Book a Place to Stay in Windsor for Your Summer Getaway
About Windsor Summer Rental on Vacation Cottage
Elevate your summer travels with 396 top-notch stay to make the most of your summer adventures? Consider a summer resort or villa rental in or near Windsor. Choosing the perfect holiday rental for your upcoming summer getaway on Vacation Cottage is a breeze. Whether you're traveling with family, friends, or a group to Windsor or its surrounding areas, Vacation Cottage offers a plethora of luxury summer accommodations to select from. Many of these accommodations boast top-notch amenities such as private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxurious bedrooms, bathtubs, and pet-friendly environments.
Searching for a tranquil retreat in Windsor for an unforgettable summer holiday? Vacation Cottage's summer rental homes are ready to provide you with the utmost comfort you deserve. Whether you're in need of a premium summer condo, luxury flat, resort, villa, bungalow, cozy cabin, RV, or cottage in Windsor, Vacation Cottage has you covered for your next summer escapade.
Frequently Asked Questions About Windsor Luxury Rentals
What are the top rated Summer Rentals in Windsor?
There are a lot of options in Windsor. If you plan on staying in the Windsor area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Windsor:
- Queens Cottage 4-Beachfront Villa - Swimming pool, staff, Newly refurbished!
- Beautiful VILLA SEAGULL in Silver Sands Beach Resortn3 bedroom 3.5 baths
- 2 bedrooms 2bath home in gated area. 24 hours security.
- MODERN BEACH SIDE VILLA
- L&V Paradise Vacation Home with Pool and Gym
- Good Hope Coach House, historic cut stone house with modern amenities
- Seaview villa at Stonebrook Manor, Falmouth, Trelawny, Jamaica
- Charming 2-bedroom house with pool, gym, room, 5 minutes away from attractions
- Home sweet home Trewlany Falmouth Jamacia a Paradise
- Simmerdown Villa is a spacious modern 4 bedroom house within a gated community
How many summer rentals are available around Windsor?
In 2025, Vacation Cottage offers 396 summer rentals in or around Windsor. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
How much does it cost to rent a summer rental in Windsor?
The average price per night for a summer rental in Windsor is $350. Check the full list of summer accommodations in Windsor.
How many summer rentals are available to book in Windsor?
There are 396 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Vacation Cottage.
Do any summer rentals in Windsor have a private pool?
Yes, here are some popular summer holiday rentals in Windsor that have a private or indoor pool:
- Queens Cottage 4-Beachfront Villa - Swimming pool, staff, Newly refurbished!
- L&V Paradise Vacation Home with Pool and Gym
- The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive
- Beautiful VILLA SEAGULL in Silver Sands Beach Resortn3 bedroom 3.5 baths
Check all holiday rentals with a pool in Windsor on Vacation Cottage.
Can I rent pet-friendly summer rentals in Windsor?
Yes, We have 396 summer rental homes in Windsor and types of place to stay in Windsor include:
- Vacation Homes: 396 available for rent
- Villas: 396 Rentals available for rent
- Holiday Apartments: 396 Rentals available for rent
- Hotels with Suites: 396 Rentals available for book
Do you have a luxury summer rental with a pool in Windsor?
Yes, of course! There are many luxury summer rental properties in Windsor. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Windsor.
