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Holiday rentals in Simcoe

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Top-rated holiday rentals in Simcoe

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Guest favourite
A serene view of the cabin is reflected in the tranquil pond, surrounded by lush trees. Red outdoor chairs are positioned nearby, inviting relaxation by the water's edge, while the cabin's simple design complements the natural landscape.
Cabin in Windham Centre
4.92 out of 5 average rating, 278 reviews

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!

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Top guest favourite
A repurposed shipping container is set within a forested area, surrounded by tall trees. A circular fire pit made of smooth stones can be seen in the foreground, with a fire crackling. A hammock is hung between two trees nearby, and two chairs are positioned on a wooden deck.
Shipping container in Simcoe
4.97 out of 5 average rating, 137 reviews

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!

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Guest favourite
A spacious bedroom features an elegant white bed with decorative pillows and a textured quilt. A woven basket sits on the bed, adding charm. Soft light is provided by hanging chandeliers, and a cozy seating area is visible, contributing to a tranquil ambiance.
Home in Waterford
4.91 out of 5 average rating, 121 reviews

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.

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Guest favourite
An exterior view showcases a modern tiny home with a combination of wooden and black siding. Large windows allow for ample natural light, and a small wooden deck is visible at the entrance. The surrounding landscape features open fields and a partly cloudy sky.
Tiny home in Cayuga
4.94 out of 5 average rating, 140 reviews

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.

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Guest favourite
A cozy sleeping area is featured with a spacious bed adorned with white linens and a patterned quilt. Soft string lights are gently draped along the wooden walls, providing a warm glow, while a window offers views of the surrounding greenery.
Cabin in Port Dover
4.84 out of 5 average rating, 130 reviews

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.

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Guest favourite
The exterior of the guest house features a wrap-around composite deck with glass railing, overlooking the direct waterfront views of Lake Ontario. The structure is surrounded by lush greenery and is complemented by large windows allowing natural light into the living space.
Guest house in Lincoln
4.96 out of 5 average rating, 309 reviews

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS JUNE 21-26 (5 nights/6 days) JUNE 27-JULY 6 JULY 8-18 JULY 26-31 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 orchards and the Lake

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Top guest favourite
Farm stay in Vittoria
4.99 out of 5 average rating, 166 reviews

Cozy and private farm loft.

Welcome to our farm! We are tucked away at the end of a dead end road in beautiful Norfolk County, located just a 10 min drive to Simcoe, Pt Dover and Turkey point, which have everything you would need. Relax in our cozy loft - stocked with all the essentials for your visit and enjoy country living! You can visit one of the many wineries or breweries we have in the county, grab some fresh produce at some of the local farm markets, or walk/bike one of the many trails in the area.

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Guest favourite
A private yard features a hot tub alongside a cozy fire pit area, surrounded by four blue Adirondack chairs set on pebbles. A wooden pergola above provides a charming touch, complemented by lush green grass and a fully fenced perimeter.
Cabin in Port Dover
4.81 out of 5 average rating, 156 reviews

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!

FamilyLocationWifi

Top guest favourite
A modern kitchen features rich wooden cabinetry and a spacious marble island with seating. Stainless steel appliances, including a refrigerator and microwave, are included. Natural light filters through two windows, illuminating the countertops. The entrance door to the side is visible, connecting to the outside.
Farm stay in Simcoe
5 out of 5 average rating, 37 reviews

Private, Peaceful Country Escape

This unique and private country apartment was created to offer our guests a place to recharge and relax in a small farm setting. Settle in and relax indoors with modern and new amenities, or step out onto your very own covered area designed to offer a comfortable space to relax and sit surrounded by nature. If outdoor cooking is something you enjoy, you have your own BBQ and backyard firepit/grill area. *Solo traveller, one bedroom rate is available upon request. Message for info*

LocationFamilyBathroom

Top guest favourite
A cottage is surrounded by vibrant red foliage, showcasing a blend of natural colors. The exterior features light wood siding and a tiled roof, with large glass doors leading to a patio area. Lattice work adorns parts of the structure, adding texture and visual interest.
Guest house in Delhi
4.97 out of 5 average rating, 177 reviews

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.

