The reasons why an Airbnb will make a lasting positive impression sound simple on paper, but it's pretty hard to pull off in reality: It has to be situated in an awesome location that gives you the essence of a destination, and every part of your stay needs to feel effortless and seamless. Ahead the R29 team has brought you the highlight reel of our best experiences from the travel powerhouse and why they are the best Airbnbs in our book. From a romantic Airbnb in the Catskills to a condo in Bangkok, you will want to bookmark these tried-and-tested stays for your next getaway.
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Tailor Loft
Location: Knoxville, Tennessee
Price Per Night: $362
Sleeps: 4
"Knoxville might not exactly be on your bucket list, but hear me out: The Great Smoky Mountains National Park is the most visited national park in the country, so while you are there, why not spend a night or two exploring Knoxville? I went recently for a concert at one of the two historic theaters South Gay Street, the heart of the city's downtown and a very walkable place for exploring restaurants, galleries, and bookshops. After the show, it was a quick walk back to our Airbnb in a historic building (the gold leaf lettering on the living room window is from when it was a tailor's shop decades ago). It also had two full-sized bedrooms plus a common area for relaxing and having a cup of coffee the next morning. You can watch the bustling foot traffic on South Gay and stroll outside to enjoy any number of great restaurants." —Marshall Bright, Affiliate Editor
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Chateau Třebešice
Location: Třebešice, Czechia
Price Per Night: $183
Sleeps: 2
Why It's Special: "My friend and I happened upon this listing of a castle when we were exploring Prague. It almost felt like a fluke at first: spending a night in a historic castle can’t possibly only cost us less than $200, right? I’m very happy to confirm that our stay at this Airbnb was very much as magical as the photos look. The castle itself dates back to the Middle Ages and is in phenomenal condition, thanks to careful restoration by the owner, an Italian architect. We did nothing but roam around the beautiful gardens and art gallery taking photos, and rummage through all the fun knick-knacks and books in our library room." —Venus Wong, Senior Travel Writer
Book Chateau Třebešice
Berkshires Lakeside Cabin
Location: Becket, Massachusetts
Price Per Night: $385
Sleeps: 7
Why It's Special: "I’m hesitant to share this Airbnb, simply because it was one of the most relaxing vacations I’ve ever been on. Set on a gorgeous, no-motor-boat lake in the Berkshires, this recently renovated house slept my family of five quite comfortably and was the perfect place for a work-from-home vacation. We spent two weeks at the lake, one working, one not, and were able to start and end every day with a float on the lake. The house has its own dock, water toys, and kayaks, and the lake, though small, was endlessly fun to explore and deeply relaxing to float on. We even saw a family of beavers one night. Plus, it’s only two hours from New York City, making it the perfect getaway for a week or a weekend." —Hannah Rimm, Senior Life Editor
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Mid-Century Getaway
Location: Palm Springs, California
Price Per Night: $475
Sleeps: 6
Why It's Special: "I've stayed in several rentals in Palm Springs, and this was by far my favorite — and it's reasonably priced! Not only is it a pristine mid-century home, full of eclectic decor and Golden Girls-themed art and memorabilia, but also it's primed for relaxation. Beyond the requisite pool and sun chairs, the grounds include a dining table for eight, fire pit with comfy chairs, hammock, and reading nook. Inside, the home has very strong AC (a must for the desert) and a meditation area, and the owner even provides his own private-label white wine, paid via Venmo for the times when you just can't pry yourself away from the pool. Add that to its location — near all the Palm Springs hot spots without being in the fray — and it's dang near perfect." — Kelsea Stahler, Content Director
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Canal View Apartment
Location: Amsterdam, Netherlands
Price Per Night: $184
Sleeps: 2
Why It's Special: "Looking at photos of this Airbnb brings back so many fond memories for me: my best friend happened to be flying into Amsterdam for work, and I had just received some amazing personal news, so we decided to meet up in Amsterdam to celebrate. We wanted to stay somewhere cute with a balcony overlooking the canal, and this is exactly the place. We spent all our time exploring The Nine Streets shopping district on foot, queuing up for stroopwafels, and looking for treasures at the nearby Albert Cuyp Market." —Venus Wong, Senior Travel Writer
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Casa Vo
Location: Brisas de Zicatela, Oaxaca, Mexico
Price Per Night: $320
Sleeps: 4
Why It's Special: "Casa Vo is incredible. It looks even better than the photos and is just overall stunning. The architecture, proximity to the beach and other restaurants, and the pool made this stay a 10/10. While there were only two of us staying during my trip, it could easily sleep four comfortably, and the pool is big enough for five or six people to be in it at the same time. The rooms and bathrooms were spotless, the beds were comfy, and Sylvia, our on-site host. was so lovely and responsive, and they helped us book excursions, like releasing baby sea turtles. My one note is that this is true indoor-outdoor living, so if you are not much of a nature person, this may not be the spot for you. We spent all our hours taking a dip in the pool." —Cortni Spearman, Social Director
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Black Point Retreat
Location: East Lyme, Connecticut, United States
