19 Coolest & Best Airbnbs in Bend, Oregon For An Adventurous Getaway. Sawmill house airbnb

Coolest Best Airbnbs in Bend, Oregon For An Adventurous Getaway

Planning an outdoorsy getaway and searching for the best Airbnbs in Bend, OR? Well, look no further, as I’ve put together the ultimate Airbnb Bend, Oregon that I’m sure you’ll find exactly what you need!

Do you always crave and seek for a heart-pumping, hair-raising adventurous getaway? Then, Bend will definitely fulfill your adrenaline rush! A small city known for its world-class recreation, Bend will not only give you a thrilling experience and activities but also a combination of spectacular views and diverse scenery, award-winning restaurants, craft beers, and shopping. This dynamic city shows off its beauty from the moment you arrive that it makes it difficult to leave.

Bend is a small city on the Deschutes River, in Oregon. It offers 300 days of sunshine a year, and offers access to more than 300 miles of mountain-biking trails, 71 parks, a thousand climbing routes and 3,600 acres of skiing and snowboarding terrain on Mount Bachelor. Other activities include kayaking, rock climbing, hiking, whitewater rafting, wild swimming, fishing and horse riding.

The city features plenty of attractive qualities for both travelers and locals to enjoy,but in order to really enjoy your experience you need great accommodation – and there are plenty of great Airbnbs in Bend. I have here a list of 18 outstanding Airbnb properties that you will surely love!


Before we jump to a long list of Airbnb properties that you could choose from, I have here my top 7 breakdown of all the “best” vacation rentals you might want to check in Bend. From the best of the best to the cheapest and the most unique accommodation you can find, I have it all here!

  • Best Cabin Vacation Rental Near Bend, Oregon –Pet Friendly, Luxury Log Cabin with Hot Tub near Sunriver!
  • Best Vacation Rental in Downtown Bend, Oregon –Historic Westside Craftsman Bungalow
  • Best Overall Airbnb in Bend, Oregon –Sink Into the Hot Tub of a Large Lovely Downtown Bend Home
  • Best Luxury Airbnb in Bend, Oregon –The Sawmill \\ Designer Cabin Vibes Glow In Natural Light
  • Best Bend, Oregon Airbnb For Groups –Modernist Mountain View Retreat in Old Mill; New Hot Tub
  • Best Cheap Bend, Oregon Airbnb –The Outside Inn – Private Studio Suite
  • Best Unique Airbnb in Bend, Oregon – Dome Sweet Dome: A Must (and safe) Experience!

I’ve also added tons of awesome, helpful, and inspiring travel videos for your upcoming getaway to Bend, Oregon! It’s such an beautiful and unique destination with lots to do, so make sure you watch a few of them to get tons of ideas for how to spend your time there! Also, be sure to read my article on the best music festivals in Oregon and best glamping Oregon for more trip ideas!

2021 Update: Due to the closure of the Airbnb Associates program, some of the properties listed here have been changed to alternative booking sites (which often have lower rates and less cleaning/services fees)!

) Pet Friendly, Luxury Log Cabin with Hot Tub near Sunriver!

Location: Bend, Oregon (20 Minute Drive from Downtown)

I’m currently planning a trip to Bend, Oregon – and this is where I’m staying! This 2-bedroom luxury cabin is what dreams are made of, and guests love everything about their stay! From the secluded location, top-notch amenities, and amazing host – this really is a cabin getaway you’ll never forget!

It’s a two-bedroom/ 2-bathroom cabin, so perfect for couples, friends, or families looking for a fun weekend getaway! Spend your days enjoying all the amazing outdoor attractions nearby, and soak up every evening in the hot tub to rest and recharge for another day of nature explorations.

While it is a bit of a drive from downtown Bend, I think there’s no better way to experience Oregon than in a beautiful log cabin!

Guest review: “Absolutely LOVED our stay at the cabin. Every detail was attended to, perfectly appointed, excellent detailed communication before, during, and at the conclusion of our stay. From the plush leather sofas to the memory foam bed, comfort was top notch and well received after a long day of getting beat up on the slopes! Could not be happier with the entire experience and look forward to booking a longer stay next season!”

