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Pinellas Trail Vacation Packages

Pinellas Trail Flight + Hotel Packages

Holiday Inn Express & Suites St. Petersburg - Madeira Beach, an IHG Hotel

Holiday Inn Express & Suites St. Petersburg - Madeira Beach, an IHG Hotel

2.5 out of 5
Price was $817, price is now $665 per person
per person
Jan 14 - Jan 21
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
Stay at this business-friendly hotel in St. Petersburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms and the overall value in our reviews. Popular attractions John's Pass Village & Boardwalk and War Veteran Memorial Park are located nearby. Discover genuine guest reviews for Holiday Inn Express & Suites St. Petersburg - Madeira Beach, an IHG Hotel, in South Pinellas Community Council neighborhood, along with the latest prices and availability – book now.
Beach House Suites by the Don CeSar

Beach House Suites by the Don CeSar

3 out of 5
Save 100% on your flightPrice was $1,120, price is now $819 per person
per person
Jan 9 - Jan 14
Roundtrip flight included
Grand Rapids (GRR) to Tampa (TPA)
Stay at this 3-star beach aparthotel in St. Pete Beach. Enjoy a beach locale, WiFi, and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and Dolphin Landings Charter Boat Center are located nearby. Discover genuine guest reviews for Beach House Suites by the Don CeSar, in Belle Vista neighborhood, along with the latest prices and availability – book now.
Home2 Suites by Hilton Tampa Downtown Channel District

Home2 Suites by Hilton Tampa Downtown Channel District

3 out of 5
Save 100% on your flightPrice was $938, price is now $708 per person
per person
Jan 10 - Jan 14
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this 3-star business-friendly hotel in Tampa. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Port of Tampa and Busch Gardens Tampa Bay are located nearby. Discover genuine guest reviews for Home2 Suites by Hilton Tampa Downtown Channel District, in Downtown Tampa neighborhood, along with the latest prices and availability – book now.
Innisbrook, A Salamander Golf & Spa Resort

Innisbrook, A Salamander Golf & Spa Resort

3.5 out of 5
Save 100% on your flightPrice was $1,046, price is now $799 per person
per person
Jan 9 - Jan 14
Roundtrip flight included
Grand Rapids (GRR) to Tampa (TPA)
Stay at this 3.5-star spa resort in Palm Harbor. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Leepa-Rattner Museum of Art and Wall Springs Park are located nearby. Discover genuine guest reviews for Innisbrook, A Salamander Golf & Spa Resort along with the latest prices and availability – book now.
Silver Sands

Silver Sands

3.5 out of 5
Save 100% on your flightPrice was $811, price is now $624 per person
per person
Jan 19 - Jan 23
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Stay at this 3.5-star condo in Treasure Island. Enjoy free WiFi, free parking, and a terrace. Our guests praise the pool and the family amenities in our reviews. Popular attractions John's Pass Village & Boardwalk and Hubbards Marina are located nearby. Discover genuine guest reviews for Silver Sands along with the latest prices and availability – book now.
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flightPrice was $844, price is now $665 per person
per person
Jan 26 - Jan 30
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this 4-star beach resort in St. Pete Beach. Enjoy free WiFi, free parking, and 5 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions John's Pass Village & Boardwalk and Splash Island Water Park are located nearby. Discover genuine guest reviews for TradeWinds Island Grand along with the latest prices and availability – book now.
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flightPrice was $675, price is now $542 per person
per person
Jan 26 - Jan 30
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this 4-star beach hotel in St. Pete Beach. Enjoy free WiFi, a marina, and 3 bars/lounges. Our guests praise the pool and the restaurant in our reviews. Popular attractions John's Pass Village & Boardwalk and Dolphin Landings Charter Boat Center are located nearby. Discover genuine guest reviews for The Hotel Zamora along with the latest prices and availability – book now.
Provident Oceana Beachfront Suites

