Holiday rentals in Trail

Earthen home in Wolf Creek

4.88 out of 5 average rating, 375 reviews

The Nest Eco-Retreat Cob Cottage

A unique stay in an earth-sculpted cottage on 46 beautiful, wild wooded acres near the scenic Rogue River, just 5 miles off I-5. Complete with kitchenette, comfy bed, wood-stove, composter outhouse, heated outdoor shower on the back deck and private space to rest and rejuvenate. Want to bring a canine companion or two? The Nest is fully fenced with plenty of space for your pooch to explore off-leash, while staying safely enclosed. If a truly rustic retreat is what you're after, The Nest is it.

4.9 out of 5 average rating, 102 reviews

Home in Trail

"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

4.96 out of 5 average rating, 247 reviews

Yurt in Eagle Point

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

Home in Trail

4.95 out of 5 average rating, 226 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.

4.96 out of 5 average rating, 298 reviews

Tiny home in Shady Cove

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.

Superhost

Guest house in Eagle Point

4.9 out of 5 average rating, 309 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!

4.85 out of 5 average rating, 39 reviews

Guest house in Trail

Adorable 1 bedroom cottage on the river.

Take it easy at this unique and tranquil getaway on the Rogue River. Situated just 35 minutes from the Medford Airport and just over an hour to Crater Lake, which is a must see. Shady Cove is only a few minutes away and offers restaurants, grocery stores, rafting, guided fishing trips, etc. Relax with a glass of wine while you enjoy the views on the deck overlooking the river. There is plenty of room to enjoy a game of horseshoes, corn hole, ladder ball or relaxing with your favorite book.

4.99 out of 5 average rating, 115 reviews

Cottage in Shady Cove

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.

4.92 out of 5 average rating, 212 reviews

Guest suite in Gold Hill

Octagon Studio / Beautiful Rogue River property

Park-like setting; Rogue River premier property. Use the Octagon Studio to enjoy the luxuries of the property or as a home base for the many amenities in the Rogue Valley. Relax by the pool or soak in the hot tub, lounge on the rivers beach, watch the river go by from the floating dock(seasonal) swing between two large pine trees, have an evening fire in the fire pit, catch trout for a morning breakfast, watch the abundant wildlife. Relaxing, romantic, fun, resort quality....enjoy

4.96 out of 5 average rating, 113 reviews

Home in Prospect

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!

4.97 out of 5 average rating, 672 reviews

Ranch in Prospect

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

4.97 out of 5 average rating, 217 reviews

Cabin in Trail

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.

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Other great holiday rentals in Trail

5 out of 5 average rating, 4 reviews

Raft & Reel Riverfront Getaway

ChristopherRating, 5 stars2 weeks ago

Colin and his team were incredible hosts. I had more questions than most travelers probably do, but every single one was answered within minutes—despite the Airbnb site saying the average response time was nine hours. That level of responsiveness was impressive on its own, but what truly stood out was the genuine kindness and compassion they showed. We were in Shady Cove under difficult circumstances due to a family loss, and Colin’s team went above and beyond to check in on us and make sure we had everything we needed. It didn’t feel like staying in a rental—it felt like staying with family. As for the property itself absolutely stunning. The home sits right on the Rogue River, and the bay window view is mesmerizing. It’s the kind of spot you could spend hours just watching the water go by. The yard is beautifully landscaped—truly magazine-worthy—and adds to the peaceful, restorative atmosphere. This was one of the warmest, most thoughtful experiences I’ve ever had through Airbnb.

Cabin in Shady Cove

4.86 out of 5 average rating, 72 reviews

A Cozy Cabin Nestled Amongst the Trees

IsabelleRating, 5 stars12 months ago

This property is incredibly beautiful, and the host was very welcoming, friendly and helpful even with my large dog which can be hard to find. I would definitely stay here again.

Home in Trail

5 out of 5 average rating, 3 reviews

Lovely eclectic Riverhouse on the Rogue River.

TorieRating, 5 stars35 months ago

We had a great stay at Carolin’s place and would definitely stay here again. The house and property are beautiful, well equipped, and just steps away from the river. Carolin was an amazing host, as she would periodically check in with us via text and email to see if there was anything we needed. Carolin, thanks for everything!

4.94 out of 5 average rating, 82 reviews

The Shady Knoll

BrandonRating, 5 stars4 days ago

The communication from host was amazing. The location is amazing. The bed was amazing. The house was amazing. Thank you!

5 out of 5 average rating, 7 reviews

Peaceful Retreat on the Rogue River

HeidiRating, 5 stars2 days ago

We had such an amazing time staying at this beautiful and serene House on the Rogue! The house is super clean, comfortable and well-stocked with amenities. Shady Cove is an awesome little fishing town and everyone is super friendly. Whether you’re staying to fish the Rogue, visit Crater Lake, reconnect with family and nature, or simply spend some solo time; this is THE place to stay! Nic and Ellen are excellent hosts! You won’t regret staying here. We will most definitely be back!

5 out of 5 average rating, 3 reviews

Rogue River Retreat

CrystalRating, 5 stars11 months ago

Steve was so accommodating to me and my friends as we were arriving way later than the deadline for check-in. The place was very spacious, and we had a comfortable stay before heading out to Crater Lake!

5 out of 5 average rating, 5 reviews

Shady Gem

ShellyRating, 5 stars9 months ago

We are a 3 person group to visit Crater Lake during Labor Day long weekend and book the house in last minutes. Michael’s house is big, clean and well-equipped with all we need. It’s around 20 minutes drive to Lost Creek Lake and around 1 hour drive to South Gate of Crater Lake National Park. There is also a grocery store near the house(around 5 minutes walk). The instruction to get into the house is clear and easy. Michael also provides a welcome book to introduce nearby sightseeing spots and things to do. My friends and I all enjoy our 2 nights stay at Michael’s house and definitely recommend people who couldn’t book the a place to stay at Crater Lake NP to stay at Michael’s house.