) Historic Westside Craftsman Bungalow – Walk to Downtown

For travelers visiting Bend looking to stay right in town, than look no further than this charming and historic 2-bedroom bungalow!

Built in 1919, this home is on the National Historical Register, making it an extra unique stay (but they’ve updated it to make it comfortable while keeping the historical elements).

It has a beautiful private backyard to enjoy a morning cup of coffee, but you’re also just minutes away from Bend’s fantastic downtown district offering amazing restaurants, cafes, bars, shopping, and lots more.

The space is well equipped with everything you’ll need, and even includes an awesome and remodeled basement that offers guests a comfy sofa, large screen TV, beer fridge and dart board. It’s fun, unique, and affordable. Just make sure you book this one well in advance, as it does get booked up quite often!

Guest review: “Nice little place right in the middle of everything. We walked everywhere. Place is super cute and nicely appointed. The beds are so comfy! Our dogs loved it too.”

) Sink Into the Hot Tub of a Large Lovely Downtown Bend Home

If you are looking for “Overall Best Airbnb in Bend, Oregon“, Green Gables is the perfect place for you! It offers all the comforts of a dream home and at the same time gets you close to the activities in the city. Located in a quiet neighborhood just 2 blocks from downtown, Green Gables boasts a home full of intricate vintage details and a mix of country and modern style, spacious rooms.

There are three rooms that sleeps up to 8 people with a king bed and queen bed, a spacious living area with an indoor fireplace and full kitchen. Take one of the complimentary bikes into town for a tour or grab a seat on the private patio while enjoying the afternoon sun, or enjoy a warm bath in the outdoor hot tub.

How Many Bedrooms Is Ideal When Purchasing An Investment Home For Airbnb

Guest review: “This is a great place for a getaway to Bend! Lots of character and plenty of room…we had everything we needed and could walk virtually anyplace we wanted to explore in downtown and the old mill district! We had an excellent experience and recommend this lovely cottage!!”

) The Sawmill | Designer Cabin Vibes Glow In Natural Light

Get spoiled with the luxurious amenities when staying at The Sawmill! This is my choice for the “Best Luxury Airbnb Bend Oregon”. Located in the heart of historic downtown, you are merely steps away from all that the city has to offer including Deschutes River for stand-up paddleboarding, kayaking, and swimming; a walk to the Old Mill for dining, summer concerts and walking trails. The house is so luxurious, with a king bed, spacious and bright living area, washer dryer combo, a walk-in shower and tub, and a beautiful view from the patio. This is the perfect spot for a small family, couples or solo adventurers!

Guest review: “Location, decor, comfort, cleanliness, etc… all awesome. My friend I loved getting to stay in this space for a night in Bend. I appreciated the coffee grinder in the AM for great, fresh coffee and overall the creative decor woodwork around the apartment left us feeling inspired. Highly recommended // would move in.”

of the Most Unique and Unusual Airbnbs in Pennsylvania

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When I’m traveling around the state, I always love finding unique places to stay on sites like Vrbo and Airbnb. Pennsylvania, believe it or not, is home to a lot of very interesting places to stay, many of which can be booked on these popular sites.

While I haven’t stayed at most of the places listed here, I’ve only picked spots that I would be excited to stay at. At the time of writing, all of them have excellent reviews, great photos, and descriptions, and look like very fun spots to stay in while exploring PA.

So, whether you want to stay in a treehouse with a slide, a bridge over a creek, or on a boat, there’s a bit of something for every adventurous traveler on this list of the coolest cabins, tents, Vrbos, and Airbnbs in Pennsylvania.

(Photo at the top of the article used courtesy of Airbnb.)

Treehouse with a Hot Tub near Ohiopyle State Park

Located in southwestern PA near Ohiopyle State Park is this incredible treehouse. Not surprisingly, it’s one of our favorite cabins in the Laurel Highlands.

Made of local lumber, this raised cabin is nestled in a beautiful woodland and has an amazing staircase leading up to it. Inside the treehouse, you’ll find a cozy space with all the amenities you need.

