Priceline’s “Name Your Own Price” Option. When using Priceline, you can enter the day you’d like to fly (or the day you’d like to stay at a hotel) and the price you’d like to spend. Priceline comes back with an offer of a flight or hotel, if there’s something available that meets your criteria. You find out the times of the flight and the star rating and general location of the hotel, but you won’t get to know the airline or specific hotel name until you book. Priceline claims that you can save 40% off published prices by using this method. Priceline also offers traditional booking services if you’d rather know exactly what you’re getting.

Why: Oaxaca de Juarez is one of the most beautiful destinations to travel to in Mexico. Colorful markets, charming architecture, cobblestone streets, fun festivals and delicious food are just part of the attraction. Stroll through Oaxaca’s main square, the Zócalo, and relax at a café, people watch and be entertained by dancers and singers in the evenings. Just a few minutes walk from the square is the Mercado Benito Juárez, where you’ll find embroidered goods and straw baskets. Continue walking the pedestrian street called Calle Macedonio, where you’ll find art galleries, cafes, shops and boutique hotels. Visit the Santo Domingo de Guzmán church and monastery that dates back to 1555. Don’t Miss the Museum of Oaxacan Cultures, where you can see the treasures found on Mont Alban — the skull covered in turquoise, carved jaguar bones, gold jewelry and ornaments for a nominal fee. Hungry? Stop by at the food market 20 de Noviembre, where you’ll find piles of fried grasshoppers (chapulines) and Oaxaca cheeses, tamales, meat-filled tortillas, tlayudas, chocolates, coffees and seven types of mole. Get a taste of local dishes at food stalls for under $5 or free Mezcal tastings at Mezcaloteca. It’s easy to find your way around this town, but if you prefer to join a guided walking tour, contact Enjoy Oaxaca — they offer several tours from city tours to day trips to see Mont Alban, Mitla Ruins, Hierve el Agua bubbling springs and the petrified waterfall, as well as cooking classes and many festival tours including the Day of the Dead. Where to Stay? There are several boutique hotels and quaint B&B’s in town. You can reserve a room at Parador San Miguel Oaxaca for as low as $86 per night.
Why: Following the devastation caused by Hurricane Maria, travelers might be reluctant to visit the territory of Puerto Rico. But, on a recent visit to the island to help rebuild some of the most popular tourist attractions, I was thrilled to see that Puerto Rico is thriving and really is open for business. If you don’t have a passport — or if you have one that’s closed to expiring or being filled — one of the best parts about visiting Puerto Rico is that no passport is needed for U.S. citizens. With plenty to see both in San Juan — from the charm and bright colors of Old San Juan to checking out where one of the most famous rums in the world is made at the Bacardi Factory ($15 for a historical tour) — and outside, such as a trip to El Yunque National Forest, you'll be kept busy. Flights to San Juan generally will run you less than $250 from the East Coast, making it a perfectly close and affordable getaway. While there are several affordable chain hotels, boutique hotels flourish — especially in Old San Juan. Check out The Gallery Inn or Decanter Hotel.
How cheap is it? Mexico’s huge, it’s right next door, and each of its 31 states has something to offer. You’re gonna take your best cheap shot? Aim for the mezcal and gastronomy capital: Oaxaca, in the south. In the capital, Oaxaca de Juarez, feast on the regional specialty: tlayudas, an oversized crisp tortilla heated on a grill, topped with lard, beans, veggies, salsa, and meat, (think combination of pizza and taco in the best possible way). It is to be eaten from a street vendor in the early hours after a night of drinking, and will set you back all of $4. For daytime noshing the markets are stacked with small vendors who serve sublime homemade moles that cost around $8 for a full portion including rice and soup. Lodging is cheaper than a movie ticket in the States; Hostel Don Nino alongside Parque Llano charges $14 per night, which includes Wi-Fi, a computer station, filtered water, clean showers, and breakfast. For free activities, there are plenty of colorful markets to stroll and art galleries to wander. The ruins of Monte Albán and the ancient Tule Tree cost around $20 for round-trip transportation plus entrance.
Why you should go: With some 6,000 islands, Greece is the Mediterranean’s powerhouse beach destination. While only 200-some are inhabited, an island-trotting adventure for everyone here, whether you’re looking for wildlife adventures, historic discoveries, or quite frankly, drinking ouzo and boogying. Athens makes an energetic springboard into the Aegean, with its own archaeological ruins, hipster cafés, and hangouts ranging from dynamic industrial to retro chic.

