Vacation rentals in Essex

4.88 out of 5 average rating, 302 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.

4.93 out of 5 average rating, 105 reviews

Home in Essex

Wine Down by the Lake -Hottub, Wineries,Lake Views

Hot tub, Lake views, wineries and golf? Sound perfect? It is and you have picked the perfect spot! A beautiful piece of heaven steps from Lake Erie. Whether you choose to relax in this amazing home, or enjoy the many wineries in walking distance, you have picked a real gem!! You can enjoy lake views from the rear deck or hot tub while sipping your wine. This home is perfect for a small bridal party, girls weekend or for couples looking to get away and explore what the area has to offer!

4.94 out of 5 average rating, 388 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! ♥️

4.96 out of 5 average rating, 118 reviews

Chardonnay Bay- June Special! stay 2 get 1 free!

Beautiful rustic cottage located in Colchester, Ontario! Chardonnay Bay offers 2 bedrooms and a loft, the master bed includes one queen bed, the 2nd bedroom has single bunk beds and the loft has a queen. We offer a full kitchen as well as laundry facilities. Outdoor patio area with hot tub, picnic table and bbq. We are located within a one minute walk to the beautiful Colchester beach, splashpad, park and marina, located on Essex County’s EPIC wine route consisting of over eighteen wineries.

4.99 out of 5 average rating, 345 reviews

Guesthouse in Essex

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.

4.97 out of 5 average rating, 175 reviews

Guest suite in Essex

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.

4.94 out of 5 average rating, 125 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.

4.93 out of 5 average rating, 223 reviews

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.

Superhost

4.93 out of 5 average rating, 156 reviews

Bright, Peaceful Lakefront ~Sunporch, BBQ, firepit

Welcome to A Day at the Lake! Relaxation, a cozy space and comfortable beds located here. Enjoy the light and airy feel of this lakefront cottage with plenty of natural light and cool breezes off Lake Erie. Located on Clark Beach in Harrow; near wineries, beaches, conservation areas, cycling and paddling routes. Welcome birders, beach goers, winery/brewing enthusiasts, cyclists and runners. Spring and summer dates book fast so be sure to reserve early to avoid disappointment.

4.93 out of 5 average rating, 130 reviews

North Shore Retreat

Welcome to North Shore Retreat! Our house sits atop an elevated bluff overlooking Lake Erie and is adjacent to a beautiful ravine surrounded by mature trees. It is a warm, modern, rustic home with a view you will never forget. Our home is walking distance to three of the most established wineries along Lake Erie (Viewpoint Estate Winery, North 42 Degrees and CREW). This space has everything you need to unwind, cook, disconnect, relax, enjoy wildlife and take care of yourself.

5 out of 5 average rating, 106 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!

4.78 out of 5 average rating, 154 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

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Essex vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Essex

5 out of 5 average rating, 53 reviews

Cottage in Kingsville

Reveries on the Lake- Kingsville cottage

FairuzRating, 5 stars1 week ago

What a wonderful place to stay! The views were incredible, it was super clean and the hosts were absolutely wonderful to talk to! They were very responsive and helpful with all of our questions. Definitely planning on coming back for a quick getaway in the future! My friends had a blast, especially when hiding Salty and coming up with a fun hint in riddle form! 10/10 would recommend!

5 out of 5 average rating, 29 reviews

Lakefront cottage in heart of wine country

JoyceRating, 5 stars1 month ago

My friends and I wanted a weekend away just to chill and catch up. We did a wine tour on the Saturday and then hung out at the house the rest of the afternoon. The place was perfect. Beds good, well stocked kitchen and beautiful deck. Wish the weather had been warmer and not rainy - would have liked to have sat outside but it was still a great weekend in a beautiful vacation rental

5 out of 5 average rating, 30 reviews

Home in South Windsor

South Windsor Luxury Home - Private Gym/Sauna

CathrynRating, 5 stars2 weeks ago

Thank you for making us feel welcome! We thoroughly enjoyed our stay in your beautifully decorated space. The flowers, snacks, water and slippers were a personal touch. Lots of room to spread out and celebrate with family. The location was perfect for getting around Windsor easily. A peaceful oasis close by everywhere you wanted to go.

4.97 out of 5 average rating, 89 reviews

Anchor down on your private Beachfront Cottage

AmitRating, 5 stars1 day ago

We visited Tessa’s place with the family on the occasion of my Mother’s birthday. Tessa’s generosity touched our heart as she gifted her with a beautiful hand written message, chocolates and local wines. We loved the her consideration and the kind gesture. I would like to start off by mentioning that her place is a rare find. Beautiful newly built house with top notch upgrades. Each and every single thing is chosen with precision. Bedding, furniture, interior design and what not. You have your personal beach in your backyard which is beautiful. BBQ, fire pit and outdoor furniture were easy to access and operate. Shining appliances and complete amenities make you feel like home away from home. I highly recommend this beautiful place to meditate, relay and rejuvenate. Kudos 👍🏻

4.95 out of 5 average rating, 22 reviews

Cottage in Kingsville

Lake front Guesthouse w/ king sz bed.

DeborahRating, 5 starstoday

We were looking for a peaceful getaway to explore the area and Amie’s place was perfect for our needs!! The cottage was spotless and had everything you would need, and also the bed was very comfy! The cottage was close to Kingsville and also to the many wineries available should you wish to do so!!

Barn in Essex

4.9 out of 5 average rating, 372 reviews

14th Homestead Barn Loft

JeremyRating, 5 stars1 month ago

The barn and the setting were more charming than I expected. the coffee shop employee Nathan greeted me when we arrived, offered me a cup of coffee on the house and directed me to how to get in the barn. Everything looked just like the photos, and it was a super charming setting. I only wish I could spend more time just enjoying the space. Highly recommend.

4.89 out of 5 average rating, 54 reviews

Guest suite in Windsor

Private/Quiet Perfect for professionals!

DilpreetRating, 5 stars1 day ago

I had a wonderful stay at Umer’s place! The location was convenient, the home was clean and comfortable, and Umer was a responsive and helpful host. Would definitely recommend to anyone visiting the area!