Vacation rentals in Sherwood

Home in Central Northeast Portland

A private patio area is featured, showcasing a wooden structure with clear roofing, surrounded by lush greenery. Two chairs with cushions are positioned near a small table, creating an inviting space for relaxation amidst flowering plants.

4.98 out of 5 average rating, 106 reviews

Heron Cottage, Urban Retreat-King Bed

The Heron Cottage was built in 1914 and was part of a network of small farms that existed in what was then the hinderlands of Portland. Now it's an urban vest pocket neighborhood with easy access to a regional hospital, light rail, bus routes and freeways. This is a pedestrian neighborhood with very narrow streets. We know our neighbors and enjoy the cultural diversity of this little enclave. The cottage's front porch beckons you to slow down, relax and maybe even make some new friends.

4.99 out of 5 average rating, 144 reviews

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

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.

Home in Northeast Portland

An outdoor patio features a long wooden dining table set with dishes and glasses, inviting shared meals. Comfortable seating arrangements include plush chairs and a sofa, surrounded by greenery. Sliding glass doors provide access to the interior, while string lights add a charming ambiance.

4.9 out of 5 average rating, 334 reviews

Huge Home with King Beds in Prime Spot with Views!

Architectural masterpiece on a safe, quiet street just blocks from Williams and Mississippi Ave, home to some of Portland’s best dining, drinking, shopping and more. Spread out across three spacious levels with multiple living areas, a large open kitchen with two eating bars, four king bedrooms and a bunk room (each with its own TV!), and 3.5 bathrooms. Relax and dine alfresco on the beautiful back patio, then watch sunrises and sunsets from the east and west facing roof decks!

Shipping container in Oregon City

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.

4.97 out of 5 average rating, 125 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.

4.93 out of 5 average rating, 106 reviews

An illuminated patio area features a covered wooden structure with string lights providing a warm glow. Comfortable seating is arranged around a central table, and a large umbrella adds color to the outdoor space. Lush plants are visible along the perimeter, enhancing the tranquil atmosphere.

Cottage in Beaverton

Cozy Cooper Mtn Cottage

Uniquely cozy with all the amenities of home but in a cottage up on Cooper Mt. Where you are surrounded by trees , feel the breezes, sunrise and sunset in the same day, and sometimes the wonderful wildlife around us. Birds in the sky , rabbits and sometimes deer, and yes our two friendly goats. Oh yes and the expansive midnight sky with the bright stars twinkling above or the big round moon shining down on you as you sit on the patio in the evening enjoying the night air.

Guesthouse in North Portland

The kitchen features stainless steel appliances, including a gas range and microwave, with a butcher block island and concrete countertops. Open shelving displays dishware, while a dining area is set with wooden stools and a table topped with a bowl of fruit and a bottle of wine.

5 out of 5 average rating, 222 reviews

Richmond Cottage in St Johns, Portland

This light, bright cottage is located in the heart of the St Johns neighborhood in Portland. Full of charm it features loads of reclaimed wood with an industrial farmhouse vibe. Complete with a private deck, keyless entry, full kitchen with eat-in island and a sleeping loft with a queen sized bed. It is a close walk to restaurants, coffee shops, bars and shopping. Easy access to downtown Portland, University of Portland, the airport and the rest that Portland has to offer.

4.76 out of 5 average rating, 189 reviews

Home in Vancouver

Style Meets Comfort in Beautiful Design

Discover unparalleled comfort and style in this beautifully designed Vancouver retreat, perfect for families and groups seeking a memorable getaway. This spacious home hosts two living rooms, king-sized beds in every bedroom, and a fully equipped kitchen, this is where comfort meets convenience. Nestled in a peaceful neighborhood with easy access to local attractions, dining, and shopping, making it the ideal home base for your Pacific Northwest exploration.

