Apartment
10.0(4 Reviews)
2 Bedrooms
4 Guests
Hot Tub
Kitchen
Air Conditioner
Internet
US $186/Night
7 Nights - US $1,300
Windsor, OH Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Windsor
10.0
House
10.0(4 Reviews)
1 Bedroom
6 Guests
Parking
Pet Friendly
Sports/Activities
Security/Safety
US $64/Night
7 Nights - US $448
House
3 Bedrooms
6 Guests
US $72/Night
7 Nights - US $501
House
10.0(2 Reviews)
1 Bedroom
6 Guests
- Parking
Spa
Balcony/Terrace- Kitchen
US $391/Night
7 Nights - US $2,739
US $360/Night
7 Nights - US $2,520
Cabin
10.0(2 Reviews)
1 Bedroom
2 Guests
- Parking
- Spa
- Balcony/Terrace
- Kitchen
US $229/Night
7 Nights - US $1,601
Cabin
10.0(2 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $223/Night
7 Nights - US $1,560
Cabin
9.6(10 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $236/Night
7 Nights - US $1,650
New
Cabin
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $282/Night
7 Nights - US $1,973
Luxury Holiday Rentals in Windsor
Over 71+ Luxury Holiday Rentals in or Near Windsor
Villa
9.8(40 Reviews)
8 Bedrooms
24 Guests
Private Pool- Hot Tub
- Parking
Pool
US $1,249/Night
7 Nights - US $8,740
House
10.0(1 Review)
6 Bedrooms
20 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,237/Night
7 Nights - US $8,659
New
House
1 Bedroom
3 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $648/Night
7 Nights - US $4,533
Cabin
10.0(1 Review)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $645/Night
7 Nights - US $4,512
New
Cottage
3 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $558/Night
7 Nights - US $3,905
House
10.0(48 Reviews)
4 Bedrooms
10 Guests
Breakfast- Parking
- Balcony/Terrace
- Kitchen
US $537/Night
7 Nights - US $3,759
House
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Air Conditioner
- Internet
Child Friendly
Laundry
US $533/Night
7 Nights - US $3,733
New
Other
6 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $492/Night
7 Nights - US $3,443
Other
9.8(6 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $459/Night
7 Nights - US $3,212
Top-Rated Holiday Rentals with a Pool in Windsor
Over 1+ The Best Private Villas and Holiday Rentals in Windsor with a Pool
House
9.6(89 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $177/Night
7 Nights - US $1,239
Pet-Friendly Holiday Rentals in Windsor
Over 18+ Pet-Friendly Holiday Rentals in or Near Windsor
RV Rental
8.0(4 Reviews)
1 Bedroom
8 Guests
- Pet Friendly
- Child Friendly
Designated Smoking Area
US $47/Night
7 Nights - US $329
House
10.0(1 Review)
4 Bedrooms
9 Guests
- Parking
- Internet
- Pet Friendly
- Security/Safety
US $274/Night
7 Nights - US $1,919
Cottage
8.0(2 Reviews)
1 Bedroom
- Parking
- Kitchen
- Air Conditioner
- Pet Friendly
US $230/Night
7 Nights - US $1,611
House
9.8(25 Reviews)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $254/Night
7 Nights - US $1,776
House
7 Bedrooms
24 Guests
- Parking
- Internet
- Pet Friendly
Accessibility
US $342/Night
7 Nights - US $2,394
New
Apartment
9.6(15 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $155/Night
7 Nights - US $1,085
Apartment
8.6(7 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $186/Night
7 Nights - US $1,302
Cabin
9.0(4 Reviews)
4 Bedrooms
9 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $454/Night
7 Nights - US $3,175
House
9.4(41 Reviews)
1 Bedroom
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $172/Night
7 Nights - US $1,204
Large Holiday Rentals and Private Villas in Windsor
Over 6+ Large Holiday Rentals and Private Villas in or Near Windsor
House
10.0(1 Review)
5 Bedrooms
16 Guests
- Air Conditioner
- Internet
- Laundry
Bedding/Linens
US $870/Night
7 Nights - US $6,088
House
10.0(1 Review)
7 Bedrooms
24 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $571/Night
7 Nights - US $3,998
Cabin
5.0(17 Reviews)
4 Bedrooms
10 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $459/Night
7 Nights - US $3,213
House
4.9(17 Reviews)
6 Bedrooms
14 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Child Friendly
US $355/Night
7 Nights - US $2,485
Other
7 Bedrooms
25 Guests
- Hot Tub
- Parking
- Spa
- Kitchen
US $450/Night
7 Nights - US $3,150
Other
4 Bedrooms
10 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $291/Night
7 Nights - US $2,035
Windsor Private Villas and Holiday Homes Under $200
Over 12+ Windsor Private Villas and Holiday Homes Under $200
House
9.8(14 Reviews)
1 Bedroom
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $169/Night
7 Nights - US $1,182
Apartment
10.0(6 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $197/Night
7 Nights - US $1,379
Apartment
10.0(5 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $186/Night
7 Nights - US $1,302
House
9.8(16 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $155/Night
7 Nights - US $1,082
Apartment
10.0(72 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $159/Night
7 Nights - US $1,110
House
8.0(1 Review)
2 Bedrooms
7 Guests
- Air Conditioner
Barbecue/Outdoor Cooking
US $168/Night
7 Nights - US $1,176
Apartment
7.0(2 Reviews)
2 Bedrooms
6 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
US $140/Night
7 Nights - US $980
Apartment
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Pet Friendly
- Child Friendly
US $182/Night
7 Nights - US $1,274
Apartment
1 Bedroom
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $120/Night
7 Nights - US $840
Instantly Bookable Holiday Homes in Windsor
Over 18+ Instantly Bookable Holiday Homes in or Near Windsor
Cottage
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $208/Night
7 Nights - US $1,456
Other
1 Bedroom
- Child Friendly
US $437/Night
7 Nights - US $3,058
Apartment
10.0(11 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $229/Night
7 Nights - US $1,603
Cabin
9.6(5 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $223/Night
7 Nights - US $1,560
New
House
1 Bedroom
6 Guests
- Hot Tub
- Parking
- Spa
Ocean View
US $394/Night
7 Nights - US $2,759
Cabin
10.0(62 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $216/Night
7 Nights - US $1,514
House
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $315/Night
7 Nights - US $2,203
New
House
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $286/Night
7 Nights - US $2,005
House
10.0(61 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $209/Night
7 Nights - US $1,464
Book a Last Minute Place to Stay in Windsor
About Casai's Private Villas and Holiday Rentals in Windsor
Discover more than 80 vacation rentals available in Windsor. 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 Windsor.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windsor, 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 Windsor. On average, places to stay near Windsor offer 750.89 ft², with nightly prices averaging US $322.
With Casai, finding and comparing holiday rentals in Windsor is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
There are 80 Windsor, OH Holiday Rentals
- Prices for a holiday home in Windsor start at US $47
- Top rated vacation home in Windsor is Geauga Maple Cottage
- Most popular short term in Windsor is Geauga Maple Cottage
- Cheapest place to stay in Windsor is The Farm at Grand River
- Most expensive holiday rental in Windsor is Cheerful Family Manor- Sleeps 25 w/hot tub and private pool in Amish Country
Recently Booked Holiday Rentals in Windsor
Frequently Asked Questions About Windsor?
What are the top holiday rentals in Windsor?
With numerous options available in Windsor, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Windsor:
- Geauga Maple Cottage
- Little house on the farm
- Located In Harpersfield twp in the heart of wine country and covered bridges
- Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
- 3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
- Historic Century Home on Chardon Square
- The Wildflower - Private cabin-wooded setting Amish Country & indoor whirlpool!
- The Thistle House off Chardon Square
- Farmhouse at Memory Lake Sleeps 6 - 3 bedrooms - 1 bath
- 4BR County Ranch w/Firepit Near Venues & Private Setting. Clean+Well-Stocked
Which holiday homes in Windsor are best for families?
If you're searching for a family-friendly holiday home in Windsor, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Windsor:
How many Casai.nz holiday rentals are available in Windsor?
As of 2026, Casai boasts over 80 properties listed in the Windsor area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Windsor.
