Vacation Rentals By Owner In Essex, ON

This downtown, grand, 1920's home is walking distance to restaurants, shops, grocery, gyms and churches. The town of Essex, centrally located in the county of Essex, is a 20 minute drive to wineries, the city of Windsor, the riverfront, Lake Erie, Lake St. Clair, Point Pelee National Park and much more. The Greenway Bike Trail can be accessed from the residence. Essex is known for being a family-friendly community in one of the safest towns in Canada. Come experience Essex for yourself.

THE ESSEX HOUSE

Essex, Ontario, Canada

Bed

3

Bath

12

Sleeps

$162.74

A home away from home. So close, but a world away. Lake Erie Escape Cottage is right on the beach. Bright and airy with lots of windows looking at Lake Erie on 2 sides. Featuring 2 bedrooms with queen size mattresses, plus a double size sleeper-sofa to accommodate 6. One and a half baths for added convenience. A well supplied (some might say gourmet) kitchen that provides everything you need to cook up the bounty of the county. LEE Cottage is here for you to enjoy Essex County and Lake Erie.

Lake Erie Escape Cottage - escape and explore

Essex, Ontario, Canada

Bed

Bath

8

Sleeps

$217.53

Take a trip back.. or better yet, just take a trip! This lakeside cottage nestled in the center (walking/biking) of the vibrant wine country of southern Ontario. A panoramic view of Lake Erie is at your doorstep. 102 Klies Beach has been fully renovated although the theme is retro. Beach and full Marina are 1/4 mile away! The cottage is shaded by mature trees which only enhances the natural lake breeze. Full amenities included (pool and foosball table; record player includes classic vinyl)brbr102 Klies Beach is a spacious 2 bedroom cottage (800 sq. feet) with a fully renovated kitchen and bathroom on the shore of Lake Erie. Keypad entry makes access easy. Clean towels, sheets, kitchen cookware and utensils allow for meals to be easily made on site. New propane BBQ grill is included. FREE FIREWOOD on site.brbrGuest accessbrAll parts of 102 Klies Beach is available when leased for your relaxation and enjoyment!brOther things to notebrWARNING: Be prepared to immediately decompress and relax without any stress or anxiety!

That 70's Cottage (on Lake Erie!) Free Firewood!

Essex, Ontario, Canada

Bed

Bath

Sleeps

$159.22

This cottage is nestled along the shores of Lake Erie in a small quite cottage community, right in the heart of epic wine Country. This cottage is perfect for a single person or a couple travelling to the area. Offers a beautiful view of Lake Erie, nice treed lot with firepit and hammock. Bikes for your enjoyment, if you wish to bike along the shore to wineries, beach, and local produce stands. The cottage is centrally located between Historical Amherstburg, beautiful Kingsville and Point Pelee National Park. There is so much to explore in the region. Fine dining, golf, bird watching, casino and so much more. Not wanting to tour around no problem, stay back and enjoy the many amenities that the cottage has to offer. Sit on the beautiful large deck to eat, have coffee, read whatever your pleasure maybe. Relax in the large treeed lot or play some yard games, hang out in the hammocks, great place for a nap while listening to lake. Many beautiful birds and if you are lucky you will see some amazing bald eagles. Nothing like ending your day sipping your favorite beverage by camp fire, not into building a fire. No problem sit lakeside and enjoy the fire table, best place to see the sunset over Lake Erie. The best part is retiring for the night with the windows open enjoy being lulled to sleep with the crashing of the waves and the beautiful lake breeze. It doesn’t matter where you are inside the cottage you will have an amazing view! Looking for a true cottage experience then this is it.

