Airbnb your place

Holiday houses in Orangeville

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Orangeville

  • Total holiday rentals

    Explore 60 holiday rentals in Orangeville

  • Nightly prices starting at

    Orangeville holiday rentals start at $52 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,550 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Orangeville holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Orangeville rentals

  • 4.7 Average rating

    Orangeville stays receive an average rating of 4.7 out of 5 from guests

Top-rated holiday rentals in Orangeville

Guests agree: these stays are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
Top Guest favourite
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.
Apartment in Orangeville
4.96 out of 5 average rating, 100 reviews

A bright & modern urban studio

Come & unwind...in comfort. "The Snug" is a 740 square foot studio-style unit, that is bright & modern. You will be on the basement level of the main house, with a completely separate entrance. Nice kitchen & Sleek 3 pc bathroom(with rainfall shower head and heated floors). The queen bed, with luxury-firm mattress, has built in storage for all your needs. Reliable wifi so you can work at home! A short hop from Toronto, Dufferin County has all you need for a relaxing getaway! Come & See :)

Superhost
A spacious glamping dome is nestled among lush green trees, showcasing large windows and a triangular design. The entrance is framed by rustic outdoor seating, and soft lighting emanates from inside, creating an inviting atmosphere amidst the surrounding foliage.
Dome in Utopia
4.95 out of 5 average rating, 277 reviews

Off-grid Glamping Dome Nestled in the Woods

Welcome to our private campsite in Utopia, ON. Our family’s glamping dome is your chance to experience a unique getaway surrounded by the sights & sounds of nature. Amenities include camping essentials & some glamping perks: king size bed, bbq, fireplace, Indoor incineration toilet, soap & water, outdoor shower (summer only), kettle, cooking utensils. Nearby is Purple Hill Lavender Farms, Drysdale's Tree Farm, Tiffin Conservation Area, Nottawasaga & golf courses. Wasaga Beach is 30 min away.

Guest favourite
A charming exterior of the Clayhill Bunkie is presented, featuring a dark blue wooden facade with a steeply pitched roof. Two windows, adorned with flower boxes, flank a central door that is decorated with a natural wreath. Lush greenery surrounds the entrance, enhancing the serene setting.
Guesthouse in Halton Hills
4.92 out of 5 average rating, 183 reviews

The Clayhill Bunkie

Looking for a place to get away that’s semi off-grid or glamping? On The Bruce Trail and minutes from Silvercreek & Terra Cotta Cons. areas, the Credit River, the villages of Glen Williams &Terra Cotta, & Georgetown. Spend your day hiking, cycling, antique hunting, tubing, or site seeing, then order in or grab take-out and come relax by a fire. 1 basket of wood is included, adding great value. You WILL hear wildlife and farm animals here. Rural property, limited electricity, beautiful views.

Top Guest favourite
Guest suite in Orangeville
4.92 out of 5 average rating, 876 reviews

Pool & Private HotTub - Headwaters Retreat

Escape to our modern-rustic 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 a quiet escape away. Book now for your ultimate getaway in comfort and nature!

Top Guest favourite
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
4.95 out of 5 average rating, 346 reviews

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!

Top Guest favourite
A modern kitchen is equipped with stainless steel appliances including a refrigerator and stove. A wooden dining table with four chairs sits in the center, complemented by a decorative vase filled with sunflowers. Ample storage is provided by the white cabinetry and countertop space.
Apartment in Orangeville
4.92 out of 5 average rating, 63 reviews

The Bee Hive - Lower Level Raised Bungalow

Kick back and relax in this calm, stylish and super equipped space. Fully self contained and private lower apartment to our home with the hosts living above. Open plan kitchen dining living area with 1 bedroom (queen bed) and 1 shower room with 8 ft ceilings. Newly renovated, almost everything new this year ready for the 2025 season. Home from home, calm and pleasant space with all the mod cons. 50" LG Smart TV, Full sized fridge freezer, dishwasher, stove, microwave and much more - Enjoy!

Top Guest favourite
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
4.95 out of 5 average rating, 155 reviews

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.

