Places to stay in Trail

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Top-rated places to stay in Trail

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Guest favorite

A modern kitchen and dining area is highlighted by a wooden table, set with a simple vase of flowers. Ample natural light enters through large windows, while sliding glass doors lead to an outdoor space. Stylish pendant lights provide functional illumination.

Guesthouse in Central Point

4.95 out of 5 average rating, 577 reviews

The Hygge Stay in the Heart of Southern Oregon

SarahRating, 5 stars3 weeks ago

We stopped off here on our way to Cali from Washington. It was very spacious for 2 adults, a toddler, and 2 pups. It was clean, had everything we needed like a full size fridge and freezer, coffee maker, microwave, and a/c in the living room. We were able to park in the driveway as we had all our gear in the back of our truck. As others mentioned it could get pretty warm in the rooms that don’t have a/c but the living room cooled off nicely and there were ceiling fans and other fans in both bedrooms. There’s an envelope for a $20 pet fee once you get there which I totally missed and didn’t have cash but was able to pay through a money app on my phone. We stayed on a weekend and heard nothing from the shop downstairs. Quiet and close to the freeway, we had a good stay!

Top guest favorite

A vibrant red maple tree is central in the garden, surrounded by lush greenery and colorful flowers. The scene is framed by wooden trellises and vines, with soft sunlight illuminating the landscaped area, creating a serene outdoor space.

Guesthouse in Medford

4.98 out of 5 average rating, 461 reviews

Comice Valley Inn With E V Charger

GerardRating, 5 stars1 month ago

Jim and Catherine were such amazing hosts. Their place was a little hidden getaway with all of their beautiful flowers and fruit trees to appreciate in the yard. Their place was exactly as described and the hospitality that they provide is second to none. I will certainly be back when it’s season for their apples and cherry and apricots are ready to be picked! Thank you guys for the stay and we look forward to coming back soon :)

Guest favorite

A rustic mountain cabin is nestled among tall evergreen trees, with a snow-covered landscape surrounding it. The structure features a brown wooden exterior and a dark green metal roof. Two garage doors are visible at the front, blending harmoniously with the natural setting.

Cabin in Ashland

5 out of 5 average rating, 16 reviews

Whispering Pines Cabin near Hyatt Lake

LaurieRating, 5 stars1 week ago

This is absolutely a gem accommodation especially if you are looking for a quiet, cabin-like feel, in the woods. The drive from Ashland was beautiful and we saw some wildlife. The cabin was perfect for our 2 families. The kids stayed upstairs in the loft area and the adults could have some quiet time on the main floor. The furniture was clean and comfortable. The patio was perfect for the early morning coffee while we waited for the kids to wake up. The host had fun puzzles and games that we enjoyed; we had brought a folding table. Having access to the garage was great so we could pack the cars without getting shoes dirty. We didn't have any issues but thought it would be good to mention. There is only 1 shower at this location. We made it work with 10 people taking quick showers & some of us had our own towels. The drive in is on a dirt road that had large puddles and over time they could get worse - our Subaru did ok.

Superhost

A living room is presented with a comfortable sofa and an accent chair. A television is mounted above a brick fireplace, while natural light streams through a large window, highlighting the greenery outside. A coffee table holds decorative items and magazines.

Home in Grants Pass

4.85 out of 5 average rating, 13 reviews

Sweet Valley Home with fully fenced backyard

RobertRating, 5 stars4 months ago

We had a great weekend! The house is beautiful, and cozy, and nestled in a very nice, quiet neighborhood. Very close to some good restaurants and stores. The host was very helpful and responsive, and even provided a list of activities to do in town. 5/5, will definitely stay again.

Top guest favorite

A mountain-side home is softly illuminated by warm outdoor lights, creating a serene atmosphere at dusk. The structure features a wooden deck with a staircase leading to the entrance, surrounded by lush trees that enhance the peaceful setting.

Home in Gold Hill

5 out of 5 average rating, 165 reviews

Hygge Hideaway. A home for rest and adventure

NicoleRating, 5 stars1 week ago

Hygge Hideaway was the perfect home for a low-key weekend full of relaxation, the home is decorated intentionally and SO cozy! Close to a few great wineries and enough places to eat without having to go far. Home with fully stocked with anything you could need to cook at home, the three of us had room to spread out and enjoy a beautiful tranquil spring weekend. We will be back if ever in the area again!

Top guest favorite

A modern fireplace is set within a white-brick structure, featuring an electric insert. Above the fireplace, a flat-screen television displays a scenic mountain landscape. A potted plant sits on the hearth, adding a touch of greenery to the space.

