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12 Large Vacation Rentals That Sleep 30 or More in Oregon

Oregon can best be described as otherworldly, mystical, enchanting, and captivating. From the striking coastal landscape to the vibrant cities that live further inland, there aren’t many U.S. vacation destinations that out-to this West Coast state. From housing the deepest lake in the United States to hosting intriguing events such as mushroom festivals, your inner adventurist will take you down endless roads of wanderlust. What better place to bring the family for a reunion, or to connect with coworkers on a retreat? We’ve gathered rentals, that can host up to 30 guests in this vacation wonderland.

12 Oceanfront, Dog-Friendly Cottages 12 oceanfront, dog-friendly cottages
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12 Oceanfront, Dog-Friendly Cottages

A compilation of cottages is lumped together to create a haven for a family retreat. The listing in its entirety can sleep up to 48 people! Another huge bonus, up to 10 dogs are allowed as well, at a $20 additional fee for each, each night. On the interior of the cottages, everything feels slightly rustic, and extremely down to earth. Rooms feature cozy wood paneling, and one of the living spaces has a large brick fireplace that serves as a focal point. Make your way down to the striking Oregon coast beaches, within reach of these conveniently located spaces.

Upscale & Newly Remodeled Oceanfront Inn Upscale & newly remodeled oceanfront inn
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Upscale & Newly Remodeled Oceanfront Inn

Time to get glam with the fam! A total of 11 separate units are combined within this one listing, and can accommodate up to 54 people! Each family can experience privacy while being right next door to beloved family members. Overall, the design is very clean, and beach chic. Bed frames, to the kitchen cabinets, feature naturalistic wood, and an airy color palette is used throughout. Massive windows bring in the coastal views as if they were a picture hanging on the wall. Guests will also have access to a private stairway that leads to the sand and water. Pets are welcome as well.

Enormous, Dog-Friendly Home Enormous, renovated, dog-friendly home
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Enormous, Dog-Friendly Home

Wooden floors, picture windows with ocean views, and bunkbeds – sold yet? Each level of the large home features it’s own kitchen, living space, and washer and dryer. A total of 14 bedrooms can accommodate up to 40 guests. So just get the family there, and enjoy sea breezes from the patio, venture out to see a movie together at the nearby cinema, and do lots of eating out at local eateries.

Deschutes Riverfront Retreat on 3 Acres with Dock Deschutes Riverfront Retreat on 3 Acres with Dock
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Deschutes Riverfront Retreat on 3 Acres with Dock

The Deschutes River is one of the countless gems located in Oregon. Rushing blue waters are gorgeous in both winter or summer. When staying at this location, you will have 3 acres among the water. The property consists of both a huge lodge, and a five-bedroom cottage, which can ultimately sleep 30 guests, and both of which display contemporary rustic decor. The hosts offer an abundance of outdoor games such as croquet, disco, and so on. It’s all about being outside, and there’s a hot tub available as well. In the winter, families can enjoy a private sledding hill and marshmallow roasting.

Large Family-Friendly House Enormous, family-friendly house
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Large Family-Friendly House

Can’t you just imagine the family working together in that huge galley kitchen, to prep a wonderful meal to enjoy at the stunning and enormous dining table? Sitting in an open environment that can be seen from the second floor, the space is simply dazzling. The home can sleep 40 guests while being able to entertain them as well! When not exploring the area, you can stay in and play pool or ping-pong, while lounging in the hot tub, or making s’mores around the fire pit. In the reviews, guests noted that the location was great, being near shops, restaurants, and other local attractions.

Scholls Valley Lodge Scholls Valley Lodge
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Scholls Valley Lodge

Stay close to both Portland and the coast while feeling relatively secluded in a serene environment. Inside the lodge, there is an abundance of intricate details, that are also extremely meaningful. Think cultural wood carvings, slate floors that were upcycled after the building of a temple, and an overall home-like atmosphere. Up to 32 guests can stay within the structure, which also features a lower apartment. Spend evenings watching the sunset, from the porch, which also overlooks a vineyard. We’ll toast to that.

