We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Trail Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    $180 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Trail area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 21 Rentals in Trail
    Sort by:
    Default
    The following rentals are within 40 kilometres of Trail.
    Medford
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Private Entrance. Clean. Comfortable.1 / 15
    (5)Excellent
    Jacksonville
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Private Mountain View Suite1 / 23
    (2)Excellent
    Jacksonville
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Red Blanket Cabin near Crater Lake National Park1 / 9
    (1)Excellent
    Prospect
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Washer
    • Central Heating
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Although the photos of the cabin are nice, they don't do justice to this spotlessly clean, thoughtfully decorated home.Decor is in the rustic style and tasteful. The kitchen is...
    See all reviews
    About this property
    The Red Blanket Cabin is a custom-built, two bedroom, one bath home located in the rural Cascade Mountains of Southern Oregon. It is nestled on a wooded acre near the town of Prospect. Peace, Quite, Beauty. Relaxation. Located 30 Miles from the South Entrance to Crater Lake. Our Cabin is the...
    View all property information
    Location Information
    Prospect, Oregon 97536
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Rogue River
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Waterfront
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Turn down the 300 foot driveway and enter a world of peace and tranquility. Our 1.5 acre property includes over 120 feet of riverfront where you can fish, float, read or just plain relax almost every day of the year. The two bedroom 2.5 bath home has a state of the art kitchen, infrared bar-b-q....
    View all property information
    Location Information
    Rogue River, Oregon 97525
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Rogue River
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Mountain Views
    • Patio
    • Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1940's Cottage has been updated to the highest standards! The Owner is a Designer and the Cottage sits in a park like setting, just a few minutes from the Rogue River and Del Rio Winery. The attention to detail never ends... a romantic claw foot tub... a pot belly stove, a full kitchen, an...
    View all property information
    Location Information
    Rogue River, Oregon 97525
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Rogue River
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Internet Access
    • Waterfront
    • Hot Tub
    • Grill
    • Mountain Views
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Turn down our 300 foot , tree lined driveway and enter into a new world. This is a one-of-a-kind property. An Oregonian Eden. This is a one bedroom one bath cottage with a full kitchen and living room. From your front deck you can relax, read a book and watch the river flow. And for those anglers...
    View all property information
    Location Information
    Rogue River, Oregon 97525
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Bella Chalet1 / 23
    (1)Excellent
    Shady Cove
    4 Bedrooms, 12 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Mountain Views
    • Washer
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 2016
    FABULOUS!!!This is a beautiful home that has it all...the house is amazing, it is beautifully decorated, its location is spectacular and it is stocked with everything! We had a...
    See all reviews
    About this property
    Magnificent Lot Home in Hilltop Setting in Shady Cove. Minutes walk to the Rogue River. All high-end amenities and details, including Gourmet Kitchen, 93 Jet Hot Tub, Soaking Tubs in all 4 Bedrooms, Private Apartment with Separate Entrance over 2 Car Garage. Gazebo, Fenced 2 Acre yard with...
    View all property information
    Location Information
    Shady Cove, Oregon 97539
    Holiday Rental House - 4 Bedrooms, 12 Bathrooms, Sleeps 10
    Make Enquiry
    Trail Creek Shady Cove 2br 2ba Woods Country Cabin1 / 60
    (5)Excellent
    Shady Cove
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    • Hot Tub
    • Washer
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 June 2017
    Nice place to stay. Fully furnished and Wi-Fi worked! Nice folks who were willing to give us input about the area.
    Reviewed 20 June 2017
    Staying at this cute Cabin in Trail Oregon, was a real treat. All amenities were there with plenty of outside chairs to sit in various shady spots along the creek. Our weather...
    See all reviews
    About this property
    You will love this beautiful 2 Bedroom (+Queen sleep sofa), two bath Cabin in the woods just off Hwy 227 on 700 feet of Trail Creek front! The Master bedroom has a huge pine log queen bed, charming antique library table writing area, lounge sofa and it's own lovely pine bathroom with a soaking...
    View all property information
    Location Information
    Shady Cove, Oregon 97541
    Cabin Holiday Rental - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Central Point
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just a short drive (or bike ride) to Downtown Jacksonville, this cottage has a queen bed in the master bedroom, full kitchen, full bathroom with shower stall and a washer and dryer in the walk-in closet. Beautiful property with wonderful mountain views. Also free-range chickens and goats live on...
    View all property information
    Location Information
    Central Point, Oregon 97502
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Save time - get the best Trail rentals sent straight to your email!
    Get the List
    Central Point
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Think Farmhouse meets Pottery Barn... A short drive (or bike-ride) to the center of Jacksonville. Close to many area wineries and the famed Britt Festival. This custom bunkhouse is part of a beautiful rural farm with goats and chickens on property. There is a daybed below and a twin sitting in the...
    View all property information
    Location Information
    Central Point, Oregon 97502
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Medford
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    No matter what your group's reason is for visiting Portland, this pair of dog-friendly downtown condos provide a combination of high-end comfort, amazing amenities, and easy access to sightseeing that your friends, family, and colleagues alike are sure to love! These upper-story downtown Portland...