Outside, there is a nice deck on the upper level and, below the main cabin, a hot tub, which is perfect for soaking your muscles after a long day of hiking.

Note that this property has a two-night minimum stay.

Haines Shoe House

The Haines Shoe House has long been one of PA’s most unique homes, and it is now open for visitors to once again spend the night inside this very unique property in York, Pennsylvania.

This structure was originally built in 1949 to advertise a local shoe business. Despite its name, it never served as a home. Instead, its first use was as a retreat for couples wanting to get away for a bit. However, in more recent decades, the Shoe House has more often been open for tours and as a popular ice cream stand.

Now, however, it is once again open for overnight guests, who will have access to this incredibly unique and historic property, which features all of the comforts of home and three bedrooms.

Octagonal Lakehouse near Scranton

Located on Roaming Woods Lake in the Poconos, only a short distance east of Scranton, you’ll find this incredible octagonal lakehouse.

The house sits in a resort community near Roaring Woods Lake, which features great fishing, boating, and even a small beach and swimming area.

Inside, the home to nicely decorated with a very retro style and features many great amenities. Outside, there is a nice deck overlooking the beautiful woods that surround the house.

Note that this property has a three-night minimum stay.

Bohemian Cabin near State College

If you love eclectic things, you’ll definitely love this Bohemian cabin in Centre County near Woodward Cave.

Located adjacent to a beautiful creek, this cabin is filled with unique and upcycled touches. Outside, enjoy the wrought iron swing, firepit, grill, and neat seating areas.

While this cabin is a bit rough around the edges, it has more than enough charm to make up for it.

Note that this cabin requires a two-night minimum stay.

Campsite Near a Waterfall near Jim Thorpe

If you love waterfalls, there are few better Airbnbs in Pennsylvania than this glamping tent near a private waterfall.

Set in the middle of a 400-acre private forest, this tent features a large bunk bed, Adirondack chairs, a picnic table, and a fire pit. It is perched close to a small but beautiful waterfall.

If that’s not enough, there are several miles of hiking trails on the property and at least one very unique bridge. Even better, the tent is located only a short drive from Jim Thorpe and Hickory Run State Park, two of my favorite spots in Pennsylvania.

Buffalo Bill’s House

If you love the movie, “The Silence of the Lambs,” then you’ll definitely want to book a stay at Buffalo Bill’s House.

Located just outside the southwestern PA community of Perryopolis, this is the actual home in which both interior and exterior scenes were filmed for the movie as the home of the antagonist, Buffalo Bill.

The home has been beautifully recreated, including several sets in the basement where you can act out your favorite scenes from the film. Upstairs, there are four bedrooms and a fantastic game room.

Lake Erie Waterfront Cottage

Enjoy the beauty of Lake Erie directly from your backyard at this amazing cottage in Erie, PA.

Located steps from the water and a short drive from popular spots like Presque Isle State Park and Waldameer Amusement Park, this cottage is a great home away from home when enjoying northwestern PA.

This home has three bedrooms, an updated kitchen, and a fantastic deck overlooking the lake.

Treehouse with a Slide near Huntingdon

There are many great spots to go glamping in Pennsylvania, but, as far as I know, this is the only one that lets you leave your treehouse by slide!

New in 2020, this elevated tent features a nice and cozy design that’s perfect for a relaxing visit to the woods. However, the highlight of this spot has to be the spiral slide that you can use during your stay. While a short walk is required to reach a bathroom, this spot does have a covered porch, picnic table, and firepit for guests to use. Updates in 2022 list private bathrooms available at each site!

This spot is located a short drive from Huntingdon, PA, and is great for exploring Raystown Lake and the Big Valley Amish community.

Covered Bridge Cabin in Lawrence County

Located in western PA near New Castle and Grove City, this Airbnb is inside a converted covered bridge that spans a small creek. That’s right, this Airbnb in Pennsylvania is located directly over a body of water!

This cabin is described as being rustic, so it’s not for everyone, though it does feature a full slate of amenities, including a great deck overlooking the stream and a half-mile nature trail directly adjacent to the property. There’s even a six-foot working waterwheel nearby.


