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Vacation rentals in Sherwood

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Top-rated vacation rentals in Sherwood

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

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Top guest favorite

The living area features a comfortable reclining couch paired with a woven chair and an upholstered armchair. A bookshelf filled with books and decorative items enhances the space. Wall art and unique decor items are displayed throughout, contributing to a cozy and inviting atmosphere.

Guest suite in Sherwood

4.97 out of 5 average rating, 118 reviews

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.

Top guest favorite

A cozy cabin with wooden exterior is set on a well-maintained grassy area, surrounded by a wooden fence. A concrete path leads to a welcoming porch with seating. A shed is visible nearby, adding to the charm of this peaceful outdoor space.

Guesthouse in Sherwood

4.99 out of 5 average rating, 164 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 (out of order), smart TV and second queen pull-out. The full bath features walk-in rain shower and full vanity.

Top guest favorite

A bright master suite features a spacious bed dressed in white linens. Natural light filters through large windows, illuminating the room. Wall sconces provide gentle lighting, while decorative items are displayed on the walls, adding character to the space.

5 out of 5 average rating, 130 reviews

Mama J's

For whatever brings you to Oregon, stay at Mama J’s comfortable, peaceful, safe and convenient spot. Portland is just ten miles away, the closest beaches, Columbia River Gorge and Mt. Hood are all about an hour, and there are numerous hikes from the forest right down the street to Silver Falls and beyond. The neighborhood is peaceful and your private patio is the perfect place for a beverage and some bird and squirrel watching. If it rains, hang out in the gazebo! Hope to host you here!

Top guest favorite

The living room features a comfortable large sofa and an armchair, arranged around a coffee table on a patterned area rug. A flat-screen TV is mounted above a brick fireplace, and natural light filters through the window, complemented by light-colored curtains.

Guest suite in Sherwood

4.98 out of 5 average rating, 301 reviews

Sherwood Hollow- Senior discount (60+) $88/night

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.

Top guest favorite

A charming craftsman home is framed by a white picket fence, with a welcoming front porch and a pergola overhead. The exterior features dark blue siding, three front-facing windows, and lush greenery surrounding the entrance.

Home in Sherwood

4.99 out of 5 average rating, 157 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.

A light-filled living area features a comfortable gray sofa with accent pillows, situated adjacent to a wooden coffee table. A large mirror reflects the space, and a dining area with blue chairs is visible in the background, enhancing the welcoming ambiance.

Townhouse in Sherwood

4.85 out of 5 average rating, 136 reviews

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.

A light blue teapot with delicate floral designs is positioned in the foreground. Behind it, several clear glass wine glasses are arranged, reflecting soft light from a nearby lamp that casts a warm glow across the surface.

Guest suite in Sherwood

4.87 out of 5 average rating, 344 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.

An outdoor picnic table is positioned on a bed of natural mulch, surrounded by towering trees. The tiny house, featuring a red and white exterior, is visible in the background, complemented by a small fenced area and a grill.

Tiny home in Sherwood

4.91 out of 5 average rating, 202 reviews

Affordable Winery Getaway ~ Charming and Cozy

🍷 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 and unique tiny space 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!

Top guest favorite

An inviting entrance showcases a fountain surrounded by lush greenery and stone pathways. The front door, framed by ornate pillars, opens to a well-lit interior. Soft lighting enhances the welcoming atmosphere, with a seasonal wreath adorning the door.

Home in Sherwood

4.96 out of 5 average rating, 138 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.

Top guest favorite

Two mini-Highlander cows are seen grazing in a grassy field, surrounded by a wooden fence and lush green bushes. A bright blue sky with fluffy white clouds creates a serene backdrop, enhancing the peaceful rural atmosphere.

Barn in Sherwood

4.97 out of 5 average rating, 178 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, unique accommodations and say hi to the mini cows. Check out our photos to imagine yourself in this peaceful paradise.

Top guest favorite

An inviting living area features floor-to-ceiling windows that offer views of the surrounding forest. Minimalist furniture includes a wooden table, lounge chairs, and a futon, creating a comfortable space to relax or entertain. Natural light enhances the cozy atmosphere.

Apartment in Newberg

4.94 out of 5 average rating, 1,004 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.