Top Guest favourite
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
4.94 out of 5 average rating, 150 reviews

L&S Comfy Suite

Beautiful inviting space for families as well as individuals. Brand New Fully renovated area with lots of amenities for the whole family. 2 Great size bedroom with queen size beds. Jack And Jill full washroom with an amazing shower that boast body jets. Comes with all the bells and whistles. Open concept with Living room, Dining room, Full Kitchen, Washer and Dryer, free parking, work area ideal for remote work, and lots more…. NO UNREGISTERED GUESTS ARE ALLOWED AS PER HOUSE RULES.

Top Guest favourite
The modern tiny home features a black exterior and a large glass front, allowing natural light to illuminate the interior. A simple outdoor seating area with two chairs is visible, surrounded by lush greenery and trees, creating a connection with the serene natural surroundings.
Tiny home in Arthur
4.97 out of 5 average rating, 400 reviews

Luxury tiny home on peaceful country estate

Escape to Heirloom Tiny Home - where macro luxury meets a micro footprint. Nestled on 23 peaceful acres, surrounded by aspen and pine forests, just 10 minutes from the picturesque town of Elora. Wake up to serene pond views as horses and sheep graze in your view. Organic linens, artisanal soaps, and a spa-like bathroom soothe the senses. Cozy up by the indoor fire and gaze at the stars. Enjoy fine dining at the Elora Mill and Spa, enjoy popular shops or hike the Elora Gorge nearby.

Top Guest favourite
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 Orangeville
4.98 out of 5 average rating, 177 reviews

Hockley Haven

Kick back and relax in this calm, stylish space. 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.

Guest favourite
Townhouse in Orangeville
4.86 out of 5 average rating, 169 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
A cozy living area features a light-colored sofa with decorative cushions, a coffee table, and a wall-mounted television. A slim electric fireplace is situated beneath the TV. To the rear, a fully equipped kitchen can be seen, enhancing the space's functionality.
Guest suite in Orangeville
5 out of 5 average rating, 201 reviews

Garden Studio Apartment

Enjoy a stylish experience at this centrally located place. Newly renovated 1 bdrm walkout apartment located in our home in downtown Orangeville. Steps to Theatre Orangeville, Orangeville farmers market, and Jazz & Blues Festival. Enjoy evenings on your own patio in a 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.

Popular amenities for Orangeville holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Orangeville's top sights

Island Lake Conservation Area

67 locals recommend

Theatre Orangeville

40 locals recommend

Galaxy Cinemas

14 locals recommend

Other great holiday rentals in Orangeville

Guest favourite
Home in Orangeville
4.81 out of 5 average rating, 16 reviews

Modern Guest Apartment near downtown Orangeville.

Top Guest favourite
An outdoor seating area features a gazebo with comfortable seating and a decorative rug. The surrounding garden showcases various plants and flowers, alongside a pathway leading to the guest home. The structure is nestled among trees, contributing to a serene setting.
Guesthouse in Mono
4.92 out of 5 average rating, 61 reviews

Mono Countryside Home & Farm

Top Guest favourite
Cabin in Guelph-Eramosa
4.99 out of 5 average rating, 92 reviews

Fern Hill Cabin

Top Guest favourite
Home in Alton
5 out of 5 average rating, 20 reviews

Little blue haven

Superhost
An aerial view of the Orangeville Retreat House is presented, showcasing the home's expansive front yard surrounded by lush greenery. A winding driveway leads to the garage, while solar panels are visible on the roof, highlighting the property's integration with nature.
Home in Orangeville
4.65 out of 5 average rating, 37 reviews

Mono Forest Stay & Event Space

Guest favourite
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.
Apartment in Orangeville
4.97 out of 5 average rating, 58 reviews

Beautiful Getaway in Orangeville

Superhost
Guesthouse in Orangeville
4.75 out of 5 average rating, 4 reviews

Ballo - GuestHouse

Superhost
Home in Caledon
4.75 out of 5 average rating, 36 reviews

8 Acre Retreat | 5 min to Canadian Open Hot Tub!

When is the best time to visit Orangeville?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$144 NZD$151 NZD$158 NZD$158 NZD$168 NZD$165 NZD$170 NZD$165 NZD$149 NZD$153 NZD$154 NZD$156 NZD
Avg. temp-7°C-6°C-1°C6°C12°C17°C20°C19°C15°C9°C3°C-3°C

Frequently Asked Questions

  • What are the best places to stay in Orangeville?