Houseboat in Old City Philadelphia

There are a lot of great hotel rooms in Philadelphia, but if you are looking for something very different, why not stay in a houseboat on the Delaware River, one of my favorite Airbnbs in Philly.

Located under the Benjamin Franklin Bridge, this custom-built floating cabin is known as the Love Shack because of its metal roof. Inside, you’ll find nearly every amenity that you could need, though the bathroom is located a short walk away at the marina. There’s even a small deck so that you can enjoy the outdoors on the water.

Streamside Cabin near Cherry Springs State Park

There is no spot in PA with darker skies than Cherry Springs State Park, and this nearby cabin is a great place to enjoy the beauty of the night sky.

This cabin is located along a beautiful creek, which you are sure to enjoy from the two large decks and the beautiful fire pit.

Of course, if you must be inside, this cabin also features many modern amenities including TV, internet, and a full kitchen.

Scandanavian Cabin near Huntingdon

There is probably no more unique treehouse in Pennsylvania than this Scandanavian-inspired treehouse.

Designed as an authentic Norwegian Stabbur, this property will have you visiting Europe without leaving Pennsylvania. This cabin is made entirely of wood and features many cozy amenities, including a sauna. On the 80-acre property, you can enjoy several miles of hiking trails, a stream, and a ton of natural beauty.

Note that this property requires a two-night minimum stay.

Dome House in Pittsburgh

Looking for somewhere unique to stay in Pittsburgh? This Yuca-Dome is a great choice.

The first of only 26 Yuca-Domes ever made, this home can withstand a 250-mile-per-hour wind (not that you have to worry about that in Pittsburgh).

This historic property includes one bedroom (though the listing states that two normally-locked bedrooms may be available for an additional cost). The home has a unique design that includes round Windows.

Note that this property has a seven-night minimum stay.

Aaron Burr’s Post-Duel Bedroom in New Hope

After the famous duel between Alexander Hamilton and Aaron Burr, Burr fled New York for a friend’s home in New Hope, Pennsylvania. Today, that home is now open as the Aaron Burr House Bed and Breakfast. You can find the BB’s rooms on Airbnb.

While there are a total of seven rooms in the house, it is said that Burr stayed in the Federalist Room during his time at the property in 1804. No matter which room you stay in, however, you might see or feel the ghost of Aaron Burr, which is said to reside at the home.

The room itself is well appointed and features a beautiful and classic style that wouldn’t have looked out of place in 1804.

Note that breakfast is an additional fee above the room rate.

Woodland Cabin near Worlds End State Park

If you are looking to explore Williamsport or the many great spots in PA’s Endless Mountains like Worlds End State Park and Ricketts Glen State Park, this woodland cabin is a perfect choice.

This 19th-century cabin has been lovingly restored and sits on the banks of the Loyalsock Creek, a popular stream for both its beauty and great fishing.

Inside, the cabin features four bedrooms and many nice touches and modern elements. Outside, there’s a great back porch overlooking the creek, a grill, and a firepit.

Note that this cabin has a three-night minimum stay.

House with Great Views of Pittsburgh’s Skyline

Pittsburgh is a city with many incredible views, but if you are looking to stay somewhere with a great view, this Vrbo in Pittsburgh is the perfect choice.

This three-bed, two-bath home is located on Mount Washington and features an awe-inspiring view over the city and the Monongahela River. This view can be enjoyed from inside the home or from the incredible top-floor deck.

There are several other outdoor spaces, including one that is perfect for outdoor games.

Treehouse in the Poconos near the Delaware River

If you’ve always wanted to spend the night in a treehouse, this Airbnb in the Poconos is a great choice.

Located near Narrowsburg, New York, but on the Pennsylvania side of the river, this elevated cabin looks quaint from the outside but is incredibly well designed on the side. Browsing through the photos of this light-filled cabin and its oversized Windows will make you feel like you are already there.

Even better, the treehouse features a clawfoot tub and a large deck with a hammock, all on nine private acres of land. It’s a great jumping-off point for exploring both the Poconos and the Catskills of New York.

