Windsor Mill Vacations from $500

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Your Windsor Mill Vacation

Our Windsor Mill vacation packages are a fast and convenient way to arrange and book your next exciting adventure. Uncover the true character of this unique neighborhood without the burden of planning it all yourself. Wondering where to go during your trip to Windsor Mill? Nearby attractions like Hudson Beach, Show Palace Dinner Theater and Cow Creek are great places to start. Stop daydreaming and start doing. When it's time to lock in your next vacation to Windsor Mill, Expedia will help get you there.

The Latest Windsor Mill Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $764, price is now $500 per person
$500
per person
Mar 9 - Mar 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (60 reviews)
Excellent customer service

Reviewed on Dec 14, 2025

Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Save 100% on your flight
Price was $1,083, price is now $645 per person
$645
per person
Mar 27 - Apr 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
No reviews
The rooms were newly renovated and the staff were very helpful. Very roomy

Reviewed on Jan 23, 2026

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,263, price is now $792 per person
$792
per person
Apr 12 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,131 reviews)
Hotel was clean and in a great location, and the rooftop pool and bar were a nice amenity. We paid extra through Expedia for a “bay view” room, but the view felt misleading: another building was directly across from our window, and the bay was only visible from a very specific spot in the room. The front desk apologized and said the bay view used to be better before the other building was built, but no alternate rooms were available. Overall we enjoyed our stay, but we would not pay extra for the bay view again—we would have preferred a standard room with a better city view and to save the added cost.

Reviewed on Jan 26, 2026

Pier House 60 Clearwater Beach Marina Hotel

Pier House 60 Clearwater Beach Marina Hotel

3 out of 5
Save 100% on your flight
Price was $927, price is now $582 per person
$582
per person
Apr 27 - May 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (1,804 reviews)
Awful breakfast but great location

Reviewed on Jan 18, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,310, price is now $831 per person
$831
per person
Apr 26 - May 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (712 reviews)
Room was excellent. Resort operations not so much.

Reviewed on Feb 4, 2026

Where to stay in Windsor Mill

Find the best Windsor Mill areas and neighborhoods for the activities you enjoy most. Learn more about Windsor Mill
Holmes Beach

Hudson Beach Estates

1 out of top 10 points of interest in this area
4/5(9 area reviews)

Though Hudson Beach Estates might not have many top sights, you can venture to the surrounding area to see attractions like Hudson Beach and Werner Boyce Salt Springs State Park.

Find hotels in Hudson Beach Estates

Windsor Mill Hotel Deals

Motel 6 Spring Hill, FL - Weeki Wachee

Motel 6 Spring Hill, FL - Weeki Wachee

2 out of 5
6172 Commercial Way Spring Hill FL
Fully refundableReserve now, pay when you stay
$51 nightly
The price is $57 total per night from Feb 16 to Feb 17
$57 total
Feb 16 - Feb 17
Total with taxes and fees
7.2/10 Good! (1,365 reviews)
Friendly staff decent room for the price

Reviewed on Feb 1, 2026

Motel 6 Spring Hill, FL - Weeki Wachee
Quality Inn & Suites Tarpon Springs South

Quality Inn & Suites Tarpon Springs South

2.5 out of 5
38724 US Highway 19 North Tarpon Springs FL
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $114 total per night from Feb 19 to Feb 20
$114 total
Feb 19 - Feb 20
Total with taxes and fees
8/10 Very Good! (1,027 reviews)
Clean room quiet area

Reviewed on Feb 4, 2026

Quality Inn & Suites Tarpon Springs South
Comfort Inn & Suites New Port Richey Downtown District

Comfort Inn & Suites New Port Richey Downtown District

2.5 out of 5
6206 US HWY 19 New Port Richey FL
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $122 total per night from Feb 12 to Feb 13
$122 total
Feb 12 - Feb 13
Total with taxes and fees
9.2/10 Wonderful! (1,154 reviews)
The entire experience was outstanding! Definitely will be back!

Reviewed on Feb 2, 2026

Comfort Inn & Suites New Port Richey Downtown District
See all 1,800 properties in Windsor Mill
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Windsor Mill

Florida’s gulf coast has some of the most beautiful sunsets. This picture was taken at Hudson Beach, luckily the weather has been beautiful all weekend and we were able to enjoy blue skies these weekend. #floridasunset #hudsonbeach #gulfofmexico #floridalifestyle #beachbum

Hudson Beach

Why not spend a carefree afternoon at Hudson Beach during your travels in Hudson? Amble around the area's parks or visit its shops.

Hudson Beach

Show Palace Dinner Theater

You can enjoy a show at Show Palace Dinner Theater during your stay in Hudson. Amble around this family-friendly area's waterfront and enjoy its top-notch restaurants.

Show Palace Dinner Theater

Beacon Woods Golf Course

Enjoy a round of golf in Hudson at Beacon Woods Golf Course. Amble around this family-friendly area's waterfront and enjoy its top-notch restaurants.

Beacon Woods Golf Course
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.