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Superhost
Home in Simcoe
4.76 out of 5 average rating, 152 reviews

Oliver's Tiny Home In The Forest | Sauna & Hot Tub

Escape to the heart of a Carolinian forest in Simcoe, Norfolk County — a private tree farm sanctuary designed for those who crave stillness. Sink into the hot tub, warm your soul in the wood-burning sauna, or brave the cold plunge bucket on warm days. Surrounded by towering trees and birdsong, this cozy retreat welcomes couples, friends, and solo adventurers year-round. Unplug. Breathe. Belong to the forest.

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Top guest favourite
A welcoming outdoor deck features a red umbrella over a dining table surrounded by four chairs. Two potted plants add greenery, while a barbecue grill stands nearby. A wooden privacy screen provides a sense of seclusion, complementing the landscaped yard.
Cottage in Simcoe
4.91 out of 5 average rating, 106 reviews

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

FamilyLocationIndoor spaces

Popular amenities for Simcoe holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Simcoe

Guest favourite
A modern guesthouse exterior is presented, featuring a contrasting white facade with black accents. Large windows allow for ample light, while the garage doors reflect a sleek design. The gabled roof adds architectural interest to the overall structure.
Guest house in Norfolk
5 out of 5 average rating, 9 reviews

Scenic & Cozy Guesthouse

LocationPetsDecor

Guest favourite
An aerial view of a stylish living area displays a light-colored sectional sofa with decorative cushions. A dark coffee table complements the space, while a patterned area rug is visible beneath. The kitchen island, featuring a dark stone countertop, is situated nearby, enhancing the contemporary design.
Guest house in Tillsonburg
4.97 out of 5 average rating, 101 reviews

BosHaven Guest House *Hot tub*

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Home in Simcoe
5 out of 5 average rating, 3 reviews

Cozy Village Retreat by the Lake - Port Ryerse

LocationFamilyIndoor spaces

Top guest favourite
Cabin in Windham Centre
4.97 out of 5 average rating, 67 reviews

The Kabin

LocationCheck-inPets

Top guest favourite
A comfortable bed is dressed in a white quilt with subtle texture, complemented by decorative pillows in various colors. A framed artwork featuring a tree hangs above the bed, while soft lighting enhances the serene environment of the room.
Flat in Port Dover
4.96 out of 5 average rating, 47 reviews

Country Apartment Retreat

LocationCheckoutAmenities

A compact living space is highlighted by a lofted bedroom area, featuring wooden beams and large windows that allow natural light to brighten the room. A cozy seating area is furnished with a dark sofa and colorful throw blankets, surrounded by art and decorative accents.
Tiny home in Simcoe
4.93 out of 5 average rating, 29 reviews

Lola Tiny House nestled on Luna Creek

FamilyLocationHospitality

Top guest favourite
A serene bedroom is highlighted by a spacious bed adorned with soft linens and fluffy towels. A decorative lantern hangs from the ceiling, and large glass panels frame a lush view of the surrounding forest. An elegant clock and mirror are positioned nearby, adding a touch of charm.
Tiny home in Vittoria
5 out of 5 average rating, 17 reviews

Secluded, Private & Truly Unique Experience

LocationValueHospitality

Guest favourite
The exterior of a two-story cabin is surrounded by lush green trees, with a spacious deck featuring a railing. Large glass doors allow visibility into the living area, revealing a warm interior. A winding staircase leads to the lower level, emphasizing the cabin's elevated position.
Cabin in Vittoria
4.89 out of 5 average rating, 80 reviews

Cabin w/ Panoramic Lake Views

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When is the best time to visit Simcoe?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price₹8,869₹13,869₹19,058₹6,699₹8,774₹8,963₹8,963₹10,189₹8,774₹10,095₹8,680₹7,642
Avg. temp-5°C-4°C0°C7°C14°C19°C21°C20°C16°C10°C4°C-2°C

Frequently Asked Questions

  • What are the best places to stay in Simcoe?

    Central neighborhoods near downtown make it easy to explore walkable shops, bistros, and historic sites. Around the outskirts, you can find stays closer to nature or peaceful community parks.

  • What are the best things to do in Simcoe with kids?

