A lighthouse by a beach with waves, trees, and a clear sky.

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Town of Essex holiday homes

A hot tub with a wooden fence and trees in the background.

1. 14th Coffee Co. Homestead Farmhouse

14th Coffee Co. Homestead Farmhouse
Essex
9.6 out of 10, Exceptional, (8 reviews)
"Fun place to stay - loved the farm house and coffee was amazing."
Canada
Sarah J.
The price is £174
includes taxes & fees
10 Nov - 11 Nov
14th Coffee Co. Homestead Farmhouse
A dining area with a view of the ocean, a ceiling fan, and a telescope on a balcony.

2. Beautiful Waterfront Lake House in the Heart of Epic Wine Country

Beautiful Waterfront Lake House in the Heart of Epic Wine Country
Essex
10.0 out of 10, Exceptional, (30 reviews)
"Very clean, full kitchen, great location"
United States
Matthew E.
The price is £247
includes taxes & fees
1 Nov - 2 Nov
Beautiful Waterfront Lake House in the Heart of Epic Wine Country
A large estate with a pond, a windmill, and a well-maintained lawn.

3. Castle On Malden - Luxury 50 Acre Private Estate

Castle On Malden - Luxury 50 Acre Private Estate
Essex
The price is £1,232
includes taxes & fees
2 Nov - 3 Nov
Castle On Malden - Luxury 50 Acre Private Estate
A neatly made bed with a white comforter and pillows, a wooden floor, and a window with dark curtains.

4. Little Belle River home

Little Belle River home
Belle River
9.8 out of 10, Exceptional, (13 reviews)
"Everything was great"
Canada
Mike
The price is £61
includes taxes & fees
15 Nov - 16 Nov
Little Belle River home
A residential area with a house, a dock, and a small boat.

5. The Cedar House. Minutes from the lake, wineries and golf. www.thecedarhouse.ca

The Cedar House. Minutes from the lake, wineries and golf. www.thecedarhouse.ca
Kingsville
10.0 out of 10, Exceptional, (92 reviews)
"Beautiful place and beautiful location"
United States
Peter C.
The price is £219
includes taxes & fees
2 Nov - 3 Nov
The Cedar House. Minutes from the lake, wineries and golf. www.thecedarhouse.ca
A modern living room with a grey sofa, wooden coffee table, and a dining area with a small table and chairs.

6. Cozy 2 Bedroom Luxury Suite

Cozy 2 Bedroom Luxury Suite
Roseland
10.0 out of 10, Exceptional, (1 review)
"We had a great stay! The place was very clean, comfortable, and in a great location with everything we needed nearby."
Canada
Lindsay M.
The price is £104
includes taxes & fees
2 Nov - 3 Nov
Cozy 2 Bedroom Luxury Suite
A modern kitchen with a large window, a coffee machine, and a sign that reads "Rise & Shine It's Coffee Time".

7. Wild Goose Landing- Located near local wineries and breweries

Wild Goose Landing- Located near local wineries and breweries
Kingsville
9.8 out of 10, Exceptional, (49 reviews)
"Great place"
United States
Bryan M.
The price is £213
includes taxes & fees
1 Nov - 2 Nov
Wild Goose Landing- Located near local wineries and breweries
A modern kitchen with white cabinetry, a central island, and a coffee bar sign.

8. Executive One-Bedroom Upper Unit

Executive One-Bedroom Upper Unit
Windsor
9.0 out of 10, Wonderful, (7 reviews)
"Property was as described. Very comfortable and in good condition. Excellent value."
Canada
Mary
The price is £108
includes taxes & fees
15 Nov - 16 Nov
Executive One-Bedroom Upper Unit
A modern kitchen with white cabinets, stainless steel appliances, and a central island.

9. Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border

Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border
Devonshire
9.0 out of 10, Wonderful, (12 reviews)
"Home was very clean, good location close to major amenities, Devonshire mall, Costco. Easy access via key pad, ample parking. "
Canada
Tony
The price is £133
includes taxes & fees
1 Nov - 2 Nov
Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border
A modern living room with a fireplace, a large flat-screen TV, a mirror, and a round coffee table with decorative plants.

10. Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.

Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.
Devonshire
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay. The host was very responsive and addressed any issues quickly. The property was very clean, and the location was very convenient. Would definitely stay again."
Canada
Junwu
The price is £133
includes taxes & fees
1 Nov - 2 Nov
Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.
A patio area with outdoor furniture, a pool, and a view of the sea.

11. Reveries on the Lake-lakefront Kingsville Cottage, Your home away from home

Reveries on the Lake-lakefront Kingsville Cottage, Your home away from home
Kingsville
9.8 out of 10, Exceptional, (30 reviews)
"Nice and relaxing stay. Good communication with the hosts and beautiful views"
Canada
Chris G.
The price is £164
includes taxes & fees
1 Nov - 2 Nov
Reveries on the Lake-lakefront Kingsville Cottage, Your home away from home
A window with a view of a brick house, a tree, and a basketball hoop.