This property has a two-night minimum stay.

Tiny House on a Farm near Shippensburg

Always wanted to experience a tiny house? This Airbnb near Shippensburg is a great choice.

Located on an organic dairy farm just east of Interstate 81 in south-central PA, this charming home provides everything you need, but in a super tiny package. Fortunately, however, there is a large outdoor deck with a nice table and grill to ensure you don’t run out of room.

This spot makes a great location for checking out Michaux State Forest, the Appalachian Trail, Harrisburg, and Gettsyburg.

Mid-Century Modern Home over a Creek near Reading

If you love Mid-Century Modern design, you won’t want to miss this incredible Airbnb near Reading, PA.

This unique home is perched directly over a small stream and features an impeccable design that is sure to wow every visitor. In fact, the design of this home looks like something straight out of a magazine.

Outside the home, you’ll find a hot tub, which is a perfect spot to relax in the evenings.

Big Al’s Pocono Creek House

Whether you love fishing, the sound of rushing water, or just relaxing, this cabin along a creek in the Poconos is for you.

This cabin looks just like the perfect log cabin out of your dreams but with all the modern amenities you could want (including Wi-Fi and a TV) while allowing you to enjoy views of the creek through the large Windows and a fireplace.

However, it’s the outside here that really shines. Step outside and go fishing right from your patio, enjoy the outdoor hot tub, or just relax on the porch.

Historic Yurt in Ohiopyle

Yurts are popping up at campgrounds and Airbnbs in PA. However, this yurt in southwestern Pennsylvania is one of the few historic yurts you can stay in.

Built in 1918, this historic yurt is located in the heart of Ohiopyle, one of the most charming tiny towns in PA and gives you quick access to the many incredible things to do in and around Ohiopyle State Park.

This spot is definitely rustic and isn’t for every traveler. However, for those that appreciate cozy and rustic accommodations, but still want quick access to hiking trails and restaurants, this is a perfect choice. There’s even a wood stove to keep you warm on chilly nights and a firepit outside.

Farm Cottage in Bethlehem

Looking for a romantic Airbnb in Pennsylvania? This 18th-century stone cottage is a great choice.

Located just outside of the charming city of Bethlehem, PA, which is known for its rich history and great Christmas celebrations, this one-room cottage is a fantastic place to stay. It has been recently renovated to provide all the necessary modern comforts and many little touches that make this a popular rental.

There’s even access to a swimming pool adjacent to the cottage.

Historic Houseboat near Pittsburgh

Located along the shores of the Allegheny River just north of Pittsburgh, this 1972 houseboat is a unique spot to stay when visiting the city.

The interior of this boat is small, but it’s been well-designed and features a kitchen and a bathroom within the confines of the boat. At the top of the boat, spread out on the deck to watch the sunset. The boat even comes with a free kayak rental!

Note that this property requires a two-night minimum stay.

coolest, best, airbnbs, bend

Renovated Church in Philly

If you’re looking for a unique property in Philadelphia to share with a whole group of people, this renovated church is a great choice.

This historic church is located south of Center City near Rittenhouse Square and is set up like a boutique hotel with eight rooms around a central living and dining space. It can easily fit your entire group. Each bedroom in this property features its own bathroom and nicely appointed bedding.

Note that this property has a two-night minimum stay.

Teepee near the Quehanna Wild Area

Located near the Quehanna Wild Area, this fun teepee is a neat spot to stay when exploring this remote part of the state.

The inside of the teepee is sparse but nicely laid out with four beds and a small kitchen area. There is also a fire pit within the teepee for warmth.

Outside, you’ll find another firepit, Adirondack chairs, a private bathhouse, and a hammock.

coolest, best, airbnbs, bend

Private Lakehouse near Cambridge Springs

Located on a peninsula on a private lake in northwestern PA, this cabin is in a very beautiful and relaxing spot. In fact, it’s surrounded on three sides by water.

This large home features a well-appointed interior, including a game room with toys for kids of all ages. The star of the show, however, is the exterior, which features a great dining area, deck, fire pit, and dock.