The Hideaway- Lake view Cottage In Wine Country

Essex, Ontario, Canada

Bed

Bath

Sleeps

$183.92

This cottage is PERFECT for a girl's getaway or for couples who wish to visit the many wineries and festivals within walking distance of this space.brbrSerenity awaits you in this newly renovated, 1000 sq foot, two bedroom lakefront cottage in the heart of Essex County's wine country. Enjoy the amazing views of Lake Erie and the lake breeze while sitting on the bluff or venture into the large treed yard for a fire, to play yard games or just to sit and enjoy the peaceful sounds of nature. Perfect for a girl's getaway or for couples who wish to visit the many wineries and festivals within walking distance of this space.brbrBeachfully decorated open concept living area with large kitchen. This cottage can accommodate up to 5 people with use of the daybed or air mattress. Main floor bedroom with queen bed and view of the lake from living room sliding door . The second storey boasts a large tranquil bedroom with a queen bed and day bed. There is a large sliding door facing the lake to enjoy the amazing view of the lake or the breathtaking sunsets all while listening to the waves while you relax and enjoy this space. Both bedrooms are equipped with high quality brand new mattresses for your sleeping enjoyment along with all new bedding.brThere is a large bathroom on the main floor with full laundry facilities. The separate dining area at the rear of the cottage faces the vast yard. You can enjoy bird watching or sit quietly to read a book on the couch in this room that also overlooks the deck and patio seating area.brThere is a large treed yard with firepit surrounded by adirondack chairs for your enjoyment as well as an outdoor grill!brbrThe cottage is within walking distance to a number of wineries, Colchester Beach and Marina, as well as a number of restaurants. It is situated right on Lake Erie bluffs, in a small cottage community surrounded by friendly neighbours and spectacular nature for the bird lovers. brThe cottage is located within driving distance to local quaint towns such as Kingsville, and Amherstburg among others. Leamington and Point Pelee are also within driving distance. brYou will find fine dining, craft breweries as well as a number amazing wineries in the area. Rent bicycles from Farm Dog cycles, And so your own wine tour or just explore the area.brbrIf you are planning a staycation around the cottage, you are within comfortable walking distance to 3 great wineries, Crew, North 42 and Lavender farms as well as Viewpointe or a short drive to a number of others such as Oxley, Coopers Hawk and Sprucewood. You can also walk to Colchester Beach and Marina and a few local favourite restaurants. br brIf you choose to drive , you are a very short drive to a number of other Erie Shores epic wineries of the region as well as local fruit stands and local towns. There are numerous festivals taking place within the area and often at the wineries themselves. There are a number of trails in the area to explore as well. Drive along County road 50 and you will not be disappointed. You can grab the Ferry to Point Pelee from Leamington May to July and Kingsville August to October.

Serenity on the Lake Completely Renovated

Essex, Ontario, Canada

Bed

Bath

Sleeps

$412.99

Experience luxury at The Castle on Malden, a modern private suite on a peaceful 50-acre estate just minutes from all Essex County wineries. Enjoy ambient lighting, a full kitchen with waterfall island, heated bathroom floors, a deep soaking tub with TV, a rain shower with jets, in-suite laundry, and a cozy bedroom plus separate living area with it’s on 55’ LED 4k TV. Perfect for romantic getaways, nature escapes, and wine-country weekends.brbrOther things to notebrThe property may not be used for weddings, ceremonies, receptions, parties, gatherings, or any event involving non-registered guests without prior written approval and a separate Event & Estate Use Agreement.brbrThe presence of unregistered guests, event equipment, décor, vendors, or increased vehicle traffic will be treated as an unauthorized event.brbrAny use of the property for an event or gathering without a separately executed Event & Estate Use Agreement constitutes a material breach of our VRBO Property Rules.brbrPlease note that the sauna, cold plunge, jacuzzi, and outdoor fire area are reserved exclusively for guests who have booked the Main Estate Experience.brbrThe Host reserves the right to immediately terminate the stay without refund and retain the security deposit.

Apartment

Luxurious Castle Suite - Private & Peaceful Escape

Essex, Ontario, Canada

Bed

Bath

Sleeps

$140.62

Serene lakeside living! A charming two bedroom, 1.5 bath cottage with spectacular view of Lake Erie. brbrSeveral beautiful wineries, apple orchards, ice cream shops, and quaint downtown Kingsville, with restaurants, breweries, and grocery stores, are only a few minutes' drive away. Point Pelee national park is within a 30-minute drive. There are also beautiful beaches within a 10 minute drive. Estate of Health, a comprehensive wellness spa, is also a 12-minute drive away.

