4.78 out of 5 average rating, 146 reviews

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

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, 358 reviews

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