448+ Vacation Rentals & Holiday Homes in Windsor |
  1. Jamaica
  2. Trelawny
  3. Windsor

Windsor Accommodations - Hotels & Rentals

About Windsor Vacation Rentals

Discover More than 448 Incredible Getaway Rentals Available in Windsor. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Windsor.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Windsor, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Windsor. The Average Size of Places to Stay Near Windsor is 1423.93 ft², with Prices Averaging US $326 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Windsor. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

Show more
Show less

Top Hotels & Vacation Rentals in Windsor

Type Count
Vacation Homes 241
Villas 108
Holiday Apartments 67
Cottages 2

Use these Quick Filters to Find a Vacation Rental in Windsor

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Windsor with Online Reservations.

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Saint Andrew Parish 623 Properties

Frequently Asked Questions About Windsor?

What are the top hotels, lake houses & vacation rentals in Windsor?

We provide an array of great vacation destinations in Windsor. If you are looking to stay in or around the Windsor area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Windsor:

How many Hotels & Vacation Rentals have private pools in Windsor?

We have 55 Hotels & Vacation Rentals featuring a private pool in and near Windsor. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Windsor is best for families?

Searching for a family-friendly getaway in Windsor? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Windsor?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 448 in the Windsor area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Windsor.


People Also Ask

Online Reservation in Windsor

Recently Booked Hotels, Resorts, or Rentals in Windsor