Holiday rentals with a kayak in Jackson County

Mountain Ave House

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!

Lanka Rose House by WanderLodges | Pet friendly!

This kid and pet friendly 3-bedroom, 1-bathroom home features a cozy living room with a wrap-around couch, a brand-new SMART TV & a fully equipped kitchen. The fully fenced yard includes a sandbox, making it a great outdoor play area. Inside, you'll find thoughtful amenities such as a pack-n-play, booster seat, kids' dishes, as well as a selection of books & toys to keep the little ones entertained. Other amenities include: -One queen room -One twin-over-full bunk bed room -One full size room

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!

Jaloma Woods, a forested retreat

This modern apartment is the former studio of the architect who designed and lives in the main house. It is on the second floor, over the garage. The home is located in a diverse forested area near the City of Rogue River, 20 miles from the Medford International Airport. Activities in the area include fishing and rafting on the Rogue river, wine tasting, ziplines, mountain biking & hiking, the Oregon Caves, Crater Lake National Park, the Shakespeare Festival in Ashland, and the Oregon coast.

2BR Pet-Friendly Retreat

This warm and inviting split floor plan offers a private 2-bedroom guest space within our home, ideal for couples, friends, or small families. • Bedroom 1: King bed with a full bathroom located right next to the room (not en-suite) • Bedroom 2: King bed with private en-suite bathroom, located on the opposite side of the house for added privacy Pet-friendly for well behaved & house trained dogs under 35 lbs (with prior approval). Please message me with details about your pet before booking.

Peach Street Inn | Downtown King Suite #3

Welcome to Suite 3 at Peach Street Inn by WanderLodges, centrally located in the heart of Medford and just 10 minutes to the airport! Enjoy the perfect blend of historic charm & modern comfort in this newly renovated suite. Relax in your spacious king-size bed, catch your favorite shows on the 65-inch Smart TV, and prepare meals in the full kitchen, complete with a cozy dining nook. Whether you're visiting Crater Lake, wine tasting, or exploring OSF in Ashland, your adventure starts here!

The Shady Knoll

Relax and Unwind at this peaceful retreat. Near the Rogue River, this beautiful property is over an acre w/ lush green grass all around. Updated home w/ nice features & a notable primary bedroom&bathroom. Both rooms have work spaces & home has excellent wifi ~ 200mbps. Start your mornings with a delicious nespresso and enjoy the bird chirping outside. Outdoor oasis with comfy patio seating and outdoor dining area, backyard lights, fire pit, BBQ, and yard games. Close to TONS of outdoor fun!

Peach Street Inn | Suite 4 | Downtown!

Welcome to Suite 4 at Peach Street Inn by WanderLodges! This cozy suite features 1 bedroom with both a queen and full bed, offering plenty of space for the whole family. Enjoy a brand new 65-inch Smart TV with access to all your favorite streaming services and a full kitchen, perfect for home-cooked meals. Conveniently located just minutes from downtown Medford and only 10 minutes from the airport, Peach Street Inn is the perfect home base for your next adventure in the Rogue Valley!

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!

Home on the River .

Take it easy at this unique and tranquil getaway home on the Rogue River. This home offers the most beautiful views of nature including fish and River otters . This one of a kind property has River access through a spiral stair case . Hang out by the fire pit on the balcony while enjoying the water views and the mesmerizing water sounds . This is the perfect place to create memories while fishing from the balcony or floating down the River .

Cozy 3BD Peaceful Retreat

This charming 3-bedroom, 2-bathroom house is the perfect retreat for families and friends. Nestled in a quiet, safe neighborhood, you'll enjoy peace and privacy just 15 minutes from the scenic mountain town of Ashland, Oregon. Come relax, recharge, and enjoy everything Southern Oregon has to offer in comfort and style.