Holiday rentals in Essex

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Top-rated holiday rentals in Essex

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

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Guest favourite
A spacious wooden deck extends towards Lake Erie, featuring a grill and two outdoor chairs. The gentle waves can be seen lapping against the rocky shoreline. Lush greenery frames the scene, adding a natural touch to the outdoor space.
Cottage in Kingsville
4.9 out of 5 average rating, 286 reviews

Lakeview Inn

The Lakeview Inn sits on the North Shore of beautiful Lake Erie. This modern lakehouse is an 8 minute drive to the centre of kingsville where there is multiple breweries and restaurants, a public beach is a 1 minute drive down the road and is right in the centre of Southern Ontario's Wine Country. If you're coming down for a weekend to relax, taste wine or to enjoy the exceptional birding the area has to offer. At the end of your day relax to the sound of the waves brushing up against the shore.

Top guest favourite
A covered outdoor seating area features a cozy arrangement of a sofa and decorative pillows, illuminated by string lights. The space is surrounded by lush greenery, with a landscaped patio and wooden railing adding to the inviting ambiance.
Farm stay in Essex County
5 out of 5 average rating, 176 reviews

The Fir&Feather Tree Farm 1Bedroom Suite & Hot tub

A unique & tranquil wooded getaway nestled on a 16 Acre working Christmas tree farm, 15 mins. from Windsor and surrounding towns. This private lower suite, part of the main house has it's own entrance & space for 4 guests with open concept Kitchen/Living room with electric fireplace,2 futons/double beds with memory foam mattresses, Queen Juno mattress in bedroom and 3 piece bath. Enjoy a covered private furnished patio w/firepit or relax in a private hot tub (netted) at a second enclosed patio

Top guest favourite
A lake house is situated on the shoreline of Lake Erie, featuring a sloped path with steps leading down to it. Soft lights illuminate the exterior during twilight, creating a warm ambiance. The tranquil water extends to the horizon, inviting a peaceful retreat.
Guest house in Kingsville
4.98 out of 5 average rating, 737 reviews

Small lake house on Lake Erie shore

Private Bachelor apartment sized house directly on Lake Erie. ULTRA FAST WI-FI, Private deck, Kayaks. The Cottage is always toasty warm all winter long. Queen bed, bathroom with shower, kitchenette. Great swimming in shallow, sandy waters. Cottage is only a few minutes from many area wineries, breweries, distilleries and fantastic restaurants serving local food. Walking distance to Pelee Island ferry. Want something completely different? This is the place. It's almost like staying on a boat.

Top guest favourite
Cottage in Essex
5 out of 5 average rating, 254 reviews

The Kiss nTell - Year round - Hot tub - Lake Views

If you “glamp” when you camp, then you’ll appreciate the finer amenities of this boutique style cottage on Lake Erie. Arguably the best views in this tiny cottage community, The Kiss n Tell graces a bluff overlooking the lake - stunning views from every room. Wake to the sound of waves crashing the shore, sunbathe in loungers, dine while the sun glistens on the water, star gaze from the hot tub or sit by a lakeside fire (firewood provided). Endless options w/out leaving this beautiful space.

Top guest favourite
Guest suite in Essex
4.98 out of 5 average rating, 206 reviews

The Loft Suite

Guests will enjoy our quaint private getaway. Our suite is set above our detached garage. Open concept. Supplied with linens, towels etc for your short getaway. Enjoy all the local wineries, golf courses, breweries, shopping, restaurants. Essex Counties best kept secret. Colchester harbour, with Colchester beach is only a minute away. A separate private sitting area for you to enjoy your stay. We supply bottled water, coffee, coffee cream. Assorted tea, sugar, freshly made banana bread.

Top guest favourite
Cottage in Essex
4.95 out of 5 average rating, 139 reviews

The Hideaway

This cosy lakeside cabin is nestled in the heart of wine country, along the Shores of beautiful Lake Erie in a very friendly cottage community. The cottage is tastefully decorated with all the amenities of home, perfect for 1 or 2 people, and an amazing view of the lake no matter where you choose to sit. Just minutes away from local wineries. Walk, bike, explore all the region has to offer. Centrally located between Leamington home of Point Pelee national park and Historical Amherstburg.

Guest favourite
A concrete patio area extends toward Lake Erie, featuring a fire pit surrounded by five red Adirondack chairs. The calm water and distant shoreline are visible, framed by trees that provide a natural border to the serene outdoor space.
Home in Kingsville
4.92 out of 5 average rating, 259 reviews

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.

