House holiday rentals in Essex County

Wine Down by the Lake -Hottub, Wineries,Lake Views

Hot tub, Lake views, wineries and golf? Sound perfect? It is and you have picked the perfect spot! A beautiful piece of heaven steps from Lake Erie. Whether you choose to relax in this amazing home, or enjoy the many wineries in walking distance, you have picked a real gem!! You can enjoy lake views from the rear deck or hot tub while sipping your wine. This home is perfect for a small bridal party, girls weekend or for couples looking to get away and explore what the area has to offer!

Location · Value · Checkout

Modern Lakefront Escape

Welcome to this charming lakefront property offering a unique blend of modern amenities and cozy comforts ensuring an unforgettable stay. This lakeside retreat is perfect for families, couples, or friends seeking a relaxing escape. Explore the great outdoors, indulge in water activities, or relax in the hot tub taking in the view. Conveniently located just 10 minutes off the 401 and only 30 minutes from Leamington, Windsor and Chatham. You're never too far from local attractions and amenities.

Location · Family · Layout

Sage On Main - Downtown Wine Country Cottage

We would love to share our Kingsville home We are located in the Heart of town on Main Street. It’s bright and cozy with a charming vintage feel. There are 3 Bdrms with Queen beds & 2 sitting areas. Each with a day bed and trundle bed under. Our kitchen is fully stocked . Enjoy mornings with a coffee on our closed In front porch,evenings around the gas fire pit in the court yard. Bike rides around town on one of our 2 cruiser bikes. Come Relax, unwind, explore, sip some local wines and enjoy

Value · Location · Air conditioning

CJ's is lakefront, pet friendly

You'll fall in love with this cozy 2 bedroom, 1 bath lakefront cottage. Situated directly on Lake Erie, CJ’s Lake House offers all the comforts of home with the charm & serenity of lakefront living. Located less than 1km from Point Pelee National Park, fun & adventure are steps away. If it's calm and relaxation you're looking for, we have a huge backyard with a large upper and smaller lower beach and a great firepit. CJ’s is all about loving the lake life, your furry family members Included!

Location · Family · Sleep quality

Heritage Lakehouse

Unwind at this modern lake house situated right on Lake Erie. The house was built with high ceilings and exposed raw steel accents throughout. Enjoy a stunning view of lake Erie from both bedrooms or through the 14 ft glass wall in the living room. The kitchen boasts all new appliances, quartz countertops and all of the cooking supplies needed. The house is located in between two public beaches and offers its own access into the lake. Wineries, Pelee Island, restaurants and golf courses.

Location · Family · Outdoor spaces

Shores of Erie Guest House

Welcome to our family-friendly vacation home in the charming village of Colchester, Ontario! Nestled in the heart of wine country, our spacious two-story house is perfect for families. Our property is renowned for its welcoming atmosphere, complete with a sandbox, an extensive collection of board games, books, BBQ, firepit, ping pong, fooseball, and even a crib for your littlest ones. We're excited to provide a memorable stay for your family, where adventure and relaxation await!

Family · Value · Laundry

Erie View Lakehouse - Serene and Spacious

Whether it is after a day of touring Essex County's Epic Wine Route, spending the day at the private beach just steps away, or exploring the abundance of nature as you hike or bike the nearby conservation areas, Erie View Lakehouse is just the place to come back to to unwind. Choose between sitting in front of the fireplace in the great room, outside on the large deck, around the firepit, or inside the . Regardless, the view is spectacular! Come, decompress, reset, and enjoy.

Location · Family · Kitchen

Walk Downtown | Fire-pit, Yard Games, Mini-put

Walk to downtown Kingsville, local restaurants, wineries, and the ferry—perfect for midweek escapes, work-from-anywhere stays, or a relaxing getaway. This fully renovated home blends modern comfort with a clean, stylish design, offering plenty of space to unwind, connect, or get ready for a day exploring wine country. Whether you’re here for a couple’s retreat, a small group stay, or a longer visit, this space is designed to feel easy, comfortable, and elevated.

Location · Family · Nearby

Lakeshore Park lakeside getaway.

Enjoy a relaxing and fun filled getaway in this 2 bedroom ranch on Lake St. Clair. Enjoy swimming and fishing off the deck, evening bonfires and more. We have all the amenities you need to enjoy your time away from a stocked kitchen to darts and board games. We are located approximately 5 minutes from the quaint town of Belle River. The house is beautifully appointed and has a spacious sunroom overlooking the lake. If you like to golf, it's 5 minutes away!

Location · Family · Nearby

The Manor on Main

Welcome to the historic Manor on Main located in the downtown core of Kingsville, Ontario. This home built in 1913 holds all its original Victorian charm with the addition of modern comfort. The space is perfect for gathering family or a large group of friends. Located on Main Street and walking distance from the town center, you will have all the best Kingsville has to offer right at your doorstep. Relax, unwind, explore, sip some local wines and enjoy!

Family · Value · Backyard

Elm St. Gardens!

Welcome to Elm St. Gardens, this historic retreat built-in 1900 is the perfect getaway in Downtown Kingsville. Walking distance to town, the beach, and the Pelee Island Ferry dock and a short drive to the many Wineries. We host 4 bedrooms, 2 full bathrooms and a pullout couch, along with a spacious entertaining space, very large yard and all the amenities to host your girls weekend, or family reunion... plenty of room for all.

Family · Location · Indoor spaces

The Lakeside house Hot tub, lake view&wine trail

Private lakefront retreat with a year-round hot tub overlooking Lake Erie. Enjoy direct lake access, golden-hour sunsets from the deck, or cozy evenings by the fireplace. Inside, the home blends cozy cabin-style charm with modern comforts, offering multiple sitting areas designed for relaxation and connection. Please review our House Rules before booking, including important details regarding pet allowances.

Value · Location · Parks