Holiday rentals in Simcoe

The Kiln - Stay Longer Save More!

Escape life's bustle & retreat to this 4-season cabin, which sits on an 80 acre farm overlooking a tranquil pond. Cozy up inside by the wood stove, play some of the many games provided, or kick your feet up & catch up on your favourite shows as satellite & wifi are accessible. Get outdoors to wonder the fields and go for long forest walks along the many trails, or sit around the fire pit roasting hot dogs and marshmallows! Make sure to keep an eye though, as you're bound to see some wildlife!

Drayton House Bachelor apartment

located at the front of the century home of Anthony's Gardens, surrounded by unusually large tropical plants and trees. It has a large private front patio, enclosed and safe for dogs, with a natural gas barbecue. Park right beside this unit. Walking distance to everything, including shopping, beach, lake, restaurants and theatre. Unit is totally complete for short visits, includes everything such as a 50 in flat screen TV, Fire Stick and Netflix. large walk-in shower, AC, electric fireplace.

Little Can in the Pines - Bunkie No. 1

*NO hydro/power/electricity *NO running water *NO flush toilet (outhouse only) *NO Wi-Fi *NO street lights (it's dark at night) *NO sheets, blankets, pillows - Queen *NO cookware, plates, utensils etc. *HEATED seasonally from Oct - May *Outdoor shower - operates seasonally *Poor cell signal (except Rogers) *Very private *Far from road - 800 ft *Dogs welcome *Firewood for sale *BBQ & propane provided w/ tongs & spatula *Bunkies are 400 ft apart from each other We look forward to hosting you!

Vintage Farmhouse with Hot Tub on Vineyard

Our tranquil Farmhouse at Bonnieheath Estate blends vintage country charm, creating a warm and inviting retreat for up to 8 guests. This beautifully styled three-bedroom, one-bathroom Farmhouse is on the main and upper floor of the building and does not share amenities with the Cellar Suite which is a separate unit on the lower floor. Perfect for relaxing, quiet gatherings, enjoying a peaceful countryside escape, steps away from the working Vineyard and Lavender farm at Bonnieheath Estate.

Luxury Tiny Home at the Farm - Botanical Oasis

Get away from it all, and enjoy time away. Spend time in the country, with all the comforts of home (and then some!). Pet / feed the animals, enjoy a campfire, walk the trails through the fields and the forest. Take an adventure outing at one of our suggested venues, or pick one of you own. Try it before you buy it! This tiny home is at the same location where True North Tiny Homes builds their homes. If you're lucky, you can tour some other tiny homes under construction while you're here.

Romantic Cabin For Two Or A Multi Family Stay

Cozy cabin for two + kids and pets. New this year is a second cabin which acts as extra sleeping space the larger family or a second family. The second cabin would not be rented to strangers to those renting the main cabin. New this year, a third building which will have outdoor movie nights with kettle popcorn over an open fire. I will also be building a pizza fire oven. Play area for the kids and a large park across the dirt road for your enjoyment. Beach is a 15min walk as most amenities.

Cobalt Hideaway| Hot Tub |Walk to beach | Bonfire

Relax & kick back in this cozy, stylish cottage in the heart of Port Dover! -Pet friendly! -Hot tub all year! -Fully Fenced in -Short walk to the beach -2 Bicycles incl. -Cornhole & Putting Green -Fireplace -AC -Fast Wi-Fi -Lg. yard -Rainshower -Solo Stove/Wood Bonfire -Gas BBQ -Deck & lounge chairs -Nearby restaurants, cafés, shops -Blackout blinds This cottage is located on the same property as the Ivory Cottage, if you want to have friends/family stay close by they can book it!

Beach-chic | Palm Springs design | Close to beach

Take up the fine art of daydreaming at “The Sun,” one of two units at the Swell House. If an easy-breezy minimalist design with a boho twist is the kind of aesthetic that makes you swoon, you’ll love staying here and soaking in everything this beachside town offers. In only 1-2 hours, you can escape the city to a historic beach bungalow just a 5-8 minute walk from the beach strip, but be warned you may never want to leave after seeing the private resort-style backyard.

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS JUNE 8-18 JUNE 21-30 JULY 1- Please mark this listing as a favourite to get notifications of last minute deals. Unwind at our cozy guest house. Beautiful 2-bedroom cottage. Enjoy the direct waterfront views from the living room, bedroom and wrap around composite deck. Outdoor fire pit and BBQ. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging. Views from the cottage include: lakefront and orchards.

R&R La Petite Rhineland Retreat

Nestled amidst a canopy of trees with a symphony of song, rests a petite cottage that offers a serene experience. This picturesque oasis is accented by a seasonal pool, private deck, and extensive landscaping adding to the air of tranquility. Whether visiting friends & family, exploring local sites or seeking a cozy little private setting for rest & relaxation, La Petite Rhineland Retreat is an impressive destination.

Quiet Cottage Near Turkey Point and Port Dover

NEWLY UPDATED Come and relax in the country. In a 115 yr old tiny home surrounded by 100 acres of farmland. You can sit by the fire and enjoy the quiet solitude of the farm, hit the local beaches, or head into town for some great restaurants. Want to stay in? We also have a few classic board games and a Wii U. Or just curl up and binge your favourite shows/movies! SEASONAL SHOWER IS NOW OPEN

Tiny House with Nature Views and Swimming Pond

Escape the city without the long drive. Our Rustic Retreat is sitting on a 137 Acre Farm just south of Caledonia, Ontario. Only a 20-min drive from Hamilton. Enjoy a romantic getaway for 2 in our cozy cottage beside the pond. Take a dip in the swimming pond (natural cement pond with plants and fish), roam the farm, and take a walk through the forest.