Windsor Mill Vacations from $308

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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.
Clearwater Suites

Clearwater Suites

2.5 out of 5
Save 100% on your flight
Price was $507, price is now $308 per person
$308
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (19 reviews)
Super convenient, clean, and right across the street from the beach. Staff was very friendly

Reviewed on Aug 25, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $675, price is now $361 per person
$361
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,006 reviews)
Location and staff were excellent. Will definitely stay here again.

Reviewed on Aug 30, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,035, price is now $597 per person
$597
per person
Nov 15 - Nov 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (609 reviews)
Loved the condo, the access to the beach, in unit laundry, and convenience of the location. Gym and beach bar on site, would definitely come back!

Reviewed on Aug 30, 2025

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,697, price is now $1,026 per person
$1,026
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,061 reviews)
It was very noisy. Inside, toilets, doors & cleaning staff. Outside, basic traffic, green car every night

Reviewed on Aug 29, 2025

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $860, price is now $528 per person
$528
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (4,285 reviews)
Affordable boutique hotel

Reviewed on Aug 30, 2025

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
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Bayonet Point

1 out of top 10 points of interest in this area
3.5/5(171 area reviews)

Shopping, waterfront views, and restaurants highlight some of the notable features of Bayonet Point. Make a stop by Beacon Woods Golf Course while you're exploring.

Find hotels in Bayonet Point

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
$60 nightly
The price is $67 total per night from Sep 7 to Sep 8
$67 total
Sep 7 - Sep 8
Total with taxes and fees
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
$89 nightly
The price is $101 total per night from Sep 7 to Sep 8
$101 total
Sep 7 - Sep 8
Total with taxes and fees
Quality Inn & Suites Tarpon Springs South
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
36750 Us Highway 19 N, Palm Harbor, FL
$199 nightly
The price is $225 total per night from Sep 1 to Sep 2
$225 total
Sep 1 - Sep 2
Total with taxes and fees
Innisbrook Resort
See all 1,665 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

Hudson Beach

4/5(32 reviews)

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.