Home in Phoenix

4.96 out of 5 average rating, 82 reviews

Phoenix Rising (Sleeps 10)

JosephRating, 5 stars1 week ago

We had a wonderful time during our stay. The home is clean, spacious and boasted a big back yard. We were able to let the kids enjoy themselves outside without worry and had enough room for us all to sleep separately. The home and location (great proximity to our family and restaurants/stores) more than met our needs.

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Popular amenities for Trail places to stay

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Trail

Guest favorite

A private balcony features a round table accompanied by two white chairs, surrounded by autumn foliage. Leaves are scattered on the wooden floor, enhancing the outdoor experience. A tranquil view of trees captures the peaceful ambiance of the setting.

Home in Roseburg

4.83 out of 5 average rating, 288 reviews

Peaceful Paradise

TinaRating, 5 stars3 weeks ago

Thanks for hosting us for our short trip again!

Superhost

A circular stone fire pit area is surrounded by four wooden chairs, positioned for evening gatherings by the river. Soft illumination highlights the natural landscape, and the water reflects the twilight sky. Trees silhouette against the background, enhancing the serene atmosphere.

Home in Gold Hill

4.81 out of 5 average rating, 86 reviews

New - Down By The Rogue River - With Fire Pit

RachelRating, 5 stars3 weeks ago

The perfect sanctuary, we especially loved morning yoga on the patio, taking a dip in the river, hanging by the firepit. Great use of space, perfect for a small group of friends coming together and wanting to reconnect with nature. Can’t wait to come back!

Guest favorite

A private outdoor space is enclosed by a wooden fence, featuring a well-maintained grassy area. A wooden deck with two chairs is positioned beneath a shaded pergola, offering a peaceful spot for relaxation.

Home in Medford

4.95 out of 5 average rating, 112 reviews

Cute, pet friendly Guest House

AaronRating, 5 stars1 week ago

Wren was a very accommodating host and appreciate her place! Very comfortable bed and she had a pack n play and high chair already. So helpful. I recommend!

Guest favorite

An outdoor patio area features a built-in gas grill and a wraparound sectional seating arrangement. A circular fire pit is positioned nearby, with string lights hanging above the space. The surrounding wooden fence provides privacy, enhancing the cozy atmosphere.

Home in Medford

4.95 out of 5 average rating, 109 reviews

Voted Guest Favorite/Fast Wi-Fi/Hiking/Shopping.

KatieRating, 5 stars1 month ago

We had a last minute booking due to a plumbing issue with our original stay. Jessica was able To quickly get us in, was responsive and easy to work with. House was clean, had the amenities we needed and met our needs. Thank you!

Superhost

Farm stay in Rogue River

5 out of 5 average rating, 4 reviews

Groups Galore - 2 Spaces Retreat

MariaRating, 5 stars8 months ago

We absolutely loved our stay, thank you for the wonderful hospitality. The location is stunning, and so peaceful. We booked both apartments and it was perfect for our two families. The kids had a wonderful time in the beautiful pool every day. The farm fresh eggs and delicious coffee were a really lovely touch. The owners weren’t there but the biggest shout out goes to the groundskeeper who made our trip unforgettable. He went above and beyond, taking us to feed their pig and chickens, and showing us around the property. Thank you so much for all of the help during our stay!! Would definitely recommend and we’re hoping to be back!

Superhost

Tiny home in Medford

4.87 out of 5 average rating, 101 reviews

Broken Chair Ranch Bungalow

JakeRating, 5 stars1 month ago

Wonderful place to stay! Very peaceful and quiet. Lots of outdoor activities nearby too, which is why we stayed. Thank you so much!

Guest favorite

A modern kitchen area features sleek cabinetry, stainless steel appliances, and a streamlined island with a sink. A gas stove is positioned next to a microwave, while a large television is mounted on the wall. Natural light illuminates the space from nearby windows.

Camper/RV in Medford

5 out of 5 average rating, 17 reviews

New Pretty 44' 5th wheel Close!

JulieRating, 5 stars3 months ago

Michelle was great - check in was easy and exactly as described. This was a beautiful RV that seemed brand new - it had a sizable sitting area with electric reclining seats, a nice kitchen although I didn’t use it, a nice bed/bedroom, 2 toilets, and a nice shower! Michelle was responsive to questions via the message app - appreciated everything!

Superhost

The exterior of a light blue two-story house is surrounded by lush greenery and landscaping. A patio area with chairs is visible, along with well-maintained flower beds and a path leading through the garden, creating a serene outdoor space.

Home in Ashland

4.86 out of 5 average rating, 126 reviews

ABBOTT'S COTTAGES - Avocet

BurakRating, 5 stars6 months ago

Second time we stayed and pretty good place ,easy check in and clean warm walkable to the down town ,we enjoyed staying in this beautiful house ,thanks again

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Places to stay in Trail

Top-rated places to stay in Trail

Vacation rentals for every style

Popular amenities for Trail places to stay

Other great vacation rentals in Trail

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