Charming Cottage with a View of Lake Erie

Essex, Ontario, Canada

Bed

Bath

Sleeps

$262.2

The Shores of Erie Wine Country Cottage is a vacation retreat like no other. The cottage has it's own private 40'x6' deck overlooking the lake. brbrIts a relaxing area with antiquing, birding and wineries just minutes away. brbrThis beautifully decorated home is suitable for couples or families/groups.brbrFeaturing a fully equipped kitchen with everything you'll need. A gas fireplace in the living room, smart TV, WiFi, all linens and laundry facilities. It can accommodate 4-6 people with lots of room for everyone. This is a smoke free home. Everything you need is right here.

Beautiful Lake Erie

Essex, Ontario, Canada

Bed

Bath

Sleeps

$218.81

Discover the charm of Lake Erie's shores and the historic County Road 50, home to numerous wineries, restaurants, and beaches. The Barn Owl Inn, situated in the heart of this scenic route, offers a comforting retreat akin to a home away from home. Whether you're unwinding, soaking up the sun on the beach, birdwatching, or touring the various wineries, the Barn Owl Inn caters to every preference. You'll be enchanted by the freshly renovated space, designed to be airy and luminous, with ample windows that invite the natural light and the beauty of the outdoors inside.

Nestled in the heart of wine country

Essex, Ontario, Canada

Bed

Bath

Sleeps

$165.7

Cute and cozy getaway in the heart of wine country! This stylish 3 bedroom home is located amongst the best wineries that Essex County has to offer, minutes from the beach, and offers multiple, peaceful sitting areas both inside and out! This cottage has all the comforts of your own home! Fully stocked and ready for you to relax and enjoy!

Sippin' & Stylin' in Wine Country!

Essex, Ontario, Canada

Bed

Bath

Sleeps

$221.27

Spacious cottage just steps from beautiful Lake Erie. This year-round gem is a perfect getaway and situated on the popular Essex County winery trail. Suitable for couples and small families. Relax and enjoy in your private 4 person hot tub under the stars. Nicely renovated throughout focusing on an open concept design boasting a stunning kitchen with everything you’ll need to wine, dine and unwind. Beach area is perfect for the kids to play and the sandy bottom “sand bar” is great for swimming.

Cozy cottage steps from beautiful Lake Erie w/Hot tub. Wine, dine and unwind!!

Essex, Ontario, Canada

Bed

Bath

Sleeps

$600.61

Escape to your own private 48-acre estate in the heart of Essex County wine country. Surrounded by orchard, forest, and open land, Villa Fiore offers a rare blend of privacy, space, and elevated comfort—perfect for small gatherings, retreats, and unforgettable stays. Villa Fiore is conveniently located in the heart of Essex County. Our 4-bedroom Mediterranean-inspired home sits on 48 acres of farmland, orchard, and Carolinian woods. brbrStroll the wooded trail, gardens, and orchard. Enjoy an afternoon cocktail, tea, or barbecue as you relax on our newly covered patio. Are you looking for a nearby birding experience, winery, park, or waterfront Though peaceful and private, this property is centrally located.brMany wineries are located 30 to 40 minutes away. Windsor Style Pizza offered at many local restaurants! brPoint Pelee National Park 35 minutes brJack Miner Migratory Bird Sanctuary 18 minutes -Fort Malden National Historic Park 30 minutesbrLakeview Marina 22 minutes brWindsor Airport 15 minutesbrAtlas Tube Centre 13 minutesbrbrEach room of Villa Fiore has been carefully curated for your comfort. Our home sleeps up to 10 people.brbrEach opulent bedroom provides freshly pressed linen, personal refrigerators, and televisions.brbrIf you are looking to be a chef for the day, the kitchen is fully equipped with all the essentials. Use the induction cooktop or oven to prepare a large meal. You may wish to use the Ninja Air Fryer/Oven to prepare a smaller meal.brbrA coffee and tea bar is conveniently located in the kitchen. Enjoy coffee, espresso and tea! Beautiful vintage tea cups are available in the kitchen to enjoy your afternoon tea!brbrA quiet space is available in the office where you might wish to work away from your desk, have an online meeting, or read quietly.brbrTwo living rooms and two dining areas are found on the main floor. Each one has either a formal or casual appeal.brbrWe are committed to keeping the home clean, sanitized, and safe for all of our guests.brbrGuest accessbrGuests will park in the driveway in front of the garages. Gain access to the house through the side entrance via key code.brbrWe welcome you to Villa Fiore!brbrOTHER THINGS TO NOTEbrAre you looking to stay at Villa Fiore for a quiet getaway for 2 to 4 people Select the room of your choice and reach out to us for more details and pricing.