    Simcoe has family-friendly parks, local playgrounds, and interactive museums where children can learn through hands-on exhibits. In summer, splash pads and community pools are frequently suggested for cooling off.

  • What are some of the best things to do in Simcoe?

    Stroll through local parks, sample harvest-fresh produce at markets, and discover heritage buildings in the historic downtown area. In summer, the town hosts outdoor events and artisanal fairs that draw both residents and visitors.

  • How is the weather in Simcoe?

    Simcoe has mild to warm summers near 79°F (26°C) and cooler autumns, with temperatures dipping to around 41°F (5°C). Rain showers are common from late summer into October, so packing a raincoat is practical.

  • When is the best time to visit Simcoe?

    Late spring through early autumn is often recommended for outdoor activities, local festivals, and farmers’ markets. Cooler temperatures in autumn bring colorful foliage and quieter town events.

  • What are the best places to visit in Simcoe?

    Downtown Simcoe is known for its heritage buildings, galleries, and vibrant markets. The town also has parks with riverside paths and small museums highlighting the region’s agricultural history.

  • What are some hiking trails in Simcoe?

    Simcoe has several forested and riverside trails, popular for walking and birdwatching. Community-maintained paths wind through conservation areas and quiet green spaces around town.

  • What are some family activities we can do in Simcoe?

    Explore the family-oriented parks, picnic at community green spaces, or visit recreational centers around town. Many families also enjoy following local walking trails and seasonal community events together.

  • What are some of the best day trip ideas from Simcoe?

    Explore nearby beaches along Lake Erie, or visit botanical gardens and conservation areas just outside town. Small lakeside communities and regional vineyards are frequently suggested for those interested in local flavors and scenic views.

  • Are there any pet friendly accommodations available in Simcoe?

    Many stays in Simcoe welcome pets, especially those near parks or on the outskirts of town. Look for accommodations with outdoor space or proximity to walking trails for convenient pet outings.

  • What are some local tips for visiting Simcoe?

    Locals often suggest visiting farmers’ markets early for the freshest produce, and layering clothing to adjust to variable weather. Neighborhood cafés are cozy spots to connect with the community or warm up on a cooler day.

  • What is Simcoe known for?

    Simcoe is known for its agricultural roots, farmers’ markets, and scenic parks. The town’s heritage architecture and annual holiday events draw visitors interested in local traditions and community gatherings.

  • What are the best hidden gems to explore in Simcoe?

    Wander nature trails along lesser-known riverside paths or discover quiet gardens maintained by local volunteers. Artisans' markets and small heritage sites around town often provide unique perspectives on Simcoe’s history.

  • What are the best foods to try in Simcoe?

    Simcoe is known for locally grown produce, artisanal cheeses, and seasonal baked goods found at farmers’ markets. Traditional dishes with Ontario-grown pork and fresh lake fish are frequently suggested in local eateries.

  • What should I bring for a trip to Simcoe?

    Pack comfortable walking shoes for exploring parks and trails, and bring layers to adjust to changing temperatures. A rain jacket is useful, especially in late summer and autumn, when showers are common.

  • What is the nightlife in Simcoe like?

    Simcoe’s nightlife has a relaxed atmosphere, with pubs, casual bistros, and community events. Some evenings feature live music or local theatre performances, creating a welcoming scene for gathering with friends.

  • What are the most popular events or festivals in Simcoe?

    The Simcoe Christmas Panorama draws visitors with festive lights during the holiday season, while summer brings music and food festivals at community parks. Agricultural fairs and classic car shows are also local traditions.

  • Are there family friendly vacation rentals in Simcoe?

    Simcoe has many family-friendly vacation rentals, including homes and apartments with kitchens and outdoor play areas. Options around parks and in quieter neighborhoods are often chosen by families looking for convenience and comfort.

Quick stats about holiday rentals in Simcoe

  • Total holiday rentals

    Explore 20 holiday rentals in Simcoe

  • Nightly prices starting at

    Simcoe holiday rentals start at ₹2,830 per night before taxes and fees

  • Verified guest reviews

    Over 160 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Wifi availability

    20 of Simcoe holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Simcoe rentals

  • 4.5 Average rating

    Simcoe stays receive an average rating of 4.5 out of 5 from guests

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Norfolk County
  5. Simcoe