Apartment in Northeast Portland

4.92 out of 5 average rating, 136 reviews

The White House in Mississippi - 95 WalkScore

Welcome to our charming three-bedroom retreat in the heart of Mississippi Street! Step outside and dive into the vibrant local scene, with endless dining, shopping, and entertainment options just steps away. After a fun-filled day exploring, return to unwind in style with a massive 4K HDTV, a fully equipped kitchen, and comfortable memory foam mattresses in all three bedrooms. Discover the best of Mississippi Street from our perfectly situated apartment!

Guesthouse in Central Northeast Portland

A modern hot tub is set against a backdrop of tall bamboo plants, creating a serene outdoor environment. Soft blue lighting illuminates the interior of the hot tub, inviting relaxation and unwinding after a long day.

4.99 out of 5 average rating, 471 reviews

LoftHousePDX w/ Sauna & Hot Tub

Debuted during Portland's Accessory Dwelling Tour, “Loft House PDX” is centrally located just off beautiful Alameda Ridge. Business and leisure travelers alike will find a peaceful retreat awaiting them in this tastefully-appointed, open and airy, modern loft house with all the accoutrements one might wish for—including a Finlandia Sauna, and STIL hot tub to enjoy after a long day of work or play, and a custom gas firepit for evening lounging...

4.97 out of 5 average rating, 241 reviews

A spacious wooden deck surrounds the cabin, showcasing large glass doors that provide an unobstructed view of the lush greenery. Sunlight reflects off the glass, enhancing the connection between indoor and outdoor spaces, while the warm wooden tones create a welcoming atmosphere.

Guest suite in Sandy

The Cedar House at Riverbend Orchard

Escape to nature’s beauty at this serene retreat on 23 wooded acres overlooking the Sandy River. Sip coffee on the heated wraparound deck, curl up by the stone fireplace, or soak in the hot tub under the stars. Hike the private trails, discover the pond, and unwind in the sauna. Thoughtfully designed for relaxation, with cozy nooks, books, and breathtaking views. Well-trained dogs welcome! No cats or other pets due to severe owner allergy.

4.82 out of 5 average rating, 125 reviews

A bright and airy room features large windows and soft curtains, allowing natural light to fill the space. A spacious bed is complemented by floral wallpaper. A small dining area with a chair is present, alongside a modern kitchen countertop and a view of the private patio through French doors.

Apartment in Portland

La Petite- BRAND NEW!

ELEGANT URBAN OASIS IN PORTLAND'S DIVISION NEIGHBORHOOD. Step into an enclave of opulence and comfort in our newly designed Accessory Dwelling Unit (ADU). This private haven, sculpted with attention to every detail, stands as a testament to luxury and comfort, offering you Portland's finest in an intimate, and sleek setting. You'll cherish our ADU's tranquil ambiance and our foodie forward neighborhood.

4.94 out of 5 average rating, 107 reviews

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

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!

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Sherwood vacation rentals

Stay near Sherwood's top sights

Target40 locals recommend

Symposium Coffee3 locals recommend

Hawks View Winery8 locals recommend

Mason3 locals recommend

Fat Milo's Family Kitchen3 locals recommend

Langer's Entertainment Center8 locals recommend

Vacation rentals with jacuzzis in Sherwood

Guesthouse in Laurelhurst

A tranquil backyard scene features a three-person hot tub beside a well-manicured lawn. A hammock hangs nearby under a wooden structure, and surrounding palm trees provide a tropical ambiance. A wooden fence encloses the area, with firewood stored in a cozy nook.

5 out of 5 average rating, 272 reviews

Cozy Getaway w/Hot tub, Fireplace, Firepit & A/C

4.86 out of 5 average rating, 291 reviews

The backyard features a spacious layout with a manicured lawn bordered by gravel pathways. A jacuzzi is positioned to the rear, complemented by a wood deck and a seating area with six lawn chairs around a fire pit. String lights are suspended above for evening ambiance.

Home in Vancouver

House By Dead End: Jacuzzi, Fire Pit, & Patio

4.88 out of 5 average rating, 152 reviews

A charming blue exterior features a bright yellow door, surrounded by lush greenery. The front porch, supported by wooden beams, showcases two comfortable chairs, inviting relaxation. Pathways lead through well-maintained landscaping, contributing to a welcoming first impression of the getaway.

