House holiday rentals in Simcoe

4.98 out of 5 average rating, 147 reviews

The exterior of the cottage is shown, featuring a combination of wood and stone textures. Wide porches wrap around the entrance, while large windows provide natural light. Snow lightly covers the ground, enhancing the peaceful countryside setting, with scattered trees visible in the background.

Home in Brantford

Langford House

Set on the front of a 7 acre country property, the cottage is minutes from Brantford & Ancaster. Enjoy the beautiful open countryside views & a cozy cottage to relax. Just around the corner from the Twin Valley Zoo, & the Rail Trail. Some other local attractions include the Historic Bell Homestead, Wayne Gretzky Sports Centre, Windmill Country Market, Grand River, Oshwegen Speedway, Grand River cruises (must be booked ahead of time), & Grand Adventures for canoeing in the nearby town of Paris.

5 out of 5 average rating, 108 reviews

A vintage schoolhouse stands in the background, showcasing its distinctive architecture and large windows. In the foreground, a well-crafted bike rack holds several bicycles under a shaded canopy, surrounded by autumn foliage and a gravel pathway.

Home in New Hamburg

The Heart of New Hamburg - Picturesque Modern Home

This newly renovated schoolhouse doubles as a picturesque live-in museum! Well lit with stately windows, the upper level delivers a fusion of classic and modern with a fully equipped kitchen, master bedroom and large bathroom with a quaint tub and hand crafted fittings. The lower level boasts of 2 bedrooms with bathrooms, a cozy living area, kitchenette, dedicated workspace and separate entrance. The back patio has heated flooring; making the winter months bearable for outdoor activities.

4.99 out of 5 average rating, 176 reviews

A bright kitchen is highlighted by clean white cabinetry and open shelving displaying dishware. A central island provides seating for four, with a fruit bowl and a potted orchid as decorative accents. Natural light enters through a window overlooking a landscaped area.

Home in Port Dalhousie

Christie St. Coach House

Located steps from Lake Ontario you will find peace and quiet at the Coach House. One of the best streets to view the sunset over Lake Ontario! A short 10min walk to Port Dalhousie business district and Lakeside Park Beach. Find all you need to eat and drink at several restaurants and cafés. Quick access to the QEW and 406 highways. Centrally located between the Wine Regions of Niagara-on-the-lake and The Bench. 15mins East or West will find you at most Niagara Wineries. Licence No: 23112230 STR

The exterior of the Secret Garden Cottage is showcased, presenting a welcoming two-story white house with dark shutters and a peaked roof. Flowering shrubs frame the entrance steps, and a pathway of stones leads to the front porch. A soft, natural backdrop highlights the charm of the home.

4.99 out of 5 average rating, 192 reviews

Secret Garden Cottage Old Town Niagara-on-the-Lake

The Secret Garden Cottage is a charming home situated right in the Historic Old Town of NOTL. In any season, enjoy the entire house AND the gifts that this beautiful area has to offer: Walk or cycle to the many high-quality wineries, outstanding restaurants, charming shops in town, and highly-acclaimed Shaw Festival productions. Or cozy up with all of the comforts of home, enjoying a glass of local wine on the back deck or in the Garden Room, while gazing out over the stunning Secret Garden.

The exterior showcases a charming brick façade with a welcoming red door. Two chairs sit on the front porch, surrounded by neatly landscaped greenery and decorative flowers. A single-car garage is visible to one side, framed by a clear blue sky.

4.94 out of 5 average rating, 224 reviews

Spacious Home in Port Dover

Welcome to your tranquil retreat! Guests enjoy our location on a quiet street. The deck overlooks a peaceful green space with a pond and a variety of wildlife. Guests have a suite downstairs, in addition to the main floor. It is a 5 minute drive to the beach, restaurants, Lighthouse Theatre, live music, and the pier. Norfolk County has 15 wineries/breweries, several beaches, a zip line, and 3 Provincial Parks. Our home is a haven from the hustle and bustle of our busy summer beach town!

A serene view of lush greenery features a winding stone path leading towards the sparkling waters of the Niagara River. Tall trees cast gentle shadows over the expansive grassy area, creating a peaceful outdoor atmosphere.