    Many guests find stays around downtown Orangeville appealing for walkable access to shops, dining, and galleries. The area near Island Lake and tree-lined neighborhoods also has a range of vacation rental options.

  • What are the best things to do in Orangeville with kids?

    Families can explore splash pads, playgrounds, and creative workshops around Orangeville. Island Lake Conservation Area also has child-friendly trails and picnic spots, while some theaters host kid-oriented performances.

  • What are some of the best things to do in Orangeville?

    Explore main street’s shops and tree carvings, spend time at local art galleries, or catch a live show at Theatre Orangeville. Nature seekers often walk the trails at Island Lake Conservation Area or nearby parks.

  • How is the weather in Orangeville?

    Orangeville has cold winters, with temperatures ranging from about 12–32°F (-11–0°C), and mild autumns around 49–70°F (10–21°C). Showers or snow are common, so layering and a waterproof jacket are helpful.

  • When is the best time to visit Orangeville?

    Late spring through early fall is often recommended for comfortable temperatures, outdoor events, and colorful landscapes. Autumn brings vibrant foliage, while summer is lively with markets and arts festivals.

  • What are the best places to visit in Orangeville?

    Many visitors explore the tree sculpture walk downtown, the Orangeville Farmers’ Market, and Island Lake Conservation Area. Theatre Orangeville is often highlighted for its performances in a historic town hall setting.

  • What are some hiking trails in Orangeville?

    Orangeville has a mix of forested walking paths and waterfront trails. Island Lake Conservation Area is frequently suggested for its scenic loops and accessible routes, while Mono Cliffs Provincial Park is also popular for varied terrain.

  • What are some family activities we can do in Orangeville?

    Families often visit splash pads, community parks, or the outdoor spaces at Island Lake Conservation Area. Downtown Orangeville sometimes hosts family-friendly festivals and public art tours.

  • What are some of the best day trip ideas from Orangeville?

    Consider exploring nearby conservation areas, touring local wineries, or discovering small towns with historic charm. Outdoor lovers often venture to Mono Cliffs Provincial Park or the Credit Valley for hiking and nature experiences.

  • Are there any pet friendly accommodations available in Orangeville?

    Pet-friendly accommodations can be found in several Orangeville neighborhoods, especially close to parks and walking trails. Hosts in the area often welcome guests with dogs, making it easy to explore outdoor spaces together.

  • What are some local tips for visiting Orangeville?

    Locals suggest exploring the public art, visiting weekend farmers markets, and trying seasonal treats at downtown bakeries. Autumn foliage and spring blooms bring extra color to nearby parks and trails.

  • What is Orangeville known for?

    Orangeville is known for its lively arts scene, locally rooted markets, and the scenic Headwaters region. Visitors frequently explore its tree sculptures, historic main street, and a range of natural retreats nearby.

  • What are the best hidden gems to explore in Orangeville?

    Discover Orangeville’s unique tree sculptures along the main streets, peek into boutique art galleries, or stroll through quiet garden spaces. Local hiking trails also reveal less-traveled corners of nearby woodlands.

  • What are the best foods to try in Orangeville?

    Locally grown produce, artisanal cheeses, and craft baked goods are frequently suggested in Orangeville. Many visitors enjoy seasonal fare at farmers markets, along with classic Canadian dishes in the town’s cafes and restaurants.

  • What should I bring for a trip to Orangeville?

    Pack layers to adapt to cooler mornings and warmer afternoons, especially outside summer. Comfortable shoes are helpful for exploring local shops, trails, or festivals, and a light rain jacket is often useful throughout the year.

  • What is the nightlife in Orangeville like?

    Orangeville’s nightlife centers around relaxed pubs, local live music, and casual eateries, especially near the main street district. Occasional performances at Theatre Orangeville or neighboring music venues bring in a creative crowd.

  • What are the most popular events or festivals in Orangeville?

    The Orangeville Blues and Jazz Festival energizes the town in early summer, while theater events, farmers markets, and seasonal fairs bring together locals and visitors year-round. Arts and busker festivals are also frequently suggested.

  • Are there family friendly vacation rentals in Orangeville?

    Orangeville has a variety of family friendly vacation rentals, especially in its residential neighborhoods and near parks. Many homes provide spacious layouts for groups or families seeking a comfortable stay.

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Dufferin County
  5. Orangeville