Holiday houses in Sherwood

4.87 out of 5 average rating, 134 reviews

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!

5 out of 5 average rating, 102 reviews

Home in Tigard

Mama J's

I've created what I think is a relaxing stay. You will sleep on a memory foam mattress with cotton linens. Additionally, there is a 55 inch smart TV with free Netflix and Apple TV, along with a selection of books and games. The patio and gazebo are also available and are the smoking areas. This master suite in my house has a private entrance and yard. There are no shared spaces and there is a lock on both sides of the sound-baffled door to the main house to value your privacy as well as mine.

4.97 out of 5 average rating, 107 reviews

Guest suite in Sherwood

Bacchus Fields - Oregon Wine Country Studio

Bacchus Fields is a private, quiet, studio in the gateway of Oregon’s wine country, with views of Mt. Hood and beautiful scenery. The studio has a queen bed, full kitchen, private bathroom and entrance. We offer self-check in, dedicated parking with complementary Level 2 EV charging, a private outdoor patio with seating, a gas grill and fire pit. The studio is nicely situated for short and long-term stays, visits to wine country, the coast, mountains, Portland, and surrounding communities.

4.98 out of 5 average rating, 286 reviews

Guest suite in Sherwood

Sherwood Hollow- Senior discount at request - 60+

Welcome to Sherwood Hollow! This completely refurbished retreat is a large 1200 square foot downstairs suite in our 1960's home. This spacious area has a large living room, eat-in kitchen, and spacious bedroom. The unit is private and completely closed off from the upstairs. Our home is located just a short walk from Old Town Sherwood and beautiful Stella Olsen park. This unit is near the bottom of a hill, a bit of a climb coming up from Old Town, and the driveway is on an incline.

4.99 out of 5 average rating, 149 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.

4.86 out of 5 average rating, 126 reviews

Townhouse in Sherwood

Cozy 2 bed, 1 bath, private backyard in Sherwood

Whether you are visiting family, on a getaway, going wine tasting, or want to be close to Portland but not in it....you will feel right at home staying in our 2 bedroom, 1 bath duplex! (This is half of the duplex- all one level- LEFT SIDE). You can 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.

4.99 out of 5 average rating, 149 reviews

Guesthouse in Sherwood

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.

4.86 out of 5 average rating, 325 reviews

Guest suite in Sherwood

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.

4.95 out of 5 average rating, 126 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.

Superhost

Tiny home in Sherwood

4.92 out of 5 average rating, 193 reviews

Sip & Stay - Charming Tiny House Near Wineries

🍷 When our fun-loving guests aren’t exploring local wineries or waterfalls, they’re unwinding—lounging at the picnic table, strolling with their pup 🐶, or cozying up with a book 📖 from our unique library. This bright, stylish retreat has it all: two comfy beds 🛏️, a fresh-air shower 🚿, ample counter space for work or dining, a fully stocked kitchen 🍽️, a large BBQ 🔥, and a pet care kit. Craving downtime in the fresh air? You’ve found it!

4.95 out of 5 average rating, 968 reviews

Apartment in Newberg

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.

4.99 out of 5 average rating, 146 reviews

Barn in Sherwood

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.

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Other great holiday rentals in Sherwood

Barn in Sherwood

4.79 out of 5 average rating, 364 reviews

Cozy barn with bedroom and loft

TylerRating, 5 stars2 months ago

The space was quant and adorable. My wife and I thoroughly enjoyed staying in the cozy barn! It stayed nice and warm, was nice and private. It was easy to access multiple different towns within minutes. Served all of our needs. Lisa was very helpful with any questions we had and was very quick to respond. Overall greatly enjoyed our stay here

4.9 out of 5 average rating, 72 reviews

Farm stay in Sherwood

Scholls Mountainside Schoolhouse

SuzanneRating, 5 stars2 weeks ago

Such a beautiful, peaceful and private location in an adorable, artfully restored and decorated old schoolhouse. Perfect place to relax and find some solitude. The one drawback is if you don't have a vehicle, which I didn't, the road is quite busy with a narrow shoulder. I like to walk and explore, which I did, but often wondered if I'd live to tell about it! Otherwise, I highly recommend it for a single person or couple.

4.97 out of 5 average rating, 89 reviews

Tiny home in Beaverton

Beaverton Vintage Tiny Home

AkhileshRating, 5 stars2 weeks ago

Loved our tiny home experience. Everything placed inside home is thoughtful and almost all the necessities for an accommodation are fulfilled by this tiny place. Parking is super easy and loved the overall experience.

5 out of 5 average rating, 8 reviews

Apartment in Beaverton

Cozy Studio in Quiet Community

KellyRating, 5 stars3 weeks ago

This place was cozy and comfortable and very clean. The host was in touch and very responsive and we enjoyed our stay!

5 out of 5 average rating, 16 reviews

Home in Newberg

Cozy Haven |Fire Pit |EV Charger |Central A/C

SusanRating, 5 stars3 days ago

Kristen was an excellent host! She was quick to respond with info on the house and stay, offered suggestions for the area, and the house was perfect for a large group that included families! Will be staying there again for sure!

5 out of 5 average rating, 29 reviews

Guest suite in Aurora

Mt Hood View near Champoeg Park!

MichaelRating, 5 stars4 days ago

If you’re looking for a peaceful retreat with stunning views, this studio is an absolute gem. Waking up to Mt. Hood glowing in the sunrise right from the window was surreal — like something off a postcard. The space is clean, modern, and thoughtfully designed. It’s small, but it doesn’t feel cramped. Everything from the cozy bed to the well-equipped kitchenette made the stay super comfortable. Bonus points for the private deck — perfect for a morning coffee or a sunset glass of wine. The host was incredibly responsive and welcoming, and the check-in process was seamless. Location-wise, it’s close enough to town for groceries and essentials, but just far enough out to feel totally quiet and disconnected in the best way. Whether you’re hiking, fishing, or just wanting to rest and reset, this place hits every mark. Highly recommend — I’ll definitely be back

5 out of 5 average rating, 52 reviews

OR Wine Country Get Away

BrentRating, 5 stars3 weeks ago

Jenn's a great host. Responding quickly to any questions. Beautiful place. Great stay.