Caledon Rentals
From $2297 per night (USD)VRBO
Caledon Country Estate 7 day family rental not available for weddings
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 10
2 story 6 Bedroom estate home on 100 acres in Caledon 2 buildings, main and separate 2 bdrm pool house Pool, Pool Hous ...
From $2297 per night (USD)VRBO
From $279 per night (USD)VRBO
Romantic Studio Hideaway • Heated Pool Option
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This beautiful lower level apartment is located in the heart of Caledon Hills on a magical country setting surrounded ...
From $279 per night (USD)VRBO
From $278 per night (USD)VRBO
Serene Country Oasis • Optional Heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Since we left the city and embraced country living, we have shared our peaceful Cannon Gates with family and friends. ...
From $278 per night (USD)VRBO
From $533 per night (USD)Expedia
Charming Log Home - 25 private acres in Caledon
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our home sits on the rolling hills of Caledon East surrounded by a serine ambiance of pure peace and quiet. Just 45 minu ...
From $533 per night (USD)Expedia
From $345 per night (USD)VRBO
PARADISE OVERLOOKING THE BUBBLING CREDIT RIVER SURRONDED BY LUSH MATURE GARDENS
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Fabulous cottage right on the Credit River in the beautiful Hamlet of Belfountain, Ont., only 50 minutes from Toronto. I ...
From $345 per night (USD)VRBO
From $278 per night (USD)Expedia
Rustic cabin-inspired residence.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Nestled in the serene landscapes of Caledon, ON, this captivating three-story cabin-style retreat offers an idyllic esca ...
From $278 per night (USD)Expedia
From $920 per night (USD)VRBO
Fields & Sunsets
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to our peaceful and chic manor, nestled amidst the serene beauty of nature. This charming retreat offers a perfe ...
From $920 per night (USD)VRBO
From $166 per night (USD)Expedia
Cozy tiny home, immersed in the forest, overlooking the pond!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
High Meadows bunkie is immersed in the forest, offering privacy from the surrounding trees and nestled up on the hill ov ...
From $166 per night (USD)Expedia
From $428 per night (USD)VRBO
Large Estate House ~ 6BR and 4.5WR ~ Sauna ~ Games ~ Pool Table ~ Hot tub - Pool
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Swimming Pool, Hot Tub, Sauna, and Pool Table. ✓ Full privacy — no shared amenities ✓ Spacious backyard with pool and g ...
From $428 per night (USD)VRBO
From $203 per night (USD)Expedia
2 Bedroom Apartment - A Full space with access to backyard, patio, and firepit
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Private 2 bedroom apartment, fully furnished with full kitchen, living room and access to outside dining area and patio ...
From $203 per night (USD)Expedia
From $271 per night (USD)VRBO
Cozy Country Spring & Summer Getaway | HotTub + Outdoor Pool & Fire Pits
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Perfect spring and early summer escapes — complete with a private hot tub, outdoor fire pit, and peaceful river views. J ...
From $271 per night (USD)VRBO
From $330 per night (USD)Expedia
#1 Best Deal in Brampton
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
• Newly constructed detached home with brand-new furniture, appliances, and decor. • Cozy living area with 4K microLED s ...
From $330 per night (USD)Expedia
From $286 per night (USD)VRBO
Opulent Estate ~ Caledon Countryside~ Small Groups
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our 3,000 sq ft modern luxury estate in Caledon. Our 2.4-acre property features: ✓ 4 lavishly furnished bedr ...
From $286 per night (USD)VRBO
From $115 per night (USD)VRBO
Luxury Retreat with Workspace & Spacious Backyard
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Enjoy our spacious and luxurious home situated in the community of Toronto Gore Rural Estate in Brampton! This home is ...
From $115 per night (USD)VRBO
From $339 per night (USD)VRBO
Alton Riverside Cottage Main Floor
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked along the gentle flow of the Credit River, Alton Riverside Cottage main floor apartment offers a calm, cozy retre ...
From $339 per night (USD)VRBO
From $88 per night (USD)Expedia
Studio Apartment in the heart of Caledon
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stylish Studio Apartment in the heart of Caledon! Check out this charming studio apartment that combines comfort, conve ...