Provident Oceana Beachfront Suites

3.5 out of 5
Save 100% on your flightPrice was $860, price is now $693 per person
per person
Jan 19 - Jan 23
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Stay at this 3.5-star beach condo in Treasure Island. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the family amenities in our reviews. Popular attractions John's Pass Village & Boardwalk and Treasure Island Golf, Tennis & Recreation Center are located nearby. Discover genuine guest reviews for Provident Oceana Beachfront Suites along with the latest prices and availability – book now.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flightPrice was $1,604, price is now $1,294 per person
per person
Feb 1 - Feb 5
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
Stay at this 3-star beach hotel in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Aluna Wellness Center & Spa and Anna Maria Sound are located nearby. Discover genuine guest reviews for Cedar Cove Resort and Cottages along with the latest prices and availability – book now.
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flightPrice was $1,381, price is now $1,115 per person
per person
Jan 26 - Jan 30
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this 4-star beach hotel in St. Pete Beach. Enjoy 2 outdoor pools, 2 restaurants, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and Dolphin Landings Charter Boat Center are located nearby. Discover genuine guest reviews for The Don CeSar along with the latest prices and availability – book now.
Shephard's Beach Resort

Shephard's Beach Resort

3.5 out of 5
Save 100% on your flightPrice was $898, price is now $730 per person
per person
Jan 24 - Jan 29
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this 3.5-star beach hotel in Clearwater Beach. Enjoy free WiFi, free valet parking, and 3 restaurants. Our guests praise the pool and the restaurant in our reviews. Popular attractions Captain Blighs Landing and Sand Key Park are located nearby. Discover genuine guest reviews for Shephard's Beach Resort along with the latest prices and availability – book now.
Comfort Suites Clearwater - Dunedin

Comfort Suites Clearwater - Dunedin

2.5 out of 5
Price was $536, price is now $439 per person
per person
Jan 19 - Jan 23
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Stay at this business-friendly hotel in Clearwater. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Florida Auto Exchange Stadium - Dunedin Blue Jays and Dunedin Stadium are located nearby. Discover genuine guest reviews for Comfort Suites Clearwater - Dunedin along with the latest prices and availability – book now.

3-4 Night Vacations in Pinellas Trail

Innisbrook, A Salamander Golf & Spa Resort

Innisbrook, A Salamander Golf & Spa Resort

3.5 out of 5
Save 100% on your flightPrice was $786, price is now $589 per person
per person
Jan 10 - Jan 14
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Home2 Suites by Hilton Tampa Downtown Channel District

Home2 Suites by Hilton Tampa Downtown Channel District

3 out of 5
Downtown Tampa
Save 100% on your flightPrice was $938, price is now $708 per person
per person
Jan 10 - Jan 14
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Beach House Suites by the Don CeSar

Beach House Suites by the Don CeSar

3 out of 5
Belle Vista
Save 100% on your flightPrice was $687, price is now $526 per person
per person
Jan 10 - Jan 14
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flightPrice was $579, price is now $453 per person
per person
Jan 27 - Jan 30
Roundtrip flight included
Boston (BOS) to Tampa (TPA)

5-7 Night Vacations in Pinellas Trail

Beach House Suites by the Don CeSar

Beach House Suites by the Don CeSar

3 out of 5
Belle Vista
Save 100% on your flightPrice was $1,120, price is now $819 per person
per person
Jan 9 - Jan 14
Roundtrip flight included
Grand Rapids (GRR) to Tampa (TPA)
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flightPrice was $1,690, price is now $1,263 per person
per person
Jan 9 - Jan 14
Roundtrip flight included
Grand Rapids (GRR) to Tampa (TPA)
Home2 Suites by Hilton Tampa Downtown Channel District

Home2 Suites by Hilton Tampa Downtown Channel District

3 out of 5
Downtown Tampa
Save 100% on your flightPrice was $1,033, price is now $774 per person
per person
Jan 9 - Jan 14
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Edge Hotel Clearwater Beach

