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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Top 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, 80 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 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, 35 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 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, 116 reviews

Cheerful 2-Bedroom, 2 Bath Home with Hot Tub

2 BR and 2 Bath, Newly Remodeled Home w/Hot Tub Autzen Stadium-Hayward Field-University of Oregon are approx.15 min and 5 miles away Eugene Airport is 10 min The Cheerful Cottage is a charming, sparkly clean home with hardwood floors; fully stocked kitchen; tasteful and comfortable furnishings and art! The hot tub is well maintained and located directly behind the cottage by the deck for easy access. Across the street is a lovely park and recreation center with an indoor pool and sauna.

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, 90 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.

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, 234 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.

Superhost
A spacious living area features a wood-burning fireplace set against a stone backdrop, complemented by a comfortable sofa and armchair. Natural light streams through large windows with shades, while a glass door leads to an outdoor seating area surrounded by trees.
Holiday home in Bend
4.85 out of 5 average rating, 26 reviews

Beautiful Resort Home- Pools, Hot Tub, Hiking, Ski

This amazing resort is the ideal getaway. This is a 1 bed 1 bath with a murphy bed and sofa bed and a single person fold out bed. 3 heated pools, hot tubs, fitness center, sauna, volleyball, and an onsite restaurant and bar. Just minutes to downtown Bend where you'll find a large array of shops, breweries, restaurants, and dozens of outdoor activities. This is the closest lodging you can get to Mt Bachelor. Just a short walk to the Deschutes River for river rafting, and paddle board.

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
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, 107 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**

Superhost
Holiday home in North Bend
4.78 out of 5 average rating, 78 reviews

Quiet coastal lifestyle | Convenient Location

Enjoy a quiet coastal lifestyle in a convenient Coos Bay–North Bend location near beaches, Oregon Dunes, dining, shops, Hwy 101, fishing, golf, and local attractions. Features include fast WiFi, easy self check-in/out, a full kitchen, ample parking, comfortable living space, and all upgraded memory foam mattresses.Great for work trips, family visits, dune adventures, road trips, and longer stays. Monthly discounts available.

Top Guest favourite
A spacious home is set against a backdrop of rolling hills, with a well-maintained yard featuring a mix of decorative stones and scattered shrubs. The house has large windows, allowing natural light to fill the interior, and a driveway that leads to a two-car garage.
Holiday home in Klamath Falls
4.93 out of 5 average rating, 73 reviews

Running Y Home, La Breeze in the Trees

Escape to sunny southern Oregon and enjoy the beauty of the outdoors while living like a local in this spacious home away from home. Located in gorgeous Running Y Ranch Resort, our guests have access to an indoor heated pool, spa, sauna, gym, tennis courts, the Ruddy Duck Restaurant, along with walking trails and Oregon's only Arnold Palmer Championship Golf Course.

Guest favourite
The exterior of the home features a welcoming entrance with a covered porch, surrounded by well-maintained landscaping. Smooth stone accents complement the wooden siding, while tall trees provide a natural backdrop. A gravel path leads up to the front door.
Holiday home in Bandon
5 out of 5 average rating, 46 reviews

5-Star Luxury Golf Retreat, 4 BDRMS (8 Queens)

This luxurious 4 BDRM (eight queens) is located on the doorstep of the world-renowned Bandon Dunes Golf Resort. Bandon Golf Villa was specifically designed for golf groups. If your group is larger than 8, please inquire about our other, almost identical home, Bandon Cottage, that also sleeps 8. We offer a 10% discount when both homes are rented by the same group.

Guest favourite
Holiday home in Shady Cove
4.96 out of 5 average rating, 69 reviews

Spectacular Cozy Cottage-3 BR, Creek, Wood Stove

Private location/outside patio and deck with BBQ. Peaceful setting and not street lights. Creek running through property. Quiet and serene with deer, foxes, birds and more. Additional bathroom located just outside the house! 1 pet per $50.00 and $25.00 each additional pet per stay.

Popular amenities for Southern Oregon holiday homes

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