House vacation rentals in Sherwood

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Quick stats about house rentals in Sherwood

  • Total vacation rentals

    Explore 20 vacation rentals in Sherwood

  • Nightly prices starting at

    Sherwood vacation rentals start at ﺩ.ﺇ 184 per night before taxes and fees

  • Verified guest reviews

    Over 730 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Wi-Fi availability

    20 of Sherwood vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Sherwood rentals

  • 4.8 Average rating

    Sherwood stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated house rentals in Sherwood

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Guest favorite
The living area features a comfortable sofa and two armchairs arranged around a coffee table, with artwork displayed on the walls. Natural light enters through a window, and a dining table for four is positioned nearby, creating an inviting environment.
Home in Sherwood
4.88 out of 5 average rating, 157 reviews

Sherwood Inn - in Charming old town Sherwood

LOCATION! We have it!! Charming 4 bed/1.5 bath house in Old Town Sherwood, the Gateway to Oregon's Wine Country and all that the Dundee Hills/and Yamhill Carlton has to offer. Our remodeled house is walking distance to local restaurants, bars, wine bars, bakeries,antiques and a super cute coffee/whiskey house with a fire pit next door. The Library as well as several parks are close by. Plan your vacation or business trip with us in Sherwood and the enjoy what surrounding areas have to offer!

Top guest favorite
A tranquil outdoor space features two wooden chairs and a round table, positioned to enjoy a breathtaking sunset. The sky is adorned with vibrant purple and orange clouds, casting a serene light over the landscape below.
Home in Newberg
4.96 out of 5 average rating, 267 reviews

Parrett Mtn Estate · Hot Tub, Sauna & Valley Views

8 private acres atop Parrett Mountain — sweeping Pinot Noir vineyard & valley views, Tempur-Pedic suites & heated stone floors. The only estate in Willamette Valley with an Oregon Red Cedar sauna, cold plunge, starlit hot tub & Universal EV Charging. Two full chef's kitchens, Egyptian cotton linens, Dyson air purifiers & hair tools, 4 bedrooms, sleeps 12. Optional add-ons available: private chef, Sommelier wine tasting & concierge services. 5 min to Newberg · 30 min to Portland · 40 min to PDX.

Top guest favorite
A spacious deck features a table set with gourmet snacks, a bottle of wine, and glasses, surrounded by comfortable seating. The lush vineyards and cherry blossoms are visible in the distance, under a clear blue sky, offering a serene outdoor setting.
Home in Newberg
4.95 out of 5 average rating, 138 reviews

Vineyard and Mountain View Wine Country Retreat

Our property is available to adults looking for some peaceful time. Conveniently located, our home will be a retreat to come back to after a day of exploring gastronomy and wineries in nearby towns. Numerous vineyards are in the immediate vicinity. On clear days enjoy views from our large deck of Mt Hood, St Helens, Rainier, and local vinery. We take great pride in maintaining a quality environment to share with others. Carefully read Additional Rules to decide if our home fits your needs.

Guest favorite
A spacious living area features a light grey couch and a coffee table with a wooden accent. A television is positioned on a dark cabinet, while a decorative wall panel adds visual interest. The dining area is visible in the background, offering a contemporary table and chairs.
Home in Sherwood
4.83 out of 5 average rating, 126 reviews

Lovely place in Sherwood!

You will be close to everything when you stay at this centrally-located place! No matter the reason you are in town, you will feel right at home staying in our 2 bedroom, 1 bath duplex! (This is half of the duplex- all one level- RIGHT SIDE). You get to enjoy the private fenced back yard, fenced front yard, and 1 car garage. It is located close to wine country, lots of parks (including dog parks), VERY close to local restaurants, shopping, family game center (Langers), and highway 99W.

Top guest favorite
Home in Tigard
4.99 out of 5 average rating, 224 reviews

Mama J's Private Neighborhood Suite

For whatever brings you through/to Oregon, stay at Mama J’s comfortable, peaceful, safe and convenient spot. Portland is just ten miles away and the beaches, Columbia River Gorge and Mt. Hood are all about an hour. There are numerous hikes, from the forest right down the street to Silver Falls and beyond. The neighborhood is peaceful and your private patio is the perfect place for a beverage and some bird and squirrel watching. If it rains, hang out in the gazebo! Hope to host you here!

Top guest favorite
A charming craftsman home is framed by a white picket fence, with a welcoming front porch and a pergola overhead. The exterior features dark blue siding, three front-facing windows, and lush greenery surrounding the entrance.
Home in Sherwood
4.99 out of 5 average rating, 187 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.