From $88 per night (USD)Expedia
From $217 per night (USD)VRBO
Cozy 1-bedroom apartment with AC, WiFi in welcoming Caledon
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This 1-bedroom apartment is perfect for your escape to Caledon. With WiFi, a washing machine, heating, AC, and an iron, ...
From $217 per night (USD)VRBO
From $670 per night (USD)Expedia
Country Caledon Charm your private oasis, your home away from home.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Private Caledon home set in the country with expansive views. You have the entire home to yourselves. Now boasting the e ...
From $670 per night (USD)Expedia
From $3268 per night (USD)VRBO
Stunning 6 bed 5 bath estate on 65 acres with Pool, Hot Tub and Tennis Court!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 11
WOODLANDS AREA Located among the rolling hills, valleys, forests and wetlands of picturesque Caledon just north of Missi ...
From $3268 per night (USD)VRBO
From $154 per night (USD)VRBO
Luxe & Cozy: Stylish Apartment in Caledon
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our 2BR, 1 Bath House in Caledon, featuring: ✓ Modern design with an open-concept layout Basement Apartment ...
From $154 per night (USD)VRBO
From $355 per night (USD)VRBO
Exclusive 100-Acre Modern Estate Designed Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Unveil the beauty of our stunning home, where modern elegance graces a private 100-acre estate. Ideally located, you're ...
From $355 per night (USD)VRBO
From $181 per night (USD)VRBO
Luxe Apartment in Caledon
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Private Suites: Spacious area with a Queen-size bed, ensuite bathrooms, premium beddings and a dedicated work desk, perf ...
From $181 per night (USD)VRBO
From $947 per night (USD)VRBO
5-Bedroom Countryside Estate in Northern GTA – Ideal for Gatherings & Getaways
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Whispering Ridge Retreat, a 4,000 sq ft luxury estate nestled in the peaceful countryside of the northern Gre ...
From $947 per night (USD)VRBO
From $1185 per night (USD)Expedia
Perfect 10 acres private quiet property for small events & family gatherings
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Only 45 minutes from Yorkdale Shopping Mall, Vintage Cottage Retreat is 10 acres of peace and quiet nestled along the pr ...
From $1185 per night (USD)Expedia
From $332 per night (USD)VRBO
Caledon family escape with Crib
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the best of Caledon in this stylish and modern townhouse. Perfect for families or groups, this spacious retre ...
From $332 per night (USD)VRBO
From $330 per night (USD)VRBO
Guesthouse Hideaway in Caledon
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 4
Welcome to your private retreat! This spacious 3-bedroom, 3-bathroom walkout basement guest suite sits on a peaceful rav ...
From $330 per night (USD)VRBO
From $304 per night (USD)VRBO
Cozy 3BR Retreat | Foosball & Lounge Chair
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your Private 3BR, 2.5WR Caledon Retreat-Perfect for Families & Peaceful Getaways! ✔ Entire home to yourself ...
From $304 per night (USD)VRBO
From $307 per night (USD)VRBO
Unwind in Bolton – Bright, Clean&Peaceful 4BR Stay
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy comfort in our private 4BR, 2.5WR Bolton home - perfect retreat for families! ✓ Entire home to yourself - complet ...
From $307 per night (USD)VRBO
From $110 per night (USD)VRBO
Charming Bed and Breakfast Rental near to the Caledon Hills, Ontario
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This charming rental is only an hour from Toronto and overlooks the Credit River. With the Caledon Hills, Ontario nearby ...
From $110 per night (USD)VRBO
From $210 per night (USD)VRBO
Unique Vacation Rental Suite with a Patio in Terra Cotta, Ontario
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This wonderful suite, within a vacation rental, has a patio and is set in the village of Terra Cotta, Ontario, just an h ...
From $210 per night (USD)VRBO
From $110 per night (USD)VRBO
Beautiful Vacation Rental overlooking the Credit River in Terra Cotta, Ontario
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This beautiful vacation rental overlooking Credit River is in the village of Terra Cotta, Ontario, and is only an hour f ...
From $110 per night (USD)VRBO
From $329 per night (USD)Expedia
Detached 5 Bedroom ~100% Spotless ~Sleeps 13
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
Enjoy Comfort in our Private 5BR & 4.5WR Caledon Home - Perfect for family & friends gatherings surrounded by nature! ✓ ...
