House holiday rentals in Dufferin County

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Top-rated house rentals in Dufferin County

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Home in Shelburne

4.66 out of 5 average rating, 29 reviews

The Old Millinery House

This rustic accommodation was formerly the Millinery House (circa 1882), once the home of Harry Jelly, the nephew of town founder William Jelly. This guesthouse is smoke free environment, its not be suitable for those who love new homes; However, it can be a charming home for ones who are passionate about the old world charm & like to make it a short time home at reasonable price (free coffee, tea, treats & parking). We do not charge for cleaning fee, so please keep the house less mess. Thank

Superhost

Home in Orangeville

4.82 out of 5 average rating, 28 reviews

Private cottage heated pool/HotTub/Games 20 Acre

Nestled in a serene countryside setting, this charming cottage offers a perfect blend of rustic charm and modern comfort. Step outside to discover a private outdoor heated pool and hot tub, each offering a soothing retreat. Whether you’re enjoying a peaceful morning swim or hosting friends for a sunset soak, this cottage with its outdoor heated pool and hot tubs is an idyllic escape for any getaway. Nearby Attractions: - TPC Toronto Opsrey Golf - Hockley Resort Ski/Spa - Provincial Park

Guest favourite

Home in Mono

4.96 out of 5 average rating, 27 reviews

Peaceful retreat on 10 acres

Forget your worries in this spacious and serene space. Very private with scenic views from all the windows. Vaulted ceiling in post and beam style home. Cosy gas fireplace in living room. Main floor bedroom with ensuite bathroom - walk in shower and free standing tub. Open loft overlooking the living room with two bedrooms, family room and bathroom. Huge deck space with 2 person hot tub and views of the wildflower gardens and surrounding woods. *Special rates for longer stays available

Guest favourite

Home in Orangeville

4.97 out of 5 average rating, 29 reviews

Orangeville 3BDRM House

This home can accommodate an escape from the city to relax/explore or offer a quiet place to work or recharge if on a business trip. This clean & cozy townhouse is perfect for the whole family. Enjoy a full kitchen stocked with coffee, sugar, honey & spices. The dining area sits 4 with some bonus additional seating at the nearby island. The living room has a large couch with 2 additional seating options that have a clear view of the television. There are 3 fantastic spacious bedrooms.

Guest favourite

Home in Badjeros

4.94 out of 5 average rating, 131 reviews

JJ’s small town country retreat

Take a step back in time to this old farm house. Located on the corner of our little town called Badjeros. This house was built in the 1930s and it’s been in our family for over 80 years. Since then there has been numerous upgrades to the house as well as a large 1200 square foot open concept addition built onto the existing house. While out in the country, this house is central to many attractions in the area 1.5 hours south of Toronto/GTA. Blue Mountain/ Collingwood is 30 minutes north.

Top guest favourite

Home in Alton

4.97 out of 5 average rating, 106 reviews

Stylish 3BR | Hot Tub • Firepit • Cozy Fall Escape

Welcome to your relaxing escape in the heart of Alton—a cheerful and spacious 3-bedroom, 1.5-bathroom home backing onto the beautiful Credit River. Perfect for families, friend groups, wedding guests, or anyone craving peace, nature, and comfort. • Sleeps up to 8 guests comfortably • 3 cozy bedrooms (2 with private decks!) • 1.5 bathrooms • Fully equipped kitchen + BBQ patio for year-round grilling • Stylish living room with fireplace & smart TV • Fast Wi-Fi, workspace-friendly

Home in Orangeville

4.77 out of 5 average rating, 69 reviews

Stunning 5 Bedroom Family Home

Beautiful and cozy home for families. This home has a fully equipped kitchen, a living & family room! You will feel completely relaxed with your family or friends. Steps from the downtown strip & top restaurants in the Dufferin Region. Just 10 minutes to Hockley Valley Ski Resort More affordable and comfortable for your kid's hockey tournaments or visiting family over the holidays! Stocked with towels, linens, a full kitchen, state of the art stainless steel appliances, & more!

Guest favourite

Home in Orangeville

4.91 out of 5 average rating, 118 reviews

Stylish 3 Bedroom Getaway in Orangeville

Nestled among tree sculptures and lakes, just steps away from downtown and minutes from the serene beauty of Island Lake Conservation Area. Our urban oasis is complete with a comfortable bed, fully equipped kitchen, chic living area, and private balconies. Be transported through time as you wander the streets of downtown, admiring vintage architecture and vibrant culture. Experience the magic of nature and city living combined in one unforgettable stay!

Top guest favourite

Home in Orangeville

4.95 out of 5 average rating, 100 reviews

Central OVille,3 bed Victorian, walk to Lake, pets

This 3 bedroom (4 beds), 1,500 sqft unit with new Gas Fireplace and central A/C sleeps 6 adults comfortably. Bedroom 1 has a queen-sized bed, another a double bed while Bedroom 3 contains two separate single beds. There is large and beautiful private deck and fenced back yard that contains a full-sized BBQ The unit contains: Washer and dryer (within the unit), hard-wood floors, and free high-speed unlimited internet and HD Cable.

Superhost

Home in Mono

4.66 out of 5 average rating, 29 reviews

Luxury Hockley Estate Spa

Kick back and relax in this calm, stylish space. This home is located in a central location close to Orangeville and hockley Valley ski/ winery/hiking. The home is just like a relaxing spa with pool, hot tub, sauna, indoor wood burning stove, outdoor BBQ, massive kitchen, lots of space. Great for family dinners and getaways, we enjoy groups with longer stays and will give monthly discounts.. This amazing property has it all:)

Guest favourite

Home in Southgate

4.9 out of 5 average rating, 41 reviews

Brand New Entire Home in Southgate ( Dundalk)

Bring the whole family to this great home with lots of room for to create good memories. Dundalk is a great cute town to go for hiking , skiing , snowboarding, snowmobiling. Nice great trails are in town. 20 minutes to Shelburne, 40 minutes to Collingwood 45 minutes to Blue Mountain. Roughly about hour to Brampton. This is where Wind Mills and farming landscapes and newer Sub division.

Guest favourite

Home in Creemore

4.97 out of 5 average rating, 37 reviews

Mulmur Getaway, outside of Creemore

A lovely and peaceful escape from city life, this 150 year old farmhouse is incredibly cozy and private. You have the entire house: 3 bedrooms, 1 1/2 bathrooms, fully equipped kitchen, wifi, wood burning fireplace and the house is air conditioned. There is a TV, VHS and DVD player (with assorted movies) but no cable service.