4.96 out of 5 average rating, 126 reviews

🥂Breathtaking Views of the Niagara River

☀️LOCATION LOCATION LOCATION Enjoy spectacular views of the Niagara River from a private contemporary home nestled in the Village of Queenston, Niagara-on-the-Lake. Situated on the renowned Niagara Parkway and centrally located this home makes it easy to enjoy all that Niagara has to offer. The entire home has been freshly painted (September 2021), with newly purchased 700 Thread Count Egyptian Cotton bedding and brand new towels........ this just listed Airbnb is guest ready to impress!

4.93 out of 5 average rating, 442 reviews

A sunroom features a mixture of wooden furniture, including a sectional sofa and lounge chairs, arranged around a central table. String lights hanging overhead provide warm illumination, while large windows offer views of the surrounding nature.

Home in Cambridge

"Cottage Home On The River" 1 Bedroom

Welcome to Speed Island Trail! Nestled on 1 Acre property in a forested area that backs onto the Speed River. Enjoy Beautiful views all season long with large floor to ceiling windows and wildlife right outside your door. It is just like being out at the cottage. This beautiful one bedroom house is beautifully decorated, has a large kitchen and a breakfast bar. Enjoy the large sunroom and deck where you can sit back and relax. Added bonus the Chickadees eat right off your hand!

A spacious outdoor area features a blend of stone and paved surfaces, surrounded by lush greenery and ornamental plants. A wooden table and chairs provide a gathering space, while a landscaped garden area creates a tranquil setting. A mature tree adds shade to the space.

4.91 out of 5 average rating, 202 reviews

Modern Farmhouse in Niagara’s Wine Country

A farmhouse with a rich history dating back to the 1800’s - fully updated with brand new modern amenities. Centrally located near the Falls, Niagara Parkway, Niagara-on-the-Lake, casinos, wineries and the largest outlet mall in Canada. (A car is recommended since the closest public transportation is 2 km away.) A great gathering spot with a full kitchen, laundry and charming outdoor space with extensive gardens for entertaining A fire pit area sits at the bottom of the garden.

4.91 out of 5 average rating, 134 reviews

A spacious bedroom features a combination of pink walls and exposed brick, enhancing the vibrant atmosphere. The area includes a large bed dressed in white sheets, a black wardrobe, and a vanity with lights. Natural light fills the room through a prominent window, creating an inviting space.

Home in Central Hamilton

Chic Oasis | Luxury Stay in the Heart of Hamilton

Step into a stunning modern-retro escape where bold red tones, playful pink accents, and vintage exposed red bricks create an unforgettable vibe. Perfectly located just steps from vibrant Hess Village, you're within walking distance to concerts, sports venues, art galleries, boutiques, and top-tier dining. Explore trendy Locke Street or hike the Escarpment nearby. With cozy bedrooms, chic outdoor spaces, and irresistible charm, this gem is a true city retreat.

4.94 out of 5 average rating, 102 reviews

A hot tub is positioned on a deck overlooking a calm, expansive lake. The water reflects soft gray skies, creating a serene atmosphere. Rocky shoreline is visible in the foreground, enhancing the tranquil lakeside setting.

Home in Hamilton

Wake Up To Lake Views!

Licence #26-000115. Book now! Bring your whole family to the lake! Need a relaxing weekend? Family Get togethers, Girl’s Trip! Guy’s weekend! Couple’s getaway! Go for a hike, a wine tour, cozy up with friends. Welcome to a beautiful, spacious Lake House. Located 20 min from the wineries in Niagara-on-the-lake, the waterfront trail 5 minutes away. Bring your bikes for a ride along the lake and a local lunch. This property has 180 degree lake views.

4.99 out of 5 average rating, 102 reviews

The exterior of a century home is highlighted, featuring a welcoming porch surrounded by lush greenery. A paved driveway leads to the entrance, with neatly trimmed grass and decorative landscaping enhancing the inviting appeal.

