Vacation rentals in Essex

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Top-rated vacation rentals in Essex

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Guest favorite

Cottage in Kingsville

4.9 out of 5 average rating, 191 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.

Mar 22 – 29

G$32,929 GYD per night

Guest favorite

Guesthouse in Kingsville

4.96 out of 5 average rating, 213 reviews

Cozy Kingsville Country Guest House

Enjoy your stay in this cozy guest house on the main strip of the charming village of Cottam, within the town of Kingsville. This attached suite will be all for you. Separated from the main house with your own private entrance in the front and rear. Relax on the spacious deck overlooking the lush green mature treed backyard, roast marshmallows at the fire pit or take a nice nap on the hammock. Located a short drive to downtown Kingsville, beaches, wineries, restaurants, craft breweries and more!

Nov 10 – 17

G$16,998 GYD per night

Guest favorite

Cottage in Essex

4.91 out of 5 average rating, 210 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.

Dec 9 – 16

G$52,411 GYD per night

Guest favorite

Guesthouse in Kingsville

4.98 out of 5 average rating, 593 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.

Oct 18 – 25

G$23,534 GYD per night

Guest favorite

Cottage in Essex

4.92 out of 5 average rating, 319 reviews

Your Soulstice Studio

Become one with nature in this cozy cottage with an expansive view of the lake. Let yourself be absorbed by the sound of waves, birds and silence in the early morning hours. Sudden urge to do some yoga? No problem you have mats, blocks and bolsters to fulfill you ever stretching need! Your Soulstice is an up and coming yoga and massage studio that has been 2 years in the making. Now that it’s ready to open it’s doors, it needs a wee income to repay the “bank of mom” to show my appreciation! ♥️

Nov 29 – Dec 6

G$30,968 GYD per night

Guest favorite

Cottage in Essex

5.0 out of 5 average rating, 120 reviews

The Kiss n Tell - We’ll Pay the HST

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.

Nov 18 – 25

G$47,827 GYD per night

Guest favorite

Home in Kingsville

4.99 out of 5 average rating, 181 reviews

La Perla - Lakefront Retreat in Wine Country!

Experience the shores of Lake Erie and it's breathtaking views! This gorgeous get-away retreat has been fully converted to a one-of-a-kind elegant vacation property. Located in the heart of Canada’s hottest wine region, and only minutes away to many craft breweries, golf courses, restaurants, shopping, Point Pelee National Park and more! We offer a zero-contact check-in, professional cleaning, and elegant furnishings! Connect with us today to let us know how we can help plan your getaway!

Oct 16 – 23

G$36,579 GYD per night

Guest favorite

Guesthouse in Essex

4.99 out of 5 average rating, 293 reviews

Private Wine Route Getaway with Hot Tub

The heart behind The Vineyard Retreat is to help our guests relax, restore, and reconnect. Located on County Road 50 we're conveniently placed on the wine route between Kingsville, Colchester, and Harrow. Our guest house is steps away from Lake Erie and close by to wineries, breweries, restaurants, tours, fruit stands, national parks, conservation areas, beaches, orchards, golf courses, bike paths, and more. Read more about what our guest house has to offer in the detailed description below.

Oct 22 – 29

G$32,938 GYD per night

Guest favorite

Cottage in Essex

4.94 out of 5 average rating, 104 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.

Sep 21 – 28

G$28,000 GYD per night

Guest favorite

Home in Kingsville

4.95 out of 5 average rating, 152 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.

Feb 27 – Mar 6

G$30,703 GYD per night

Guest favorite

Guest suite in Essex

4.97 out of 5 average rating, 136 reviews

The Loft Suite

Guests will enjoy our quaint private getaway. Our suite is set above our detached garage. Open concept. Perfect for a short getaway to 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, sugarFreshly made banana bread. Some snacks.

Jun 12 – 19

G$24,269 GYD per night

Guest favorite

Farm stay in Essex

5.0 out of 5 average rating, 133 reviews

Luxury Farm Stay - Hot tub - Allow pets - Firepits

-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 with frontage onto majestic Lake Erie. Bathe in our farm and forests' healing power. Town of Essex License #STR-2022-28

Nov 23 – 30

G$46,000 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Essex vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Essex's top sights

Colchester Harbour/Beach20 locals recommend

Oxley Estate Winery93 locals recommend

Garfield's34 locals recommend

Cooper's Hawk Vineyards and The Vines Restaurant61 locals recommend

Tim Hortons14 locals recommend

Viewpointe Estate Winery68 locals recommend

Other great vacation rentals in Essex

Guest favorite

Cottage in Kingsville

4.97 out of 5 average rating, 258 reviews

Sage On Main - Downtown Wine Country Cottage

Jan 19 – 26

G$31,150 GYD per night

Guest favorite

Bungalow in Kingsville

4.96 out of 5 average rating, 210 reviews

Singor Shores, Canada

Aug 5 – 12

G$25,217 GYD per night

Guest favorite

Guesthouse in Essex

5.0 out of 5 average rating, 39 reviews

Premiere Cottage-Heart of Wine County/ Lake Access

May 16 – 23

G$28,575 GYD per night

Guest favorite

Farm stay in Essex County

5.0 out of 5 average rating, 82 reviews

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

Jun 13 – 20

G$18,092 GYD per night

Guest favorite

Cottage in Essex

5.0 out of 5 average rating, 47 reviews

Blue Haven at Colchester Harbour

Sep 27 – Oct 4

G$33,938 GYD per night

Guest favorite

Home in Essex

4.91 out of 5 average rating, 32 reviews

Cheerful 2-bedroom home minutes from the Lake!

Mar 28 – Apr 4

G$18,297 GYD per night

Guest favorite

Home in Essex

4.95 out of 5 average rating, 20 reviews

Hideaway in Harrow with 2 person Air-jet Tub

Sep 3 – 10

G$19,289 GYD per night

Guest favorite

Home in Essex

4.9 out of 5 average rating, 58 reviews

The Blues Barn on the Wine Trail w/ FirePit & BBQ

Dec 8 – 15

G$30,887 GYD per night

Show all

Quick stats about vacation rentals in Essex

Total rentals
110 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
70 properties are a good fit for families
Total number of reviews
6.7K reviews
Nightly prices starting at
G$10,449 GYD before taxes and fees

Frequently Asked Questions

Do cottage rentals in Essex have a kitchen?
Absolutely! We offer over 50 cottage rentals with a kitchen in Essex. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Essex have free parking?
Absolutely! We offer over 30 house rentals with free parking in Essex. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Essex have air conditioning?
Absolutely! We offer over 50 cottage 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 50 homes with air conditioning, over 50 homes with free parking, over 50 homes with a kitchen, over 50 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 20 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 40 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 60 vacation rentals in Essex featuring dedicated workspaces. Stay connected and productive in your home away from home.

Vacation rentals in Essex

Top-rated vacation rentals in Essex

Vacation rentals for every style

Houses

Cottages

Hotels

Popular amenities for Essex vacation rentals

Stay near Essex's top sights

Other great vacation rentals in Essex

Cottage in Kingsville

Bungalow in Kingsville

Guesthouse in Essex

Farm stay in Essex County

Cottage in Essex

Home in Essex

Home in Essex

Home in Essex

Quick stats about vacation rentals in Essex

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do cottage rentals in Essex have a kitchen?

Do house rentals in Essex have free parking?

Do cottage rentals in Essex have air conditioning?

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

Are there family-friendly vacation rentals in Essex?

Do house rentals in Essex have wifi?

Are there pet-friendly vacation rentals in Essex?

Are there vacation rentals with a dedicated workspace in Essex?

Destinations to explore