Sherwood vacation rentals

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Top-rated vacation rentals in Sherwood

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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.

Sep 12 – 19

G$21,240 GYD per night

Guest favorite

Farm stay in Hillsboro

5.0 out of 5 average rating, 360 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, great restaurants and exceptional vineyards. The Willamette Valley is recognized as one of the best Pinot Noir producing regions in the world. Enjoy hand-feeding alpacas and exploring paths in enchanting gardens and natural wetlands. Located six miles from Hillsboro and 14 miles from Portland. Offering seven unique and private accommodations. Please read all information.

Oct 7 – 14

G$25,272 GYD per night

Guest favorite

Cottage in Newberg

4.96 out of 5 average rating, 122 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.

Apr 15 – 22

G$23,333 GYD 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.

May 28 – Jun 4

G$29,958 GYD per night

Guest favorite

Tiny home in Sherwood

4.96 out of 5 average rating, 180 reviews

· Quaint and Quiet Sip and Stay in Wine Country

When our delighted guests are not planning a local wine tour or waterfall hike, relaxing at the picnic table, or walking their furry family member; they're napping or cuddling or reading a book from our unique library in one of the two comfy beds. This bright and stylish space truly has it all with an amazing fresh air shower, plenty of countertop space for working or dining, a fully stocked kitchen, a large BBQ, and a pet care kit. Seeking down time in the great outdoors? You've found it!

Aug 7 – 14

G$18,758 GYD 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 4 – 11

G$25,523 GYD 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 12 – 19

G$33,222 GYD 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 9 – 16

G$17,505 GYD 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.

Jan 20 – 27

G$22,041 GYD 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.

Mar 26 – Apr 2

G$18,343 GYD per night

Guest favorite

Apartment in Newberg

4.94 out of 5 average rating, 841 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.

Oct 22 – 29

G$22,879 GYD 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.

Jul 10 – 17

G$22,785 GYD 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, 194 reviews

Entire House in Wine Country

Oct 6 – 13

G$25,999 GYD 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

Mar 20 – 27

G$54,729 GYD per night

Guest favorite

Guesthouse in Canby

4.95 out of 5 average rating, 180 reviews

Cozy Country Bungalow

Apr 13 – 20

G$19,539 GYD per night

Guest favorite

Apartment in Newberg

4.92 out of 5 average rating, 252 reviews

GFU neighborhood / Oregon Wine Country studio

Jun 20 – 27

G$19,331 GYD per night

Guest favorite

Guesthouse in Wilsonville

4.95 out of 5 average rating, 407 reviews

Willow Creek Cottage

Jul 27 – Aug 3

G$26,090 GYD per night

Guest favorite

Cabin in Beaverton

4.98 out of 5 average rating, 330 reviews

Cooper Mountain Tiny Cabin

Jan 6 – 13

G$26,437 GYD per night

Guest favorite

Guest suite in Newberg

4.85 out of 5 average rating, 252 reviews

Hoover Park Studio-Great Wine tasting location

Sep 14 – 21

G$22,538 GYD per night

Guest favorite

Guesthouse in Wilsonville

4.96 out of 5 average rating, 241 reviews

Creekside Haven

Apr 6 – 13

G$29,738 GYD per night

Show all

Other great vacation rentals in Sherwood

Guest favorite

Guesthouse in Beaverton

4.98 out of 5 average rating, 256 reviews

Park Cottage

Nov 6 – 13

G$26,416 GYD per night

Guest favorite

Apartment in Hubbard

4.96 out of 5 average rating, 140 reviews

Peace and Quiet on a Farm in the Country

Oct 10 – 17

G$19,532 GYD per night

Guest favorite

Loft in Newberg

4.88 out of 5 average rating, 490 reviews

Vintage 2 Bedroom Loft | Above Boutique | GFU

Mar 5 – 12

G$31,204 GYD per night

Guest favorite

Guesthouse in Beaverton

4.98 out of 5 average rating, 134 reviews

SCHOLLS VALLEY RETREAT

Jun 26 – Jul 3

G$23,954 GYD per night

Guest favorite

Cottage in Lake Oswego

4.93 out of 5 average rating, 224 reviews

Peacock Grove Cottage in Lake Oswego, OR

Oct 23 – 30

G$16,468 GYD per night

Guest favorite

Place to stay in Brush Prairie

4.97 out of 5 average rating, 412 reviews

Spaceship Destination!

Nov 12 – 19

G$29,466 GYD per night

Guest favorite

Guest suite in Sherwood

4.97 out of 5 average rating, 78 reviews

Bacchus Fields - Oregon Wine Country Studio

Aug 28 – Sep 4

G$19,855 GYD per night

Guest favorite

Townhouse in Sherwood

4.91 out of 5 average rating, 74 reviews

Cozy 2 bed, 1 bath, private backyard in Sherwood

Dec 3 – 10

G$21,000 GYD per night

Show all

Quick stats about vacation rentals in Sherwood

Total rentals
30 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.2K reviews
Nightly prices starting at
G$6,253 GYD before taxes and fees

Frequently Asked Questions

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 10 vacation rentals for guests traveling with pets.
Are there family-friendly house rentals in Sherwood?
Sherwood has more than 10 family-friendly house rentals. 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.
Do house rentals in Sherwood have wifi?
Absolutely! We offer over 10 house rentals with wifi in Sherwood. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Sherwood have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Sherwood. Enjoy a tailored experience with all the comforts you desire.

Sherwood vacation rentals

Top-rated vacation rentals in Sherwood

Vacation rentals for every style

Cottages

Hotels

Unique stays

Popular amenities for Sherwood vacation rentals

Stay near Sherwood's top sights

Other great vacation rentals in Sherwood

Home in Newberg

Home in Sherwood

Guesthouse in Canby

Apartment in Newberg

Guesthouse in Wilsonville

Cabin in Beaverton

Guest suite in Newberg

Guesthouse in Wilsonville

Other great vacation rentals in Sherwood

Guesthouse in Beaverton

Apartment in Hubbard

Loft in Newberg

Guesthouse in Beaverton

Cottage in Lake Oswego

Place to stay in Brush Prairie

Guest suite in Sherwood

Townhouse in Sherwood

Quick stats about vacation rentals in Sherwood

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Sherwood?

Are there pet-friendly vacation rentals in Sherwood?

Are there family-friendly house rentals in Sherwood?

How much does it cost to stay in house rentals in Sherwood?

Do house rentals in Sherwood have wifi?

Do house rentals in Sherwood have air conditioning?

Destinations to explore