Vacation rentals in Jefferson

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Top-rated vacation rentals in Jefferson

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Guest favorite

A charming yellow cottage with a white picket fence is showcased. A stylish mailboxes stands prominently, featuring a heart-shaped accent. The entrance is marked by a white door and steps leading up to the porch, surrounded by neatly arranged rose bushes.

Cottage in Newberg

4.95 out of 5 average rating, 150 reviews

The Valley Wine Cottage - Walk to Tasting Rooms

A cozy cottage in the heart of wine country. Walk to restaurants and tasting rooms and then relax on your own front porch or private back deck. The cottage has two bedrooms, both with Christopher Knight (tm) queen-sized beds for a great night's sleep and you can rent it as a one or two bedroom. Although we're walkable to many attractions, our street is tranquil and you'll enjoy sitting in a porch rocker with a glass of wine (in our varietal-correct Riedel glasses), or relaxing in the hammock.

Top guest favorite

A well-lit upper hallway leads to a cozy bedroom, featuring sloped ceilings. Artwork hangs on the wall, while a wooden chair and bedside table accompany a spacious bed adorned with light bedding. Natural light enters through an adjacent window.

Home in Sherwood

4.99 out of 5 average rating, 144 reviews

Old Town Retreat - Best place in Old Town Sherwood

At the gateway to wine country, our peaceful Old Town 1916 craftsman home brings historical charm with many amenities right in the heart of Old Town Sherwood. Sleeps 9 with 6 new beds, 2.5 remodeled baths and an open kitchen with gas range, everything you need for a few or many. Owner occupies the basement and rear separated dwelling on property. However, both the basement and rear dwelling are completely locked off and have entirely separate entrances. The best place in town.

Guest favorite

Guesthouse in Salem

4.96 out of 5 average rating, 126 reviews

Willamette Valley Luxury Chateau

Escape! Voted as one of the Salem’s luxurious places to stay. Treat yourself to “Ritz Salem” This will likely be one of the best Airbnb experience. This place is quiet and relaxing, as you enjoy the views, nature, and time alone. Great place to celebrate your birthday or anniversary with a quiet retreat, wine tasting, or visit nearby restaurants or nature. It offers king size bed, gas fireplace, large space, full couch, high ceilings, and fast internet. No contact self-check in.

Top guest favorite

A modern container home is nestled among trees, featuring a deck with railing and large windows. Soft outdoor lighting highlights the structure against a colorful twilight sky, while the surrounding bamboo adds a lush green contrast.

Shipping container in Oregon City

4.97 out of 5 average rating, 123 reviews

Sustainable Dream Container Getaway with a View

A private green-luxury container home inside a bamboo grove and lavender field overlooking a serene valley. This brand-new, single-level home features picture windows leading out to a quiet deck with sunset views every night. Situated in the heart of the Pacific Northwest between the mountain, lakes and coast - exploration, wine tasting and the best nature spots are just a short drive away. This private home can comfortably host couples or up to 3 people including the couch.

Superhost

A dining area is featured with a wooden table set for four, complemented by dark chairs. Bright views of the landscape are visible through three large windows, adorned with elegant floral arrangements and a simple table setting.

Guesthouse in Dundee

5 out of 5 average rating, 3 reviews

Red Hills Vacation | 3BR Hot Tub, Sauna & Views

Surrounded by breathtaking valley views, Red Hills Vacation is a serene retreat designed for those seeking both relaxation and adventure. This newly listed three-bedroom guest suite offers two full bathrooms, a private hot tub, and a sauna, making it the perfect getaway for couples, friends, families, and their four-legged companions. Located in the heart of Oregon’s Wine Country, this inviting escape provides a seamless blend of comfort, convenience, and natural beauty.

Guest favorite

An expansive gaming area is highlighted by vibrant blue and orange lighting. Rows of slot machines are positioned along a sweeping carpet, while colorful table games are visible in the background. Decorative lanterns suspend from the ceiling, enhancing the lively atmosphere.