Top guest favorite

An open studio space features a queen bed with decorative pillows and a cozy lounge couch. A kitchenette is visible in the background, along with a wooden table and chairs. Natural light floods in from the window, highlighting the warm wooden flooring.

Home in Newberg

5 out of 5 average rating, 658 reviews

Newberg Garden View Suite – Peace, Rest, Enjoy

This updated suite is a totally private unit ready to enjoy. Your own separate entrance, large deck overlooking the garden, and enough space to relax. A 10-minute walk to the center of Newberg with a country feel. In the heart of Chehalem Valley within a 10-minute drive to 50+ wineries, and many beautiful areas to explore close at hand. Designed for individuals or a couple.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodations with great services and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Sherwood vacation rentals

Laptop-friendly workspace

Air conditioning

Other great vacation rentals in Sherwood

A picturesque vineyard landscape features rows of young grapevines leading up to a charming two-story house. The property is adorned with lush greenery and trees, set against a cloudy sky that hints at a tranquil atmosphere.

Farm stay in Sherwood

4.88 out of 5 average rating, 190 reviews

Ariniello Vineyard - Private 2 Bedroom Suite

Top guest favorite

A cozy living area features a sectional grey sofa with soft throws draped over it. A flat-screen TV is mounted on a wooden wall. Natural light enters through a yellow door, illuminating the open space, which includes a round dining table set with clear glasses.

Apartment in Tualatin

4.96 out of 5 average rating, 280 reviews

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

A charming two-story cottage features light yellow siding and is adorned with lush greenery. An inviting entrance is framed by a trellis, leading into the home. Nearby, the landscaped garden showcases a mix of plants and flowers, contributing to a serene outdoor environment.

Cottage in Newberg

4.97 out of 5 average rating, 174 reviews

Oxberg Lake Retreat, lake & farm view in wine ctry

Top guest favorite

A vibrant outdoor space features a patio set with black metal chairs and a table, overlooking a lush garden. Colorful autumn foliage surrounds the area, with greens, oranges, and reds, while a double rainbow arcs gracefully over the scene, enhancing the landscape.

Guest suite in Hillsboro

4.99 out of 5 average rating, 246 reviews

Willamette Valley Wine Country Hub

Top guest favorite

A bedroom is featured with a spacious bed adorned in an orange coverlet. Light streams through a large window with a view of outdoor greenery. A nightstand with a lamp and a decorative plant enhances the room's simplicity, while a large mirror reflects the inviting space.

Apartment in Tigard

4.99 out of 5 average rating, 149 reviews

Private one-bedroom unit with living space.

Top guest favorite

A spacious studio is depicted, featuring a comfortable sofa and a day bed placed near a large window. A king-size bed is positioned thoughtfully in the room. The floor is adorned with a decorative area rug, and dark curtains frame the windows, allowing natural light to filter through.

Guesthouse in Murray Hill

4.99 out of 5 average rating, 323 reviews

Park Cottage

Top guest favorite

A charming sign reading 'Willow Creek Cottage' is mounted on a yellow wooden wall. Lush greenery surrounds the entrance, adding a touch of nature to the welcoming facade.

Guesthouse in Wilsonville

4.95 out of 5 average rating, 541 reviews

Willow Creek Cottage

Top guest favorite

A charming farmhouse exterior is depicted, featuring a spacious front porch adorned with hanging flower pots. Lush green lawns and vibrant flower beds enhance the inviting landscape, while an American flag adds a touch of character. The building boasts multiple stories and classic architectural details.

Apartment in Tigard

4.93 out of 5 average rating, 174 reviews

Private Apartment at the Farmhouse

Quick stats about vacation rentals in Sherwood

Total rentals
30 properties
Nightly prices starting at
R524 ZAR before taxes and fees
Total number of reviews
1.8K 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 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.
Do house rentals in Sherwood have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Sherwood. Enjoy a tailored experience with all the comforts you desire.
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.
Do house rentals in Sherwood have free parking?
Absolutely! We offer over 10 house rentals with free parking in Sherwood. Enjoy a tailored experience with all the comforts you desire.
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 wifi, over 10 homes with a kitchen, over 10 homes with free parking, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
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.

Destinations to explore