Seven Separate Cozy Cottages, Minutes to Beach Seven separate cozy cottages - minutes to beach
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Seven Separate Cozy Cottages, Minutes to Beach

Seven cottages are clustered together, in their own cute little nook, mere minutes away from Rockaway Beach. Each little abode has a fresh and vibrant appeal, while also offering comfortable sleeping arrangements, and kitchenettes. Either 27 adults, or 41 people when accounting for kids, can call this little haven home for their vacation. Restaurants and shops are also within walking distance, so just park your car on the street, and enjoy days of strolling. Dogs are welcome in the cottages but will be an additional $20 a night for each.

Taylor Creek Lodge, Entire Facility Taylor Creek Lodge, Entire Facility
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Taylor Creek Lodge, Entire Facility

Stay on 35 forested acres of Oregon beauty! Guests will also find a majestic waterfall on the property, creating the feel of a true fairy forest. Much of the accommodations are in the lodge itself, but there is also a lovely treehouse that is available to four additional guests. We have a feeling all of the kids are going to want to meander up that magical entryway. Local ingredients are used to prepare breakfast in the morning, which will be a great start to a day of adventure, whether that be in the surrounding area, or just playing on the trampoline, or sitting around the fire pits.

26,000 Square Foot Villa on 46 Acres in Heart of Oregon Wine Country 26,000 sqft Villa on 46 acres in the heart of Oregon Wine Country
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26,000 Square Foot Villa on 46 Acres in Heart of Oregon Wine Country

Escape to Kensington Palace—eh, we mean this jaw-dropping mansion in Oregon wine country! Dripping with ornate attributes, rooms feature intricate tiling, chandeliers, while other parts of the home welcome guests into dramatic entryways, or onto manicured foliage surrounded patios. That’s a mouthful. Inspired by an Italian château, the breathtaking home wows with 11 bedrooms and show-stopping attributes, like the ballroom! Get your gowns ready. Prep elaborate meals in the chef’s kitchen, and spend extra time hanging out by the pool table or on the sports courts. All of the suites can accommodate up to 30 people and will have all the guests feeling like they are staying at a high-end spa.

7,000 Square Feet on 15 Acres 7k sq Ft. on 15 acres. Socially distance with style
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7,000 Square Feet on 15 Acres

So much of this rental is centered around stunning views, whether that be while soaking in the master bathroom tub, lounging in a bedroom, or sipping morning coffee in the sunroom, while reading through some of the property’s books. However, golf is also front and center, as the rental is near one of the United States’ top golf courses. The overall theme of this home feels cozy and rustic, while still having plenty of lavish upgrades. With 11 bedrooms, the informational section details the home can sleep up to 30 people, but the description mentions it accommodates 24 guests. Often working with local chefs, the hosts can arrange incredible catered meals.

Mt Hood Lodge, Perfect for Large Groups, Sleeps 48 Maximum Mt Hood Lodge: Perfect for Large Groups: Sleeps 48 Maximum-Two Deluxe Hot Tubs
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Mt Hood Lodge, Perfect for Large Groups, Sleeps 48 Maximum

How cool is it that you can book an entire lodge? The charming structure backs up against evergreen foliage while being close to the downtown amenities of Government Camp, Oregon. A shuttle stops at the museum across the street and will whisk ski enthusiasts to Timberline Resort. Inside, the structure can house a maximum of 48 guests, while having a comfortable yet low-key feel. Kids can hang out in the game room, eating snacks at the picnic table while playing rounds of ping-pong and pool. Two hot tubs serve as a wonderful gathering place at the end of the day as well.

A Perfect Location to Get Away A Perfect Location to Get Away
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A Perfect Location to Get Away

Want to explore Bend, but would rather avoid the hustle and bustle of crowds? Stay in La Pine, which is close to both the city, and Sunriver. This area of the United States is an outdoor playground, with an abundance of biking, skiing, hiking and kayaking opportunities, just to name a few. Presenting traditionally, this home is welcoming. With a variation of bedding, such as fold-down couches, day beds, and just regular ole beds, this dwelling can accommodate up to 30 people. When not out playing in the snow, or basking in the seemingly endless sunshine in the summer, everyone can enjoy the game room complete with a bar, or the outdoor hot tub with barbecue. Kombucha and grass-fed burgers anyone?

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