Price Per Night: $424
Sleeps: 10
Why It's Special: "I stayed at this adorable Connecticut Airbnb with my wedding party leading up to the big day and had the most relaxing time. There are so many individual and family rooms you can comfortably spread out with ten people, and the beach is only a walk away. My friends and I particularly enjoyed using the outdoor grill and having midday BBQs while chatting on the outdoor patio. I'll definitely be revisiting this Airbnb with family next time and would highly recommend it if you're looking for a peaceful retreat away from the big city." —Vivien Lee, Fashion Writer
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Rosa's Place
Location: Madrid, Spain
Price Per Night: $65
Sleeps: 2
Why It's Special: "If you want to do a European city break on the cheap, it's hard to beat the culture, food, and prices in Madrid. Staying at Rosa's spare room in the stylish Alonso Martinez area was such a blessing. It was very conveniently located in the midst of trendy eateries and lively bars, and with some seriously top-tier neighborhoods nearby. We loved walking around Chueca and went on the best tapas crawl in Malasaña. The best part was definitely the two friendly cats and the pretty balcony — the perfect spot to enjoy breakfast." —Venus Wong, Senior Travel Writer
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Desert Delight
Location: Cathedral City, California, United States
Price Per Night: $368
Sleeps: 6
Why It's Special: "My best friend and I realized that it had been literal years since we’d taken a day off, so we decided to meander down to Palm Springs for an ultra-relaxing girls’ weekend. All we wanted was something that had a pool (because Palm Springs in August is hot AF) and was dog-friendly (because my pet is an integral member of our girls’ group). Because we booked it at the last minute, there were very few options available, but we managed to find this incredible house.
"Everything about the stay was perfect. From the discounted rate the host gave us (because of the off-peak exorbitantly hot weekend we booked for) as well as the immaculate kitchen, ultra-powerful A/C, and luxe private pool and backyard, there was nothing about the stay that didn’t make us feel like we were lounging in style. Just a short drive from downtown Palm Springs, we were easily able to go into town for thrift shopping, brunch, etc. But the house was so nice, we ended up spending most of our time there. It was definitely more than our original budget, but it sleeps up to six people. So for a bigger group, it’s more than reasonable for the luxury accommodations." —Charlotte Lewis, Sexual Health & Wellness Writer
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Redondo Farm House
Location: Redondo, Évora, Portugal
Price Per Night: $208
Sleeps: 4
Why It's Special: "I went on a European road trip with my best friends from school and drove from Lisbon to the Algarve with a pit stop in the medieval town of Évora. We spent the night at this traditional farmhouse in Alentejo, a region that produces some of my favorite Portuguese white wines. The place was downright magical: antique furniture and family memorabilia gave the space a retro, lived-in vibe, and there were so many cute farm animals we could say 'hi' to. The owners live on the premises, which is a working cork farm and vineyard. The infinity pool had an amazing front-row view of the dramatic natural landscape of Alentejo. We only stayed for one night, but I wish we were there for much longer." —Venus Wong, Senior Travel Writer
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The Eddy
Location: Morristown, Vermont, United States
Price Per Night: $371
Sleeps: 8
Why It's Special: "This was a perfect spot for a getaway for my family in Vermont. My mom wanted to go back to Stowe, where she grew up skiing, so full credit goes to her for finding this location. It feels modern while still feeling like a classic cabin, which is rare — no cheesy signs or sagging, overstuffed couches. There are also so many spots to hang out around the property, whether you want to curl up with a good book, toast a s'more, or stretch out by the creek." —Marshall Bright, Affiliate Editor
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Apple Tree Cottage
Location: Nailsworth, Gloucestershire, England
Price Per Night: $93
Sleeps: 2
Why It's Special: "My partner and I were so charmed by our stay at this 18th-century cottage that we've made a pact to come back every year (we're now on our third annual stay). It's the perfect size for a couple, with dramatic sloped ceilings framing the upstairs bedroom and the softest, comfiest bed. Our favorite things to do when we spend time here are soak up the sun and read in the patio garden, take a long afternoon nap, and then pick up lobsters from the local seafood monger and bake it for dinner.
"Hotels in the Cotswolds — a famously picturesque region in England — are quite expensive in general, so we feel really good about having this little place at our disposal, which costs less than $100 a night. It's set in Nailsworth, a peaceful small town with just a small but solid selection of restaurants but is still close enough to the 'scenier' spots in the Cotswolds, like Soho Farmhouse in Chipping Norton." —Venus Wong, Senior Travel Writer
Book Apple Tree Cottage
Three Sisters Sanctuary
Location: Goshen, Massachusetts, United States
Price Per Night: $196
Sleeps: 4
Why It's Special: "I’ve stayed in plenty of Airbnbs in various parts of the world, but I’ve never seen anything as unique as this one in rural Massachusetts. I booked this stay when visiting some friends in the area who were expecting a baby, and it’s really an experience unlike any other. The apartment itself is comfortable and clean, albeit somewhat modest (although it does have some very beautiful and ornate woodwork in it), but the grounds that surround it are truly spectacular.
