Vacation rentals in Orangeville

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Top-rated vacation rentals in Orangeville

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Guest favorite

Guesthouse in Orangeville

4.96 out of 5 average rating, 309 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.

Feb 12 – 19

G$38,062 GYD per night

Guest favorite

Dome in Bradford West Gwillimbury

4.98 out of 5 average rating, 208 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...

Nov 12 – 19

G$24,859 GYD per night

Guest favorite

Apartment in Horning's Mills

4.96 out of 5 average rating, 255 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.

Nov 7 – 14

G$16,496 GYD per night

Guest favorite

Loft in Mono

4.98 out of 5 average rating, 59 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.

Jul 11 – 18

G$19,717 GYD per night

Guest favorite

Apartment 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.

Feb 10 – 17

G$20,437 GYD per night

Guest favorite

Tiny home in Belwood

4.93 out of 5 average rating, 191 reviews

Uniquely Pure Bunkie Getaway in Belwood

Stay on a quiet property amongst trees at the Uniquely Pure Bunkie in Belwood. Enjoy your own space with a firepit, a cozy place to sleep, and a seasonally available outdoor shower (closes Oct 1st until spring). The owner lives on same property as Uniquely Pure Studio, where you can book massage therapies & yoga classes, or purchase products from our aromatherapy and culinary creations line during your stay (contact in advance for availability). Sorry, NO KIDS (for safety) & NO PETS!

Jan 2 – 9

G$19,765 GYD per night

Guest favorite

Guesthouse 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 :)

Sep 8 – 15

G$14,054 GYD per night

Guest favorite

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!

Dec 8 – 15

G$15,542 GYD per night

Guest favorite

Apartment in Orangeville

4.97 out of 5 average rating, 37 reviews

Beautiful Getaway in Orangeville

Enjoy some time away at this unique and tranquil getaway. Beautiful and spacious 1 bedroom apartment (plus 2 futons), a 5 minute walk to Island Lake Conservation. Located in a quiet neighbourhood close to the downtown area full of amazing restaurants and shops. A short driving distance to nature getaways Mono Cliffs, Cheltenham Badlands, Bruce Trail, Hockley Valley and Adamo Estate & Winery. Perfect for nature lovers, ski enthusiasts, hikers, kayakers, and families.

Dec 11 – 18

G$21,713 GYD per night

Guest favorite

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

Dec 2 – 9

G$34,686 GYD per night

Guest favorite

Guest suite in Mono

4.98 out of 5 average rating, 268 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.

Aug 28 – Sep 4

G$20,638 GYD per night

Guest favorite

Apartment in Shelburne

5.0 out of 5 average rating, 112 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.

Dec 24 – 31

G$16,710 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Orangeville vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Orangeville's top sights

Island Lake Conservation Area31 locals recommend

Walmart Orangeville Supercentre5 locals recommend

Zehrs10 locals recommend

Bluebird Café & Grill10 locals recommend

Mill Creek Pub and Restaurant6 locals recommend

Sobeys Orangeville5 locals recommend

Other great vacation rentals in Orangeville

Guest favorite

Guest suite in Mono

4.98 out of 5 average rating, 65 reviews

Welcome to a Sweet Suite

Jun 13 – 20

G$16,623 GYD per night

Guest favorite

Home in Orangeville

4.78 out of 5 average rating, 49 reviews

A Modern 3 Bedroom Home with Free Parking & Wifi

Nov 8 – 15

G$22,656 GYD per night

Guest favorite

Guesthouse in Mono

4.92 out of 5 average rating, 89 reviews

Mono Studio

Sep 20 – 27

G$21,945 GYD per night

Guest favorite

Home in Orangeville

4.89 out of 5 average rating, 53 reviews

Vibrant & Stylish 3 Bedroom Home with Free Parking

May 6 – 13

G$28,595 GYD per night

Guest favorite

Home in Orangeville

4.97 out of 5 average rating, 58 reviews

HotTub & Private Suite - Casa Facciolo

Jun 2 – 9

G$26,372 GYD per night

Guest favorite

Cabin in Orangeville

4.98 out of 5 average rating, 66 reviews

Hockley Valley Cozy Cottage

Feb 7 – 14

G$36,792 GYD per night

Guest favorite

Home in Orangeville

4.96 out of 5 average rating, 48 reviews

2 BR Century Home in Downtown Orangeville

Aug 26 – Sep 2

G$31,399 GYD per night

Guest favorite

Guesthouse in Orangeville

5.0 out of 5 average rating, 27 reviews

Island Lake Guest House

Apr 26 – May 3

G$14,589 GYD per night

Show all

Quick stats about vacation rentals in Orangeville

Total rentals
50 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
2.1K reviews
Nightly prices starting at
G$8,356 GYD before taxes and fees

Frequently Asked Questions

Do house rentals in Orangeville have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Orangeville. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Orangeville?
Four-legged friends are welcome in Orangeville. Choose from more than 10 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Orangeville?
Experience the best of Orangeville with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Orangeville?
Orangeville has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Orangeville have wireless internet?
Absolutely! We offer over 20 house rentals with wireless internet in Orangeville. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Orangeville?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Orangeville

Top-rated vacation rentals in Orangeville

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Orangeville vacation rentals

Stay near Orangeville's top sights

Other great vacation rentals in Orangeville

Guest suite in Mono

Home in Orangeville

Guesthouse in Mono

Home in Orangeville

Home in Orangeville

Cabin in Orangeville

Home in Orangeville

Guesthouse in Orangeville

Quick stats about vacation rentals in Orangeville

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Orangeville have air conditioning?

Are there pet-friendly vacation rentals in Orangeville?

How much does it cost to stay in house rentals in Orangeville?

Are there family-friendly vacation rentals in Orangeville?

Do house rentals in Orangeville have wireless internet?

What are the most popular amenities for House Rentals in Orangeville?

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