Holiday houses in Sherwood

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Top-rated holiday rentals in Sherwood

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

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Top Guest favourite
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
4.98 out of 5 average rating, 127 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 favourite
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, 184 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 favourite
A cozy bedroom setup includes a spacious bed with white linens, a 55-inch smart TV mounted on the wall, and a black mini-fridge. A wooden cabinet holds books and games, while a decorative rug covers the dark wood floor. Wall art and a calendar are also visible.
Home in Tigard
5 out of 5 average rating, 176 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 favourite
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, 312 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.

Guest favourite
A well-lit bedroom features a spacious bed with neutral bedding. A large window allows natural light to illuminate the room, complemented by plants visible outside. Decorative wall art adds character, while a cozy chair in the corner invites relaxation.
Guest suite in Beaverton
4.9 out of 5 average rating, 409 reviews

Suburban Retreat in Beaverton,Or.

Private entrance.into a a small one bedrm apartment or mother In law space. Stacked washer/gas dryer ..refrigerator.. cooktop.. microwave ..everything you need to cook or Grill a meal. While your out for the day I empty trash...collect recyclables... and tidy up kitchen and bath areas for you. You come back each day to a Clean quiet Space and relax. Sit in the Hot tub or sauna or sit on the deck and enjoy the beauty of nature and listen to the sounds of birds and wildlife around you.

Top Guest favourite
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, 172 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.

Top Guest favourite
The living area features a soft brown sofa adorned with patterned cushions, situated on a neutral-toned area rug. Two stylish chairs with orange accents flank the sofa. Warm light is provided by two lamps, enhancing the cozy atmosphere of the room.
Guest suite in Cedar Mill
4.99 out of 5 average rating, 132 reviews

Jason & Susie's private guest suite w/ kitchenette

Located in NW Portland, our space is in a quiet neighborhood, next to a park and tennis courts. We are 7 minutes from the Nike Headquarters, 2 minutes from Columbia Sportswear Headquarters, and 15 minutes from Intel, making it a perfect stay for your business needs. We are within walking distance to a grocery store, pubs, small restaurants, and the Saturday Cedar Mill Farmers Market. Close by is the entrance to Forest Park, one of the largest urban parks, with 80 miles of trails.

Guest favourite
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, 365 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.

Guest favourite
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, 209 reviews

Charming Winery Getaway ~ Comfy and Cozy

When guests aren’t exploring local wineries or hiking 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 and stylish tiny space has it all: two comfy beds, a refreshing open-air shower, generous 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 the perfect getaway!

Top Guest favourite
The spacious bedroom is characterized by brown walls and soft carpeting. A large bed with neutral bedding is complemented by a decorative wall art piece above. A comfortable window seat is adorned with patterned pillows, and bedside lamps provide gentle lighting.
Guest suite in Sherwood
4.97 out of 5 average rating, 103 reviews

Carly's Comfort Inn

Great location for wine country enthusiasts, and so much more. Five minutes to Old Town Sherwood for dining and wine tasting. Nearby wineries include Hawk's View, Blakeslee Vineyard Estate and Alloro Vineyard. Carly's Comfort Inn is the hub for exploring Willamette Valley wineries, the coast, Silver Creek Falls, Columbia Gorge or Mount Hood. A day trip in any direction and a cozy place to return to at the end of the day.

Top Guest favourite
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, 209 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 favourite
The exterior of the Tiny Home features a welcoming wooden deck with stairs leading up. Flower pots filled with greenery flank the steps, while large windows allow natural light to illuminate the interior. A vibrant front door adds a pop of color against the dark siding.
Tiny home in Beaverton
4.96 out of 5 average rating, 183 reviews

Beaverton Vintage Tiny Home

Have you ever wondered what it's like to stay in a Tiny Home? Our Tiny Home away from Home has everything you need to relax, live a little and have fun. Our location is in the burbs just 15 minutes west of downtown Portland and minutes to Nike World Headquarters. The Tiny Home has a kitchenette, full bath, w/d, living area, queen bed loft, and personality galore!

Popular amenities for Sherwood holiday rentals

When is the best time to visit Sherwood?

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Avg. price$128 AUD$122 AUD$158 AUD$149 AUD$143 AUD$248 AUD$169 AUD$248 AUD$163 AUD$152 AUD$138 AUD$150 AUD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Sherwood?

    Sherwood has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there Sherwood vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Sherwood, available on Airbnb. Make a splash and soak up the sun in style!

  • Do hotel rentals in Sherwood have a gym?

    Absolutely! We offer over 10 hotel rentals with a gym 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 30 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 30 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 air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do hotel rentals in Sherwood have wifi?

    Absolutely! We offer over 10 hotel rentals with wifi in Sherwood. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Sherwood

  • Total holiday rentals

    Explore 40 holiday rentals in Sherwood

  • Nightly prices starting at

    Sherwood holiday rentals start at $43 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,930 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Sherwood holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Sherwood rentals

  • 4.8 Average rating

    Sherwood stays are highly rated by guests—averaging 4.8 out of 5!

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