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 favorite

Guest suite in Hillsboro

4.98 out of 5 average rating, 158 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.

Oct 5 – 12

ﺩ.ﺇ374 per night

Guest favorite

Guesthouse in Wilsonville

4.95 out of 5 average rating, 404 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.

Oct 1 – 8

ﺩ.ﺇ358 per night

Guest favorite

Cottage in Newberg

4.96 out of 5 average rating, 121 reviews

Oxberg Lake Retreat, lake & farm view in wine ctry

A storybook oasis with lake/farm views. Enjoy your morning coffee or evening wine while listening to the sheep and chickens. One loft bedroom, one full bath with large living room/kitchen. * 5 min to George Fox University * 2 min to The Allison Inn & Spa * 50+ wineries within 10 min drive *Walk to Farm Craft brews at Wolves and People on Benjamin *Enjoy canoeing, feeding the sheep, or reading a book by the fire pit. (wood provided) We also have a roll-away bed that is available upon request.

Feb 16 – 23

ﺩ.ﺇ446 per night

Guest favorite

Farm stay in Sherwood

4.88 out of 5 average rating, 158 reviews

Ariniello Vineyard - Private 2 Bedroom Suite

Perfect location for wine tasting and touring the beautiful Pacific NW. A unique opportunity to stay on a newly planted small vineyard in your own private suite. Enjoy your very own 1st floor living quarters. The property is also located on a small farm. You will enjoy your own entry with two private bedrooms (1 king and 1 queen), living room and private bathroom. Basic kitchen set up -NO oven. The space can easily sleep 4 (6 includes an air mattress). No smoking allowed in the suite.

Oct 3 – 10

ﺩ.ﺇ511 per night

Guest favorite

Home in Sherwood

4.98 out of 5 average rating, 102 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.

Feb 18 – 25

ﺩ.ﺇ964 per night

Guest favorite

Tiny home in Newberg

5.0 out of 5 average rating, 603 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.

Sep 25 – Oct 2

ﺩ.ﺇ450 per night

Guest favorite

Guesthouse in Sherwood

4.98 out of 5 average rating, 100 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.

Jun 8 – 15

ﺩ.ﺇ579 per night

Guest favorite

Guest suite in Sherwood

4.88 out of 5 average rating, 249 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.

Aug 5 – 12

ﺩ.ﺇ306 per night

Guest favorite

Guest suite in Newberg

4.98 out of 5 average rating, 131 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.

Sep 15 – 22

ﺩ.ﺇ388 per night

Guest favorite

Guest suite in Sherwood

4.98 out of 5 average rating, 239 reviews

Sherwood Hollow

Welcome to Sherwood Hollow! This completely refurbished retreat is located in a large downstairs In-Law suite of our 1960's home. The unit is private and closed off from the upstairs. Our home is located just a few blocks from Old Town Sherwood and the beautiful Stella Olsen park. Please note that because our home is older you will hear footfall from the upstairs. We will do our best to be respectful of sound.

Oct 10 – 17

ﺩ.ﺇ323 per night

Guest favorite

Apartment in Newberg

4.94 out of 5 average rating, 840 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.

Nov 13 – 20

ﺩ.ﺇ375 per night

Guest favorite

Apartment in Tualatin

4.96 out of 5 average rating, 251 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.

Aug 29 – Sep 5

ﺩ.ﺇ401 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Sherwood vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Sherwood's top sights

Walmart Supercenter4 locals recommend

Regal Sherwood7 locals recommend

Fat Milo's Family Kitchen13 locals recommend

Langer's Entertainment Center12 locals recommend

Handels Homemade Ice Cream6 locals recommend

Crazy Sushi Restaurant4 locals recommend

Other great vacation rentals in Sherwood

Guest favorite

Home in Newberg

4.94 out of 5 average rating, 192 reviews

Entire House in Wine Country

May 30 – Jun 6

ﺩ.ﺇ493 per night

Guest favorite

Apartment in Newberg

4.92 out of 5 average rating, 249 reviews

GFU neighborhood / Oregon Wine Country studio

Jun 20 – 27

ﺩ.ﺇ351 per night

Superhost

Tiny home in Sherwood

4.96 out of 5 average rating, 180 reviews

· Quaint and Quiet Sip and Stay in Wine Country

Jul 27 – Aug 3

ﺩ.ﺇ331 per night

Guest favorite

Farm stay in Hillsboro

5.0 out of 5 average rating, 359 reviews

Oakwood Gardens Studio •Alpaca Farm• Wine Country

Oct 7 – 14

ﺩ.ﺇ447 per night

Guest favorite

Guest suite in West Linn

5.0 out of 5 average rating, 206 reviews

Private Casita in Historic Willamette

Sep 20 – 27

ﺩ.ﺇ441 per night

Guest favorite