
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.

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!

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.

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.

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.

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!

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.

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.

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

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.

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.

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.

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
House rentals with a pool

The Staycation House

Frankie's Place; Walkable Craftsman luxury!

One level Entertainers Dream *Heated Pool*

The Starburst Inn: Enclosed Heated Pool, Theater

An Entertainment Oasis!

5bdrm,Heated Pool, Hot Tub, Sauna.

Private Pool & Hot Tub Oasis | Cowboy Retreat

Rose City Hideaway
Weekly house rentals

School Street Cottage

River Wine Farmhouse

The Farm Cottage

Spacious Forest Retreat w/ Hot Tub & Views

The Fox Bungalow

Portland Modern

❤️ CLEAN ★ LUXURY OASIS ★ NEAR DOWNTOWN

Little farm on the peak
Private house rentals

Pet-Friendly Sherwood Home with Mountain Views

OR Wine Country Get Away

Updated & Private 3 bed, 3 bath

Wine Country Studio|Walk to Dundee Wineries

Lake Oswego Luxury Retreat

Milwaukie Easy-Centrally located, Close to PDX

The Walking Woods Retreat in Lake Oswego

The Lemon Drop Lair - PetFriendly SpaciousBackyard
Destinations to explore
- Fitness-friendly rentals Sherwood
- Rentals with a patio Sherwood
- Rentals with pools Sherwood
- Rentals with a washer and dryer Sherwood
- Cottage rentals Sherwood
- Pet-friendly rentals Sherwood
- Cabin rentals Sherwood
- Family-friendly rentals Sherwood
- Rentals with breakfast Sherwood
- House rentals Washington County
- House rentals Oregon
- House rentals United States
- Silver Falls State Park
- Moda Center
- Laurelhurst Park
- Oregon Zoo
- Oregon Convention Center
- Providence Park
- The Grotto
- Beacon Rock State Park
- Portland Japanese Garden
- Enchanted Forest
- Airplane Home
- Tom McCall Waterfront Park
- Wonder Ballroom
- Oaks Amusement Park
- Washington Square
- Reed College
- Sellwood Riverfront City Park
- Arlene Schnitzer Concert Hall
- Tryon Creek State Natural Area
- Powell's City of Books
- Pittock Mansion
- Evergreen Aviation & Space Museum
- Hoyt Arboretum
- Wings & Waves Waterpark





