Hill 'n Dale Vacation Packages for 2026

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Hill 'n Dale Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

$567
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, a rooftop terrace, and a 24-hour fitness center. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
New hotel 1 yr old Perfect condition

Reviewed on Aug 27, 2026

CW Resort

CW Resort

Save 100% on your flight
$627
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

Save 100% on your flight
$828
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this beach hotel in Clearwater Beach. Enjoy a full-service spa, 3 restaurants, and a beach locale. Our guests praise the breakfast and the pool in our reviews. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
Captiva Beach Resort

Captiva Beach Resort

South Village
Save 100% on your flight
$614
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Our stay was perfect! The room was beautiful with good AC and very clean. Housekeeping went above and beyond. Very close to the beach and the free trolley to the village. It was very quiet and we enjoyed great sleeps. This was our second time here and I can only hope we get to come back again.

Reviewed on Aug 27, 2026

Residence Inn By Marriott Tampa Downtown

Residence Inn By Marriott Tampa Downtown

Downtown Tampa
$582
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this business-friendly hotel in Tampa. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Tampa Riverwalk and Benchmark International Arena are located nearby.
This is my second time staying at this location. I like the convenience of being close to everything downtown. There was construction this time around so a little more hectic and loud. I do not love the parking situation and that I have to go across the street, use a parking garage and if it is a busy time you may not find a spot since you can only park in designated areas. Would like to see the breakfast be a little more upgraded. Overall I give it a good rating because it is a good hotel choice.

Reviewed on Aug 26, 2026

Crystal Palms Beach Resort

Crystal Palms Beach Resort

Sunshine Beach
Save 100% on your flight
$611
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Stay at this aparthotel in Treasure Island. Enjoy a 24-hour front desk, dry cleaning or laundry services, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
Overall Bad.

Reviewed on Aug 27, 2026

Don't see what you're looking for?
See all available trips from Columbus to Hill 'n Dale
View all trips

Top Hotel Deals

Motel 6 Spring Hill, FL - Weeki Wachee

Motel 6 Spring Hill, FL - Weeki Wachee

6172 Commercial Way Spring Hill FL
27.26 km from Hill 'n Dale
Stay at this motel in Spring Hill. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Days Inn by Wyndham Brooksville/Dade City

Days Inn by Wyndham Brooksville/Dade City

6320 Windmere Rd Brooksville FL
5.85 km from Hill 'n Dale
Book a stay at this golf motel in Brooksville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
Microtel Inn & Suites by Wyndham Spring Hill/Weeki Wachee

Microtel Inn & Suites by Wyndham Spring Hill/Weeki Wachee

4881 Commercial Way Spring Hill FL
29.17 km from Hill 'n Dale
Book a stay at this business-friendly hotel in Spring Hill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Holiday Inn Express Hotel & Suites Brooksville West by IHG

Holiday Inn Express Hotel & Suites Brooksville West by IHG

14112 Cortez Blvd Spring Hill FL
19.74 km from Hill 'n Dale
Book a stay at this business-friendly hotel in Spring Hill. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
Hampton Inn Dade City - Zephyrhills

Hampton Inn Dade City - Zephyrhills

13215 Us Highway 301 Dade City FL
21.87 km from Hill 'n Dale
Stay at this hotel in Dade City. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions The ...
Microtel Inn & Suites by Wyndham Zephyrhills

Microtel Inn & Suites by Wyndham Zephyrhills

7839 Gall Blvd Zephyrhills FL
29.83 km from Hill 'n Dale
Book a stay at this business-friendly hotel in Zephyrhills. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Microtel Inn & Suites by Wyndham Brooksville

Microtel Inn & Suites by Wyndham Brooksville

6298 Nature Coast Blvd Brooksville FL
5.35 km from Hill 'n Dale
Book a stay at this business-friendly hotel in Brooksville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Fairfield Inn & Suites by Marriott Brooksville Suncoast Parkway

Fairfield Inn & Suites by Marriott Brooksville Suncoast Parkway

14082 Cortez Blvd Spring Hill FL
19.75 km from Hill 'n Dale
Book a stay at this business-friendly hotel in Spring Hill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Quality Inn & Suites Brooksville I-75/Dade City

Quality Inn & Suites Brooksville I-75/Dade City

30307 Cortez Blvd Brooksville FL
5.31 km from Hill 'n Dale
Book a stay at this business-friendly hotel in Brooksville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Microtel Inn & Suites by Wyndham Bushnell

Microtel Inn & Suites by Wyndham Bushnell

2612 West County Road 48 Bushnell FL
21.51 km from Hill 'n Dale
Book a stay at this business-friendly hotel in Bushnell. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Holiday Inn Express Hotel & Suites Brooksville by IHG

Holiday Inn Express Hotel & Suites Brooksville by IHG

30455 Cortez Blvd Brooksville FL
5.66 km from Hill 'n Dale
Stay at this hotel in Brooksville. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Quality Inn Weeki Wachee - Spring Hill

Quality Inn Weeki Wachee - Spring Hill

9373 Cortez Blvd Brooksville FL
26.67 km from Hill 'n Dale
Book a stay at this business-friendly hotel in Brooksville. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Our guests praise the helpful staff in ...
Hampton Inn Brooksville Dade

Hampton Inn Brooksville Dade

30301 Cortez Blvd Brooksville FL
5.18 km from Hill 'n Dale
Book a stay at this business-friendly hotel in Brooksville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Don't see what you're looking for?
See all available properties in Hill 'n Dale
View all properties
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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Delta
Southwest Airlines
Sun Country Airlines
Breeze Airways