
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.

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.

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

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.

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.

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.

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.

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

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.

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.

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.

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.

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**
Popular amenities for Southern Oregon holiday homes
Family-Friendly holiday homes

Mood in Wood with private serenity in the city

Coastal Shenanigans!

Bar Run Golf House With pool

Newly Constructed Apartment in Prime Location!

Oceanfront Home, Lighthouse, Beach Access, Sunsets

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

Running W Ranch home on the Sprague River.

The Crows Nest + Complimentary Farm Breakfast
Holiday home rentals with a patio

Dorothy's place

Cozy 1 bedroom cottage with free parking on site

Beautiful Oceanfront w/ Private Beach Access

Central Modern Escape - Walk to SHARC & Village!

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

Peaceful Relaxing Retreat

The Crows Nest + Complimentary Farm Breakfast

Be In The ♥️ Of Bend, 3🛏+AC+5min Walk Drake P/DT
Holiday home rentals with a washing machine and dryer

Walk to the Deschutes, 8 SHARC passes DCCA#824522

Coastal Getaway | 30% OFF Monthly Stay

2BR Lakeside Home in Town walk to Lake near Dunes

Après-ski Haus 20 mins to MTB w/ FP & Dog friendly

New Prime Location Home In The Heart Of Eugene!!
Destinations to explore
- Northern California Holiday rentals
- Gold Country Holiday rentals
- Eastern Oregon Holiday rentals
- Portland Holiday rentals
- Willamette Valley Holiday rentals
- Willamette River Holiday rentals
- Wine Country Holiday rentals
- South Lake Tahoe Holiday rentals
- Sacramento Holiday rentals
- Sacramento River Holiday rentals
- Deschutes River Holiday rentals
- Reno Holiday rentals
- Loft rentals Southern Oregon
- Villa rentals Southern Oregon
- Rentals with outdoor seating Southern Oregon
- House rentals Southern Oregon
- Family-friendly rentals Southern Oregon
- Rentals with an EV charger Southern Oregon
- Chalet rentals Southern Oregon
- Luxury rentals Southern Oregon
- Beachfront rentals Southern Oregon
- Serviced apartment rentals Southern Oregon
- Waterfront rentals Southern Oregon
- Rentals with a sauna Southern Oregon
- Cabin rentals Southern Oregon
- Rentals with a kayak Southern Oregon
- Rentals with beach access Southern Oregon
- RV rentals Southern Oregon
- Rentals with a fire pit Southern Oregon
- Bed and breakfasts Southern Oregon
- Rentals with a fireplace Southern Oregon
- Apartment rentals Southern Oregon
- Yurt rentals Southern Oregon
- Rentals with lake access Southern Oregon
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- Fitness-friendly rentals Southern Oregon
- Rentals with a patio Southern Oregon
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- Townhouse rentals Southern Oregon
- Guesthouse rentals Southern Oregon
- Boutique hotels Southern Oregon
- Rentals with pools Southern Oregon
- Ski-in/ski-out rentals Southern Oregon
- Rentals with an accessible height toilet Southern Oregon
- Rentals with breakfast Southern Oregon
- Private suite rentals Southern Oregon
- Pet-friendly rentals Southern Oregon
- Hotel rooms Southern Oregon
- Rentals with a hot tub Southern Oregon
- Rentals with a washing machine and dryer Southern Oregon
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- Holiday home rentals Oregon
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