Edge Hotel Clearwater Beach

3.5 out of 5
Save 100% on your flightPrice was $1,203, price is now $907 per person
per person
Jan 24 - Jan 29
Roundtrip flight included
Boston (BOS) to Tampa (TPA)

Pinellas Trail Last Minute Hotel Deals

Grand Shores West
Grand Shores West
3.5 out of 5
17350 Gulf Blvd, North Redington Beach, FL, 33708
Stay at this 3.5-star hotel in North Redington Beach. Enjoy free WiFi, free parking, and a private beach. Popular attractions John's Pass Village & Boardwalk ...
Grand Shores West
Holiday Inn Hotel & Suites Clearwater Beach S-Harbourside, an IHG Hotel
Holiday Inn Hotel & Suites Clearwater Beach S-Harbourside, an IHG Hotel
3 out of 5
401 2nd St, Indian Rocks Beach, FL, 33785
Stay at this 3-star family-friendly hotel in Indian Rocks Beach. Enjoy free WiFi, a marina, and 3 bars/lounges. Our guests praise the helpful staff and the overall ...
Holiday Inn Hotel & Suites Clearwater Beach S-Harbourside, an IHG Hotel
Legacy Vacation Resorts - Indian Shores
Legacy Vacation Resorts - Indian Shores
3 out of 5
19607 Gulf Blvd, Indian Shores, FL, 33785
Stay at this 3-star beach aparthotel in Indian Shores. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean ...
Legacy Vacation Resorts - Indian Shores
Barefoot Beach Resort
Barefoot Beach Resort
3.5 out of 5
19417 Gulf Blvd., Indian Shores, FL, 33785
Stay at this 3.5-star aparthotel in Indian Shores. Enjoy free WiFi, free parking, and a terrace. Our guests praise the pool and the spacious rooms in our reviews. ...
Barefoot Beach Resort
Sandalwood Beach Resort
Sandalwood Beach Resort
3 out of 5
17100 GULF BOULEVARD, North Redington Beach, FL, 33708
Stay at this 3-star beach hotel in North Redington Beach. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the comfy ...
Sandalwood Beach Resort
Holiday Inn Express & Suites St. Petersburg - Madeira Beach, an IHG Hotel
Holiday Inn Express & Suites St. Petersburg - Madeira Beach, an IHG Hotel
2.5 out of 5
4816 100th Way North, St. Petersburg, FL, 33708
Stay at this business-friendly hotel in St. Petersburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms and the overall ...
Holiday Inn Express & Suites St. Petersburg - Madeira Beach, an IHG Hotel
Belleair Beach Resort Motel
Belleair Beach Resort Motel
3 out of 5
2040 Gulf Blvd, Belleair Beach, FL, 33786
Stay at this 3-star beach hotel in Belleair Beach. Enjoy free WiFi, free parking, and a private beach. Our guests praise the pool and the helpful staff in our ...
Belleair Beach Resort Motel
Clearwater Beach Hotel
Clearwater Beach Hotel
2 out of 5
504 S. Gulfview Blvd., Clearwater Beach, FL, 33767
Stay at this business-friendly hotel in Clearwater Beach. Enjoy free WiFi, onsite parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
Clearwater Beach Hotel
See all 9,793 properties in Pinellas Trail
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.

Book the perfect getaway to Pinellas Trail

With Hotwire, booking your next trip to Walsingham is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Pinellas Trail while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Pinellas Trail flight and hotel package for as low as $439.

Living it up in Walsingham means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Pinellas Trail, Walsingham vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Pinellas Trail for some of the best accommodations and flight deals.

FAQs about cheap Pinellas Trail packages:

How to get cheap vacation deals to Pinellas Trail?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $91.

How much are Pinellas Trail packages?

Vacation packages to Pinellas Trail vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $439.

How to find cheap car rentals near Pinellas Trail?

Hotwire partners with some of the most reliable car rental companies in Walsingham to bring you the best car rental deals in Pinellas Trail for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Pinellas Trail now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Pinellas Trail right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

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