Maidstone Holiday Rentals
Apartment
- Windsor
- ·
- East Windsor
- 0.69 mi to center
10.0Exceptional
(33 Reviews)
1 Bedroom
1 Bath
1 Guest
450 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
R1,527/Night
7 Nights - R10,683
House
10.0Exceptional
(3 Reviews)
4 Bedrooms
3 Baths
8 Guests
3003.13 ft²
Oceanfront
Pool
Ocean View- Balcony/Terrace
R7,341/Night
7 Nights - R51,387
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Air Conditioner
R4,890/Night
7 Nights - R34,225
Apartment
- Windsor
- ·
- Walkerville
- 0.24 mi to center
10.0Exceptional
(29 Reviews)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R2,734/Night
7 Nights - R19,142
Villa
10.0Exceptional
(2 Reviews)
7 Bedrooms
3 Baths
16 Guests
322.92 ft²
- Fireplace/Heating
View- Parking
- Air Conditioner
R14,374/Night
7 Nights - R100,614
House
10.0Exceptional
(17 Reviews)
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R2,242/Night
7 Nights - R15,700
House
10.0Exceptional
(16 Reviews)
1 Bedroom
1 Bath
2 Guests
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R2,881/Night
7 Nights - R20,165
Apartment
10.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
3 Guests
450 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R2,801/Night
7 Nights - R19,613
Condo
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R2,580/Night
7 Nights - R18,054
Luxury Holiday Rentals in Maidstone
Over 566+ Luxury Holiday Rentals in or Near Maidstone
House
- Ontario
- ·
- Town of Essex
- 7.98 mi to center
3 Bedrooms
4 Baths
10 Guests
Pet Friendly- Air Conditioner
Internet
Laundry
R16,012/Night
7 Nights - R112,076
House
3 Bedrooms
2 Baths
10 Guests
5995.5 ft²
- Hot Tub
- Pool
- View
- Pet Friendly
R14,677/Night
7 Nights - R102,741
Cabin
6 Bedrooms
3 Baths
10 Guests
4000 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R14,004/Night
7 Nights - R98,032
House
10.0Exceptional
(5 Reviews)
4 Bedrooms
4 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
R12,613/Night
7 Nights - R88,291
House
10.0Exceptional
(7 Reviews)
6 Bedrooms
3 Baths
12 Guests
4000 ft²
Private Pool- Hot Tub
Spa- Fireplace/Heating
R12,175/Night
7 Nights - R85,222
House
- Lakeshore
- ·
- Belle River
- 0.68 mi to center
5 Bedrooms
4 Baths
10 Guests
2002.09 ft²
- Pool
- Pet Friendly
- Parking
- Air Conditioner
R10,936/Night
7 Nights - R76,552
House
4.0Average
(1 Review)
7 Bedrooms
5 Baths
19 Guests
2723 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R10,411/Night
7 Nights - R72,883
House
8.6Fabulous
(4 Reviews)
4 Bedrooms
3 Baths
10 Guests
6000 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R9,958/Night
7 Nights - R69,701
House
4 Bedrooms
4 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
Breakfast
R9,467/Night
7 Nights - R66,275
Top-Rated Holiday Rentals with a Pool in Maidstone
Over 48+ The Best Private Villas and Holiday Rentals in Maidstone with a Pool
House
- Ontario
- ·
- North Ridge
- 6.13 mi to center
10.0Exceptional
(18 Reviews)
3 Bedrooms
2 Baths
10 Guests
1700 ft²
- Private Pool
- Spa
- Fireplace/Heating
- Pool
R7,246/Night
7 Nights - R50,721
House
10.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R9,307/Night
7 Nights - R65,155
House
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
8 Guests
3500 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
R6,547/Night
7 Nights - R45,834
Hotel
9.8Exceptional
(73 Reviews)
1 Bath
- Pool
- Breakfast
- Parking
- Internet
R2,133/Night
7 Nights - R14,937
House
9.7Exceptional
(124 Reviews)
2 Bedrooms
2 Baths
6 Guests
301.39 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R1,730/Night
7 Nights - R12,112
Ski Chalet
- Ontario
- ·
- North Ridge
- 6.15 mi to center
9.6Exceptional
(6 Reviews)
3 Bedrooms
2 Baths
10 Guests
1679.17 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R4,968/Night
7 Nights - R34,777
Hotel
9.4Exceptional
(1003 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
R2,112/Night
7 Nights - R14,791
Hotel
9.4Exceptional
(591 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
R2,291/Night
7 Nights - R16,041
Bed & Breakfast
- Ontario
- ·
- Town of Essex
- 5.50 mi to center
9.4Exceptional
(39 Reviews)
3 Bedrooms
3 Baths
6 Guests
211.69 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
R3,099/Night
7 Nights - R21,691
Pet-Friendly Holiday Rentals in Maidstone
Over 174+ Pet-Friendly Holiday Rentals in or Near Maidstone
Apartment
- Windsor
- ·
- Walkerville
- 0.54 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
650 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R1,799/Night
7 Nights - R12,599
House
- Windsor
- ·
- Walkerville
- 0.71 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
2 Baths
5 Guests
13928.5 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R2,856/Night
7 Nights - R19,986
Apartment
- Windsor
- ·
- Walkerville
- 0.65 mi to center
7.4Very Good
(11 Reviews)
1 Bedroom
1 Bath
- Hot Tub
- Spa
- Fireplace/Heating
- Balcony/Terrace
R1,996/Night
