Vacation rentals in Trail

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Top-rated vacation rentals in Trail

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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, 106 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

An open interior of a modern yurt is shown, featuring a kitchen island with bar stools, wooden cabinetry, and a cozy seating area. Large windows allow natural light to fill the space, highlighting the unique vaulted ceiling and bamboo flooring.

Yurt in Eagle Point

4.97 out of 5 average rating, 262 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!

Superhost

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, 236 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

4.96 out of 5 average rating, 316 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 cozy studio is nestled among tall pine trees, illuminated softly by warm outdoor lights. The clear night sky is filled with stars, adding a serene backdrop to the natural surroundings. A pathway leads to the entrance, inviting exploration of the tranquil setting.

Treehouse in Jacksonville

4.97 out of 5 average rating, 270 reviews

Tree Top Studio

Find your Peace in this cozy light filled studio in the treetops of the Siskiyou mountains. The studio is very private with views in every direction of trees, earth and sky (no other buildings in sight). You have direct access to trails leading to old growth forest and a refreshing year long creek. The studio space is an inspiration for artists and lovers of fine details. The kitchen meets all your basic culinary needs. Living room has cozy nooks. Bedroom upstairs has a comfy queen size bed.

Guest favorite

The interior of the guesthouse features warm wooden walls and high ceilings, creating a cozy ambiance. A dining table with fresh roses sits on a wooden surface, while a well-equipped kitchen and an inviting sitting area are visible, complemented by natural light from the doorway.

Guesthouse in Eagle Point

4.91 out of 5 average rating, 321 reviews

Free Bird Ranch-Oregon Adventures Home Base

Crater Lake National Park is NOT closed, only the 2 mile walking path that leads to a boat ramp is closed for renovation. The rim drive is open all year round. Find peace and serenity in the Rogue Valley. Enjoy stunning valley, Cascade views, and sunsets from the deck. Minutes from vineyards, a short drive to Table Rocks (10 min) & the Rogue River (2 min). On the way to Crater Lake (50 min) & near Ashland skiing (45 min). Unwind in comfort after your adventures. Long-term inquiries welcome!

Guest favorite

A bright bedroom features a spacious bed with neutral bedding layered with a green throw. Large windows allow natural light to fill the room, complemented by a ceiling fan. A wall-mounted TV is positioned above a modern desk area with a computer.

Home in Shady Cove

4.93 out of 5 average rating, 104 reviews

The Shady Knoll

Relax and Unwind at this peaceful retreat. Near the Rogue River, this beautiful property is over an acre w/ lush green grass all around. Updated home w/ nice features & a notable primary bedroom&bathroom. Both rooms have work spaces & home has excellent wifi ~ 200mbps. Start your mornings with a delicious nespresso and enjoy the bird chirping outside. Outdoor oasis with comfy patio seating and outdoor dining area, backyard lights, fire pit, BBQ, and yard games. Close to TONS of outdoor fun!

Top guest favorite

The tranquil Upper Rogue River is captured, reflecting a vibrant blue sky. Lush green trees line the riverbank, with a distant view of a cottage nestled among the foliage, creating a serene and natural setting.

Cottage in Shady Cove

4.99 out of 5 average rating, 121 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.

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, 123 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!

Top guest favorite

The entrance pathway is lined with blooming purple irises, leading to a rustic cabin framed by vibrant green trees. A gravel drive meanders toward the building, partly obscured by lush foliage, with hints of a paddock visible in the background.

Ranch in Prospect

4.97 out of 5 average rating, 693 reviews

Crater Lake "Bunkhouse" on 100 acre ranch & trails

The private Ranch "BunkHouse" sits on a meadow near the horse paddocks & barn w/ views of valley, mountains, & access to gorgeous woodsy hiking trails. The "BunkHouse" retains the rustic charm of the original Bunkhouse but inside it enjoys new comfort, style & amenities! It's an up-dated large (20X40) open studio/bedrm w/ kitchenette & private bath (clawfoot shower/tub). A king-sized bed & extra twin bed if you have a 3rd traveling w/you, all in one room. Also, TV and WiFi

Top guest favorite

A spacious dining area features a large wooden table surrounded by six chairs. Natural light fills the room through two large glass doors that open to a deck with forest views. A bowl sits at the center of the table, adding a welcoming touch.

Home in Gold Hill

4.99 out of 5 average rating, 193 reviews

Hygge Hideaway. A home for rest and adventure

In Scandinavia, "hygge" represents contentment & coziness. Settle into this sun-soaked, mountain-side, madrone forest & valley view home for relaxation on the deck, wine by the fire, & mineral baths. This solar powered home has easy access to outdoor adventures. Options include Laundry, Wood Stove (fire logs avail $), & fully equipped Kitchen. Whether you're looking for a getaway, family event, road stop, or retreat - you're welcome here. Pets require PRE-APPROVAL.

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, 224 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.