Guesthouse in Portland

SE City Spa Retreat

4.95 out of 5 average rating, 143 reviews

An outdoor courtyard is illuminated by soft lighting, creating a serene evening ambiance. A picnic table and chairs are positioned under a wooden pergola, with a hammock suspended nearby. Lush greenery surrounds the space, enhancing the natural setting.

Guesthouse in Woodstock

Romantic Casita, Hot tub, Movie loft & Chiminea!

Guesthouse in Northeast Portland

A cozy bedroom is visible with a spacious bed draped in soft bedding and a decorative wall art piece. A desk with a computer is situated beside a window adorned with a neutral-toned shade, allowing natural light to enter the room. A plush throw is draped over the chair.

4.99 out of 5 average rating, 146 reviews

The Portland Sun House

4.99 out of 5 average rating, 135 reviews

A spacious hot tub is nestled under a modern gazebo, surrounded by lush greenery and decorative landscaping. The inviting space features potted plants and a serene atmosphere, offering an ideal spot for relaxation. The nearby open area emphasizes the tranquility of the natural surroundings.

Home in North Plains

2 Acre, Pond View Home, with Hot-tub & BBQ FOR 16

4.89 out of 5 average rating, 344 reviews

A hot tub with soft, pulsating purple lights sits on a patio, surrounded by trees. In the background, a vibrant sunset paints the sky in shades of orange and pink, providing a serene atmosphere.

Guest suite in Damascus

Fireshaker Guesthouse (with hot tub!)

4.91 out of 5 average rating, 101 reviews

A hot tub is positioned under a covered area, with sheer curtains allowing light to filter through. The view reveals a spacious lawn, a fire pit area in the background, and surrounding greenery, enhancing the outdoor experience.

Guesthouse in Cedar Mill

Warm Cedar Cottage Oasis with Hot Tub on Request

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Other great vacation rentals in Sherwood

5 out of 5 average rating, 22 reviews

A community park is depicted, featuring a wide grassy area bordered by trees and pathways. A sign indicating 'Central Park' is visible in the foreground. Bicycle racks are positioned near the entrance, while a pavilion can be seen in the background, surrounded by shaded seating areas.

Home in Orenco Station

Orienco home, steps to Intel RA, winter discount!

4.87 out of 5 average rating, 23 reviews

Home in Clackamas

Rose Meadow Oasis

4.9 out of 5 average rating, 10 reviews

The dining area features a rectangular wooden table surrounded by six green chairs. Decorative place mats are laid out on the table. Light streams through large windows framed in dark wood, illuminating the space. A cozy living area is visible through the open space, enhancing the home's layout.

Home in Portland

Fresh Belmont Charmer w/ 95 WalkScore

5 out of 5 average rating, 12 reviews

A bright hallway is featured, showcasing a blend of modern design with a light color palette. A console table holds decorative items, while soft lighting from a table lamp creates an inviting ambiance. Archways lead toward a dining area, enhancing the sense of spaciousness.

Home in Newberg

Cozy Haven |Fire Pit |EV Charger |Great Location

5 out of 5 average rating, 9 reviews

Two white Adirondack chairs are positioned on a gravel path, surrounded by lush vegetation and softly illuminated by strategically placed lighting. Tall trees and shrubs create a serene and inviting garden atmosphere.

Home in Carlton

Carlton Gates- Luxury Vacation Home

4.93 out of 5 average rating, 15 reviews

An elegant dining area with a glossy black floor is showcased, featuring a round table surrounded by plush velvet chairs. Natural light enters through tall windows, and a grand piano is visible nearby, enhancing the room's spacious feel.

Home in Tigard

Stunning Former Street Of Dream

5 out of 5 average rating, 184 reviews

A spacious family room features soft furnishings in neutral tones arranged around a central coffee table. Natural light floods in through large windows, illuminating the wood-beamed ceiling and stone fireplace. A dining area with white chairs is visible in the background.

Guesthouse in Dayton

Modern Farmhouse - Country living in wine country.