Home in Brant

Paris Oasis-The Maples on Brock

Stay in this immaculately renovated century home, which is just a short walk from downtown Paris and comes with all the perks and white-glove service of a 5 Star Hotel. If you’re searching for the perfect home for your next family vacation, stay-cation, business trip, or long-term rental that satisfies both luxury & location, then look no further. Save your dates now and secure a Paris holiday you’ll always remember!

A charming red cottage features a white deck and railing, leading to a welcoming entrance. Large windows allow natural light to fill the space. The sloped roof and surrounding trees create a cozy and inviting outdoor environment.

4.88 out of 5 average rating, 125 reviews

Sandy Shores Cottage *with hot tub*

Welcome to your cozy beach retreat. This charming 2 bedroom plus loft is a short walk to the sparkling shores of Lake Erie. Being centrally located from the beach, provincial park,restaurants, wineries, breweries and much more gives you the option of a peaceful retreat or an adventure filled getaway. This cozy cottage has it all. Book now to secure your perfect vacation spot. Sandy Shores Cottage.

Popular amenities for house rentals in Simcoe

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.85 out of 5 average rating, 121 reviews

An indoor heated saltwater pool is featured in a bright room with natural light streaming through skylights. The pool's clear water reflects playful patterns on the ceiling. Comfortable seating, including a hammock and lounge chairs, is arranged around the pool area.

Home in Aylmer

Indoor pool, hottub & video game room, near beach

A spacious living area features a plush brown couch and a cozy white lounge chair next to a modern black coffee table. A well-lit dining area with seating for eight is visible, along with a bright kitchen and stylish decor elements.

4.87 out of 5 average rating, 135 reviews

Luxury Family Oasis W/ GameRoom/King Bed/Hot Tub

A serene view of a heated saltwater swimming pool reflects sparkling blue water under clear skies. The pool area is accompanied by a gazebo adorned with blooming wisteria, while comfortable chairs offer seating around the space.

4.8 out of 5 average rating, 246 reviews

WhiteOrchid LuxuryHome WithSaltHeatedSwimmingPool

4.84 out of 5 average rating, 162 reviews

A private backyard space features a swimming pool with steps leading in. Comfortable lounge chairs sit nearby on the concrete patio, while vibrant green trees and a well-maintained lawn surround the area. A shaded seating area can be seen in the background.

Home in Waterloo

Entire Guest Unit+Free Parking by Glenbridge Plaza

A private pool is surrounded by a secure fence, featuring a concrete deck with steps leading into the water. Comfortable lounge chairs are positioned nearby, set against a backdrop of lush greenery and a clear blue sky.

4.9 out of 5 average rating, 103 reviews

Wine country Cottage 15 min drive to old Town NOTL

4.81 out of 5 average rating, 113 reviews

The image features a diamond-shaped solar-heated swimming pool reflecting the soft colors of sunset. Comfortable blue lounge chairs are positioned nearby, overlooking a serene lake. The distant skyline can be faintly seen across the water, blending into the horizon.

Home in Hamilton

California Chic +Breathe +Unwind +Restore

4.87 out of 5 average rating, 99 reviews

Hot Tub/Outdoor Sauna/Heated Pool/5 Min To Falls

A comfortable living room features a dark brown leather sofa and loveseat arranged around a wooden coffee table. A neutral area rug lies beneath the furniture. A white brick fireplace with a wooden mantel is adorned with decorative pieces, and natural light enters through sheer-curtained windows.

4.78 out of 5 average rating, 153 reviews

sunset 1100

Weekly house rentals

A spacious backyard is featured, showing a dark green cottage with a metal roof. The deck is equipped with a patio umbrella, outdoor seating, and barbecue. Lush grass surrounds the area, and a dog rests contentedly on the lawn under the dappled shade of mature trees.

4.79 out of 5 average rating, 19 reviews

Tamarack Cottage by the Beach

5 out of 5 average rating, 11 reviews

A bright cedar sunroom features a swim spa with clear water, set against wood-paneled walls. Natural light floods in through the windows, illuminating the space. Nearby shelves hold decorative items, and a cozy sitting area can be glimpsed through an open doorway.