Private 48-Acre Estate | Luxury Retreat near Wine Country

Essex, Ontario, Canada

Bed

Bath

Sleeps

$220.47

Our 4-season waterfront home is a beautiful gathering spot with memories at every turn. It sits on the shores of Lake Erie, on a quiet private road in the heart of Essex wine country. The moment you step into the cottage and see the lake view, relaxation soon follows.brbrThe cottage has an open-concept layout for easy entertaining. It offers a large fully equipped kitchen, a dining room with a gas fireplace, a living room with stunning lake views, three generous-sized bedrooms, and all the luxuries of home with high-speed Wi-Fi. Outside you will enjoy a beautiful outdoor space with a covered porch, new 12x25 deck, a gas BBQ, sitting area, and a dining space to enjoy outdoor meals.brbrEnjoy the sun, take a dip in the lake, experience local attractions, and end your evenings with breathtaking sunsets while you relax by the outdoor fire pit.

Beautiful Waterfront Lake House in the Heart of Epic Wine Country

Essex, Ontario, Canada

Bed

Bath

Sleeps

$282.37

Hot tub, lake views, wineries brSound perfect It is and we are waiting to host you!brA Beautiful piece of heaven steps from Lake Erie. Whether you choose to relax in this amazing home, or enjoying the many wineries in walking distance, you have picked a real gem!brbrYou will have full access to the home with three large bedrooms rear deck, hot tub. This home accommodate six people with one king bed one queen bed and one double bed. All bedrooms have high-quality brand new mattresses and new bedding for your comfort. There are full laundry facilities for your convenience. The master bedroom has an en suite with beautiful shower in the main bath is a full bath with tub. Both amazing bathrooms have in floor heating.brYou can enjoy dinner in the dining area that seats 6 or chill at the breakfast bar with seating for 4. brThe gorgeous kitchen has all the amenities you need with granite countertops and high-end appliances. Off the kitchen you’ll find a side deck with barbeque for grilling!brbrThere is a great lake view from the living and dining area as well as from the third bedroom. Sit and relax and enjoy the sounds of nature in the rear yard or on the large deck with sectional as well as patio table and chairs. brYou can enjoy a fire at the outdoor propane fire pit or relax in the hammock while listening to the sounds of nature. End the day with a soak in the hot tub with your favourite glass of wine!

Wine Down By the Lake

Essex, Ontario, Canada

Bed

Bath

Sleeps

$306.17

Welcome to The Gatehouse, our family cottage since 1970 - that grew! It is a large 4 bedroom vintage/rustic cottage that offers three bedrooms on the upper floor, and the largest bedroom on the main floor. The living room and dining room features a cozy gas fireplace with 20 ft ceilings. Three wineries are within easy walking distance. Relax on the large deck facing a huge yard with a view of the lake in the distance. The public beach and harbour are a 10-15 minute walk and it is a short stroll to a country diner located in quaint Colchester Village, in Ontario Canada. There are designated bike paths on road side for those seeking exercise. We are a year-round cottage and invite you to stay in all seasons.br***NEW for 2022*** New vinyl plank flooring in all the bedrooms and bathrooms!!br****COMING SOON IN 2024**** New kitchen and upstairs powder room. Stay tuned for updated pictures!!brbrApril 2024 - kitchen remodel and powder room addition are now complete! Check out the pictures of our new kitchen, with all new floors, cupboards and appliances. The large fridge has an ice maker (made with filtered water). The microwave above the new range is also a range fan. The new coffee / bar features a filtered water tap for easy filling of coffee pots and drink pitchers. The mini fridge is perfect for all your cold drinks needs.brThe new powder room upstairs is between the east and middle bedrooms.

Wine country cottage - The Gatehouse

Essex, Ontario, Canada

Bed

Bath

Sleeps

$143.15

Welcome to our “labour of love”. Our completely renovated 550 sq. ft. 2 bedroom cottage on the bluffs, with views of Lake Erie. Our cottage is a 10 minute walk to the sandy shores of “Colchester Beach Park and Splash Pad” and sits on historic “Latitude 42” along famous County Road # 50. We are nestled in the heart of wine country, just minutes from many local wineries. You can walk, bike or ride to explore all the region has to offer. We are centrally located between Leamington (home of Point Pelee National Park) and the historical town of Amherstburg.