    View all property information
    Location Information
    Medford, Oregon 97205
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Medford
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Patio
    • Private Garden
    • Washer
    • Wi-Fi
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The home is a Classic Craftsman, conveniently located in Downtown Medford... just minutes away from restaurants, coffee shops, retail stores, and both the Craterian and Holly Theaters. The home features a large Living Room with Fireplace, Dining Room, Kitchen, Two Bedrooms and a Full Bath. There...
    View all property information
    Location Information
    Medford, Oregon 97501
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
    Make Enquiry
    Waverly Cottage 1898 Historic Victorian1 / 34
    (1)Excellent
    Medford
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Balcony
    • Parking
    • Porch
    • Terrace
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 August 2017
    What a neat place. The cottage has very comfortable beds and offers you the convenience of having your own house while visiting Medford. My parents and I had to be in Medford...
    See all reviews
    About this property
    Waverly Cottage is a restored Victorian in Historic Downtown Medford. It is a Boutique Style Museum/B&B. Your stay at Waverly Cottage will be a step back in time. Enjoy a house full of antiques with many artifacts for the guests viewing pleasure. Waverly Cottage has just the right amount of modern...
    View all property information
    Location Information
    Medford, Oregon 97501
    Private Room - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Tina's Luxury Studio I1 / 7
    (3)Very good
    Medford
    Studio, 1 Bathroom, Sleeps 3 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Patio
    • Washer
    • Grill
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2016
    Traveling with 2 small dogs is not the easiest thing unless you find Tina's Luxury Studio in Medford Oregon. Then life is easy. This studio is comfortable and the hostess is...
    Reviewed 2 July 2016
    We stayed several nights and really enjoyed the quiet neighborhood. Overall the place was very comfortable for two. We cooked a lot of our own food and used the mini-refrig a...
    See all reviews
    About this property
    This is a very comfortable and home like experience in a quiet, residential neighborhood that is close to downtown and the I-5. It is a very well planned out 400 sq ft that takes advantage of the space and feels much larger than what it is. From the very nicely equipped kitchenette that can...
    View all property information
    Location Information
    Medford, Oregon 97501
    Condo/Apartment - 1 Bathroom, Sleeps 3
    Make Enquiry
    Tina's Luxury Studio II1 / 5
    (1)Excellent
    Medford
    Studio, 1 Bathroom, Sleeps 3 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Porch
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Washer
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 December 2016
    Very nice private second floor apartment! Excellent well equipped modern kitchen! The washer and dryer were a plus! Host Tina very accommodating to my allergy to fragrances...
    See all reviews
    About this property
    This is a very comfortable and home like experience in a quiet, residential neighborhood that is close to downtown and the I-5. This is an upstairs unit. It is a very well planned out 400 sq ft that takes advantage of the space and feels much larger than what it is. From the very nicely equipped...
    View all property information
    Location Information
    Medford, Oregon 97501
    Condo/Apartment - 1 Bathroom, Sleeps 3
    Make Enquiry
    Jacksonville
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    • Satellite TV
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely remodeled two-bedroom cottage in historic Jacksonville, Oregon. Walk to fantastic restaurants, quaint shopping, and beautiful parks. Perfect getaway to enjoy Jacksonville surrounded by lovely vineyards, fabulous wine, hiking and so much more! Relax and unwind in comfortable luxury!...
    View all property information
    Location Information
    Jacksonville, Oregon 97530
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Medford
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Patio
    • Private Garden
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious home with a huge back yard featuring a hot tub, patio, BBQ, and garden that you can help yourself to. Our place is close to restaurants and dining, the city center, lots of shopping, the mall, and Oregon's first and only In-N-Out! You’ll love our place because of the cozy feel, the...
    View all property information
    Location Information
    Medford, Oregon 97504
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Plymale Cottage, Bed & Biscotti1 / 14
    (1)Excellent
    Jacksonville
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Satellite TV
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 October 2016
    We stayed here and had a stay of a lifetime. Loni treated us like we knew her our entire life. She gave us a tour of upstairs on arrival and gave excellent advice on restaurants...
    See all reviews
    About this property
    Jacksonville, OR. combines the gentle ambiance of a designated Historic Town in a vibrant setting. The area features numerous wineries, tasting rooms, the famous Britt Music Festival, a summer long music performing arts festival and the incredible Rogue River for the avid fisherman. Award winning...
    View all property information
    Location Information
    Jacksonville, Oregon 97530
    Private Room - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Medford
    1 Bedroom, 1 Bathroom, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Grill
    • Washer
    • Mountain Views
    • Hot Tub
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The perfect place from which to explore the wonders of Southern Oregon and the Rogue Valley. Homestead Woodland Cottage is a spacious, modern bungalow nestled on 60-acres of private property in the Griffin Creek area between Medford and Jacksonville. It’s at the end of a country road (now paved),...
    View all property information
    Location Information
    Medford, Oregon 97501
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 8
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Center of Town!1 / 8
    (1)Terrible
    Jacksonville
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Parking
    • Satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ideally located within a block of first class grocery store, all shops and across the street from beautiful former Court House now becoming City Hall. This is a lovingly cared for Historic Home. Private exterior stairs lead to room with new kitchen counter plus microwave, convection oven and...
    View all property information
    Location Information
    Jacksonville, Oregon 97530
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 2
    Make Enquiry
    List your property
    Owner log in