Why: Colombia isn’t usually thought of as a value destination, but due to the strong U.S. dollar, it has become one of the most compelling destinations in the world for those willing to venture off the beaten track. Travelers in the know are loving Barichara, one of the most beautiful small colonial villages in the Andes. Stay at Casa Barichara for under $200 a night and dine at El Carambolo, a quaint B&B rich with personality and the perfect fit for those searching for authentic, Colombian hospitality. Though not a typical tourist destination, Barichara is perfect for adventure travelers who enjoy activities like paragliding. A trip to Barichara can be paired with the town of Salamina, where travelers will find quirky architecture and a renowned coffee production, and/or the vibrant city of Medellin, which boasts music, museums, nightlife and friendly people.
The Big Island of Hawaii, or simply "the Big Island," is the largest island in the island chain. Due to its size, the Big Island's regions vary considerably. There are twelve distinct climate zones here, ranging from East Hawaii's tropical rain forests and the frozen slopes of Mauna Kea to Kau's arid desert in the south. The dramatic size of the largest Hawaiian Island creates a microcosm of environments and activities. Read more about the Big Island

When the lure of a tropical paradise beckons, the Caribbean is second to none. Immerse yourself in the laid-back island lifestyle, and enjoy wonderful all-inclusive resorts, fantastic beaches, marvelous diving and snorkeling, challenging golf and great shopping. Whether you are looking for the perfect atmosphere for a romantic getaway or an exciting adventure for the whole family, Caribbean vacations are fun for everyone.  
Why: While the devastating hurricanes of 2017 impacted just a portion of the Caribbean region, it damaged some of its more cruise-popular spots, like Tortola in the British Virgin Islands, St. Martin, Puerto Rico, St. Bart's, and the U.S.V.I.’s St. Thomas, St. Croix and St. John. While all are under significant rehab and rebuilding — and most are actually now open to cruise ships and tourists, this could be a perfect year to explore more exotic islands. That’s because lines like Windstar, which had, pre-hurricanes, planned to offer BVI-centric trips, relocated ships to other parts of the Caribbean. The winning trip? We love Wind Surf, one of the line’s sailing vessels, with its trip out of Barbados; ports include Martinique, Guadeloupe, and Montserrat — all islands that heretofore have often been bypassed by established cruise lines. And get this: There’s plenty of cruise capacity in this region, particularly when it comes to small ship sailings. In part, excess cabins are available because many skittish travelers canceled their bookings. As well, they can typically be more expensive (look for $300 per person, per day) than big ship vessels. But do the math: Windstar, and other small ship lines like Crystal, Regent Seven Seas, Seabourn, Azamara, Oceania and Viking Oceans, can actually be quite a good value when compared to land-based properties because they’re more price inclusive. Look for deals that include cocktails, gratuities and shore excursions not to mention pre- and post-cruise hotel stays and, in some cases, airfare to the ships’ port of embarkation.
The Big Island of Hawaii, or simply "the Big Island," is the largest island in the island chain. Due to its size, the Big Island's regions vary considerably. There are twelve distinct climate zones here, ranging from East Hawaii's tropical rain forests and the frozen slopes of Mauna Kea to Kau's arid desert in the south. The dramatic size of the largest Hawaiian Island creates a microcosm of environments and activities. Read more about the Big Island
Then, sit back and wait. Some (but not all) websites are set up to automatically send a coupon or other offer to people who almost make a purchase but change their minds at the last minute. Coupon values vary dramatically, so you have to know what will be enough to sway you. You might only get a token discount, but it’s not unreasonable to see 10%, 15%, or even 25% off.
Hawaii.com is proud to offer Hawaii vacation packages, most with rates under $1,000. These vacation packages include air, car rental, and hotel stay for six to eight days on one or more of the Hawaiian Islands. Visiting different islands, or "island-hopping" as we call it, is highly recommended because each Hawaiian Island has its own distinct "personality." We invite you to peruse the travel packages on this page to see which one might fit your needs.
*Savings based on all holiday package bookings with Flight + Hotel on Orbitz.com from July 2017 to December 2017, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.
Why: For an affordable and sun-soaked vacation, southern Portugal’s Algarve region should be hot on your radar. The city of Albufeira boasts a beautiful climate, fabulous beaches, inexpensive apartment-style hotels and a central location within the Algarve. There are over 100 different restaurants, bars and nightclubs, and Albufeira even has a charming Old Town with traditional Portuguese streets and plazas within the city center. The prices for both food and wine are extremely reasonable; be sure to sample the wines of Portugal. While summer remains the busiest and most popular time to visit, I love visiting in late spring — the weather is pleasant and sunny, there are fewer tourists and hotel rates are very affordable. Albufeira also offers easy access to nearby towns such as Loulé, with its famous market and an authentic slice of Portuguese culture. Rent a car to see the church of São Lourenço in Almancil, famous for its exquisite blue tile. Head north of Lagos to see Ponta da Piedade, with its towering red rock formations against the sea. Play a round of golf in one of the many beautiful courses in the Algarve. The place to stay: the Epic Sana Algarve overlooking Praia da Falésia, where you can bask in the sun at one of its five outdoor pools and indulge at the beautiful spa.
Vacation rentals are becoming increasingly popular. Sites such as Airbnb, VRBO, and HomeAway permit homeowners to put their own properties up for rent whenever they won’t be using it. This is a good way to experience life as a local, because you’ll be staying in a residential area instead of one that caters to tourists. While some properties are tiny, cheap, and perfectly suitable for one person, vacation rentals are also a great way for a large group to get away together in a big house without having to pay for individual hotel rooms.
Vacation rental prices vary as much as hotel prices. Case in point: A search of one-bedroom vacation rentals in Manhattan during September results in options ranging from $60 per night to $2,800 per night. Vacation rentals are ideal for longer stays (seven nights or more). Many vacation rentals require minimum stays, so if you’re hoping for a weekend getaway, you may have to look elsewhere.
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