Holiday rentals with a kayak in Jackson County

Mountain Ave House by WanderLodges

Welcome to this beautifully renovated turn of the century 3 bed/ 2 bath house in Ashland, OR. Featuring one king bed on the main floor and two king rooms upstairs, this functional layout is great for the whole group to spread out. Share the space with ease with a full bathroom on each level, open kitchen, and bright living room. At just a half mile from the downtown plaza, you’ll have the quiet solitude of suburban living while being a quick walk to restaurants, OSF, Lithia Park, & so much more!

Medford Oasis by Wineries, Airport & Crater Lake

Escape to your private Medford oasis—where comfort, convenience, and style come together. Perfectly located near top wineries, downtown, and Crater Lake, this home is ideal for relaxing getaways, long term work contracts in booming southern oregon, business trips, or weekend adventures. Dog-friendly home perfect for family road trips! Includes a large fenced dog run in the front yard so your pets can safely enjoy the space, It’s designed for everyone to relax, recharge, and feel right at home.

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!

The Shady Knoll | Crater Lake Basecamp | Hot Tub

Unwind on a fenced, gated acre just up from the Rogue River. Private year-round hot tub, fire pit, BBQ & string lights over a huge lawn. Updated home w/ king suite, spa-style rainfall shower, fast wifi (150+ Mbps) & 2 workspaces. Raft or fish world-class Chinook & steelhead water minutes away, Lost Creek Lake in 10, Crater Lake in about an hour, and tons of waterfalls and hikes under an hour. Mornings: Coffee on the deck. Nights: stargazing from the hot tub. Your Southern Oregon basecamp.

Upper Rogue Cool Creek Cottage

Relax with the whole family at this peaceful place to stay. COOL CREEK COTTAGE Welcoming Cool Creek Cottage is situated in the mountains of the Rogue River Siskiyou National Forest, along Oregon Highway 62 on the Rogue River, in the heart of Prospect Oregon, population 500. Located 45 miles from Medford, Oregon, and just 32 miles from, Crater Lake National Park South entrance, Prospect is the gateway to year-round natural beauty and recreational opportunities.

Ashland Lodge w/ Lake Views & Game Room Loft

Make memories that last a lifetime by booking this extravagant Ashland home, a 4-bedroom, 3-bath vacation rental with plenty of offer! The property boasts an impressive and spacious interior with a full kitchen and game room loft. Spend days barbecuing on the private patio enjoying spectacular views of the nearby lake or relaxing in the fresh mountain air. With natural surroundings and a prime location, this gem lets you have your pick of outdoor adventure!

Comfortable cozy private space, country setting!

We are just far enough out of town to enjoy the peaceful country feel. Perfect for your visit to this beautiful area! Turkey and deer cruise around our 3.5 acre property at their leisure! Lots of birds to listen to. The deck faces our seasonal creek and it's a nice comfortable private space to enjoy morning coffee or tea and a firepit at night under the stars. We have a quaint downtown with several restaurants. Easy access to I-5 for your adventures!

Custom Rogue River Cabin

Nestled in a secluded bend of the Rogue River just outside Gold Hill, Oregon, this custom 3-bedroom, 2-bath riverfront cabin feels like it was plucked straight out of a Pacific Northwest dream. As you wind down the private gravel drive, the home reveals itself: a handsome two-story cedar and river-rock cabin with a wrap-around 2,000 sq ft redwood deck that practically hangs over the rushing Rogue.

Applegate Riverfront Farmhouse. Winter Oasis

Welcome to your ultimate haven on the Applegate River! This top-notch rustic home is your basecamp for adventure, boasting 2,000 feet of riverfront and prime access to game trails. Whether you're tracking deer or casting a line, you'll find everything you need right here, with plenty of parking for your trailers and gear.

Owl Creek Cabin near Ashland OR

Looking to inspire creativity through nature? Check out this cozy cabin rental in a scenic forest near Ashland, Oregon, for your next writer's retreat.

Cabin near Crater Lake NP OR

Check out this rustic cabin, found just a hop, skip, and a jump from the stunning Crater Lake National Park, in Oregon.