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Sherwood vacation rentals

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Top-rated vacation rentals in Sherwood

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

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Guest suite in Hillsboro

4.99 out of 5 average rating, 208 reviews

Willamette Valley Wine Country Hub

Located in the heart of the Willamette Valley wine country the 1100 SqFt private unit provides a unique opportunity to experience the north west. We are at the center of a hub with equal access to Hillsboro, Sherwood, Newberg and Beaverton for all of the night life and restaurants while being within a few miles of 100+ wineries. We also offer a wood fired pizza making experience (see below for details). All of this while experiencing rural Oregon. We are on 6 acres with only a few neighbors.

Guesthouse in Wilsonville

4.95 out of 5 average rating, 475 reviews

Willow Creek Cottage

Enjoy country living in our charming and unique 1890s guest house. Situated on 12 acres in horse country. Great location - 20 minutes to Portland, 25 minutes to Oregon Wine Country, 90 minutes to the coast and five minutes from I-5 and Wilsonville. Bedroom with comfy pillow top queen bed. Breakfast nook with refrigerator, microwave and Keurig coffee maker. Direct TV and WiFi. **Please be assured that we continue to take all steps necessary to sanitize and air the cottage before your visit.

Farm stay in Hillsboro

5 out of 5 average rating, 403 reviews

Oakwood Gardens Studio •Alpaca Farm• Wine Country

Experience an immersive farm adventure on 70-acres in the quaint community of Scholls, while being close to quality markets and great restaurants. The Willamette Valley is recognized as one of the best Pinot Noir producing regions in the world with exceptional vineyards to tour. Enjoy hand-feeding alpacas and exploring paths in enchanting gardens and natural wetlands. Offering six private accommodations, just 14 miles from Portland. Please read details prior to making an inquiry or booking.

Home in Sherwood

4.98 out of 5 average rating, 133 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.

Tiny home in Newberg

5 out of 5 average rating, 644 reviews

Garden Spa Getaway in Wine Country-Newberg

Enjoy the hot tub and sauna for relaxation! The Tiny Home is privately tucked in a garden oasis, in a quiet residential neighborhood. Only 13 blocks to downtown Newberg 's lovely wine boutiques and restaurants, 6 blocks to George Fox University, 45 min. from PDX Airport. Spacious and comfortable with 192 sq. feet modern atmosphere. Complimentary specialty cheese & oatmeal cups for breakfast. Nice bikes to tour beautiful Newberg and local wine boutiques. *Two night minimum stay.

Guesthouse in Sherwood

4.98 out of 5 average rating, 120 reviews

Cozy Willamette Valley Cabin With Modern Comforts

A cozy retreat on the brink of Oregon's wine country, walking distance to local restaurants and shops. Enjoy being less than 30 minutes from Portland International Airport and some of the most acclaimed wineries in Oregon's Willamette Valley. This luxurious cabin features a full sized kitchen, washer/dryer, bedroom with queen bed and separate office/dressing room, gas fireplace, smart TV and second queen pull-out. The full bath features walk-in rain shower and full vanity.

Guest suite in Sherwood

4.87 out of 5 average rating, 300 reviews

Cozy Wine Country Suite

A cozy suite with private, separate entrance and garden, located a short walk to Sherwood’s charming downtown. Quick access to coffee shops, restaurants, and a local brewery. Close to many of the valley’s best tasting rooms and vineyards. Relax with a glass of Pinot Noir and watch the sunset on your private deck, or take a short drive to Portland and explore the city. Sherwood is centrally located and the perfect distance for a day trip to the coast or the mountains.

Guest suite in Newberg

4.98 out of 5 average rating, 152 reviews

Sarah's Suite at Woods & Vine Farm

Property is a 35-acre farm located between Newberg and Carlton on Highway 240 in the heart of Oregon's Pinot Noir wine country. Currently, half of the farm is in hay production and the other half is densely wooded. Exceptional location at the edge of the Dundee Hills AVA in close proximity to Newberg, Dundee, and Carlton. There are more than 80 wineries and 200 vineyards in Yamhill County, representing the largest wine producing region in Oregon.

Home in Sherwood

4.95 out of 5 average rating, 116 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.

Rental unit in Newberg

4.95 out of 5 average rating, 913 reviews

Bright, Unique Apartment in Heart of Wine Country

*4 Min to George Fox University *10 Min walk to wine tasting rooms & restaurants *50+ wineries within 10 min drive This adorable daylight basement apartment is like walking into a storybook oasis. You’ll love the forest views from the floor to ceiling windows. Enjoy your morning coffee (or evening wine) from the private seating area and take in the sounds of chirping birds and babbling brook.

Barn in Sherwood

4.99 out of 5 average rating, 107 reviews

Rustic Barn | Country Getaway

Nestled atop Parrett Mountain is our countryside barn ready for you to enjoy! Conveniently located to many vineyards, and a picturesque drive to close by cities. This space offers a fully stocked kitchen and plush bedding (1 Queen/ 1 Double). Come and slow down with our rural pace of life and unique accommodations. Check out our photos to imagine yourself in this peaceful paradise.

Rental unit in Tualatin

4.96 out of 5 average rating, 263 reviews

Elk Place - Heart of Wine Country. Bdrm & Lvg Rm

Our place offers a quiet, beautiful, park-like setting. This space is completely separate with a Private Entrance. You will enjoy a private living room, kitchenette area ( NOT A KITCHEN FOR COOKING & CLEANING UP), bedroom, bathroom & outdoor Patio. Our place is good for couples, solo adventurers, business travelers, and families. NOTE: Owners live on property. NO Pets Allowed.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

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Unique stays

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Homes

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Popular amenities for Sherwood vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Sherwood's top sights

Target40 locals recommend

Symposium Coffee25 locals recommend

Tualatin River National Wildlife Refuge25 locals recommend

Hawks View Winery20 locals recommend

Mason14 locals recommend

Fat Milo's Family Kitchen13 locals recommend

Other great vacation rentals in Sherwood

Farm stay in Sherwood

4.89 out of 5 average rating, 56 reviews

Scholls Mountainside Schoolhouse

Guesthouse in Beavercreek

4.98 out of 5 average rating, 193 reviews

Muse Cabin in old growth forest w/cedar hot tub

Guest suite in Sherwood

4.99 out of 5 average rating, 77 reviews

Carly's Comfort Inn

Dome in Amity

4.97 out of 5 average rating, 236 reviews

Round House Retreat in the Woods

Guesthouse in Canby

4.95 out of 5 average rating, 198 reviews

Cozy Country Bungalow

Guesthouse in Beaverton

5 out of 5 average rating, 156 reviews

~The Backyard Bounty ADU~*Private 5 Star Space*

Guest suite in Milwaukie

4.99 out of 5 average rating, 339 reviews

Light Filled Garden Studio

Rental unit in Tigard

4.99 out of 5 average rating, 112 reviews

Private one-bedroom unit with living space.

Quick stats about vacation rentals in Sherwood

Total rentals
30 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
1.5K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Frequently Asked Questions

Are there family-friendly vacation rentals in Sherwood?
Sherwood has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Sherwood?
Experience the best of Sherwood with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Sherwood?
Yes! Work meets play with ease at over 20 vacation rentals in Sherwood featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Sherwood?
Four-legged friends are welcome in Sherwood. Choose from more than 20 vacation rentals for guests traveling with pets.
What are the most popular amenities for House Rentals in Sherwood?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Sherwood have wifi?
Absolutely! We offer over 20 house rentals with wifi in Sherwood. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore