Vacation rentals with outdoor seating in Dufferin County

4.92 out of 5 average rating, 127 reviews

A winding path is framed by tall trees, leading to a rustic cabin nestled among the forest. Lush greenery flanks the path, creating a serene and secluded ambiance, inviting exploration into the natural surroundings.

Tiny home in MONO

Whispering Pines Cabin in Woodland Acres

Experience this nature retreat just 60 km from Toronto and feel like you’re thousands of miles away. The perfect glamping experience for any nature lover looking for a relaxing getaway. There is power in the bunkie which offers the convenience of lighting, cell phone charging, an electric fireplace, a kuerig coffee maker and mini fridge with freezer. Pursue your favourite outdoor activities during the day and then return to your cozy queen size bed and sofa bed just steps away from the bonfire.

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, 353 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

Guesthouse in Orangeville

A studio room features a spacious bed with crisp linens and a decorative throw. Comfortable seating areas include armchairs and a small table. Natural light filters in through the windows, enhanced by a ceiling fan overhead. The kitchen and dining area are visible in the background.

4.96 out of 5 average rating, 133 reviews

A bright & stylish urban studio

Come & relax...in privacy. In the "Carriage House" you will be away from the main house, in your own building! Its a 634 square foot studio-style unit, that is unique & intimate. A nice sized kitchen, complete with gas range. Spacious & bright over-sized bathroom. The Murphy bed has a luxury-firm queen mattress, & stows away in a snap for more room. A diner booth for meals, or working at home! A short hop from Toronto, Dufferin County has all you need for a relaxing getaway! Come & See :)

Guest suite in Orangeville

This inviting bedroom features a spacious bed adorned with soft linens and a textured throw. A large armoire stands alongside, complemented by decorative plants and soft lighting. Natural light is welcomed through an adjacent glass door leading to a private entrance.

4.92 out of 5 average rating, 764 reviews

Hot Tub & 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!

4.83 out of 5 average rating, 114 reviews

A cozy sleeping area features a queen-sized bed adorned with a patterned blanket. Two pieces of wall art depicting nature hang above the bed. A bedside lamp provides soft lighting, and recessed ceiling lights contribute to a bright ambiance.

Guest suite in Shelburne

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!

Apartment in Horning's Mills

A private wooden deck is shown with an umbrella-covered table and four chairs, surrounded by lush greenery. Windows on the building's façade allow natural light, while potted plants add a touch of color, enhancing the outdoor space for relaxation.

4.95 out of 5 average rating, 288 reviews

Beautiful Riverside Country Apartment

Bright, warm and newly renovated, this 900sqft apartment, a private floor of a charming country home with separate entrance and garden patio, awaits you in Melancthon. SmartHDTV, Wifi, tranquil surroundings, and next to the Bruce Trail. Close to Shelburne, Mansfield, Creemore, and many excellent restaurants (like The Globe and Mrs Mitchels). Only 40 minutes to the Scandinave Spa, Collingwood, Blue Mountain, and Wasaga Beach. Golf Courses are close by. A perfect retreat just north of Toronto.

4.98 out of 5 average rating, 120 reviews

A spacious living area features a blue sofa with a light throw, positioned beside a circular coffee table. Wall art adorns the white walls, and natural light filters through a decorative window. A white cabinet and a small plant complete the cozy atmosphere.

Loft in Mono

Hockley Haven

Kick back and relax in this calm, stylish space. Newly renovated cozy 1 bedroom carriage house loft (appx 650 sq ft) above detached 3 bay garage in serene country setting on 5 acres of pine and cedar with a river running thru it. Pullout couch can accommodate 2 additional people. Walk across the road to Pollinator Garden & Island Lake Trails. 6 min drive to Hockley Valley Resort and Adamo Estate Winery, as well as beautiful downtown Orangeville boasting fabulous restaurants and quaint shops.

4.93 out of 5 average rating, 114 reviews

An open concept living area showcases large panel doors that fully open to the outdoor deck. Inside, a comfortable seating arrangement is visible, along with a cozy area rug and a neutral color palette. Natural light floods the space, enhancing the connection to nature.

Cottage in Mono

Hockley Riverside Cottage • Loft and Bunkie

Needing an unforgettable escape? This cozy cottage is nestled in nature along the Nottawasaga river and has large panel doors that fully open for picture worthy views & peaceful sounds of the river. A new incredible outdoor fire-pit with hanging egg chairs. A cozy indoor wood burning fireplace along with a comfy pull out couch that has a projector above for the best movie nights. Heated floors if you aren't interested in maintaining a fire, fully equipped kitchen, Wi-fi, AC and washer/dryer.

4.97 out of 5 average rating, 145 reviews

A covered gazebo with dark curtains offers a shaded area equipped with seating. Lush greenery surrounds the space, featuring mature trees and vibrant plants, creating a serene outdoor environment. The grassy area leads to a rich landscape of ferns and decorative shrubs.

Cabin in Orangeville

Hockley Valley Cozy Cottage

Take it easy at this unique and tranquil setting where the entire property is yours! Freshly renovated cottage only 600M from Hockley Valley Resort and also close to restaurants and hiking trails. This cottage sleeps 4 comfortably with separate bedroom. Picturesque setting directly on Nottawasaga river with mature gardens and plenty of outdoor space. Morning coffee or afternoon drinks under the covered gazebo at the waters edge or relax in the hammocks, this place truly has it all.

4.98 out of 5 average rating, 217 reviews

A modern living area features a sleek gray sofa flanked by decorative pillows. A glass coffee table sits atop a circular patterned rug, with decorative items placed on it. Natural light enters through two windows dressed with sheer curtains, while a door leads to another room.

Apartment in Shelburne

A&M Cozy Home Away From Home

Bring the whole family to this great place with lots of room for fun. Guests can enjoy this beautiful modern 2 bdrms with queen size beds, legal/separate entrance apartment equipped with kitchen appliances, microwave, stove, dishwasher, fridge, toaster, coffee maker, pots, plates, utensils, separate laundry. Equipped with your comfort in mind. It offers shampoo, conditioner, body wash, towels, keyless entry. Ignite TV premier PKG, Netflix, free 500 mbps Wifi.

4.95 out of 5 average rating, 217 reviews

The spacious bedroom features a king bed with a striped blanket and a decorative area rug. Large windows allow natural light, which brightens the neutral walls. French doors lead to an outdoor area, complemented by a seating arrangement and a wooden furniture set.

Place to stay in Mono

Rural Estate Coach House Apartment

Peaceful secluded guest house in forest property 5 minutes from Orangeville. We have three active dogs who often demand attention! Can be arranged as a two bedroom with privacy or a one bedroom with extra room. King bed in the large bedroom. Double futon in the sitting room. Fabulous bathroom with views. The guest house is 70 feet from main house. Quiet, nice forest walks. NOT a 'corporate Airbnb' - managed by owner. Near Bruce Trail and Hockley.

4.98 out of 5 average rating, 114 reviews

A private detached apartment is visible nestled among tall trees and lush greenery. The wooden exterior of the structure blends harmoniously with the natural surroundings. A pathway leads towards the entrance, framed by a vibrant landscape of ferns and colorful shrubs.

Guest suite in Caledon

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

Vacation rentals for every style

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Popular amenities for Dufferin County outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.97 out of 5 average rating, 38 reviews

A restored stone farmhouse is framed by lush greenery and colorful flower beds. A well-maintained stone wall borders the property, providing a rustic charm. The approach features a paved path leading up to the welcoming porch, inviting guests to explore the landscaped surroundings.

Home in Mono

Country Family Getaway with Pool and Trails

Cory & GinetteRating, 5 stars7 months ago

We had an amazing stay! Communication with the hosts was quick, and they were very attentive to all our needs, ensuring we had everything we required. The house was perfectly suited for our group of 8, offering plenty of space and comfort. The property itself is beautiful, with easy access to scenic walks and hikes right on the grounds. Plus, it was just a short drive to Hockley Valley, where we attended our event. This place was ideal for our weekend getaway, and we’d definitely stay here again!

4.98 out of 5 average rating, 126 reviews

A modern living area features a large, dark sectional sofa adorned with blue and orange cushions. A floral area rug adds a splash of color beneath the furniture. Natural light enters through two windows, and a mirror reflects the space, enhancing the open feel.

Home in Orangeville

HotTub & Private Suite - Casa Facciolo

MarianaRating, 5 stars2 weeks ago

Sherry is an exceptional host who truly goes the extra mile. From the moment we arrived, we were greeted with thoughtful decorations and a personalized sign celebrating our anniversary. The attention to detail was remarkable, and it made us feel incredibly special. The Airbnb itself was a peaceful , offering a divine escape from our everyday lives. We felt right at home in the cozy and inviting space. Sherry's warm hospitality and the atmosphere created an unforgettable experience. We highly recommend her Airbnb to anyone seeking a truly special getaway!

4.92 out of 5 average rating, 25 reviews

A spacious bed is elegantly dressed in a fluffy white blanket, complemented by decorative pillows. A bedside table holds a lamp and a star-shaped decor item. Light-colored walls and vinyl flooring create a serene ambiance, with natural light filtering in from an unseen window.

Home in Orangeville

Serenity In The Hills

ElsieRating, 5 stars1 day ago

Monique was very attentive and stayed in touch to make sure I had what I needed for my stay. Great host!

4.94 out of 5 average rating, 36 reviews

An expansive three-story brick triplex is shown, featuring distinct architectural details, including a turret and a sloped roof. The grounds display a mix of grass and patches of snow, while nearby trees and sidewalk complete the scene of a charming residential neighborhood.

Home in Shelburne

Tranquil 2BR Triplex in the Heart of Shelburne

TrishaRating, 5 stars1 week ago

We had a wonderful stay at Jeff’s lovely Airbnb over the weekend for my friend’s son’s wedding. The home was spotless, beautifully decorated, and had everything we needed to feel comfortable and relaxed. The host was incredibly welcoming and responsive, which made the experience even better. The location was perfect—close to the wedding venue and local amenities, yet peaceful enough to unwind after the celebrations. We especially appreciated the cozy touches that made it feel like a home away Thank you for helping make such a special weekend even more memorable. We would absolutely stay here again!

Superhost

A covered hot tub area features wooden paneling and a vaulted ceiling with skylights, allowing natural light to fill the space. The hot tub, surrounded by stone tiles, creates a tranquil environment for relaxation, providing views of the greenery outside through large windows.

Home in Caledon Village

4.88 out of 5 average rating, 16 reviews

Charming and Peaceful Retreat with Hot Tub

AndresRating, 5 stars4 weeks ago

My family and I all stayed here for my sisters wedding ceremony. We had a phenomenal time here and everyone enjoyed the place. Highly recommend staying here for family gatherings. Thank you for everything, Andres

4.93 out of 5 average rating, 107 reviews

Home in Badjeros

JJ’s small town country retreat

CodyRating, 5 stars4 weeks ago

Took my family away for an extended weekend and ended up choosing Jer’s place to stay. The kids enjoyed all of the things to do: pool table, games, fooseball, sauna and the hot tub. The weather didn’t cooperate as we would have hoped but we still had lots to keep us entertained while there. Cool set up from the new construction addition to the old farmhouse. Kitchen was loaded with anything you would need to prepare a meal and the space was clean and tidy. Thanks for the opportunity to enjoy your space Jer, we all had a blast!

