Deals on vacations and trips to Trail

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Trail flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
My Place Hotel-Medford OR

My Place Hotel-Medford OR

3 out of 5
Price was $1,115, price is now $1,028 per person
$1,028
per person
Sep 21 - Sep 25
found 19 hours ago
Roundtrip non-stop flight included
Sioux Falls (FSD) to Medford (MFR)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. A snack bar/deli, a picnic area, and a computer station are also on offer.
The Bard's Inn, BW Signature Collection by Best Western

The Bard's Inn, BW Signature Collection by Best Western

2.5 out of 5
Historic Downtown District
Price was $1,342, price is now $1,212 per person
$1,212
per person
Sep 21 - Sep 25
found 19 hours ago
Roundtrip non-stop flight included
Sioux Falls (FSD) to Medford (MFR)
A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A 24-hour business center, a garden, and luggage storage are also on offer.
Prospero's Flagship Inn

Prospero's Flagship Inn

2.5 out of 5
Price was $1,158, price is now $1,058 per person
$1,058
per person
Sep 21 - Sep 25
found 19 hours ago
Roundtrip non-stop flight included
Sioux Falls (FSD) to Medford (MFR)
A restaurant and a seasonal outdoor pool are featured at this hotel. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Grandview of Ashland

Grandview of Ashland

3 out of 5
Price was $1,958, price is now $1,800 per person
$1,800
per person
Sep 21 - Sep 25
found 19 hours ago
Roundtrip non-stop flight included
Sioux Falls (FSD) to Medford (MFR)
This vacation home features a hot tub and a sauna. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, a picnic area, and laundry facilities are also on offer.
Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges

4 out of 5
Price was $1,774, price is now $1,635 per person
$1,635
per person
Sep 21 - Sep 25
found 19 hours ago
Roundtrip non-stop flight included
Sioux Falls (FSD) to Medford (MFR)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a picnic area, and barbecue grills are also on offer.

Top Trail hotels deals

*Riverfront* "Cabin on The Rogue", Gateway to Crater Lake! Sleeps 2-4

*Riverfront* "Cabin on The Rogue", Gateway to Crater Lake! Sleeps 2-4

Trail OR
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This cabin features a garden, laundry facilities, and barbecue grills.
Romantic & private cabin on Rogue River, 1 hr from Crater Lake

Romantic & private cabin on Rogue River, 1 hr from Crater Lake

Trail OR
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This cabin features a hot tub and a sauna. Barbecue grills are provided for your convenience.
"Home on The Rogue" - Gateway to Crater Lake!

"Home on The Rogue" - Gateway to Crater Lake!

Trail OR
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This vacation home featured laundry facilities and barbecue grills.
Fish, Raft & Hike: Southwest OR Couple’s Retreat!

Fish, Raft & Hike: Southwest OR Couple’s Retreat!

Trail OR
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This apartment includes a garden and barbecue grills.
'RIVER HAVEN' is a serene riverside cabin on the Rogue River

'RIVER HAVEN' is a serene riverside cabin on the Rogue River

Trail OR
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This vacation home includes a garden and laundry facilities.
Cozy retreat on 3 acres near Lost Creek Lake. Pet Friendly

Cozy retreat on 3 acres near Lost Creek Lake. Pet Friendly

Trail OR
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This cabin features laundry facilities.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Trail attractions

Lost Creek Park

9.2/10 (5 reviews)
Explore the great outdoors at Lost Creek Park, a lovely green space in Trail. Wander the riverfront in this relaxing area.
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Frequently asked questions

How much are vacation packages to Trail?
With a Travelocity vacation package, you can live it up in Trail for as little as $1,028. Hotels, flights and experiences — we have it all. You'll save loads just by combining your bookings together. And with everything taken care of before leaving, you won't have to worry about a thing.
How long should my Trail vacation be?
Typically, 2 nights is how long most people spend discovering the attractions of Trail. Wondering if you'll have sufficient time to fit in everything on your to-do list? Stay a few extra nights so you don't miss a thing.
Where can I get the best vacation package deals for Trail?
Travelocity is the place to go to score an amazing Trail package deal. Choose from 400 airlines and 1,000,000 properties worldwide and create a vacation package that fits your style. With so many options, now's the time to book your next exciting getaway.
Why should I book my Trail vacation package with Travelocity?
We have destinations and experiences for every kind of traveler, superb service and customer support available 24/7. On top of that, we'll match any lower price you come across with our Price Match Guarantee.
Will I save money on my Trail car rental if I bundle it with a hotel or flight?
Sure can. And our Trail vacation packages are the best way to do it. With just a few clicks you can save money and time by booking everything in one place. Collect the keys to your rental car and do your vacation your way. Need to fill your itinerary? Add some activities or experiences to your package and make savings on those too.
Which airport is best for Trail?
Rogue Valley Intl. Airport (MFR), the major terminal in Trail, is where you'll stroll through arrivals. You'll find it 20 mi south of the center of town.
What is there to do in Trail?
While veering off the tourist trail can be rewarding, you really shouldn't miss the well-known sights that make a place famous. Joseph H Stewart State Park and Cole M. Rivers Hatchery are just two of them in Trail.
Where should I stay when visiting Trail?
If you're looking for a place to spend your nights, have a look at the Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!. It's the top pick for many visitors.

Photos of local treasures

Browse Trail vacation photos for more inspiration

A mountain range with a prominent peak, dense forest, and a clear sky.
A forest trail with moss-covered rocks and dense green foliage.
A forested trail with dense greenery and tall trees.
A forested trail with dense ferns and tall trees.
A serene pond surrounded by large evergreen trees, a stone bridge, and a grassy area with a tent.