Top guest favourite
The exterior view of the guesthouse showcases a single-story structure with green siding and a gray shingled roof. The house is surrounded by freshly landscaped areas featuring small shrubs and plants. A gravel pathway leads to the front entrance, with open green lawn surrounding the property.
Home in Essex
4.96 out of 5 average rating, 179 reviews

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!

Superhost
A private guest suite features a spacious bed with a dark blue coverlet, a cozy sofa, and a TV mounted on the wall. Natural light enters through large sliding doors, complemented by dark blue curtains. A small round table stands nearby, adding to the inviting atmosphere.
Guest suite in Windsor
4.82 out of 5 average rating, 120 reviews

Private unit for professionals! Seperate access

Discover comfort in this private guest suite w/ self-check-in and a separate entrance, located in the tranquil Southwood Lakes neighborhood. Close to golf courses and Devonshire Mall, it’s perfect for relaxation or exploring nearby amenities. Enjoy a swivel mount TV with Netflix from the cozy sofa or bed. Step into the spacious backyard with a stunning gazebo and elegant seating, ideal for unwinding. Luxury bathroom w/ supplies. Coffee bar! Book your peaceful escape today!

Guest favourite
A dining table made of wood is set with two jars filled with decorative materials, positioned on a blue table runner. Sheer white curtains frame a large window, providing a view of Lake Erie and the surrounding landscape.
Cottage in Essex
4.82 out of 5 average rating, 130 reviews

Cute BeachHouse with a Personal Beach/Fire Pit/BBQ

This Cute BeachHouse on Lake Erie is Super Adorable with Lots of Character. It has gorgeous panoramic water views and a private beach on the premise! We are located on Lypps Beach Road, a private lakeside community minutes away from award winning wineries, golf, beaches, hiking, biking, fishing and restaurants. This Cute BeachHouse is PERFECT for a romantic getaway, family & friends, wine lovers, nature lovers and those looking to relax

Top guest favourite
Farm stay in Essex
5 out of 5 average rating, 200 reviews

Relax at Bridgewood Farms I Hot Tub & Wine Country

-Breathe in the presence of nature- You will quickly fall in love with the quiet pace, beautiful nature, and fabulous food and wine on County Road 50. This luxurious cottage hideaway is surrounded by wildlife and farmland. Private access to idyllic grounds that span over 225 acres of farmland, creeks, and frontage onto majestic Lake Erie. Bathe in the healing power of our farm and forests. Town of Essex License #STR-2025-20

Top guest favourite
Loft in Kingsville
5 out of 5 average rating, 313 reviews

The Hudson Loft

Loft above our garage, situated along Essex county’s wine route. Guests have a parking spot right outside their separate entrance (Please do not park in front of the garage doors as we need access to them). Please note: no gatherings, events, or video productions. Check out our feature on “Best air bnb” https://www.bestairbnb.ca/properties/hudson-loft-kingsville

Popular amenities for Essex holiday rentals

When is the best time to visit Essex?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$175 SGD$176 SGD$178 SGD$183 SGD$188 SGD$206 SGD$213 SGD$211 SGD$198 SGD$185 SGD$184 SGD$202 SGD
Avg. temp-4°C-2°C2°C8°C15°C20°C23°C21°C18°C11°C5°C-1°C

Frequently Asked Questions

  • Do cottage rentals in Essex have a kitchen?

    Absolutely! We offer over 40 cottage rentals with a kitchen in Essex. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Essex have free parking?

    Absolutely! We offer over 40 cottage rentals with free parking in Essex. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Essex have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in Essex. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Cottage Rentals in Essex?

    Enhance your stay in our Cottage Rentals with the most popular amenities: over 40 homes with a kitchen, over 40 homes with air conditioning, over 40 homes with free parking, over 40 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly vacation rentals in Essex?

    Essex has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Essex have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Essex. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Essex?

    Four-legged friends are welcome in Essex. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Essex?

    Yes! Work meets play with ease at over 40 vacation rentals in Essex featuring dedicated workspaces. Stay connected and productive in your home away from home.

Quick stats about holiday rentals in Essex

  • Total holiday rentals

    Explore 100 holiday rentals in Essex

  • Nightly prices starting at

    Essex holiday rentals start at $76 SGD per night before taxes and fees

  • Verified guest reviews

    Over 8,140 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    90 of Essex holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Essex rentals

  • 4.9 Average rating

    Essex stays are highly rated by guests – averaging 4.9 out of 5!

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