Superhost
A welcoming living area features a modern gray sofa, accent table, and decorative plants. Warm lighting is provided by two floor lamps. A dining table with white chairs is visible, along with an elegant area rug. A sliding barn door leads to additional spaces.
Home in Tigard
4.95 out of 5 average rating, 240 reviews

Spectacular Choice: Sleeps 6, Your Dog Welcome Too

This bright, clean and stylish home has everything you need to make your visit comfortable and welcoming. Relax in the living room after your travels with Firestick/Roku TV. Prepare meals and mix cocktails in the well-equipped, functional kitchen. Enjoy the pristine bathroom with tub/shower and elegant marble vanity. Two bedrooms and a living room sofa bed will sleep up to 6 guests. Washer/dryer. Large deck with patio and BBQ. Dog friendly backyard. Parking for up to four cars.

Guest favorite
A spacious outdoor deck features a white Adirondack chair overlooking a vast landscape. The view encompasses rolling hills and a horizon that fades into the distance under a clear sky. Hues of autumn are visible in the trees and ground, adding color to the scenery.
Home in Newberg
4.94 out of 5 average rating, 230 reviews

Spectacular Valley View in Wine Country

Relax and enjoy the best of what Oregon Wine country has to offer in our newly renovated country home. With a stunning view overlooking the Willamette Valley, you are close to over 300 wineries and tasting rooms, local craft beer, and a great social atmosphere in our small town. Enjoy soaking in the hot tub or having dinner outside under the gazebo. Have your pets outside, worry free with a large fenced back yard. A pellet grill is on the deck as well for outside cooking.

Top guest favorite
An aerial view captures a sprawling estate surrounded by lush greenery and mature trees. The main house stands prominently among manicured lawns, while additional outbuildings are visible nearby. A winding driveway leads to the entrance, enhancing the serene country atmosphere.
Home in Wilsonville
4.98 out of 5 average rating, 229 reviews

Beautiful Dog Friendly Cottage on a 10 Acre Estate

A little slice of heaven. Stay near the heart of wine country on a 20 acre estate and Hazelnut Orchard. Enjoy a complimentary bottle of Oregon wine and treats upon arrival. Settle in and sit on your personal porch surrounded by Hazelnuts and Dahlias. Or take a dip in the hot tub by the garden and play a little basket ball on the sports court. Close to numerous wineries, breweries, equestrian centers, just 20 miles south of Portland and 60 minutes from the beautiful coast.

Top guest favorite
A charming outdoor area is visible, featuring a stone pathway leading to a cozy seating arrangement with two black chairs. The bungalow is framed by lush greenery, with warm light emanating from the windows, inviting a peaceful ambiance.
Home in Southwest Portland
4.97 out of 5 average rating, 167 reviews

Multnomah Village Hideout

Explore our new, artist-built bungalow in Multnomah Village, Portland. This cozy space sleeps four with a queen bed upstairs and a pullout couch downstairs. Steps away are charming cafes, shops, and a park with hiking trails and dog parks. Enjoy local activities like bingo and dining on pet-friendly patios. Complete with essentials including laundry and a breakfast nook, this bungalow is perfect for both short and extended stays, offering a unique Portland experience.

Top guest favorite
An inviting entrance showcases a fountain surrounded by lush greenery and stone pathways. The front door, framed by ornate pillars, opens to a well-lit interior. Soft lighting enhances the welcoming atmosphere, with a seasonal wreath adorning the door.
Home in Sherwood
4.95 out of 5 average rating, 165 reviews

Chateau Chardonnay:Tuscan home in NW wine country

Equipped with two HEPA air filtration systems that work continuously to filter and sanitize the air, this home is a clean and safe space to relax and enjoy nature! The house sits on 4 acres in the picturesque Oregon wine country. The back deck looks out over a lush back yard that cascades down to a lazy creek. Gaze out the large kitchen window to the paver patio, vibrant lawn and rimmed with beautiful mature landscaping, koi pond and fountain.

Top guest favorite
A single-story house with a welcoming front porch is surrounded by a lush, green lawn. The exterior features a mix of white siding and dark roofing, with two garage doors on one side. Tall trees provide a natural backdrop, enhancing the tranquil setting.
Home in Lake Oswego
4.96 out of 5 average rating, 154 reviews

Completely updated home in Lake Oswego!

I have a 3 bedroom, 2 full bath house with a family room, dinning area & open kitchen. The master has a king bed, the other two have queen beds, I also have an air mattress if additional sleep space is needed. All bedrooms have closets & TVs, there is a desk and chair for a work space if needed in garage. High speed internet and a fully fenced in back yard with a covered space, table and chairs for relaxing or entertaining.

Popular amenities for Sherwood house rentals

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