7 Nights - R13,979
House
- Windsor
- ·
- East Windsor
- 0.97 mi to center
9.8Exceptional
(27 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R2,281/Night
7 Nights - R15,976
Apartment
- Windsor
- ·
- Walkerville
- 0.16 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
6 Guests
150.69 ft²
- View
- Pet Friendly
- Parking
- Air Conditioner
R2,792/Night
7 Nights - R19,548
House
9.6Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R3,654/Night
7 Nights - R25,572
House
9.4Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
R2,020/Night
7 Nights - R14,141
Apartment
- Windsor
- ·
- Walkerville
- 0.78 mi to center
8.0Excellent
(2 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R2,362/Night
7 Nights - R16,528
Apartment
- Windsor
- ·
- Walkerville
- 0.58 mi to center
6.8Good
(3 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
R1,571/Night
7 Nights - R10,992
Large Holiday Rentals and Private Villas in Maidstone
Over 62+ Large Holiday Rentals and Private Villas in or Near Maidstone
House
- Windsor
- ·
- Amherstburg
- 7.77 mi to center
10.0Exceptional
(4 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R4,937/Night
7 Nights - R34,566
House
9.7Exceptional
(3 Reviews)
5 Bedrooms
2 Baths
10 Guests
118.4 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
R3,914/Night
7 Nights - R27,406
House
9.8Exceptional
(26 Reviews)
5 Bedrooms
2 Baths
10 Guests
2200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R2,951/Night
7 Nights - R20,652
Villa
- Ontario
- ·
- Boblo Island
- 3.40 mi to center
9.5Exceptional
(2 Reviews)
4 Bedrooms
4 Baths
11 Guests
3003.13 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
R3,621/Night
7 Nights - R25,344
House
- Windsor
- ·
- Walkerville
- 0.88 mi to center
9.8Exceptional
(18 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R5,890/Night
7 Nights - R41,239
House
- Windsor
- ·
- Bridgeview
- 0.72 mi to center
9.6Exceptional
(19 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R3,488/Night
7 Nights - R24,419
House
9.6Exceptional
(14 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R4,032/Night
7 Nights - R28,218
House
- Ontario
- ·
- Boblo Island
- 3.65 mi to center
9.6Exceptional
(5 Reviews)
4 Bedrooms
3 Baths
11 Guests
2800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R4,849/Night
7 Nights - R33,949
House
9.6Exceptional
(5 Reviews)
5 Bedrooms
2 Baths
10 Guests
2200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,403/Night
7 Nights - R23,818
Wheelchair Accessible Holiday Homes in Maidstone
Over 30+ Wheelchair Accessible Holiday Homes in or Near Maidstone
Condo
- Windsor
- ·
- Sandwich Towne
- 0.70 mi to center
9.6Exceptional
(21 Reviews)
1 Bedroom
1 Bath
2 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R1,484/Night
7 Nights - R10,391
Hotel
9.0Exceptional
(126 Reviews)
3 Baths
426.97 ft²
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Pet Friendly
R2,167/Night
7 Nights - R15,164
Apartment
8.2Excellent
(403 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R1,026/Night
7 Nights - R7,176
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
Child Friendly
Wheelchair Accessible
R2,586/Night
7 Nights - R18,103
Hotel
8.9Fabulous
(232 Reviews)
8 Baths
372.7 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
R2,620/Night
7 Nights - R18,347
House
- Windsor
- ·
- Walkerville
- 0.59 mi to center
4.0Average
(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R1,772/Night
7 Nights - R12,404
Condo
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
R1,831/Night
7 Nights - R12,810
House
- Ontario
- ·
- Kingsville
- 9.73 mi to center
5.0Average
(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Air Conditioner
R3,636/Night
7 Nights - R25,458
House
3 Bedrooms
1 Bath
7 Guests
3000 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Air Conditioner
R4,381/Night
7 Nights - R30,670
Maidstone Private Villas and Holiday Homes Under $200
Over 410+ Maidstone Private Villas and Holiday Homes Under $200
Apartment
- Windsor
- ·
- East Windsor
- 0.58 mi to center
10.0Exceptional
(7 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R1,737/Night
7 Nights - R12,161
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
1700.7 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
R1,775/Night
7 Nights - R12,420
Bed & Breakfast
- Windsor
- ·
- Walkerville
- 0.56 mi to center
9.6Exceptional
(380 Reviews)
1 Bedroom
1 Bath
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
R1,779/Night
7 Nights - R12,453
Apartment
- Windsor
- ·
- Walkerville
- 0.36 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R1,746/Night
7 Nights - R12,226
House
- Windsor
- ·
- South Central
- 0.29 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
96.88 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Kitchen
R682/Night
7 Nights - R4,773
Bed & Breakfast
- Windsor
- ·
- East Windsor
- 1.80 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R2,168/Night
