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9 Ways to Find the Most Interesting Place to Stay in a City

By:  Colleen Oakley Aug 5, 2014
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Clear Blue Ocean
Jan Schneider

Vacation relaxation to the extreme in Moorea, French Polynesia

Sure, that chain hotel you always book when you’re going on vacation has all the necessities, and there certainly is something to be said for the security in knowing what you will be getting. But if you want to be more adventurous for your next vacation consider looking for a one-of-a-kind hot spot to hole up in for a night or week. Just click on one of these websites or download the related app and start searching — a fun, hip room rental (or house) is just a finger tap away.

1. AirBnB

Best for: Unusual rentals and great deals
Want to experience the heart of the city you’re visiting? Skip the hotel and stay at a condo or house in the heart of it all. As you are probably already aware, AirBnB connects travelers with people who have places to rent out at every price point in more than 34,000 cities and 190 countries. Need a room for one or two? You can find that. Need a villa for 16? You can find that, too. And each listing has user reviews to give you a better idea of what you’re getting.
AirBnB: Website, iPhone app, Android App

2. Tripping

Best for: One-stop shoppers
If you like using Kayak to book flights because it allows you to compare prices at several travel sites at once, you’ll love using the similar features on Tripping to book vacation homes. You’re sure to find one-of-a-kind digs among their 1.5 million rentals across 50,000 cities worldwide, thanks to their compilation of top rental sites including HomeAway, FlipKey, Housetrip, Interhome, Roomorama, Booking.com and more.
Tripping: Website

3. Jetsetter

Best for: Luxury boutique hotels
This (free!) membership-only magazine/vacation-planning tool, which is part of tripadvisor, highlights the cream of the crop when it comes to luxurious accommodations across the globe. If 5-star service mixed with exotic scenery is what you’re looking for, look no farther.
Jetsetter: Website, iPhone app, iPad app

4. Couchsurfing

Best for: College kids on a budget
When all you need is a free place to rest your weary head (we’re looking at you, students backpacking across Europe on summer break), check out Couchsurfing, a website that connects you with locals who have a couch, futon or room (if you’re lucky) in 100,000 cities where you can catch some ZZZZs — and a once-in-a-lifetime experience.
Couchsurfing: Website, iPhone app, Android app

5. Vacationist

Best for: Deals on high-end resorts
Do you crave luxury but don't have the credit limit to get you there? Head to Vacationist, a members-only website created by the folks who brought us Luxury Link. Here, you’ll find up to 60% off stays at stunning, off-the-beaten-path luxury resorts that cater to your every desire in paradise.
Vacationist: Website

6. VRBO

Best for: One-of-a-kind vacation homes
Imagine waking up at a farmhouse in Tuscany, with the sun kissing the rolling hills of grapevines just outside your window. That dream can be a reality with VRBO (Vacation Rentals By Owners), a HomeAway property. From farmhouses to condos to cottages, you can find a unique house to call your very own on vacation, rent it directly from the owner and — better still — pay as little as half the price of a hotel room.
VRBO: Website, iPhone app, Android app

7. Dwellable Vacation Rentals

Best for: Domestic travelers
Need a staycation? Use Dwellable’s search-by-map feature to find a slice of heaven in your own backyard. Or catch the nearest train, plane or bus to any of their 80,000 beach houses, condos, cottages and summer homes in the United States as well as rentals in Europe, Mexico and the Caribbean. The app has more than a million photos in its system so you can browse to your heart’s content — or until you find the perfect match for your next trip.
Dwellable Vacation Rentals: Website, iPhone app, iPad app

8. Bid Vacation Rental

Best for: Negotiators
With thousands of destinations all over the world, Bid Vacation Rental (BVR) is sure to have the vacation rental of your dreams. The bonus? You set the price. Users can tell owners what they’re willing to pay for a specific home and wait and see if the bid is accepted.
Bid Vacation Rental: Website, iPhone app, iPad app

9. BeWelcome

Best for: A real local experience
When you’re a stranger in a new town — or a new country — it helps to have a friend to show you the ropes. BeWelcome.org can introduce you to that friend. The non-profit organization connects like-minded travel enthusiasts. Be a guide for a foreigner in your city or find a guide for your upcoming trip. The best part? You’ll get to be a guest in their home and get a true sense of their culture — for free.
Bewelcome: Website