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

Search Holiday Homes in Town of Essex

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 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 £206
includes taxes & fees
28 Oct - 29 Oct
14th Coffee Co. Homestead Farmhouse
A large estate with a pond, a windmill, and a well-maintained lawn.

2. Castle On Malden - Luxury 50 Acre Private Estate

Castle On Malden - Luxury 50 Acre Private Estate
Essex
The price is £1,431
includes taxes & fees
21 Oct - 22 Oct
Castle On Malden - Luxury 50 Acre Private Estate
A dining area with a view of the ocean, a ceiling fan, and a telescope on a balcony.

3. 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, (29 reviews)
"Very clean, full kitchen, great location"
United States
Matthew E.
The price is £264
includes taxes & fees
1 Nov - 2 Nov
Beautiful Waterfront Lake House in the Heart of Epic Wine Country
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
10.0 out of 10, Exceptional, (12 reviews)
"Everything was great"
Canada
Mike
The price is £78
includes taxes & fees
22 Oct - 23 Oct
Little Belle River home
A modern living room with a grey sofa, wooden coffee table, and a dining area with a small table and chairs.

5. 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 £107
includes taxes & fees
21 Oct - 22 Oct
Cozy 2 Bedroom Luxury Suite
A residential area with a house, a dock, and a small boat.

6. 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, (91 reviews)
"Beautiful place and beautiful location"
United States
Peter C.
The price is £218
includes taxes & fees
23 Oct - 24 Oct
The Cedar House. Minutes from the lake, wineries and golf. www.thecedarhouse.ca
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 £212
includes taxes & fees
21 Oct - 22 Oct
Wild Goose Landing- Located near local wineries and breweries
A patio area with outdoor furniture, a pool, and a view of the sea.

8. 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 £176
includes taxes & fees
21 Oct - 22 Oct
Reveries on the Lake-lakefront Kingsville Cottage, Your home away from home
A modern kitchen with white cabinetry, a central island, and a coffee bar sign.

9. 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 £107
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.

10. 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
2 Nov - 3 Nov
Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border
A kitchen with white cabinets, a black tiled backsplash, a window with a view of trees, and a stainless steel stove.

11. 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, (21 reviews)
"Beautiful stay "
United States
Mohamad C.
The price is £137
includes taxes & fees
22 Oct - 23 Oct
Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.
A modern living room with a fireplace, a large flat-screen TV, a mirror, and a round coffee table with decorative plants.

12. 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
21 Oct - 22 Oct
Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.
A gazebo with a tiled roof, surrounded by greenery and a view of the water.

13. Stylish Getaway - Walk to downtown + Parks, Fenced yard + Firepit + Smart TVs

Stylish Getaway - Walk to downtown + Parks, Fenced yard + Firepit + Smart TVs
Kingsville
10.0 out of 10, Exceptional, (25 reviews)
"Great house, so clean and it was the perfect location to walk to town!"
United States
Katie F.
Stylish Getaway - Walk to downtown + Parks, Fenced yard + Firepit + Smart TVs
A window with a view of a brick house, a tree, and a basketball hoop.

14. 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 £264
includes taxes & fees
21 Oct - 22 Oct
Cozy, trendy, beachfront loft
A modern interior with a sliding glass door leading to a balcony with a view of the sea.

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

Lakefront Wellness Retreat - Sauna + Cold Plunge + Paddleboards + Lake Access
Kingsville
9.6 out of 10, Exceptional, (5 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 £345
includes taxes & fees
22 Oct - 23 Oct
Lakefront Wellness Retreat - Sauna + Cold Plunge + Paddleboards + Lake Access
A kitchen with a central island, pendant lighting, and a view into the dining area.

16. 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 £335
includes taxes & fees
26 Oct - 27 Oct
Historic Luxury Retreat in Downtown Kingsville
A two-story brick house with a garage, a covered patio, and a small front yard.

17. 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)
"Exactly as described. Easy check in. Easy to find. Nice space between bedrooms when staying with other couples. Fully stocked kitchen."
Canada
Brenda
The price is £154
includes taxes & fees
21 Oct - 22 Oct
Modern 2BR Basement Appartment. Near Point Peele. Free Parking. Kitchen
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.

18. 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 £254
includes taxes & fees
22 Oct - 23 Oct
Modern Spacious 1 bedroom and a den home (Lower Unit)
Relax in the living room and watch your favorite shows, lounging is a great way to unwind after a long day.

19. 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.
Modern 1BR Guesthouse | Near Marina & Golf
A modern living room with a sofa, coffee table, and dining area.

20. 3 bdr upper, prime location

3 bdr upper, prime location
Remington Park
The price is £159
includes taxes & fees
31 Oct - 1 Nov
3 bdr upper, prime location
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Town of Essex Hotel Reviews

Hampton Inn & Suites by Hilton Windsor

Hampton Inn & Suites by Hilton Windsor

10/10 Excellent
"Friendly and cheerful staff. Clean and tidy room Fresh and hot food."
Rosa 2-night trip
Posted 1 hour ago
Hampton Inn & Suites by Hilton Windsor

Find out more about Town of Essex

Town of Essex Holiday Homes information

Number of reviews
223
Accommodation
220 Holiday Homes
Lowest Price
£78
Highest Price
£1,431