From $329 per night (USD)Expedia
From $770 per night (USD)VRBO
Beautiful Villa on Hill
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Beautiful Villa on Hill, a secluded paradise nestled on App. 3 acres of ravine property in Caledon East. Surr ...
From $770 per night (USD)VRBO
From $145 per night (USD)Expedia
Golf & Spa Retreat w/ Jacuzzi near TPC Toronto
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Experience a warm and luxurious countryside retreat in Caledon, perfectly suited for family stays, well ...
From $145 per night (USD)Expedia
From $1305 per night (USD)VRBO
Fun Villa | Pool, Theatre, Gym & BBQ | Sleep 14
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to Caledon Villa — your private luxury escape, perfect for unforgettable group stays with premium comfort and en ...
From $1305 per night (USD)VRBO
From $378 per night (USD)Expedia
Luxury 5-Bed Home w/ Office & 5 Baths | Peaceful Caledon Escape
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 11
Welcome to your home away from home in beautiful Caledon — a peaceful, upscale community surrounded by rolling countrysi ...
From $378 per night (USD)Expedia
From $662 per night (USD)VRBO
Luxury 4BR Stay with Swim Spa, Golf & Fireplaces
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Just a heads up: The primary guest must be at least 28 years of age to book this stay. Kick back in style a ...
From $662 per night (USD)VRBO
From $519 per night (USD)Expedia
Private 5-Bedroom Caledon Home Comfort, Style, and Nature!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
Rental basis: Entire house or apartment Number of bedrooms: 5; Number of other rooms with beds: 0 Number of bathrooms: 4 ...
From $519 per night (USD)Expedia
From $837 per night (USD)VRBO
Caledon Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 16
✨ Luxury 6-Acre Country Estate in Caledon — Modern Comfort Meets Rustic Charm ✨ Escape to your private 6-acre oasis in ...
From $837 per night (USD)VRBO
From $514 per night (USD)Expedia
100 % privacy 7 bedrooms with 6 bathrooms and 2 master bedroom with 2 king beds
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 15
100 percent privacy 7 bedrooms with 6 bathrooms almost 4000 square feet finished area including legal basement. This is ...
From $514 per night (USD)Expedia
From $162 per night (USD)VRBO
Cozy 3BR Caledon Retreat with Patio & Outdoor BBQ
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in this beautifully curated Caledon home, where modern comfort and a warm atmosphere come together to create the pe ...
From $162 per night (USD)VRBO
From $148 per night (USD)Expedia
Live Lavishly: Modern Studio, 5G, Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Welcome to Caledon’s Finest Studio Retreat! Enjoy a cozy and thoughtfully designed space in the peaceful community of C ...
From $148 per night (USD)Expedia
From $272 per night (USD)VRBO
⭐ Premium 5⭐ Luxury Stay Near Brampton
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
🏡 Spacious 3-Bedroom Home – Ideal for families, groups, and business travelers 🛏️ Luxury Sleeping Setup: 👑 Master Bed ...
From $272 per night (USD)VRBO
From $2231 per night (USD)VRBO
Perfect Group Getaway Large House with Style
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
This spacious property comfortably accommodates up to 16 guests - basement not included. Perfect for weddings, birthdays ...
From $2231 per night (USD)VRBO
From $380 per night (USD)VRBO
Countryside Meet City - New Luxe 4BR Cozy Home in Caledon - EV Charger and More
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
Where suburb meets countryside — experience the best of both at this stunning brand-new home. Welcome to your Caledon ...
From $380 per night (USD)VRBO
From $197 per night (USD)Expedia
Modern 2BR Private Suite |Prime Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our Stylish & Modern 2BR,1WR basement Retreat in Southfields, Caledon -Perfect for all Families, Couples & Bu ...
From $197 per night (USD)Expedia
From $468 per night (USD)VRBO
Modern Luxury 5 ⭐ Space near Brampton | Sleeps 8
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
⭐ Elegant 5⭐ Detached Home in Prime Caledon Location – Designed for comfort, space & a refined stay 🏡 Spacious 4-Bedroo ...
From $468 per night (USD)VRBO