Holiday Homes in Southern Oregon

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Top-rated Holiday Homes in Southern Oregon

Guests agree: These holiday homes are highly rated for location, cleanliness and more.

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Guest favourite
A cozy living area is highlighted by a modern fireplace and a large television built into a white cabinetry. Soft seating is provided by a sectional sofa and accent chairs. Natural light flows through the large windows, illuminating the room's neutral decor.
Holiday home in Bend
4.82 out of 5 average rating, 98 reviews

Cozy 3-BR house w/ EV charger & trailer parking

Enjoy a peaceful retreat while staying at this centrally located home. Modernly decorated and cozy, with updated features to accommodate any and all guests. Conveniently located 2 blocks from Farewell Bend Park, 1 mile from Old Mill, 1.5 miles from Hayden Homes Amphitheater, and 20 minutes to Mt. Bachelor. Enjoy listening to concerts nearby, strolling along the river trails, getting a bite to eat at a number of tasty restaurants, or revel in a number of water activities on the Deschutes River.

Guest favourite
A spacious living area features a comfortable couch and armchairs, arranged around a central coffee table. A wood-burning stove and television are positioned against a textured stone wall. Large windows allow natural light to fill the room, with a view of the surrounding trees outside.
Holiday home in Bend
4.95 out of 5 average rating, 73 reviews

Dog friendly home, with A/C, near Deschutes River

Cozy home nestled in a grove of Aspen trees on a 1 acre lot. Sunriver Village, fishing, hiking, golfing, & more all within 10 min. Mt.Bachelor is a 30 min. drive. The master bedroom has a king size bed and it’s own bathroom. The other 2 bedrooms have queen beds. The couch in the living room has a queen pull out bed. While drinking your morning coffee or eating your evening dinner keep an eye out for the majestic wildlife. Peaceful quiet neighborhood. Pets allowed. Pet fee $15 per night per pet

Top Guest favourite
A charming single-story cottage is surrounded by well-maintained gardens, featuring a blend of green lawn and vibrant landscaping. The exterior showcases a mix of wood and siding with multiple windows, allowing natural light to brighten the interior. A paved path leads to the welcoming entryway.
Holiday home in Eugene
4.99 out of 5 average rating, 107 reviews

Cheerful 2-Bedroom, 2 Bath Home with Hot Tub

The Cheerful Cottage is a charming, sparkly clean home with hardwood oak floors; fully stocked kitchen; tasteful and comfortable furnishings and lots of art! The hot tub is well maintained and located directly behind the cottage next to an attached deck for easy access. Across the street is a lovely park and recreation center with an indoor pool and sauna. You are 10 minutes from the airport, blocks from the bike trail along the river, and a few miles to shopping centers and downtown Eugene.

Top Guest favourite
A newly constructed two-story building features a spacious exterior with a combination of wood and stone siding. The property boasts two large garage doors and an expansive gravel driveway. Surrounding pine trees provide a natural backdrop, creating a serene outdoor environment.
Holiday home in Crescent Lake
4.97 out of 5 average rating, 33 reviews

Newly Constructed Apartment in Prime Location!

Turnkey, newly constructed 1BR/1BA that sleeps 4. Includes primary BD w/a king bed, American Leather queen size sleeper sofa in living room, full BA w/tub & shower, full kitchen w/dishwasher, oven, microwave, coffee maker and more. Additional amenities include washer/dryer, Wi-Fi, TV, 40’ covered RV parking, outdoor balcony, & fire pit. Great location in Diamond Peaks. Enjoy easy access to lakes, hiking, biking, and snowmobile trails, Willamette Pass Ski Area, the PCT, & easy access to Hwy 58.

Top Guest favourite
A comfortable living area features a plush sofa and a reclining chair, arranged around a wooden coffee table. Natural light enters through the large windows, illuminating the stone fireplace and highlighting the warm wood paneling on the walls.
Holiday home in Gold Beach
4.97 out of 5 average rating, 35 reviews

Coastal Charm: SW Oregon home on 2+ quiet acres

Relax in this recently remodeled country home on the gorgeous Southern Oregon "Wild Rivers" Coast. This 3 bdm, 2 bth spacious home is situated on a quiet 2+ acre property, minutes away from the world famous Meyer's Creek Beach; one of the many State Parks in the area. In addition to ocean beaches, other area interests include amazing old growth forests, hiking trails, whitewater jetboat trips, ocean & river fishing, kayaking and much more! Located minutes from the Crook Point Wedding Venue.

Top Guest favourite
Two wooden chairs are positioned on a grassy area, facing a serene ocean view. In the distance, a lighthouse stands atop a rocky outcrop, surrounded by calm waters and a clear sky, providing a scenic backdrop.
Holiday home in Coos Bay
5 out of 5 average rating, 86 reviews

Oceanfront Home, Lighthouse, Beach Access, Sunsets

This private 1 BR/1BA apartment is the first floor of a 3-story house perched directly above the crashing Pacific Ocean waves. Only 200 feet away, there is private access to Lighthouse Beach, a ½ mile sandy beach between rocky headlands from the north or south, it is the closest thing to a private beach in Oregon. Enjoy amazing views of Gregory Point, the historic Cape Arago lighthouse on Chiefs' Island, and Lighthouse Beach from every room in this spectacularly located one bedroom apartment.

