Vacation Rentals By Owner In Essex, ON

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

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Exceptional(4)

$298.26

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

Agritourism

14th Coffee Co. Homestead Farmhouse

Essex, Ontario, Canada

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Bath

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Exceptional(3)

$142.69

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

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$112.91

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

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Exceptional(68)

$305.05

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

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Exceptional(1)

$263.46

Enjoy the country side on a horse ranch in the suburbs of Windsor and 45 to Detroit city, surrounded by trees with hay field in your backyard, enjoy the horse ride if you are up to it.brEnjoy the Hot tube watching sunset, or go in the steam of the wood burning sauna,brWatch the firefly dance over the hay in the field,or go on horse back ride around the farm, the ranch is close the award winning wineries and restaurants located on Lake Erie shores on highway 50 the renowned wine route of Essex county,brTaste the fresh fruits from the fruit wagon,brAnd take a dip in Lake Erie at Colchester beach among other beach close to the farm, after all that relax at the luxury of the house have a relaxing evening in the sun room, or watch your favourite game on the big screen TV.

The horse ranch living and if you climb into the saddle be ready for the ride

Essex, Ontario, Canada

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Bath

Sleeps

Exceptional(51)

$281.7

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

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Bath

Sleeps

Exceptional(10)

$147.63

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

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Exceptional(20)

$246.02

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

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Bath

Sleeps

Exceptional(3)

$372.83

This recently renovated and professionally designed 3-bedroom home is set on 4 sprawling acres of land, offering plenty of room for adventuring, BBQ’s and gathering around the fire pit area. It boasts 2.5 luxury bathrooms, including a jet shower for the ultimate relaxation experience, 2 large living room spaces & and a pullout couch for additional sleeping arrangements. The spacious chef worthy kitchen and dining room provide a welcoming atmosphere for all guests to enjoy shared meals together. We are conveniently located right between CREW (Colchester Ridge Winery Estates) and North 42 Degrees Winery Estates, with their vineyards providing the perfect backdrop for photos. To make exploring the EPIC wine country even more enjoyable, we have provided 6 bikes for our guests to use at their leisure. We are also less than a 10-minute walk to Colchester Harbour and Beach, enjoy easy access to waterfront activities on Lake Erie. This space is a wine connoisseur's dream escape. Perfect for a girls' weekend, couples' getaway, or accommodation for weddings in the area, our home promises an unforgettable experience in EPIC Wine Country.

Situated Between 2 Wineries In The Heart of Wine Country. Minutes From The Beach

Essex, Ontario, Canada

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$695.94

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

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Exceptional(18)

$100.56

This charming guest house (a licensed short-term rental) will have you feeling at home the moment you walk through the door. Perfect for a couples getaway, or even room to bring one extra guest for the couch. You will wish you could stay longer. And for those still working remotely we offer high-speed fiber connected internet WHC (Work from Cottage)! br

Apartment

Adorable Guest House near EPIC Wineries!

Essex, Ontario, Canada

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Bath

Sleeps

Exceptional(22)

$192.63

This charming cottage will have you feeling at home the moment you walk into the door. Peaceful sunsets, lake views and bonfires alongside the lake are captivating at anytime of the year. This licensed short-term rental is conveniently located near 2 public beaches for you to enjoy. Nearby golf courses include Oxley Beach Golf Course, a walking only, 18-hole Par 3 course, and close to Kingsville Golf & Country Club. And for those still working remotely we offer high-speed fiber connected internet WHC (Work from Cottage)!

Erie Breeze Cottage, right on Lake Erie, EPIC wine route!

Essex, Ontario, Canada

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$165.14

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

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Bath

Sleeps

Exceptional(24)

$301.61

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

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$125.38

Serene Lakeside living! A charming three bedroom one bath cottage with spectacular view of Lake Erie. Several beautiful wineries, ice cream shops and quaint downtown Kingsville with restaurants breweries and grocery stores nearby. Point Pelee national park is within a 30-minute drive. Estate of Health comprehensive wellness spa is also a 12-minute drive away.

Serene Lakeside living! A charming three bedroom one bath cottage

Essex, Ontario, Canada

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Bath

Sleeps

$242.56

Charming Colchester Cottage | 5-Min Walk to Beach | brExperience the heart of Lake Erie’s North Shore in this peaceful village retreat.brbrWhether you’re here for the world-class birding, the EPIC wine trail, or a classic family beach getaway, our quaint cottage is the perfect home base. Located in the quiet village of Colchester, you are steps from the sand and minutes from the vines.brbrThe SpacebrOur cottage blends authentic charm with a functional, open-concept layout—perfect for reconnecting with family or friends.brbrLiving & Dining: An open-concept living room and fully equipped kitchen create a bright, airy hub for your stay.brbrThe Back Nook: A multi-purpose utility room featuring a laundry suite, sitting area, books, records, and games.brbrSleeping: Two comfortable bedrooms designed for a restful night's sleep after a full day adventuring.brbrIndoor-Outdoor Flow: Step out onto our beautifully screened-in porch. It’s the ultimate spot for morning coffee without the bugs, accompanied only by the sound of the waves and the local birds.brbrOutdoor Living & Lake AccessbrThe Backyard: End your evenings at our private fire pit, perfect for stargazing and s'mores.brbrBeach Access: While we aren't directly on the water, the views are steps away, and Colchester Beach is an easy 5-minute walk away.brbrThe Village Vibe: You are truly in the heart of it. Three local restaurants and bars are within 3 blocks, making it easy to grab dinner or a drink without needing the car.brbrExplore Colchester & BeyondbrYou are walking distance to:brbrColchester Harbour: Splash pad, playground, basketball/volleyball courts, and bike rentals.brbrLocal Treats: Ice cream shops and village bars/restaurants.brbrBirding & Nature: We are centrally located between Holiday Beach and Point Pelee, right in the path of major migrations.brbrAgritourism: Essex County is famous for its fresh flowers and farm-gate produce—all just minutes away by car or bike.

Crabapple Cottage

Essex, Ontario, Canada

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Bath

Sleeps

Exceptional(10)

$226.21

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

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Sleeps

$237.89

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

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Most popular vacation rentals in Essex

$364.32

Lake Erie & EPIC Wineries

Essex, Ontario, Canada

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Bath

Sleeps

$142.69

Charming Cottage with a View of Lake Erie

Essex, Ontario, Canada

Bed

Bath

Sleeps

$147.63

Cottage On The Bluffs (Olive’s Place)

Essex, Ontario, Canada

Bed

Bath

Sleeps

$168.14

The Hideaway- Lake view Cottage In Wine Country

Essex, Ontario, Canada

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Bath

Sleeps

$221.63

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

Essex, Ontario, Canada

Bed

Bath

Sleeps

$226.21

Nestled in the heart of wine country

Essex, Ontario, Canada

Bed

Bath

Sleeps

$263.46

The horse ranch living and if you climb into the saddle be ready for the ride

Essex, Ontario, Canada

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Bath

Sleeps

$301.61

THE ESSEX HOUSE

Essex, Ontario, Canada

Bed

Bath

Sleeps

$298.26

Agritourism

14th Coffee Co. Homestead Farmhouse

Essex, Ontario, Canada

Bed

Bath

Sleeps

$246.02