Holiday rentals in Orangeville

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Orangeville

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Guest house in Orangeville

4.95 out of 5 average rating, 310 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.

14–21 Aug

₹11,473 per night

Guest favourite

Dome in Bradford West Gwillimbury

4.98 out of 5 average rating, 213 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

2–9 Mar

₹9,989 per night

Guest favourite

Yurt in Mono

4.98 out of 5 average rating, 227 reviews

Yurt Soaring Heart Wellness Spa

Sustainable Yurt Lodging close to the Bruce Trail. There is plenty of privacy and nature to experience our 10-acre property. We harvest and sell teas from our herb gardens. Check online at Escarpment Gardens. Enjoy a soak in the hot tub, float on our pond, practice yoga, book a massage, relax by the wood stove, or an outdoor campfire under the stars. Check massage services online : Soaring Heart Wellness Simple camp style cooking or eat at a great local restaurant within a 5 minute drive.

2–9 Jun

₹9,258 per night

Guest favourite

Loft in Mono

4.97 out of 5 average rating, 60 reviews

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.

12–19 Oct

₹9,345 per night

Guest favourite

Flat in Mono

4.95 out of 5 average rating, 197 reviews

Rural Estate Coach House Apartment

Peaceful secluded guest house in forest property 5 minutes from Orangeville, 1 hour from downtown Toronto. 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.

12–19 Mar

₹8,212 per night

Guest favourite

Farm stay in Essa

5.0 out of 5 average rating, 118 reviews

The Schoolhouse

Kick back and relax in this calm, stylish space. This school portable turned into a modern guest home is situated on acreage boasting with gorgeous views of forests, fields, grazing animals and sunsets. In warmer months, cool off in the stock tank pool, play on the volleyball court, and enjoy meals on the deck accessed from the bedroom and main entry. Relax by the campfire, walk nearby trails, visit restaurants, markets and shops. Planning your wedding? Ask about our wedding package!

4–11 Nov

₹14,222 per night

Guest favourite

Guest house in Orangeville

4.97 out of 5 average rating, 98 reviews

A bright & stylish urban studio

Come & relax...in privacy. The "Carriage House" is a 634 square foot studio-style unit is unique & intimate. You will be away from the main house, in your own building. Amazing kitchen, complete with gas range. Spacious & elegant over-sized bathroom. The Murphy bed has a luxury-firm queen mattress, & stows away in a snap for your convenience. 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 :)

11–18 Mar

₹5,770 per night

Guest favourite

Guest suite in Orangeville

4.92 out of 5 average rating, 656 reviews

Private Hot Tub - Headwaters Retreat

Escape to our cozy and rustic queen suite with a modern touch. Private entrance & hot tub steps from your door, overlooking our peaceful conservation area. Spacious fireplace in main suite with en-suite bathroom, Apple TV, Netflix, and second bedroom with two twin beds. Steps from the hiking trails and just minutes from the town center. Perfect for outdoor adventures, art gallery visits, wine tours, weddings, sporting events, work trips or just a quiet getaway. Your getaway awaits!

8–15 Dec

₹6,245 per night

Guest favourite

Guest suite in Mono

4.98 out of 5 average rating, 66 reviews

Welcome to a Sweet Suite

Forget your worries in this spacious and serene space. Enjoy the hiking trails at Mono Cliffs and Island Lake or an afternoon of wine tasting at Adoma Winery. Golf/ski is only 5km away at beautiful Hockley Valley. Enjoy a 5 star dinner at one of the fabulous restaurants in Orangeville. After a busy day return to your cozy queen size bed for a great night sleep. In the morning no need to head out for coffee as it is available for brewing on site. Cream and sugar provided.

7–14 Sep

₹6,680 per night

Guest favourite

Cabin in Mono

4.94 out of 5 average rating, 272 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 and yoga studio, minutes to the Bruce Trail, Hockley Ski & Resort, and Mansfield Ski Club, enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Chef's creations and Private yoga and group classes available

25 Dec – 1 Jan

₹13,938 per night

Guest favourite

Guest suite in Mono

4.98 out of 5 average rating, 269 reviews

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.

17–24 Jun

₹7,524 per night

Guest favourite

Flat in Shelburne

5.0 out of 5 average rating, 114 reviews

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.

22–29 Mar

₹6,715 per night