Vacation rentals in Trail

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Trail

Guests agree: these stays are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Guest favorite
The image captures the Upper Rogue River, framed by lush greenery on either side. Sunlight reflects gently on the water’s surface, creating a serene atmosphere. Tall trees line the riverbank, enhancing the natural beauty of the scene.
Home in Trail
4.91 out of 5 average rating, 108 reviews

"Home on The Rogue" - Gateway to Crater Lake !

Strongly advise Travel Insurance offered thru Airbnb due to our strict cancellation policy. Riverfront 3 bdrm/2 bath home perfectly located on the picturesque Upper Rogue River. Centrally located 50 min. from Crater Lake National Park, the Famous Shakespearean Theater in Ashland, and the ever-so Popular Jet Boat trips in Grants Pass. Parking for boat, recreational, travel trailers NO DUMPING OF ANY KIND. Great for families, locals, couples or groups, ABSOLUTELY NO PETS, Non-AD & NO CABLE TV

Top guest favorite
The exterior of the guest suite features a covered porch with white railings and a set of wooden steps leading to the entrance. Lush greenery surrounds the property, providing a natural setting in the hills of east Medford.
Guest suite in Medford
4.97 out of 5 average rating, 201 reviews

Angel Crest Casita Guest Suite - East Medford

Enchanting, large, private 1 bedroom guest suite with a view In Upper East Medford. Beautiful, open concept living /dining area has plenty of room to relax and unwind. This space also includes a semi private queen bed. There is a large luxurious shower, kitchenette, and other amenities (microwave, fridge, and coffee maker). Outside there is a large private covered deck with outside seating and a fire pit. Close to wineries, golf, restaurants, and great hiking. This is a non smoking property.

Guest favorite
A large log home is nestled among lush greenery, surrounded by trees. The structure features multiple large windows that allow natural light to fill the interior. The expansive deck is supported by sturdy columns, while a gentle slope leads to the landscape below.
Home in Trail
4.95 out of 5 average rating, 248 reviews

Log Cabin w/Treehouse & Zip Line on Rogue River

Serene, large log home in the woods w/matching tree house fort. Located in Trail, Oregon on 120 acres of forest views and has a 1/2 mile of river frontage on the wild and scenic Rogue River. The property is near to several lakes, waterfalls and scenic hiking trails and is located directly on the way to Crater Lake National Park. Home is located at the end of the road and provides lots of privacy, peace and quiet. The nearby river can be heard from the cabin providing a peaceful environment.

Guest favorite
A new tiny home is situated among tall pine trees, featuring a clean exterior with large windows adorned by flower boxes. A gas grill is positioned on a patio area, framed by a wooden fence and lush green grass.
Tiny home in Shady Cove
4.95 out of 5 average rating, 341 reviews

Modern Tiny House w/ Hot Tub and Putting Green

Located on a hillside in Shady Cove. This is a spacious brand new 300 sq foot tiny home. The tiny house is located on our private property. We request for our guests to be respectful of our home, our neighbors, and surroundings. It is important that our guests treat the outdoor space as if they were camping and not leave any food outside as there is some wildlife in the area. Included is a covered gazebo with curtains on a private deck with a spa, and gas fire pit that also heats your legs.

Top guest favorite
A charming entrance showcases double French doors framed by decorative lanterns. A small patio area features a round table and two chairs, surrounded by planters filled with vibrant flowers. The exterior blends rustic stone with smooth siding against a backdrop of abundant greenery.
Guest suite in Grants Pass
4.9 out of 5 average rating, 757 reviews

The Hideaway - A Private Entrance Suite

Escape to this charming private EDU cottage with its own entrance and convenient parking. This cozy retreat includes a mini-fridge, microwave, Keurig, WiFi, and TV with Netflix. The soothing décor, custom-tiled bathroom, and spa-style shower make it a relaxing getaway. Located 3 miles from historic downtown Grants Pass in Oregon's beautiful farm country, the property features a tranquil pond alive with birds in spring and summer. Unwind and enjoy the perfect blend of comfort and nature.

Top guest favorite
The exterior of the lodge is showcased, featuring a blend of natural wood and stone accents. A spacious driveway is visible, surrounded by tall trees, with a backdrop of rolling hills. Large windows invite natural light, creating a welcoming entrance.
Home in Prospect
4.96 out of 5 average rating, 130 reviews

Ripple Rock Ranch Lodge

The Ripple Rock Lodge offers amazing views of The Rogue River Gorge and Lost Creek Lake. The lodge has a large patio with ambient lighting, and both gas and charcoal grills! It is located on a 10 acres parcel of woodlands to explore with access to the Rogue River and numerous hiking trails. Medford International Airport is approximately 40 miles from the Lodge and Crater Lake National Park is approximately 35 miles. Now offering as a wedding venue, please message with any inquiries!