Top Guest favourite
A spacious green house is positioned amid lush greenery, framed by tall trees. The structure features large windows, allowing for abundant natural light. A lawn with small white flowers grows in the foreground, enhancing the inviting ambiance of the surrounding landscape.
Holiday home in Crescent City
4.93 out of 5 average rating, 46 reviews

Mid-century modern private hideaway in the woods.

Forget your worries on this 8.5 acres of serene redwoods, fir, and alder. Very private , yet close to town, the beach, and the river. Very spacious and clean 5 bedrooms gives everyone plenty of room to breathe . Play a round of disc golf or wander through our forest. Bbq on the deck , roast marshmallows at the fire pit, or just post up and watch a movie with the Family. Brookings Oregon is just 20 minutes to the north for great shopping. Surf South Beach or fish the clear water of the Smith

Guest favourite
The exterior of the vacation house is surrounded by lush greenery, showcasing a multi-level design with a spacious parking area. Stairs lead from the ground level to the entrance, which is framed by wooden railings and decks. A unique house number is displayed prominently.
Holiday home in Eugene
4.91 out of 5 average rating, 222 reviews

Mood in Wood with private serenity in the city

Nestled within the serene embrace of a picturesque landscape, Mood in Wood is a charming vacation house that promises a harmonious blend of modern luxury and natural beauty and offers a perfect escape from the bustling city life. Built by an artist and craftsman, the house has private entrance, nice open view, fully equipped kitchen, washer/dryer, double-bed futon(2 guests), WiFi, TV, close to scenic hiking trails, 20 min to winery farm to enjoy beautiful scenery of Willamette Valley.

Top Guest favourite
A charming wooden home is set against a backdrop of towering pine trees on a sprawling green lawn. A paved driveway curves around, leading to the garage. The soft hues of dawn reflect on the house, creating a serene rural landscape.
Holiday home in Chiloquin
4.98 out of 5 average rating, 41 reviews

Running W Ranch home on the Sprague River.

4 bedroom, 2.5 bath on a 460 acre working cattle ranch. 3 miles of the Sprague River. Beautiful decorated home overlooking the Sprague River. Our home has a open and spacious layout with a large covered deck to enjoy the view. Seating and a Gas BBQ. Room to roam. Ten miles out of the town of Chiloquin, Or. with abundance of relaxation, fishing and hunting in the area. Property is 18 miles from the Yamsi Ranch with guided fly fishing and 40 miles from beautiful Crater Lake.

Guest favourite
The exterior of a single-story home is featured, characterized by brown siding and a peaked roof. A wooden fence surrounds the front yard, and an American flag is displayed near the entrance. Soft evening light casts a warm glow over the inviting porch area.
Holiday home in Reedsport
4.93 out of 5 average rating, 107 reviews

Coastal Shenanigans!

This home is right in the middle of everything to do on the coast. Whether it's fishing the Umpqua river or the ocean, riding the dunes or shopping old town Florence. It's all 10- 30 minutes away. Go for a sunset walk on the beach! There is a nice little coffee shop close and some very good restaurants close by. There is free parking on the premises and on the street. Our driveway is 38' L x 20' W. If you are a boater, we have towels in the garage to wipe your boat off.

Superhost
A wooden deck is visible, featuring Adirondack chairs arranged around rustic stumps. The deck leads to a modern lodge set against a backdrop of dense greenery. Soft lighting fixtures are mounted on posts, enhancing the inviting entrance of the lodge.
Holiday home in Days Creek
4.9 out of 5 average rating, 147 reviews

The Lookout •Complimentary Farm Breakfast

⸻ The Lookout is a cozy cedar-lined studio with mountain and forest views. It features a full bathroom, kitchenette with essentials, and a comfy futon that folds out to sleep 2–4 guests. We provide a continental breakfast for your first morning: fruit, yogurt, oatmeal, croissants, and coffee. Set on a peaceful, chemical-free mountain ranch with pure spring water, you’ll enjoy stargazing, fresh air, privacy, and access to trails, creeks, and wild herbal plants.

Guest favourite
An indoor heated pool features inviting blue water and gently sloping steps. The surrounding space includes large windows allowing natural light, and two orange chairs are situated nearby for relaxation. Soft lighting enhances the area, creating a calm and welcoming environment.
Holiday home in Roseburg
4.98 out of 5 average rating, 105 reviews

Bar Run Golf House With pool

Bring the whole family to this great place with lots of room for fun. Indoor heated pool for year round swimming, hot tub on the deck with great views, large TV’s for watching the game, and just a short walk or golf cart ride to the newly opened Bar Run Golf and RV Resort. Surrounded by Umpqua valleys beautiful wine country. There is truly something here for everyone.**For parties or events you need permission first and there maybe an added charge**

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