Holiday houses in Collingwood

Newly Built Woodsy Retreat - Your Perfect Escape

Welcome to Woodsy Loft, an ideal home base for not just the beach and stunning sunsets, but Blue Mtn, Scandinave Spa, Collingwood, brand new casino, all close by. Many bars, restaurants, beach and other things to do, within 5 min. Great place to stay in, too. Packed with amenities like screened in patio, XL bathtub w/ towel warmer, King size bed, 'The Frame' Smart TV, full kitchen, fast WIFI, motorized blind...and the list goes on. Situated and designed to offer max. privacy and relaxation.

Luxurious Creek Retreat With Hot Tub

Welcome to this luxury cottage on the water. The perfect place to relax and unwind while listening to the waterfall and babbling brook flowing past only a few feet away. If you're looking for privacy and tranquility along with all the pleasures of a luxury stay then look no further. This property boasts a propane fireplace inside as well as one outside, in-floor heat and A/C. Fully equipped kitchen, two bedrooms with hotel quality mattresses and a bathroom that exudes high-end style and decor.

Dear Napier Street

Our colourful upper studio private suite is located on a quiet treed street in beautiful Collingwood. The vibrant, nostalgic decor of this Wes Anderson inspired space is an evolving at project, setting a happy vacation tone. It's a ten minute walk of the historic downtown, offering unique shops, galleries and creative places to eat and drink. Sunset Point Park is closeby and a network of more than sixty trails is one block away, connecting you to the iconic terminal, downtown and beyond.

Suite 67

This beautiful couples retreat is a 900 sq. ft., 1 bedroom upper apartment located in the heart of downtown Collingwood. Steps to shops and restaurants and a short drive to all the major ski hills in the area. Featuring, vaulted ceilings, sectional couch and 65” TV. The kitchen comes complete with all cooking needs and dishes supplied, a breakfast bar and dining area, Master bedroom with a King size bed, 5-piece ensuite, 2 piece powder room with laundry and door to large outdoor deck.

Tiny A-Frame near the Bruce Trail

Find yourself nestled among white pine trees just steps off the Bruce Trail! This tiny A-Frame is 100 sq.ft providing enough room for cozy comfort. The cabin is equipped with 2 stackable twin beds converting into a queen bed when desired. Our amenities contain all the essentials, including a BBQ, drinking and dish water, and an outhouse with a composting toilet. Centrally located to Old Baldy Lookout, Beaver Valley, Blue Mountain and Duncan Caves. The perfect spot to relax and unwind!

The Klinck House 2| Collingwood +Add on Amenities

1 of two private suites (see our other listing) Between the stunning Blue Mountains and the picturesque Georgian Bay. Each suite features a private balcony, 3pc bathroom, queen sized bed, kitchenette, living space with TV and outdoor spaces Plus, our property borders the scenic Georgian Trail. Unwind with one of our add on on-site amenities such as massage sauna cold plunge yoga and hot tub see additional photos for price list. Minutes to everything the area has to offer.

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 *2 Year Round Hot Tubs *Seasonal Pool (open as of May 31st 2025) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)!

"Paddle" at Hills | Scenic Escape Near Blue Mtn

Welcome to Hills! Once known as Hill's Dairy in Meaford, this historic building has been converted into four rental units with an adventure shop. Steps to downtown Meaford, and minutes to Georgian Bay, Georgian Trail cycling route, the infamous Trout Hollow Trail, shops and restaurants, beaches, and 25 mins from Blue Mountain. This modern suite is the perfect year-round getaway spot to unwind after a day of exploring the area.

The Beach Button

Cute as a Button, this cozy home inspired by beach house vibes is nestled in the quaint town of Meaford. This town offers some of the most amazing waterfront to explore! 2 minutes east is a spacious public beach, 2 minutes towards the west is the beautiful Harbor or step out the door and enjoy a 3min walk down to the lake! This property is also located a scenic 25min to the famous Blue Mountain Ski Resort! and Scandinave Spa!