Guest favorite
A private cabin is nestled alongside the Rogue River, surrounded by lush greenery and mature trees. A spacious deck overlooks the water, providing a serene outdoor space. A pathway leads from the cabin to the river's edge, enhancing accessibility.
Cabin in Trail
4.96 out of 5 average rating, 235 reviews

Rogue River Lodge, Riverside Cabin

One of the Upper Rogue's most popular private cabins along the Rogue River. Cabin built in 1937 & recently refurbished with all of modern conveniences - family & pet friendly, with large deck overlooking the Rogue River. Private cabin located just steps from the Rogue River - fully equipped cabin, with private hot tub and dry/moist sauna. Only 52 miles to Crater Lake National Park, with local fishing, rafting, hiking, wineries, golfing & more.

Guest favorite
Home in Trail
4.95 out of 5 average rating, 221 reviews

Eagle’s Nest Cottage | 40 mins to Crater Lake

Rogue River Retreat enjoy a cozy weekend of unplugging and quality time with loved ones! - 60 minutes to Crater Lake National Park - Riverfront retreat on the tranquil Rogue River - Wake up to breathtaking river views - Lounge in the hammock while watching rafters, ducks, and fish drift by - Play Ping-pong - BBQing on the patio - Fishing off the dock (BYO poles) - Cook family meals together - Play board games - Stream movies on the Roku TV

Top guest favorite
The exterior of the yurt is highlighted by warm light emanating from the windows, creating a welcoming ambiance in the evening. A wooden deck leads to the entrance, while a nearby chair rests under a small tree. Soft landscaping and a hammock are visible in the background.
Yurt in Grants Pass
4.98 out of 5 average rating, 790 reviews

Sunset View Yurt of Applegate Valley with HOT TUB!

NO CLEANING FEE! Large 24 ft yurt located on our 5 acre property. Gorgeous views to the west. Includes a king size bed, and queen sofa bed. Located in Applegate Valley. Many fabulous wineries nearby. We're 6 miles south of downtown Grants Pass, and 2 miles north of Murphy. Enjoy the hot tub under the stars, or catch a spectacular sunset. It's all good! Please note: Well behaved, non destructive children are welcome.

Top guest favorite
A cozy living area features a leather couch, a lounge chair, and a barrel chair arranged around a wooden coffee table. A large window provides views of the outdoors, while a patterned area rug lies on the warm-toned floor, enhancing the tranquil ambiance.
Home in Myrtle Creek
5 out of 5 average rating, 131 reviews

Peaceful Nights with Highland Cows & Horses

Meet friendly Highland Cows and beautiful horses on a lush green ranch nestled in rolling hills. Just 13 miles east of I-5, this peaceful retreat offers total nature immersion. Even the drive delights—with farms, grazing sheep, and scenic views at every turn. Step out, breathe deep, and let the fresh country air melt your stress away. It’s more than a getaway—it’s a soul-refreshing retreat!

Guest favorite
A spiral staircase leads to an upper level, crafted with wooden steps and a sleek black railing. The open floor plan reveals a modern kitchen with bar seating, large windows providing natural light, and views of the surrounding nature.
Home in Trail
4.79 out of 5 average rating, 115 reviews

Oregon Riverfront Oasis •Pool •Hot Tub •Sleeps 10+

✨ Soak in riverfront & mountain views from the hot tub ♨️ or private balconies 🌄 at this luxury retreat! This 3BR 🛏️, 4BA 🛁 getaway features 2 master suites, a pool house with private bath 🏠, and sleeps up to 12. Enjoy the pool 🏊‍♂️, sauna 🧖‍♀️, theater 🎬, gym 🏋️, pool table 🎱, Traeger grill 🍖 & more — all behind a gated entry for total privacy 🔐.

Guest favorite
The geodome is illuminated at night, showcasing its unique architectural design. Inside, warm lighting highlights a spacious bed and a round dining table with chairs. The backdrop features a cloudy sky, with the moon visible, adding to the serene atmosphere of the surrounding nature.
Dome in Ashland
4.82 out of 5 average rating, 162 reviews

The Acorn dome

Nestled in the trees, the geodome has mini split ac, heat, WiFi, tv, kitchen area, stove, fridge and private detached bathroom/shower. Three miles to Ashland, yet surrounded in nature. Take advantage of the Incredible views and bird watching on the wrap around deck. Barrel sauna available for use, shared with adjacent tiny house airbnb

Popular amenities for Trail vacation rentals

  1. Airbnb
  2. United States
  3. Oregon
  4. Jackson County
  5. Trail