Guesthouse holiday rentals in Southern Oregon

Ranch Cottage: Desert, Forest, Horses, Hot Tub

Beautiful guest cottage studio, with mountain views, in the southeast Bend neighborhood of Sundance. 15 minutes to town and 45 minutes to Mt. Bachelor ski area. This special ranch property is two blocks away from endless recreation in the Deschutes National Forest. (PLEASE NOTE; national forest access has been closed as of May 1, 2025-May 2026 for fuel reduction and restoration. blm trails are open) Includes one king Sleep Number bed and one queen Murphy bed. Private hot tub out the back door.

Hillside Cabin Retreat

Immerse yourself in nature at our serene tiny cabin in the woods. Secluded & private, yet minutes to the city & university! Enjoy your meals & watch the wildlife & sunsets from the large front deck. Relax & read a book in the hammock or watch the birds & enjoy the view from the terraced gardens. Fall asleep to the calls of the great horned owl! Large windows, well stocked kitchenette & outdoor shower create the perfect nature escape. Only 4 miles to Hayward Field, the U of O & Downtown Eugene!

Free Bird Ranch-Oregon Adventures Home Base

Crater Lake National Park is NOT closed, only the 2 mile walking path that leads to a boat ramp is closed for renovation. The rim drive is open all year round. Find peace and serenity in the Rogue Valley. Enjoy stunning valley, Cascade views, and sunsets from the deck. Minutes from vineyards, a short drive to Table Rocks (10 min) & the Rogue River (2 min). On the way to Crater Lake (50 min) & near Ashland skiing (45 min). Unwind in comfort after your adventures. Long-term inquiries welcome!

Oceanfront Luxury Guest House | King Bed Retreat

ALWAYS 5 STARS CLEAN, no pets, fresh. Come here, enjoy a luxurious, ultra private Guest House in garden. Safe, serene, green, gorgeous, meticulous grounds, private patio, big yard. NO CHORES FOR YOU! Contactless check-in. CalKing bed, luxury linens. Access to huge cliffside oceanfront deck & yard. Equipped gourmet kitchen. Personal gas BBQ, utensils, lawn & picnic area, safe, secure parking, estate lighting, washer, dryer, soap. Free fast dedicated WiFi. NOT SAFE FOR CHILDREN OPEN CLIFF.

TheBliss/2 blks to DT food/wine/no cleaning fee

Welcome to the Bliss! Crisp, clean, & ready for your arrival! Thoughtfully curated with high-end linnens & amenities, ensuring you feel pampered from the moment you arrive. Tucked in behind our main residence, this cozy, private, studio style, sanctuary provides a peaceful escape while keeping you close (2 blks down)to the vibrant energy of local restaurants, wineries, boutique shops, & the lively Sat farmers market. 9am-1pm Waterfalls, (1 hr)Crater lake (90 min)Wildlife safari (10 min)

La Petite Maison + Hot Tub

Welcome to La Petite Maison! Come take it easy at our unique and tranquil home away from home. Located in the heart of the Applegate with nearby wineries and exquisite views of the mountains. Our guest house is equipped with 1 master bedroom, full kitchen/bath, dining and living room with and private SPA on your very own deck! Only a 10 minute drive from the historic town of Jacksonville. At La Petite Maison you will have the peace and quiet of the country, and all that you may need.

Cozy Jacksonville Cottage

This cozy, rustic one bedroom cottage (325 sq. ft.) is just a 15 min. walk from downtown Jacksonville (3/4 mile) and 30 min. from Ashland. It has private parking, on the property. The owner is happy w/ pets in the cottage, but needs to know in advance that a pet is coming (maximum 35lbs) too. There isn't a full kitchen but it has a kitchenette with sink, fridge, microwave, hot plate and coffee maker, so cooking basics won't be a problem. Relax in the outside patio in the summer.

Most Spectacular Ocean Views - Studio East Upper

The Point provides the most amazing OMG view of the ocean and beach of the Oregon South Coast and possibly the world. You sit 100 feet above the water on our beach front property looking at the dolly dock pier and harbor to the east and Battle Rock and and a long stretch of beach to west. You can walk to the end of the property and enjoy your favorite beverage on the deck on the cliff above the water. You have truly magnificent views from our top-of-the-line studios.

BEE WELL Organic Spa Garden Studio w/ Hot Tub

This detached 420 sf apartment is perfect for 1-2 guests. Light-filled studio (from two solar tubes) on over 1/3 acre of flowers and fruit trees, three blocks from downtown, and craft foods and wine. Very close and easy access from the highway. Jacksonville is 6 miles, and the Ashland plaza is 17 miles. Southern OR is filled with playhouses, delicious wine, yummy local restaurants, scenic rivers, and miles of wilderness. Come enjoy! We celebrate diversity!