7 Nights - R15,181
House
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
3 Guests
600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R1,208/Night
7 Nights - R8,459
House
- Windsor
- ·
- East Windsor
- 0.82 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
R2,114/Night
7 Nights - R14,807
House
- Windsor
- ·
- East Windsor
- 0.81 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
R1,953/Night
7 Nights - R13,671
Instantly Bookable Holiday Homes in Maidstone
Over 274+ Instantly Bookable Holiday Homes in or Near Maidstone
House
- Windsor
- ·
- Walkerville
- 0.83 mi to center
10.0Exceptional
(7 Reviews)
2 Bedrooms
1 Bath
5 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R5,464/Night
7 Nights - R38,252
Apartment
- Windsor
- ·
- Walkerville
- 0.82 mi to center
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R3,044/Night
7 Nights - R21,302
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R1,886/Night
7 Nights - R13,200
Apartment
- Windsor
- ·
- Walkerville
- 0.91 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R3,204/Night
7 Nights - R22,438
House
- Windsor
- ·
- Walkerville
- 0.84 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R2,642/Night
7 Nights - R18,493
Apartment
- Windsor
- ·
- South Central
- 0.49 mi to center
9.8Exceptional
(6 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R1,570/Night
7 Nights - R10,992
Apartment
9.6Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R1,832/Night
7 Nights - R12,826
Apartment
- Windsor
- ·
- East Windsor
- 0.31 mi to center
9.4Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R1,999/Night
7 Nights - R13,995
House
9.0Exceptional
(11 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R1,899/Night
7 Nights - R13,297
Book a Last Minute Place to Stay in Maidstone
About Casai's Private Villas and Holiday Rentals in Maidstone
Discover more than 575 vacation rentals available in Maidstone. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Maidstone.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Maidstone, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Maidstone. On average, places to stay near Maidstone offer 492.37 ft², with nightly prices averaging R2,804.
With Casai, finding and comparing holiday rentals in Maidstone is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Show more
Show less
Top Accommodation Types in Maidstone
| Type | Count |
|---|---|
| Vacation Homes | 273 |
| Holiday Apartments | 206 |
| Villas | 5 |
| Cottages | 3 |
Use these Quick Filters to Find a Holiday Rental in Maidstone
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Maidstone.
Weather in Maidstone, ON
View the weather forecast for Maidstone before booking your Maidstone Vacation Rentals to confirm your best time to go.
December - February
High 23°F Low 2°F
March - May
High 65°F Low 12°F
June - August
High 76°F Low 49°F
September - November
High 65°F Low 8°F
Top Attractions Around Maidstone, ON
Casai offers a large selection of top attractions around Maidstone . Research things to do on your vacation before you visit Maidstone.
Frequently Asked Questions About Maidstone?
What are the top holiday rentals in Maidstone?
With numerous options available in Maidstone, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Maidstone:
- The Boho Oasis: Luxurious Studio Apartment, Quiet Court, Close to All Amenities!
- Beautifully renovated home in historic Walkerville.
- Woodland Retreat with Pool, Sauna & Event Space
- Luxury 2BR home with high ceilings with BBQ/patio in beautiful South Windsor.
- Perfect hideaway with a hot tub and a fireplace
- Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel
- Luxury Condo Windsor/LaSalle Ontario
- Large quiet estate property in beautiful natural surroundings.
- Unique 2-BDR Historic Warehouse Loft with Terrace and Fireplace ! ! !
- The Boho Oasis: Spacious Deluxe Apartment, Close to All Amenities, Safe & Quiet
How many holiday rentals have private pools in Maidstone?
Discover a selection of holiday rentals with private pools near Maidstone with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Modern Spacious 1 bedroom and a den home (Lower Unit)
- Hyatt Place Windsor
- Cozy Farmhouse Escape – Ideal for a Peaceful and Relaxing Getaway!
- Holiday Inn Express Windsor Waterfront by IHG
Which holiday homes in Maidstone are best for families?
If you're searching for a family-friendly holiday home in Maidstone, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Maidstone:
- Park View Retreat with Hot Tub and King Size Bed
- Executive 2BR Lower Suite Private & Spacious Close to USA Border
- Housing Albert
How many Casai.co.za holiday rentals are available in Maidstone?
As of 2026, Casai boasts over 575 properties listed in the Maidstone area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Maidstone.
People Also Ask
Finding the best prices in Maidstone
Map
