Holiday rentals in Essex

A serene outdoor space features several Adirondack chairs arranged in a circle, facing a calm lake. A fire pit is centered among the seating, with a hot tub visible in the background. Sunlight reflects on the water, creating a peaceful ambiance.

4.88 out of 5 average rating, 344 reviews

Year Round Hot Tub & Beautiful Views Cottage

Welcome to the Cozy Lakeside Cottage! Located within the village of Colchester, right on Lake Erie, nestled in the middle of Essex Wine Country. This cottage features 4 beds (A queen bed in the primary bedroom, one bunk bed with a queen base and a full upper bunk in the 2nd bedroom, plus an additional murphy bed on the main floor) Full kitchen, indoor dining, outdoor dining, 4 person hot tub & stunning views! Colchester Beach, Restaurants, Park & Marina just steps away! A truly relaxing escape.

4.9 out of 5 average rating, 282 reviews

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

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.

4.85 out of 5 average rating, 114 reviews

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

Private/Quiet Perfect for professionals!

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 and Amazon Prime 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 house in Kingsville

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.

4.98 out of 5 average rating, 731 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.

A bright living space is presented with large windows offering stunning lake views. Comfortable seating is arranged around a central coffee table. A dining table for four is positioned nearby, with decorative accents complementing the airy atmosphere. Light floods the room, enhancing its open feel.

5 out of 5 average rating, 243 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.

4.92 out of 5 average rating, 256 reviews

A spacious living area features a comfortable sectional sofa and an ottoman. Large glass doors provide a view of Lake Erie. A natural wood TV stand and wall art accents are present, along with a patterned area rug and a touch of greenery from a nearby plant.

Home in Kingsville

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.

4.99 out of 5 average rating, 369 reviews

A charming brick guest house is surrounded by lush green lawns and mature trees. The property features a rustic wagon as a decorative element, with warm lights illuminating the exterior. A spacious driveway provides easy access to the home, enhancing its inviting appeal.

Guest house in Essex

Wine Country Retreat w/ Hot Tub & Fire Pit

Welcome to The Vineyard Retreat, your peaceful, private escape along Essex County’s wine route between Kingsville and Colchester. This thoughtfully designed guest house feels like a private retreat, with its own entrance, outdoor living space featuring a hot tub, fire pit, and barbecue, overlooking a serene farmers’ field. Just steps from Lake Erie, you’ll be close to wineries, breweries, beaches, parks, orchards, and markets. It’s the perfect place to relax, restore, and reconnect.

4.95 out of 5 average rating, 177 reviews

The two-story green house features a generous front porch with seating and is surrounded by a grassy lawn. A detached garage is visible to the right, framed by landscaping. The overall setting is tranquil, with trees lining the background under an overcast sky.

Home in Essex

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!

4.99 out of 5 average rating, 118 reviews

Barn in Kingsville

Cozy Forest Retreat • Sauna • Hiking • Event Space

Escape to Kings Woods Lodge for a cozy winter getaway! Enjoy hiking in the woods, bird watching, crackling fires, heated blankets, rejuvenating sauna sessions, and nights filled with board games and shuffleboard. Surrounded by peaceful forest views, it’s the perfect spot to relax and reconnect. Hosting an event? Kings Woods Hall, our boutique on-site venue, is just steps away and can host up to 80 guests. Great for Christmas parties, bridal or baby showers or intimate weddings.

Adirondack chairs are arranged on a spacious deck overlooking Lake Erie, with a fire pit nearby. Lush greenery frames the scene, enhancing the connection to nature, while the calm water reflects the sky, creating a serene view.

5 out of 5 average rating, 123 reviews

Waterside Lakehouse - Lake Erie & EPIC Wineries

Welcome to Waterside Lakehouse on the shores of Lake Erie and nestled among the EPIC Wineries of Essex County. Take in the magnificent views of Lake Erie from the 'infinity deck' or take a short walk (5 min.) to the public beach, harbour and marina in the Village of Colchester. The harbour features a park with a splash pad for the kids, pirate ship climbers and a pier that can be the perfect spot for fishing. You are minutes away from a number of the best Ontario wineries. Enjoy!

A charming cottage is presented with a welcoming front porch and a neatly paved pathway leading to the entrance. Lush greenery and carefully arranged landscaping surround the home, while a tall chimney adds character. Bright blue skies peek through the trees, creating a serene setting.

4.8 out of 5 average rating, 176 reviews

Lakeside getaway

Welcome to Lake Erie and the village of Colchester. Enjoy this premier location with views of the lake and easy access to many local amenities. Families will enjoy the splash pad, play center, public beach, harbour and public changerooms/toilets so close you can see from the window. Friends and couples are well situated to explore local wineries and breweries, 3 of which are less than 10 minutes away by bicycle, and many more accessible via bike lanes along the HWY 50 wine route

A welcoming entryway is presented, featuring a sign reading 'THE BEACH' mounted on a wooden panel. The dining area is visible in the background, showcasing a long table with seating for six and large windows offering a glimpse of natural light.

4.81 out of 5 average rating, 128 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

Popular amenities for Essex holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Essex

5 out of 5 average rating, 52 reviews

A modern kitchen features light wood cabinetry and a spacious island with seating for four. Pendant lights hang above the counter, illuminating the area. Stainless steel appliances, including a refrigerator and oven, are visible, while the open layout extends into a bright living space with large windows.

Home in South Windsor

Luxury South Windsor Home- Gym & Sauna -2 King Bed

4.97 out of 5 average rating, 98 reviews

Anchor down on your private Beachfront Cottage

Superhost

Home in Kingsville

4.84 out of 5 average rating, 19 reviews

Hideaway at Cedar Island

5 out of 5 average rating, 39 reviews

The exterior of The Stone Cottage is highlighted by its striking stone façade and black shutters. A covered porch extends across the front, supported by decorative beams. Potted plants flank the entrance, while a brick-paved walkway leads to the entry door, enhancing the inviting atmosphere.

Home in Amherstburg

The Stone Cottage

4.98 out of 5 average rating, 47 reviews

A spacious bedroom features a king bed with a plush white comforter, accented by decorative pillows. Framed floral artwork adorns the walls above the bed. Soft lighting is provided by two bedside lamps, and a window dressed with light curtains allows natural light to enter.

Flat in Kingsville

Hello Gorgeous

5 out of 5 average rating, 27 reviews

The exterior of a cottage is shown, featuring a light grey facade and a bright yellow front door. A welcoming sign is positioned by the entrance, with flourishing flower beds on either side. A well-maintained lawn is bordered by wooden fencing and trees provide a natural backdrop.

Home in Essex

Waterfront Lake House Oasis in EPIC Wine Country

4.93 out of 5 average rating, 46 reviews

A modern kitchen is showcased with sleek white cabinetry and a central island. Ingredients for a meal are spread across the counter, including fresh produce, wine bottles, and glasses. A decorative plant adds a touch of greenery, and a chandelier provides soft illumination.

Home in Essex

Lake Erie Wine Route Home: Private HotTub Retreat

A two-story lakefront cottage is depicted, featuring a grey exterior and a welcoming front porch. A paved pathway leads to the entrance, with grassy areas surrounding the home. Outdoor grilling equipment is positioned near the entrance, and other cottages are visible in the background.