"The apartment is located in the Three Sisters Sanctuary, an eight-acre art sanctuary featuring more than 250 sculptures and other pieces of outdoor art, nestled among stunning gardens. During my stay, we had access to the full sanctuary space, giving us plenty to explore without having to leave the property. Did I mention the space has a giant fire-breathing dragon? As far as amenities go, that one’s pretty hard to top in my book." —Sarah Crow, Affiliate Director
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Athens Dream Studio
Location: Athens, Greece
Price Per Night: $67
Sleeps: 3
Why It's Special: "For my partner's 30th birthday, I surprised him with an impromptu city break to Athens. I was about to quit my last full-time job to travel in Asia, so I knew that the accommodation for this trip would have to be on the affordable side. Luckily, this studio checked off all the boxes. It was incredibly cheap for having a whole place to ourselves, and it came with a balcony that pours open to the bustling streets of Exarchia, a hip neighborhood known for its anarchist roots and happening street market on the weekends.
"Our unit is also connected to two other spacious patio gardens on the other floors of the building, which we were welcome to use. The studio itself was small but artfully decorated and had everything we needed. The biggest flex about this place? It was formally a rock bar in the 1980s, where rock stars like Nick Cave performed on stage." — Venus Wong, Senior Travel Writer
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East Nash Poolhouse
Location: Nashville, Tennessee, United States
Price Per Night: $301
Sleeps: 10
Why It's Special: "Nashville has bachelorette Airbnbs aplenty, and it can be hard to tell the difference between the good ones and the houses that have had a coat of paint, some double bunk beds, and a few neon signs slapped on the walls but little else. This rental property is a rare balance of luxe and group-friendly — and in a great location. I haven't actually stayed here myself (I live in Nashville!), but I always recommend it to groups visiting town. You could have your family stay in it for Thanksgiving (and even prep an impressive feast in that kitchen!) or have a bachelorette group getaway, and enjoy it either way." — Marshall Bright, Affiliate Editor
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Catskills Retreat
Location: Olivebridge, New York, United States
Price Per Night: $223
Sleeps: 8
Why It's Special: "We booked this gorgeous secluded Catskills house for my best friend’s bachelorette party, and it was absolutely perfect. Surrounded by woods and fields, you feel like you’re in your own (gorgeous) world when you stay here. The house gets so much light, and it feels cozy and airy at the same time. Our group spent most of our home time in the hot tub (which somehow fit all eight of us!), but I was a particular fan of the screened-in porch, which has a great view of the deck but is far enough removed for a moment alone (necessary in a large group setting). The price was super-reasonable, and I would definitely recommend it to anyone looking for a low-key bachelorette location." —Charlotte Lewis, Sexual Health & Wellness Writer
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Fawley Court
Location: Wye Valley, Herefordshire, England
Price Per Night: $1,636
Sleeps: 16
Why It's Special: "Me and my best friend have the same birthday, so we booked this incredible manor house and pool in Herefordshire, England, with 34 of our friends. It only came down to just over $200 for three nights, which is a bargain. When we arrived, I nearly fell over: We couldn’t believe the size of the place. Each couple had their own room with their own en suite bathroom. It felt like we were living an IRL game of Cluedo.
"Even though the price has increased, I’d recommend this for a long weekend away in the English countryside with a big group of friends. It’s perfect for a big birthday (like a 30th) or a bachelor or bachelorette party. The carpets have definitely seen some wear and tear with it being a ‘party house’ — but the giant heated swimming pool, games room, and vast gardens definitely make up for it. If you want a magical, luxurious escape to the country with a big group, I’d 100% recommend." —Kelly Washington, Social Editor
Book Fawley Court
The Binocular
Location: Bolton-Ouest, Quebec, Canada
Price Per Night: $299
Sleeps: 2
Why It's Special: "When my husband and I booked this rural Airbnb about 30 minutes outside Montreal during the height of lockdown, people thought we’d secretly flown to the Swiss Alps. The view is so gorg — you’ll never want to leave this little cube house or its hot tub, but the surrounding countryside, which is close to the Vermont border, is full of charming towns and shops, trails, and restaurants." —Carli Whitwell, Senior Director of Editorial
Book The Binocular
Khet Khlong Toei Condo
Location: Bangkok, Thailand
Price Per Night: $55
Sleeps: 2
Why It's Special: "I went on a solo trip to Bangkok last summer and had the best time exploring the city's street food, gilded palaces, and skyscraper malls. A big part of me feeling safe while going on daily adventures on my own was the fact that I stayed at a one-bedroom condo in this gated community. It came with all the amenities you would expect from a luxury high-rise building, including a gym and an incredible rooftop pool, and it's so well-connected on public transit. There were lots of new day spas within easy walking distance (my fave was Plant Day Spa), so I spoiled myself with affordable aromatherapy massages daily after a long day of exploring." —Venus Wong, Senior Travel Writer
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