Apartment in Willamina

4.94 out of 5 average rating, 68 reviews

Fort Hill Outpost

*1 MILE FROM SPIRIT MOUNTAIN CASINO!* Discover a hidden gem in Grand Ronde, with our remarkable Airbnb. This retreat is a perfect blend of relaxation and adventure. Within 10 miles, explore the captivating Drift Creek Falls, hike picturesque trails, or take a scenic drive along the breathtaking Oregon Coast. Immerse yourself in the local wineries, and exploring nearby museums. Unwind in your very own private oasis, your extraordinary vacation awaits!

Top guest favorite

A modern two-story home is showcased, featuring a combination of light and dark exterior materials. A garage door and front entryway are clearly visible. The surrounding landscape is neatly maintained, with lawn areas and a small garden near the entrance.

Home in Newberg

4.98 out of 5 average rating, 175 reviews

Villa Fontana: Modern, Wine-Country Comfort

Welcome! Enjoy a fresh, clean, retreat while you sip your way through Oregon's Wine Country. A modern home nestled amid local historic landmarks, you will be 6 blocks from the downtown Newberg strip and within a 5 mile radius of the closest wineries, making this home the perfect choice for accessibility. Enjoy complimentary Prosecco to toast your arrival and plan to cook meals that pair with your local wine purchases using our high-end appliances!

Top guest favorite

Home in Dayton

4.97 out of 5 average rating, 236 reviews

The Historic Dayton Wine House

Stay in one of the top rated vacation rentals located in the heart of the Willamette Valley wine country. This majestic 1885 Victorian style home sits prominently on the charming town square of Dayton, Oregon, 30 miles from Portland, a perfect location for winery exploring! The beds and linens are of high quality for a great nights sleep. The small details are not forgotten in this large home with plenty of room for everyone to spread out.

Top guest favorite

Guesthouse in Silverton

4.96 out of 5 average rating, 177 reviews

Buena Vista Guest House.

Take it easy at this tranquil getaway. Stay at our beautiful lavender farm located in the rolling hills 8 miles south of Silverton Oregon. Our guesthouse is a private, quiet, and cozy get-away that is surrounded by beautiful views of the Willamette Valley and coastal range. Enjoy the quiet evenings on the private patio enjoying the amazing views! Pictures do not do it justice. This is a hidden gem.

Guest favorite

The exterior of the recently renovated home is shown, featuring a two-story structure with a welcoming entrance and a spacious deck. Large windows allow light to fill the rooms, while surrounding trees enhance the natural setting. The view includes gentle hills in the background.

Home in Carlton

4.94 out of 5 average rating, 107 reviews

Lofty Vibes | Vineyard Views

Porch Light Vacation Rentals is proud to present Summers Hill Retreat, a peaceful escape with stunning vineyard views. This charming property features two queen bedrooms, two bathrooms, and a well-equipped kitchen. Outdoor spaces include a covered firepit, hot tub, and large patio, and a game cottage for cards and board games add to the fun. Book your stay now and experience this special retreat!

Guest favorite

The cabin features a warm wooden exterior with large windows allowing ample natural light. It is set among tall trees, providing a sense of seclusion. A small wooden deck extends out, enhancing the connection with the surrounding nature.

Cabin in Gaston

4.96 out of 5 average rating, 589 reviews

Great Cabin- Heart Of Wine Country!

Overlooking a 40 acre vineyard, this beautiful cabin is the epitome of Pacific Northwest craftsmanship. Come enjoy views of the Willamette Valley and it's sprawling vineyards, sample wine in our tasting room and most importantly sit back and relax! Looking for an event venue? Contact us for great options for your next event - we offer both indoor and outdoor space - plus you can stay on site!.

Guest favorite

A wooden staircase leads up to the entrance of a treehouse, framed by lush greenery. Large glass doors provide a view into the inviting interior, while natural light filters through the surrounding trees, creating a serene atmosphere.

Cabin in Dallas

4.94 out of 5 average rating, 197 reviews

Oregon Treehouse Getaway!

The perfect cozy treehouse oasis! Wake up surrounded by greenery next to a cozy fire overlooking a peaceful pond. From the fireplace outside on the balcony to the beautiful octagon windows bringing in all natural light! You will be able to un-plug and truly wake up feeling like you’re in paradise. Come, relax, unplug, and reset!