12. Cozy, trendy, beachfront loft

Cozy, trendy, beachfront loft
Kingsville
10.0 out of 10, Exceptional, (8 reviews)
"Great location absolutely beautiful loaf..."
Canada
Rebecca
The price is £280
includes taxes & fees
2 Nov - 3 Nov
Cozy, trendy, beachfront loft
A modern kitchen with dark wood cabinets, stainless steel appliances, and a marble backsplash. There are two bar stools and a small island with a sink.

13. Modern Spacious 1 bedroom and a den home (Lower Unit)

Modern Spacious 1 bedroom and a den home (Lower Unit)
Roseland
8.0 out of 10, Very good, (9 reviews)
"Very clean and everything that we thought it would be from the pictures"
United States
Dannavan C.
The price is £200
includes taxes & fees
1 Nov - 2 Nov
Modern Spacious 1 bedroom and a den home (Lower Unit)
A kitchen with white cabinets, a black tiled backsplash, a window with a view of trees, and a stainless steel stove.

14. Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.

Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.
South Windsor
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful stay "
United States
Mohamad C.
The price is £137
includes taxes & fees
2 Nov - 3 Nov
Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.
A two-story brick house with a garage, a covered patio, and a small front yard.

15. Modern 2BR Basement Appartment. Near Point Peele. Free Parking. Kitchen

Modern 2BR Basement Appartment. Near Point Peele. Free Parking. Kitchen
Leamington
10.0 out of 10, Exceptional, (7 reviews)
"The basement apartment was lovely decorated, the bath/shower had updated fixtures and the kitchen had all the amenities of home, not to mention that the hosts were kind and gracious!"
United States
Todd S.
The price is £154
includes taxes & fees
2 Nov - 3 Nov
Modern 2BR Basement Appartment. Near Point Peele. Free Parking. Kitchen
A modern living room with a sofa, coffee table, and a view of the outside.

16. Premium Stay Near Windsor Employers & Hospital

Premium Stay Near Windsor Employers & Hospital
Ford City
9.0 out of 10, Wonderful, (11 reviews)
"Nice stay overall."
United States
Adam Y.
The price is £175
includes taxes & fees
1 Nov - 2 Nov
Premium Stay Near Windsor Employers & Hospital
A kitchen with a central island, pendant lighting, and a view into the dining area.

17. Historic Luxury Retreat in Downtown Kingsville

Historic Luxury Retreat in Downtown Kingsville
Kingsville
10.0 out of 10, Exceptional, (2 reviews)
"Everything was perfect."
United States
Ray P.
The price is £282
includes taxes & fees
1 Nov - 2 Nov
Historic Luxury Retreat in Downtown Kingsville
A grassy outdoor area with wooden Adirondack chairs, a small fire pit, and a view of the ocean.

18. CJs Lakehouse is 1km to Point Pelee. Huge yard, firepit, pets welcome!

CJs Lakehouse is 1km to Point Pelee. Huge yard, firepit, pets welcome!
Leamington
9.8 out of 10, Exceptional, (91 reviews)
"We really enjoyed our stay."
United States
Andrew W.
The price is £240
includes taxes & fees
17 Nov - 18 Nov
CJs Lakehouse is 1km to Point Pelee. Huge yard, firepit, pets welcome!
A waterfront property with a deck, lounge chairs, a hot tub, and a small boat docked by the water.

19. Lakefront Wellness Retreat - Sauna + Cold Plunge + Paddleboards + Lake Access

Lakefront Wellness Retreat - Sauna + Cold Plunge + Paddleboards + Lake Access
Kingsville
9.8 out of 10, Exceptional, (6 reviews)
"The property had a lovely lakefront location with lots of privacy. The decor was contemporary but cozy and everything was very clean. The host Dylan was very friendly and quick to respond to any questions and and the online guidebook was much appreciated. It was the perfect place for our family to relax together at the end of a busy summer. Would definitely consider returning."
Canada
Susan
The price is £309
includes taxes & fees
1 Nov - 2 Nov
Lakefront Wellness Retreat - Sauna + Cold Plunge + Paddleboards + Lake Access
Relax in the living room and watch your favorite shows, lounging is a great way to unwind after a long day.

20. Modern 1BR Guesthouse | Near Marina & Golf

Modern 1BR Guesthouse | Near Marina & Golf
Windsor
7.6 out of 10, Good, (4 reviews)
"To get from the driveway to the side entrance into the apartment is unsafe. There is a steep step going down from the driveway and there are no stepping stones. The apartment is lovely and we enjoyed our stay."
Canada
Maria C.
The price is £122
includes taxes & fees
1 Nov - 2 Nov
Modern 1BR Guesthouse | Near Marina & Golf
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Town of Essex Hotel Reviews

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

10/10 Excellent
"❤️"
Jason 1-night trip
Posted 1 hour ago
Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

Find out more about Town of Essex

Town of Essex Holiday Homes information

Number of reviews
291
Accommodation
220 Holiday Homes
Lowest Price
£61
Highest Price
£1,232