Cottage On The Bluffs (Olive’s Place)

Essex, Ontario, Canada

Bed

Bath

3

Sleeps

$111.27

Welcome to your dream lakeside retreat! Experience the Magic of Colchester by Lake Erie, Nestled in the Essex County Wine Route at the Perfect 42° Parallel. Enjoy easy access to local wineries, tastings, fine dining, and Essex County’s stunning landscapes.brThis charming 3-bedroom house is ideal for working from home, offering a productive environment with great Wi-Fi signal, allowing you to stay connected while enjoying the relaxed lakeside vibes . The house is conveniently situated within a 30 km radius of Windsor, Essex, Amherstburg, LaSalle, Leamington, and Kingsville, making it perfect for mid-term rentals and business purposes.brThe open-concept layout connects the living, dining, and kitchen areas, ideal for both relaxing and working. The kitchen is fully equipped with modern appliances and ample counter space for preparing delicious meals.brEach bedroom is thoughtfully decorated for a restful night’s sleep, with comfortable beds and plenty of natural light. Step outside to a quaint backyard with a cozy patio, perfect for enjoying your morning coffee or an evening glass of wine amidst lush greenery.brLocated just one block from the lake, this home offers the ultimate in lakeside living. Whether swimming, sunbathing, or strolling along the shore, the lake is right at your doorstep. Nearby local shops, restaurants, and cafes provide everything you need for a comfortable stay.brWe’d be delighted to host you in our serene and beautiful home :)

Dreamcatcher Coast House

Essex, Ontario, Canada

Bed

Bath

Sleeps

$340.47

The Farmhouse is the first building on the 14th Coffee Co. Homestead, a two-acre property in Essex, Ontario. It's a lovely century home, that's been renovated with modern conveniences & timeless design. Experience stunning open-landscape views, surrounded by nature and located near many local wineries.brbrThis three bedroom, two bath house has lots of natural sunlight, original hardwood floors, tin ceilings, barn board walls, and locally produced artwork & decor. brbrThe 14th Coffee Co. Homestead includes this Farmhouse, and separate buildings - the Coffee House and century-old Barn that has been newly renovated. brbrThe Grounds: Relax on the front porch with picturesque skylines throughout the day or retreat to the expansive back deck, patio and fenced yard. The garden grows seasonal vegetables, flowers, plants, and trees. For your use and enjoyment, there is a hot tub, hammock, a covered pavilion, and lots of space for lawn games (bocci, frisbee, etc.).brbrStrictly no parties or events and a maximum of six-eight guests.brbrEntire Farmhouse and yard. Beyond the fenced yard is the 14th Coffee Co. Coffee House. It has staff throughout the week and limited public hours

Country House

14th Coffee Co. Homestead Farmhouse

Essex, Ontario, Canada

3

Bed

Bath

6

Sleeps

$1061.41

Escape to The Castle on Malden, a 50-acre private estate of pure luxury. Hand-carved, custom painted trim and graceful arches lead beneath two grand chandeliers; custom LED lighting accents every detail. Enjoy 8-seater hot tub, custom barrel-globe sauna, a private wine cellar and the secret poker room, “Lion’s Den.” Entertainment includes a high-end pool table, fire-pit beneath starlit sky, panoramic views, total privacy—perfect for weddings, proposals, events, or a photo-filled getaway.brbrOther things to notebrThe property may not be used for weddings, ceremonies, receptions, parties, gatherings, or any event involving non-registered guests without prior written approval and a separate Event & Estate Use Agreement.brbrThe presence of unregistered guests, event equipment, décor, vendors, or increased vehicle traffic will be treated as an unauthorized event.brbrAny use of the property for an event or gathering without a separately executed Event & Estate Use Agreement constitutes a material breach of Property RulesbrbrThe Host reserves the right to immediately terminate the stay without refund and retain the security deposit.

Castle On Malden - Luxury 50 Acre Private Estate

Essex, Ontario, Canada

5

Bed