Private suite holiday rentals in Dufferin County

HotTub & Pool Getaway - Headwaters Retreat

Escape to our rustic-modern Queen Suite, perfect for your getaway. Relax in the private hot tub right outside your door, unwind by the fireplace & enjoy Netflix & Amazon TV. This cozy retreat features a private entrance, ensuite bathroom, and a second bedroom with twin beds. Steps from scenic hiking trails, minutes from the town center, your stay is ideal for outdoor adventures, wine tours, weddings, work trips or just quiet escape away. Book now for your ultimate getaway in comfort and nature!

Entire spacious basement with Kitchenet

Relax with the family or friends at this peaceful and immaculate place. Accommodates up to 4 people with the comfortable sofa bed in den. NON-SMOKING NO PETS. FULL KITCHEN NOT AVAILABLE. KITCHENET AVAILABLE. Full, clean washroom. Spacious room, a queen size bed, dining table sits six, kettle, grill, basic utensils and kitchen wear, linen, towels, and drinking water. 50 minutes away from Collingwood, Wasaga Beach, Berrie, Blue Mountain & Brampton. Lots of food options available in Shelburne!

New "Country Escape" Guest Suite

Beautiful and well-equipped 2-bedroom guest suite in a peaceful rural setting. The guest suite is situated in a quiet country neighborhood, offering tranquility and a connection to nature. The proximity to many trails is a great bonus for outdoor enthusiasts. The proximity to essential amenities, shopping, grocery store, pharmacy, hospital, and restaurants in Orangeville, is a practical advantage. The 12-minute drive to these facilities ensures that guests have easy access to necessities.

Cedar Trail Cottage Suite

The Cedar Trail cottage suite is the perfect mindfulness retreat! This tranquil space is a great way to enjoy a night…or more! Enjoy being cozied up in bed, while your windows offer stunning views of tall cedar trees and a stream-fed pond. Step outside to a glass-railing deck overlooking a magical vista. Nestled on a large acreage, explore private trails through an enchanting forest and open meadows. Located 25 min to Hwy 410, 30 min to Hockley Valley Resort, 6 min to Cambium Farms.

Executive Suite

Enjoy easy access to great local eateries and shops from our central home. We take great pride in our home as we live right upstairs! Provided For You -Coffee, decaf, tea, sugar, salt, pepper, oil. -Dishwasher -Queen size bed -Smart TV with Netflix & Disney+ -Full washer/dryer -New bathroom with tub & shower -Small private fenced in yard & patio -1 Parking spot (additional parking on street April 1st - November 30th) -Welcome book with local fun recommendations -Keypad Entry

Mono - Charming, Rustic 150 Year Carriage House

This rustic space is perfect for a weekend getaway, year round. Close to ski hills, nature trails and the quaint town of Orangeville the Carriage house will provide you the authentic feel of our iconic cabin in the woods with the sophistication and comforts of your personal retreat for the weekend. The interior design is eclectic, funky and perfectly contrasts the rustic charm of the 140 year old, hand cut wooden beams and the overall log cabin environment.

Casa Caledon-Secluded Suite Surrounded by Nature

Take it easy at this unique and tranquil getaway on 3 acres of land The suite is close to conservation areas Cheltenham Badlands, Fork of the Credit and Terra Cotta Bruce trail, golf courses, restaurants, bakeries, butchers, farm produce and city needs are close Each season is wonderful Spring/summer has lush forests, the pond and fire pit Fall walks with the beautiful colours Winter has a white blanket and access to winter sports

Garden Studio Apartment

Enjoy a stylish experience at this centrally located place. Newly renovated 1 bdrm apartment located downtown Orangeville. Steps to Theatre Orangeville, Orangeville farmers market, and Jazz & Blues Festival. Enjoy evenings on your own private backyard overlooking the garden. Enjoy walks on the Island lake Conservation Park.. Dine at any of the many fine restaurants or cook at meal in your own fully equipped kitchen.

Dew Drop Inn

Welcome to your temporary home away from home! Separate apartment within our home (930 square feet). Separate entrance with large foyer. Two bedrooms, 1 with a queen bed and kitchen, the other with a queen bed, futon and T.V. (sitting area). Three piece bathroom with step-in shower. Tons of parking. Hardwood floors throughout. Spectacular views and 2 firepits to use. Please see pictures. No pets allowed.