
Holiday rentals in Trail
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Trail
Guests agree: these stays are highly rated for location, cleanliness and more.

"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
LocationFamilyAir conditioning
4.91 out of 5 average rating, 111 reviews
Tiny Groove with plunge pool and soaking tubs
A unique off grid experience awaits you at our eco-friendly solar powered tiny home on 6 secluded acres. The home site is perfectly cut into a groove in the hillside 200 feet above the valley below allowing for beautiful Mountain views and amazing privacy with no visible neighbors other than the variety of local wildlife. Enjoy the outdoor soaking tubs, wood fired sauna and a seasonal plunge pool. Just a short 5 minute drive to the lovely town of Rogue River and access to I-5. Pet friendly too!
LocationConditionOutdoor spaces
4.86 out of 5 average rating, 132 reviews
Starlight Meadow Yurt
The yurt is a modern, light, space with a deck. It's nestled between a mixed conifer forest and Starlight Meadow. We're at the end of a private road on 20 acres. The property is gated for your comfort and peace of mind. There's a large trampoline at the edge of the meadow perfect for stargazing and sunsets. The creek flows October thru June depending on rainfall. Six miles from Shady Cove where you'll find restaurants and a grocery store. 40 miles to Crater Lake. 26 to Ashland. Treat yourself!
ValueLocationShared spaces
4.96 out of 5 average rating, 291 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.
LocationFamilyTV
4.95 out of 5 average rating, 264 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.
FamilyLocationWalkability
4.94 out of 5 average rating, 387 reviews
Peaceful Retreat on the Rogue River
Entire House in Shady Cove Enjoy time with your feet up overlooking the beautiful Rogue River from the deck or snuggled up in the family room near the fireplace. Over 400 feet of river frontage with direct river access for fishing, swimming, rafting, kayaking, or just sitting on the river’s edge taking in the natural beauty of this serene location. Location Just 5 minutes from the small quaint town of Shady Cove & 30 minutes from downtown Medford where there is a local airport/car rental.
LocationFamilyGetting around
4.97 out of 5 average rating, 39 reviews
Rogue River Retreat
Located on the Upper Rogue River, this riverfront cottage is perfect whether you seek a quiet weekend away or fishing for steelhead, (plus, there's a great run right in front of the cottage). We're just down the way from the Riverhouse and bridge, close to town. It is a very quiet and serene atmosphere, perfect for unwinding. The geese will wake you up in the morning and the deer and raccoons will amuse you. Feel free to pick fruit from the trees if in season. Sorry, no children.
LocationValueBathroom
4.98 out of 5 average rating, 131 reviews
Ripple Rock Lodge- Gateway to Crater Lake
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!
LocationFamilyKitchen
4.97 out of 5 average rating, 151 reviews
Eagle’s Nest Cottage | 60 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 is allowed—please bring your own line and tackle. - Cook family meals together - Play board games - Stream movies on the Roku TV
FamilyLocationCheck-in
4.95 out of 5 average rating, 238 reviews
The Shady Knoll | Crater Lake Basecamp | Hot Tub
Unwind on a fenced, gated acre just up from the Rogue River. Year-round private hot tub, BBQ & string lights over a huge lawn. Updated home w/ king suite, spa-style rainfall shower, cozy pellet stove, fast wifi & 2 workspaces. Boat & raft trailer parking inside the gate — fish or float world-class Chinook & steelhead water minutes away. Lost Creek Lake in 10, Crater Lake ~1 hr, waterfalls & hikes all around. Mornings: coffee on the deck. Nights: stargazing from the hot tub.
FamilyLocationGrill
4.92 out of 5 average rating, 170 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.
LocationValueHot tub
4.96 out of 5 average rating, 256 reviews
Rogue River Retreat
A nature lovers retreat on the beautiful Rogue River. Watch osprey from the sprawling cedar deck, fish for salmon right on the river bank, or take a soak in the deep tub, this peaceful cabin you won't want to leave. Located half way between Grants pass and Medford with easy access to the 5 freeway, you can enjoy all that Southern Oregon has to offer. The cabin has one deluxe bathroom and one cozy bedroom that has a king size bed with a water view.
LocationFamilyWifi
4.97 out of 5 average rating, 298 reviewsPopular amenities for Trail holiday rentals
Other great holiday rentals in Trail

The Uphill Ranch
LocationFamilyView
5.0 out of 5 average rating, 21 reviews
Private Ranch Log Cabin Lakeside Escape
ValueFamilyCleanliness
4.98 out of 5 average rating, 57 reviews
3 Pines Cabin | Hot Tub & Forest Retreat
FamilyLocationComfort
4.89 out of 5 average rating, 28 reviews
Spectacular Cozy Cottage-3 BR, Creek, Wood Stove
FamilyValueAccuracy
4.91 out of 5 average rating, 74 reviews
The Renovated Retreat -hot tub
LocationComfortOutdoor spaces
5.0 out of 5 average rating, 3 reviews
Comfortable cozy private space, country setting!
LocationValueNearby
5.0 out of 5 average rating, 61 reviews
Forest retreat skoolie
FamilyLocationCondition
4.79 out of 5 average rating, 38 reviews
Rogue Valley Retreat
LocationValueCheck-in
5.0 out of 5 average rating, 30 reviewsDestinations to explore
- Portland Holiday rentals
- South Lake Tahoe Holiday rentals
- Bend Holiday rentals
- Sacramento Holiday rentals
- Eugene Holiday rentals
- Reno Holiday rentals
- Lincoln City Holiday rentals
- Seaside Holiday rentals
- Cannon Beach Holiday rentals
- Truckee Holiday rentals
- Rockaway Beach Holiday rentals
- Sunriver Holiday rentals