Superhost

A spacious living area features a contemporary stone fireplace as a focal point. A large television is mounted above it, while a comfortable sectional couch and two wooden tables provide seating. Glass doors open to a private outdoor deck surrounded by greenery.

Home in Mono

4.76 out of 5 average rating, 17 reviews

Custom home that feels like the Spa

NickRating, 5 stars5 months ago

Great place to stay and very the host was awesome. Exactly as described.

4.94 out of 5 average rating, 88 reviews

A charming yellow house features a wide front porch with wooden seating and a grill. Lush greenery surrounds the porch, enhancing the outdoor space. The entrance is framed by a pair of glass doors flanked by symmetrical windows, inviting guests into the home.

Home in Orangeville

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

JamieRating, 5 stars1 month ago

We loved staying at George’s place. Easy to find and clean. Host was great. We will be back!

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Apartment rentals with outdoor seating

4.9 out of 5 average rating, 20 reviews

The kitchen features modern white cabinetry complemented by light granite countertops. An island with two stools is positioned centrally, while stainless steel appliances are situated against the wall. Under-cabinet lighting enhances the bright and inviting atmosphere of the space.

Apartment in Alton

Cataract Comfort!

ElizabethRating, 5 stars5 months ago

We had a very comfortable stay. We loved the fireplace and heated bathroom floor. Kitchen is very organized with the drawers labelled so that you can easily find items. Thank you for the added touches such as muffins and clearing our car windows of snow.

Superhost

A peaceful outdoor space is surrounded by lush greenery and tall trees. Red chairs are positioned on a gravel area near a small pond, which is lined with rocks. A wooden table can be seen, adding a functional element to the serene setting.

5 out of 5 average rating, 3 reviews

Country estate one bed suite

DeniseRating, 5 stars21 months ago

we need a last minute place to stay and this was perfect. we loved the peaceful location and the fact that it had a full location. if you are looking for a countryside getaway at an extremely affordable price, this is it. we were traveling under extenuating circumstances and Colin was very compassionate and sympathetic. Thank you so much!!!

A spacious dining area features a wooden table surrounded by upholstered chairs. Natural light fills the room through large windows, highlighting the modern décor and vaulted ceiling. A comfortable seating area with a couch and armchair sits adjacent, creating an inviting open-plan layout.

4.91 out of 5 average rating, 35 reviews

A bright & chic 2 bedroom urban apartment

Karen And RayRating, 5 stars1 day ago

We really enjoyed our stay at the Cooper. It is very spacious, comfortable, and has everything needed to make you feel welcomed and at home. It is in a great location, a short walk to downtown Orangeville restaurants and shops.

4.9 out of 5 average rating, 69 reviews

A modern living area is presented with two light grey sofas facing a glass coffee table, which rests on a decorative rug featuring shades of blue and neutral tones. Natural light enters through two windows, highlighting the stylish wall decor.

Apartment in Shelburne

L&S Comfy Suite

OburuRating, 5 stars1 day ago

Great place, helpful instructions, beautiful surroundings, peaceful neighbourhood…highly recommended.

A bright living room area features a comfortable beige sofa with decorative cushions. A glass coffee table sits at the center, displaying a light blue decorative bowl. Natural light flows through a large window, highlighting the artwork above the sofa.

4.98 out of 5 average rating, 45 reviews

Beautiful Getaway in Orangeville

CelesteRating, 5 stars11 months ago

I loved my stay in Orangeville. This airb&b was clean and spacious. The host was proactive in the communication and made sure to help in anyway. Thank you!!

A sleek bathroom features a modern vanity with a vessel sink and polished faucet. Clean white tiles adorn the walls, complemented by a spacious walk-in shower. Minimalist accents include a framed decorative piece and neatly arranged white towels on shelves.

4.95 out of 5 average rating, 73 reviews

A bright & modern urban studio

CharleneRating, 5 stars2 weeks ago

Very pleasant place to stay. Worked well for what I needed.