Shady Hills Vacation Packages

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Your Shady Hills Vacation

Organizing your next break is a cinch with a Shady Hills vacation package. The neighborhood of Heritage Pines, which is good for golfing, makes a terrific base to discover the delights of this unique city. If seeing the sights is a must during your trip to Shady Hills, make sure you find your way to leading attractions like Nature Coast Botanical Gardens and Strong Tower Vineyard. Whoever you're taking time off with and whether your budget is big or small, your dream Shady Hills vacation is just a few clicks away with Expedia.

Top Holiday Package Deals in Shady Hills

Price found within the past 48 hours. Click for updated prices.
The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Central Sarasota
Price was CA $1,173, price is now CA $735 per person
CA $735
per person
May 14 - May 19
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
8.2/10 Very Good! (515 reviews)
All of those and the wonderful, helpful staff

Reviewed on Feb 19, 2026

Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was CA $1,446, price is now CA $793 per person
CA $793
per person
Apr 1 - Apr 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
8.6/10 Excellent! (60 reviews)
Staff was very responsive although we did not meet in person. Very old but clean Florida Motel which is all we needed for the night and the price was good!

Reviewed on Feb 26, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $2,452, price is now CA $1,446 per person
CA $1,446
per person
Apr 18 - Apr 25
found 3 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.6/10 Exceptional! (712 reviews)
Room and view was outstanding. The guest services were very friendly.

Reviewed on Feb 27, 2026

Family Home Tampa

Family Home Tampa

2 out of 5
Forest Hills
Price was CA $2,273, price is now CA $1,411 per person
CA $1,411
per person
May 22 - May 29
found 1 hour ago
Roundtrip non-stop flight included
Hamilton (YHM) to Tampa (TPA)
7.6/10 Good! (4 reviews)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was CA $1,715, price is now CA $1,083 per person
CA $1,083
per person
May 14 - May 19
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.2/10 Wonderful! (1,097 reviews)
Overall it was a good

Reviewed on Feb 17, 2026

Where to stay in Shady Hills

Find the best Shady Hills areas and neighborhoods for the activities you enjoy most. Learn more about Shady Hills
Beautiful spring water, perfect for kayaking and paddleboarding!

Weeki Wachee

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

Unique features of Weeki Wachee include the shopping and restaurants. Make a stop by Weeki Wachee Springs or Weeki Wachee Springs State Park while you're exploring the area.

Find hotels in Weeki Wachee

Shady Hills Hotel Deals

Days Inn by Wyndham Brooksville/Dade City

Days Inn by Wyndham Brooksville/Dade City

2 out of 5
6320 Windmere Rd Brooksville FL
Fully refundableReserve now, pay when you stay
The price is CA $103 per night from Mar 5 to Mar 6
CA $103
CA $115 total
Mar 5 - Mar 6
includes taxes & fees
7.6/10 Good! (46 reviews)
The rooms here are always spotless and the staff very accommodating.

Reviewed on Mar 1, 2026

Days Inn by Wyndham Brooksville/Dade City
SPOT X Hotel Tampa - Wesley Chapel by The Red Collection

SPOT X Hotel Tampa - Wesley Chapel by The Red Collection

3 out of 5
5703 Oakley Blvd Wesley Chapel FL
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Mar 2 to Mar 3
CA $161
CA $180 total
Mar 2 - Mar 3
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
The whole facility was clean. The furniture needs to be updated but I wasn’t there for luxury. Beds were hard too. Overall stay was great and food was good!!

Reviewed on Feb 25, 2026

SPOT X Hotel Tampa - Wesley Chapel by The Red Collection
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
5700 Saddlebrook Way Wesley Chapel FL
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Mar 23 to Mar 24
CA $174
CA $236 total
Mar 23 - Mar 24
includes taxes & fees
7.4/10 Good! (26 reviews)
Did not like the fact that you had to valet our car and shuttled to our room. The rooms were kind of dates.

Reviewed on Feb 28, 2026

Saddlebrook Resort
See all 2,348 properties in Shady Hills
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
Family Vacations
Family Vacations

Frequently asked questions

How much does a Shady Hills vacation package cost?
The most affordable Shady Hills vacation package is CA $735, so your dream escape can become a reality — without the high price tag. Combine flights, hotels, car rentals and more to custom build a package that matches your traveling style.
How do I get a cheap travel package to Shady Hills?
One of the simplest ways to save money (and time) is to bundle your bookings with Expedia. Flights, rental cars, hotels and activities — we've got them all covered. Select the combination that best fits you and see your savings stack up. Of course, a travel package is never a one-size-fits-all. That's why we offer more than 550 air carriers and 1,000,000 hotel options throughout the world, which lets you customize your Shady Hills vacation.
Where should I stay in Shady Hills?
A vacation in Shady Hills wouldn't be complete without visiting Strong Tower Vineyard, Bayfront Health Spring Hill and Adventure Coast Fun Park. Stay near these top sights and make sightseeing simple.
What are the top hotels in Shady Hills?
Get your vacation off to a great start by booking a room at Unique Vacation Rv Living, Usd70 Per Nights. It's one of most popular properties in Shady Hills. Another welcoming option is Little Taste Of Country Living.
How far in advance should I book my Shady Hills vacation?
It can be difficult to know exactly when is the ideal time to book your Shady Hills trip. But typically the earlier you book, the lower the prices. In some cases, you can reserve your flights and hotels up to 12 months before departure. If you're thinking of a last-minute getaway, no need to fret! There are fantastic deals featured on Expedia every day.
What does an Expedia Shady Hills travel package include?
Expedia has everything you need to lock in Shady Hills trip, but what your package looks like is up to you. Pick from a combination of flights, hotels and rental cars. Looking for a few activities to keep you on the move? Once you've made your booking, you can add them on too. No matter your style or budget, there's a package deal to suit your needs.
What should I know before booking a Shady Hills travel package?
So many places to venture to, so many things to experience. With a package, you'll be able to cross more of them off your list. Bundle your flights, rental cars and hotels and enjoy big savings.
Can I choose my airline with a Shady Hills Expedia vacation package?
You can, and with more than 550 airlines to pick from worldwide, it's all about choice. Look through the available options and find out which airline best fits your needs and budget.
If I'm not able to travel, can I cancel my Shady Hills vacation package?
Yes, you can cancel your Shady Hills booking if your travel plans have been upended. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. You may be able to change or cancel your booking free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

Discover the most popular places to visit in Shady Hills

Beautiful spring water, perfect for kayaking and paddleboarding!

Weeki Wachee Springs

Explore the great outdoors at Weeki Wachee Springs, a lovely green space in Spring Hill. Wander the riverfront in this family-friendly area.

Weeki Wachee Springs

Bayport Park Boat Ramp

Explore the great outdoors at Bayport Park Boat Ramp, a lovely green space in Bayport. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.

Bayport Park Boat Ramp

Silverthorn Country Club

Enjoy a round of golf in Spring Hill at Silverthorn Country Club. While in this family-friendly area, you can savor the top-notch restaurants.

Silverthorn Country Club

Things to do

Clear Kayak Tours in Weeki Wachee

Clear Kayak Tours in Weeki Wachee

CA $108
per adult
100% of travellers recommend
Clear Kayak Tours in Weeki Wachee
See all activities in Spring Hill
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.