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It's time to fly. What's waiting for you in Windward Side?

Perhaps you’re searching cheap flights to Windward Side for a much-needed vacation or you simply have to roll in to see the relatives. Either way, we say rock that family reunion. Tell one too many stories at the hotel bar. Traveling for work? Crush it. If you lie back and relax without your cell phone, we won’t tell.

In the end you want to score a great deal and have a fantastic time, right? Flying is a small part of the whole adventure. We get that. Wherever you’re excited to go – or get away from – start this story with Hotwire’s cheap flights to Windward Side.

Not sure how to get the best price on plane tickets to Windward Side?

We know there are some airline aficionados out there. If you don’t know the industry like the back of your hand, don’t worry. You can make spending less look good with our booking tips.

Search certain days of the week for Windward Side flights

For better savings, consider departing on a Wednesday, Thursday or Saturday. Return on a Sunday, Tuesday or Wednesday. International deals are often available when departing Monday through Thursday.

Change up your days for cheaper weekend getaways

Jetting off on Thursday and returning on Sunday is generally less expensive than flying on Friday and returning on Monday.

Stay a Saturday night to play more

Spending the weekend at your destination will generally result in lower airfares. We’re all for that.

Consider alternate airports when searching Windward Side flights

Other nearby airports may offer different fares from your current search results. Clicking “Nearby Airports” after your initial search will give a list of the closest options.

See a fare that you like? Pounce!

Coordinate with your travel buddies before searching and you’ll be able to act quickly when it’s time to book. Airline ticket prices often change in minutes. We know you’re combing for the best prices but so is everyone else! If the deal is right, snag it and feel the sweet satisfaction of booking victory.

Fly during the off-peak season

Certain travel destinations have especially high volume during particular seasons. For example, Europe, Hawaii and Alaska are big hits in the summer. Florida, New Orleans and Southern California are the most popular in springtime. Winter is prime for Mexico and the Caribbean, as well as ski and snowboard destinations like the Colorado Rockies. In the autumn, Northern California, the Pacific Northwest and New England draw visitors. Flying during less popular periods can mean extra money in your wallet – yes, please!

Last Minute Hotel Deals in Windward Side

See all 10 Properties in Windward Side
Scout's Place Hotel

Scout's Place Hotel

Windwardside, Windward Side
    2.5 out of 5.0
     
     

    Situated near the airport, this hotel is 0.1 mi (0.1 km) from Dutch Museum of Saba and 2.9 mi (4.7 km) from Cove Bay Beach. Well's Bay Beach is 3.8 mi (6.1 km) ...

    Scout's Place HotelGet Rates

    El Momo Cottages

    El Momo Cottages

    Booby Hill, Windward Side
      2.5 out of 5.0
       
       

      Situated in Windward Side, this guesthouse is 0.3 mi (0.5 km) from Dutch Museum of Saba and within 6 mi (10 km) of Cove Bay Beach and Well's Bay Beach.

      El Momo CottagesGet Rates

      Selera Dunia Boutique Hotel

      Selera Dunia Boutique Hotel

      Wall Street, Windward Side
        3.0 out of 5.0
         
         

        Located in the heart of Windward Side, this bed & breakfast is 0.1 mi (0.2 km) from Dutch Museum of Saba and 2.9 mi (4.6 km) from Cove Bay Beach. Well's Bay ...

        Selera Dunia Boutique HotelGet Rates

        Queen's Garden Resort & Spa

        Queen's Garden Resort & Spa

        Troy Hill #1, The Bottom
          4.0 out of 5.0
           
           

          Situated near the bay, this spa resort is 2.1 mi (3.4 km) from Well's Bay Beach and 2.6 mi (4.1 km) from Dutch Museum of Saba. Cove Bay Beach is 5.3 mi (8.5 ...

          Queen's Garden Resort & Spa$221

          Queen's Garden Resort & Spa$221