Holiday rentals in Trail

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Top-rated holiday rentals in Trail

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Guest favourite

Yurt in Eagle Point

4.97 out of 5 average rating, 216 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!

29 Aug – 5 Sep

$180 SGD per night

Guest favourite

Guest house in Central Point

4.97 out of 5 average rating, 887 reviews

The West Wing Guest House

Located next to the main home, this detached guest house has a separate driveway/parking & hosts kitchen/living downstairs, with bedroom & bathroom upstairs. We are located 5 miles from Jacksonville, home of the Britt Festival & the best local wineries. About 20 minutes south is the town of Ashland, well known for the Shakespeare Festival. Downtown Central Point is just a mile away, where you will find the renowned Rogue Creamery. The house is also only 10 minutes from the Rogue Valley Airport.

30 Jun – 7 Jul

$100 SGD per night

Guest favourite

Home in Trail

4.95 out of 5 average rating, 210 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.

8–15 Oct

$587 SGD per night

Guest favourite

Tiny home in Shady Cove

4.95 out of 5 average rating, 199 reviews

Modern Tiny House w/ Hot Tub

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.

28 Sep – 5 Oct

$205 SGD per night

Guest favourite

Cabin in Prospect

4.98 out of 5 average rating, 259 reviews

The Get Away

Located in the beautiful Cascade Mountains is your "Get Away". The cabin is in the small town of Prospect. Just 40 min. to Crater Lake the cabin is complete with Central Heat/Air. Wood stove in Living Room (1 bun provided). The 900 sq. ft. cabin has 2 Bedrooms with Brand New Queen beds. Kitchen is fully stocked , New full size appliances. The Cabin sits back off the road with large front yard and has Horseshoe Pit & BBQ area with Picnic Table. Great for kids. Circular Driveway easy in & out.

18–25 Nov

$251 SGD per night

Guest favourite

Farm stay in Eagle Point

4.97 out of 5 average rating, 250 reviews

Shadow Bear Lodge - Crater Lake Home Base!

We designed an incredible comfy studio-the Shadow Bear Lodge, perfect for a weekend get away! On the path to CRATER LAKE (50 MIN TO ENTRANCE). This private space offers serenity, comfort and peace away from home. Enjoy beautiful SUNSETS and breath taking MOUNTAIN VIEWS of Table Rock and the Cascades on the private patio. The ROGUE RIVER is minutes away to enjoy fishing. Hiking is popular all around us with the table rocks only minutes away. Or enjoy a glass of wine from Vineyards near by!

1–8 Jun

$164 SGD per night

Guest favourite

Home in Trail

4.94 out of 5 average rating, 153 reviews

Eagle’s Nest Cottage | 40 mins to Crater Lake

Only 40 minutes to Crater Lake National Park! Nestled directly on the tranquil Rogue River, this riverfront retreat is the perfect spot for a cozy weekend away. Wake up to breathtaking views and lounge in the hammock as rafters, ducks, and fish drift by. Spend your days unplugging with family and enjoying outdoor activities like ping-pong, BBQing on the patio, or fishing off the dock (BYO poles!). In the evenings make a family meal and play board games or stream a movie on the Roku TV.

9–16 Oct

$324 SGD per night

Guest favourite

Guest house in Eagle Point

4.91 out of 5 average rating, 252 reviews

Free Bird Ranch-Oregon Summer Adventures Home Base

You’ll love the peace and serenity this private guest house brings! We are minutes away from beautiful vineyards. On the path- (50 minutes) to CRATER LAKE where you can sightsee, hike, and snow shoe. Go fishing on the Rogue 5 minutes away! Enjoy the deck that overlooks the views of the valley and view’s of the CASCADES AND TABLE ROCK which is a 5 minute drive to the entrance. Ashland ski resort is 45 minutes away. Come back to a relaxing and cozy home after your adventures in the Rogue!

19–26 Sep

$170 SGD per night

Guest favourite

Guest house in Gold Hill

4.92 out of 5 average rating, 165 reviews

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

13–20 Sep

$197 SGD per night

Guest favourite

Yurt in Grants Pass

4.97 out of 5 average rating, 654 reviews

Sunset View Yurt of Applegate Valley with HOT TUB!

NO CLEANING FEE! Large 24 ft yurt located on our 5 acre horse 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: ONLY well-behaved children are welcome. If your kids are destructive or abusive, you will be asked to leave.

30 Mar – 6 Apr

$137 SGD per night

Guest favourite

Ranch in Prospect

4.97 out of 5 average rating, 597 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

11–18 Apr

$196 SGD per night

Guest favourite

Cabin in Grants Pass

4.98 out of 5 average rating, 413 reviews

The Cozy Cabin (with own private hot tub!)

Come relax and unwind in our cozy, peaceful cabin, tucked away in the beautiful hills of Grants Pass. With mountain views, stunning sunsets and a private wooded environment, it’s the perfect place to get away. Relax, read a good book, take a soak in the hot tub located just steps outside the master suite. The Cozy Cabin is filled with thoughtful touches, from throw blankets to high quality linens and towels, selected to create a welcoming and comfortable atmosphere.

14–21 Aug

$189 SGD per night