This house is also close to a ski resort for wintertime adventures.

Historic Barn in the Philadelphia Suburbs

Want to stay in a tranquil rural setting but within reach of downtown Philly? This historic barn is a great choice.

coolest, best, airbnbs, bend

Located in Bryn Mawr, only a 35-40 minute drive from the city and near train lines directly into Center City Philadelphia, this spot feels away from it all while being close to the many amazing things to do in Philadelphia and its suburbs.

This PA vacation rental is located in the loft of a historic dairy barn. Inside, this light-filled space features all the amenities you could want and a lot of great little touches.

Have you ever stayed in one of these Airbnbs in Pennsylvania or do you have a favorite one to share? Let us know in the Комментарии и мнения владельцев below.

Guest Houses

For additional lodging options to fit your accommodation needs, see our Hotels Motels and Bed Breakfasts pages.

Berger’s Bungalow

Enjoy your stay in our cozy, two bedroom, one bathroom bungalow. Built in the mid 1940s, our 900 sq. ft., pet friendly home is ideal for singles, families and business travelers. We also are conveniently located 15 minutes from EPIC.

We have updated the entire home to make your stay enjoyable. Spend time in the newly remodeled kitchen or sit outside, overlooking the large backyard while you watch the kids or the dogs play. Our charming home has hardwood floors and beautiful, original Windows.

Berger’s Bungalow, LLCBeth and Bruce Berger, membersPhone: 608-558-4104Email: bergersbungalow@gmail.com

Hidden Bluff Lodge

It’s a nature lover’s paradise! The rustic charm of a log cabin with all the amenities you would expect in a comfortable family home. The property features a 2150 square foot, 4 bedroom, and 3.5 bath well-appointed log home on 40 acres of prime driftless area land with hiking trails leading through rock cliffs, pollinator prairie and oak savannas.

With our homestead-inspired simplicity, you’re sure to enjoy any stay with us, whether you’re here to attend one of the many area festivals or just relaxing. We are located in the hills west of New Glarus, a mile off the paved road, but you won’t feel isolated unless you want to be.

Two-night minimum; weekly rates also available. Accommodates 1–6 people, children stay free. The Lodge address is Blanchardville, but this property is very close to New Glarus. For more information visit our website.

Kennedy’s Guest House

Kennedy’s Guest House offers all the comforts of home to enjoy your vacation! Amenities include an open air view of New Glarus from the edge of our downtown district. Newly updated with a free flowing floor plan. A full kitchen, large bathroom, a queen bedroom with two living room sleeper sofas to accommodate up to five. Enjoy the ample deck with a barbecue grill and comfortable seating. Located above Kennedy’s Ice Cream Grill, the park and pool across the street and being on the Sugar river trail head, come for fun, hiking, biking or snowmobiling and enjoy our town’s charm.

Kennedy’s Guest House400 Railroad StNew Glarus,WI 53574

New Glarus Deck Retreat

Best location in town! You’ll be right downtown where the fun is, but quiet. You get a recently remodeled, one king bedroom apartment with all the amenities. Nice deck and off street parking. You can walk to everything.

New Glarus Loft Retreat408 2nd StNew Glarus, WI 53574

New Glarus Garten Retreat

This large 2 bedroom street level New Glarus getaway is in a prime location within downtown New Glarus. You are within steps from all downtown shops and restaurants. You will be across the street from the village park and a block from the bike trail. The iconic Swiss United church is in your backyard and most festivals are within a block from your residence. If relaxing on the deck you will hear chimes, music, and the occasional alphorn.

New Glarus Garten Retreat402 2nd StNew Glarus, WI 53574

New Glarus Loft Retreat

A newly remodeled one bedroom apartment overlooking the Village Park. Contains a spacious bathroom with a walk in shower and a kitchenette with a refrigerator, microwave, Keurig coffee maker and a toaster. You can set out on the deck and enjoy your morning coffee or relax watching the large TV with 20 channels plus internet television.

New Glarus Loft Retreat402 2nd StNew Glarus, WI 53574

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