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, 160 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 11 – 18

G$21,337 GYD per night

Guest favorite

Farm stay in Hillsboro

5.0 out of 5 average rating, 363 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$25,277 GYD per night

Guest favorite

Cottage in Newberg

4.96 out of 5 average rating, 124 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 22 – 29

G$23,338 GYD per night

Guest favorite

Farm stay in Sherwood

4.88 out of 5 average rating, 159 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.

Sep 14 – 21

G$25,070 GYD per night

Guest favorite

Home in Sherwood

4.98 out of 5 average rating, 104 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.

Oct 1 – 8

G$54,740 GYD per night

Guest favorite

Tiny home in Newberg

5.0 out of 5 average rating, 606 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.

Oct 24 – 31

G$25,528 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.

Aug 29 – Sep 5

G$28,870 GYD per night

Guest favorite

Guest suite in Sherwood

4.88 out of 5 average rating, 253 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.

Mar 17 – 24

G$16,093 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.

Nov 2 – 9

G$21,832 GYD per night

Guest favorite

Home in Newberg

5.0 out of 5 average rating, 256 reviews

The Fox Bungalow

Make yourself comfortable in this charmingly updated 840 sq. ft. home in the heart of wine country. This house has everything you need to rest, relax, and enjoy your stay in Newberg. Just 4 short blocks from Newberg's quaint downtown area with its many locally-owned restaurants, coffee shops, bakeries and wine tasting, you will also be centrally located to George Fox University and minutes away from hundreds of beautiful wineries.

Feb 26 – Mar 5

G$33,900 GYD per night

Guest favorite

Guest suite in Sherwood

4.98 out of 5 average rating, 241 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 1 – 8

G$18,347 GYD per night

Guest favorite

Apartment in Newberg

4.92 out of 5 average rating, 255 reviews

GFU neighborhood / Oregon Wine Country studio

Cozy studio apartment with private locked entrance right in the middle of Oregon Pinot Noir Wine country. Perfect for a one or two person getaway to experience all that Yamhill County has to offer. This apartment is attached to our house on a very quiet cul-de-sac. You’ll have a slider that opens up to our backyard space where you can enjoy your own partially private patio. * Newly renovated bathroom.

Jun 1 – 8

G$17,662 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

Guesthouse in Wilsonville

4.95 out of 5 average rating, 413 reviews

Willow Creek Cottage

Sep 19 – 26

G$20,100 GYD per night

Guest favorite

Farm stay in Newberg

4.98 out of 5 average rating, 327 reviews

Amani Acres in the heart of wine country

Dec 29 – Jan 5

G$31,840 GYD per night

Guest favorite

Home in Newberg

4.94 out of 5 average rating, 197 reviews

Entire House in Wine Country

Oct 25 – Nov 1

G$25,972 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

Aug 8 – 15

G$18,762 GYD per night

Guest favorite

Guesthouse in Wilsonville

4.96 out of 5 average rating, 241 reviews

Creekside Haven

Nov 23 – 30

G$30,798 GYD per night

Guest favorite

Guesthouse in Canby

4.95 out of 5 average rating, 183 reviews

Cozy Country Bungalow

Apr 27 – May 4

G$22,816 GYD per night

Guest favorite

Cabin in Beaverton

4.98 out of 5 average rating, 332 reviews

Cooper Mountain Tiny Cabin

Feb 9 – 16

G$26,442 GYD per night

Guest favorite

Guest suite in West Linn

5.0 out of 5 average rating, 207 reviews

Private Casita in Historic Willamette

Mar 9 – 16

G$26,798 GYD per night

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Other great vacation rentals in Sherwood

Guest favorite

Guesthouse in Tigard

4.95 out of 5 average rating, 181 reviews

The Cottage at River Run!

Sep 17 – 24

G$27,559 GYD per night

Guest favorite

Guesthouse in Beaverton

4.98 out of 5 average rating, 257 reviews

Park Cottage

Sep 20 – 27

G$28,800 GYD per night

Guest favorite

Cottage in Lake Oswego

4.93 out of 5 average rating, 227 reviews

Peacock Grove Cottage in Lake Oswego, OR

Oct 26 – Nov 2

G$16,472 GYD per night

Guest favorite

Apartment in Hillsboro

4.94 out of 5 average rating, 602 reviews

Wine country retreat with amazing views

Feb 20 – 27

G$21,088 GYD per night

Guest favorite

Apartment in Newberg

4.91 out of 5 average rating, 307 reviews

Red Hills Retreat — Lower Carriage House

Oct 2 – 9

G$28,805 GYD per night

Guest favorite

Guest suite in Sherwood

4.97 out of 5 average rating, 78 reviews

Bacchus Fields - Oregon Wine Country Studio

Sep 25 – Oct 2

G$19,828 GYD per night

Guest favorite

Townhouse in Sherwood

4.91 out of 5 average rating, 77 reviews

Cozy 2 bed, 1 bath, private backyard in Sherwood

Mar 10 – 17

G$21,039 GYD per night

Guest favorite

Barn in Sherwood

4.95 out of 5 average rating, 39 reviews

Tree Top Studio- *Brand New* in Wine Country

May 24 – 31

G$22,536 GYD per night

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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$6,254 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

Hotels

Unique stays

Homes

Popular amenities for Sherwood vacation rentals

Stay near Sherwood's top sights

Other great vacation rentals in Sherwood

Guesthouse in Wilsonville

Farm stay in Newberg

Home in Newberg

Tiny home in Sherwood

Guesthouse in Wilsonville

Guesthouse in Canby

Cabin in Beaverton

Guest suite in West Linn

Other great vacation rentals in Sherwood

Guesthouse in Tigard

Guesthouse in Beaverton

Cottage in Lake Oswego

Apartment in Hillsboro

Apartment in Newberg

Guest suite in Sherwood

Townhouse in Sherwood

Barn 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