Estate Windsor Vacation Rentals from $183: Search Short-Term Rentals

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Our top choices for Estate Windsor vacation rentals

A living room with a wooden entertainment center, a glass coffee table, and a sofa.

1. Windchime Estates

Christiansted

Alexis daniel

$163 nightly

Oct 31 - Nov 1

Total with taxes and fees

A modern kitchen with white cabinets, a white refrigerator, a microwave, and a stove. There is a dining area with a white table and turquoise chairs.

2. The Cottage at Green Cay - Walk to the Beach - King Bed - AC

Gallows Bay

Patricia F.

$306 nightly

Oct 31 - Nov 1

Total with taxes and fees

A small room with a sliding glass door leading to a garden, a wooden table, and a bench.

3. Buck Island Views on North Shore: Windsors Rest

Northcentral

Tom M.

$147 nightly

Oct 31 - Nov 1

Total with taxes and fees

A pool area with lounge chairs, a small table, and a pathway leading to a building with illuminated windows.

4. Your Caribbean home away from home

Christiansted

Breanna S.

$288 nightly

Oct 31 - Nov 1

Total with taxes and fees

A wooden swing with cushions against a yellow wall, a white door, and an air conditioning unit.

5. Buck Island Views on North Shore: The Mermaid

Northcentral

Amy L.

$161 nightly

Oct 31 - Nov 1

Total with taxes and fees

6. Best Buck Island Views on North Shore: The View

Northcentral

Lori C.

$177 nightly

Nov 2 - Nov 3

Total with taxes and fees

A stone wall, a concrete pathway, and a white picket fence.

7. Large & Comfortable 1 Bed/Bath Guest Room on St. Croix

Christiansted

Anthony B.

$198 nightly

Nov 4 - Nov 5

Total with taxes and fees

A modern bedroom with a large bed, two bedside tables with lamps, a potted plant, and artwork on the walls.

8. Town Treasure - King Bed - Walkable - AC

Christiansted Historic District

"I have tears in my eyes writing this because we’re on the sea plane leaving st croix. I had the greatest time ever and it was mainly thanks to our stay. The accommodations were more than I ever would have expected… And we have stayed thousands of places.this was one of my favorite experiences of my life and I owe a great huge thanks to the host for all that she did for us. Thank you so much."

Kate M.

$177 nightly

Nov 2 - Nov 3

Total with taxes and fees

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Top Estate Windsor Hotel Reviews

Palms Resort and Beach

8/10 Good

"So peaceful. Location is beautiful. They are revamping the place so the pool was not open to my disappointment. I was supposed to have gotten a notice from Expedia but I did not. Any compensation??"

The Waves at Cane Bay

8/10 Good

"Overall, we had a great stay, but there are definitely areas that need improvement! The restaurant and bar staff were AMAZING and truly made our stay! The food was pricey but REALLY good. Our room was nicely decorated and felt homey, the balcony views were incredible, and housekeeping did a fantastic job. Unfortunately, maintenance and attention to detail were lacking. The bathroom sink was clogged, the stopper wouldn't come up, and the shower leaked water all over the floor. Towels were limited, the bed was too firm, and the blankets were stiff and itchy. The balcony was my biggest disappointment. The paint was chipped, cracked, and faded, and the furniture cushions were so dirty that I didn't even want to sit outside and enjoy the gorgeous view. Such a shame! We also had a few bugs in the room, although that's somewhat expected on an island. We only received bottled water on our first day of an eight-day stay. The Keurig didn't accept standard pods, so we wasted money purchasing them. Wish they had laundry service. Management really needs to focus on maintenance and the overall appearance of the property. It's the little things that add up and take away from what could be an amazing experience. Would I stay again? Absolutely, but mainly because of the incredible restaurant and bar staff, delicious food, and beautiful views. They made our stay memorable! I'd just return with lower expectations regarding the property's upkeep and overall aesthetics."

The Buccaneer Beach & Golf Resort

10/10 Excellent

"The Buccaneer was gorgeous. We appreciated all that it had to offer. Our ocean view room was stunning with a view of the ocean, beach and Christinstead. We loved the Grotto pool and The beaches,and the restaurants. The overally friendly staff were helpful.As were the drivers both at the hotel and into town. Especially Lockhart and Paul and the helpful staff like Leah at the Concierge and the waiters at the Terrace and Mermaid restaurant. On the downside it was off season which made it made it nice and quiet but also we experienced some concerns. The Grotto pool closed our first couple of days. Also, the service at the Mermaids restaurant seemed to be under staffed which made service slow. The waiters did a good job though. The terrace restaurant closed and the seating area outside the Terrace was closed off for renovations as well. Definitely on our bucket list to come back."

Ruff Resort at Victoria House

8/10 Good

"We had a good stay. The property was good. The surrounding areas near rhe property looks like an older town, so we did not venture over there. Resurfacing of the road was in progress while we were there. Location is far away from Christiansted; we took around 35 to 40 mins to get to Christiansted by car."

Find out more about Estate Windsor

Everything you need to know about Estate Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Estate Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Estate Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Estate Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Estate Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Estate Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $183 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Estate Windsor rentals

At Expedia, we put the best Estate Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Estate Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Estate Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Estate Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Estate Windsor?

Yes, you can find vacation rentals close to the most popular points of interest in Estate Windsor, or you can choose a secluded option if you're looking for relaxation.

What are some of the best vacation home rentals that Estate Windsor has to offer?

Beachfront. Just a Few Steps to the Sand. Walk to Restaurants. Near Downtown.: Visitors like this Estate Windsor vacation home rental. It is located on the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

What’s there to see and do in Estate Windsor?

While you're exploring the area, Cane Bay and Cane Bay Beach are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Carambola Golf Club and Sugar Beach.

What’s a vacation rental in Estate Windsor like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Estate Windsor. Vacation rentals feature amenities such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a small group gathering.

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Check prices for these dates

Our top choices for Estate Windsor vacation rentals

1. Windchime Estates

2. The Cottage at Green Cay - Walk to the Beach - King Bed - AC

3. Buck Island Views on North Shore: Windsors Rest

4. Your Caribbean home away from home

5. Buck Island Views on North Shore: The Mermaid

6. Best Buck Island Views on North Shore: The View

7. Large & Comfortable 1 Bed/Bath Guest Room on St. Croix

8. Town Treasure - King Bed - Walkable - AC

9. Cozy Retreat by Chenay Bay

10. "Spectacular Ocean Views" at Calypso Castillo!

11. Buck Island Views on North Shore: View & Windsors

12. Lovely 1-bedroom condo with Fresh Water Pool

13. Caribbean View Style 1 Bedroom Condo by RedAwning

14. Beach-Food-Resort 2 min walk l Patio lOcean View

15. Moko Jumbie House - "Guesthouse" - Cozy 1-Bedroom

16. Buck Island Views North Shore: Mermaid & Windsors

17. Buck Island Views on North Shore: Mermaid & View

18. Moko Jumbie - "Premier Suite" - Entire Condo

19. Private & Cozy 1 Bed/1 Bath Apartment

20. Historic Apt in Heart of Christiansted

Find vacation rentals that suit your style

Top Estate Windsor Hotel Reviews

Palms Resort and Beach

The Cove Hotel St.Croix

King Christian Hotel

The Waves at Cane Bay

The Frederiksted Hotel

Holger Danske Hotel

The Buccaneer Beach & Golf Resort

Ruff Resort at Victoria House

Windchime Estates

Find out more about Estate Windsor

Frequently asked questions

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