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Holiday rentals in Caledon

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Top-rated holiday rentals in Caledon

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

Wooden guesthouse in the forest
SUPERHOST
Entire guest house · 2 guests · 2 beds · 1 bathroom

Wooden guesthouse in the forestThe guesthouse is the perfect getaway. Like living at a cottage, minutes away from the city. This loft guest house is fully equipped with bedrooms, own kitchen and private bathroom. We are just 45 minutes from Toronto. Centrally located with a short drive to both Georgetown & Acton. Ten Minutes To 401/407. This exclusive retreat is nestled in a hill with spectacular views, surrounded by 16 acres of towering trees overlooking a creek with a private waterfall and walking trails.

Sunny Pines Farm Designer Studio
SUPERHOST
Entire guest house · 2 guests · 1 bed · 1 bathroom

Sunny Pines Farm Designer StudioPerfect 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, a small wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge/freezer; 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.

A spectacular cabin setting in the woods
SUPERHOST
Tiny house · 2 guests · 1 bed · 1 bathroom

A spectacular cabin setting in the woodsThis cozy cabin in the woods is the perfect couples weekend retreat. Set on 15 acres the cabin is your personal oasis to relax and unwind in nature around your private 1/2 acre pond. Only minutes from Orangeville, Hockley Valley and less than one hour from downtown Toronto this private cabin is the perfect setting for a weekend getaway.

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Popular amenities for Caledon holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Caledon

SUPERHOST
  1. Tiny house
  2. Schomberg
BEAR CABIN (rustic, 'off-the-grid')
SUPERHOST
  1. Entire cabin
  2. Palgrave
Hockley valley, up country guest cottage
SUPERHOST
  1. Entire loft
  2. Schomberg
Rustic Country Escape for the Nature Lover
SUPERHOST
  1. Entire cabin
  2. Mono
The Trails Retreat (Private Cabin)
SUPERHOST
  1. Entire house
  2. Orangeville
Charming & Spacious Hockley Valley Coach House
SUPERHOST
  1. Entire cabin
  2. Caledon
Caledon Cabin Cottage
  1. Entire flat
  2. Brampton
Sunny 1 Bedroom Apartment with your own Sun Room
  1. Entire flat
  2. Mississauga
Executive suite
SUPERHOST
  1. Entire guest house
  2. Mono
A charming, rustic 140 year old Carriage house
SUPERHOST
  1. Tiny house
  2. Mono
Post & Beam Tiny Home with Pond and Trails
  1. Entire bungalow
  2. Erin
Country Cottage House, Cozy and Private
SUPERHOST
  1. Entire flat
  2. Mono
Rural Estate Coach House Apartment

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