Home in Brantford

Hot Tub ~ Pool Table ~ 30 Mins to Port Dover

5 out of 5 average rating, 15 reviews

The kitchen features an expansive island with seating for six and modern pendant lighting. White cabinetry is complemented by warm wood accents, while a large window allows natural light to illuminate the space. Essential appliances are neatly arranged, enhancing functionality and openness.

Home in Selkirk

Blue Water Haven Cottage

The exterior of a modern three-story house is showcased, featuring a combination of stone and wood materials. A balcony extends from the second floor, providing a view of the surrounding greenery. A gravel driveway leads to a garage area, surrounded by well-maintained landscaping.

4.88 out of 5 average rating, 8 reviews

Brick House by the water

4.75 out of 5 average rating, 139 reviews

Home in Simcoe

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

5 out of 5 average rating, 45 reviews

Home in St. Thomas

lost + found under the pines

An inviting living area is featured with a high ceiling and natural light streaming through large front windows. Two sofas, one in dark fabric and another in a lighter tone, flank a glass coffee table. Decorative elements and a ceiling fan add to the cozy atmosphere.

5 out of 5 average rating, 24 reviews

Erie Shores

The living area features modern furnishings, including a leather sofa and armchair. A round coffee table with a gold accent lies at the center, and a flat-screen TV is mounted on the wall. Natural light filters through the shutters on the windows.

5 out of 5 average rating, 31 reviews

NEW! Luxury 3BR - 5 minutes to Port Dover Beach

Private house rentals

4.86 out of 5 average rating, 14 reviews

A covered porch extends along the side of the cottage, revealing a view of the private sandy beach and the gentle waves of Lake Erie. The grassy area leads to the shoreline, where a firepit is situated, surrounded by Muskoka chairs, creating a welcoming outdoor space.

Home in Dunnville

Lakefront Cottage w/ Private Beach and Porch views

A modern kitchen and living area are showcased, featuring light-colored cabinetry and a central island with seating for four. Natural light floods the space through large windows, and a cozy seating arrangement is positioned to the side. Warm wooden accents create a welcoming ambiance.

5 out of 5 average rating, 44 reviews

Lakefront Couples Cottage | Romantic Views

4.95 out of 5 average rating, 81 reviews

A spacious deck features a large hot tub, surrounded by lounge chairs and illuminated by string lights above. The cottage is situated in the background, with large windows offering views of the outdoor area. The wooden deck provides ample space for relaxation.

Home in Port Rowan

Sandhill Cottage - Hot Tub (6P) Renovated / Beach

4.83 out of 5 average rating, 63 reviews

A comfortable living area is highlighted by two plush sofas and a large area rug, with soft natural light illuminating the space. A cozy fireplace with a white brick surround is visible, alongside a wooden coffee table and decorative wall art.

Home in Simcoe

Quaint Lakehouse 1.5 Hours from GTA

4.91 out of 5 average rating, 34 reviews

An outdoor deck offers a tranquil space for relaxation, furnished with comfortable seating and a dining table beneath an umbrella. A stunning sunset casts warm colors across the sky, while the waterfront view enhances the serene atmosphere.

Home in Dunnville

Beachfront Bliss~ Erie~ Patio~ Piano~ BBQ~ Firepit

The open kitchen and dining area feature a wooden dining table surrounded by white chairs. A kitchen island with stools provides additional seating. Modern appliances are integrated into the cabinetry, and warm lighting complements the space, connecting to a cozy living area in the background.

4.9 out of 5 average rating, 42 reviews

The Main Street Family Retreat

4.95 out of 5 average rating, 21 reviews

A spacious living area features a large sectional sofa with soft, striped upholstery, positioned against light-colored walls. Natural light filters through dual-layered window treatments, complementing the contemporary design. A mounted TV hangs above a slim electric fireplace, adding to the modern ambiance of the room.

Home in St. Williams

Grey Haven cottage

An expansive open-style bedroom area features multiple spacious beds arranged throughout the room. Natural light floods in through large windows, illuminating the polished wooden floor. Simple white bedding contributes to a clean and inviting atmosphere, ideal for communal lodging.