Home Vacation Rentals By Owner In Sherwood, OR

Showing 20 Of 28 Vacation Rentals
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Exceptional(6)

$769.31

/ Nightly
Private Vacation Home

Luxury Wine Retreat • Spa Sunroom • Walk Downtown

Sherwood, Oregon, United States

Sherwood Retreat | Elevated Wine Country LivingbrbrWelcome to Sherwood Retreat — a beautiful luxury home just one block from downtown Sherwood. Walk to cafés, tasting rooms, breweries, and parks, then return to your private wine-country oasis featuring a light-filled sunroom with a spa-style hot tub framed by expansive windows.brbrDesigned for groups, families, and wine lovers who want comfort, style, and unbeatable walkability.brbrWhy Guests Love ItbrGlass-Enclosed Sunroom Hot Tub – Soak year-round in a bright, window-lined retreatbrBackyard Fire Pit – Perfect for evenings under the starsbrFull Game Room – Arcade games, foosball, air hockey & Nintendo SwitchbrCozy Media Lounge + Fireplace – Movie nights made easybrChef’s Kitchen – Ideal for hosting dinners & wine tastingsbrPet-Friendly + Fenced Yard – Travel easily with dogsbrbrSleeps 12 ComfortablybrThoughtfully designed for privacy and group comfort:br• 2 King Bedrooms – spacious primary retreatsbr• 2 Queen Bedrooms – each with two queen bedsbr• Bunk Room – full-over-full bunk (perfect for kids & teens)br• 3 Full Bathrooms – plush towels + essentials providedbrbrEntertainment for All Agesbr• Large living room with sectional & Smart TVbr• Dedicated game room with multiple arcade optionsbr• Separate media lounge with fireplacebr• Board games + puzzles for relaxed afternoonsbr• High-speed WiFi throughoutbrbrGather, Cook & CelebratebrOpen-concept layout perfect for connection:br• Fully stocked chef’s kitchen with stainless appliancesbr• Large island for prep, appetizers & conversationbr• Keurig + drip coffee makerbr• Wine glasses & bar tools for tasting nightsbr• Seamless flow between kitchen, dining & living areasbrbrIndoor–Outdoor LivingbrThe highlight of the home: a sunroom lined with windows, creating a bright spa atmosphere around the hot tub — rain or shine.br• Window-filled sunroom with hot tub & lounge seatingbr• Deck with dining furniture + grillbr• Fire pit for cozy eveningsbr• Private fenced yardbr• EV charger in garage (bring your own cable)brbrPrime Wine Country Locationbr1 block to downtown Sherwood shops & tasting roomsbrMinutes to Willamette Valley wineriesbrEasy drive to Newberg, Dundee & PortlandbrQuiet, charming neighborhoodbrbrThe Perfect Wine Country Home BasebrSpend your days exploring vineyards and your evenings soaking in the sunroom spa, gathering around the fire pit, or enjoying dinner with friends.brSherwood Retreat blends luxury, location, and entertainment — all within walking distance of downtown.brbrBook your wine country escape today.
Bed 5

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Bath 3

Bath

Sleep 12

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Exceptional(19)

$98.33

/ Nightly
Mobile Home

Charming Winery Getaway ~ Comfy and Cozy

Sherwood, Oregon, United States

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!brbrWelcome to the Wine Wagon - Nestled on the edge of a quiet forest, not far from Hiway 99, next to a gravel driveway, this tiny home has easy access to everywhere you`ll need to go. br brOur tiny house with a big personality and a love letter to both wine and whimsy. Every corner here has a story: a chandelier dripping with wine glasses (because why not), towels tucked into a wine rack, and yellow pops of cheer sprinkled throughout. The space sleeps 3 comfortably, with a queen + twin bunk perfect for kids, friends, or anyone who likes their own nook. br brClever design makes this tiny retreat mighty: a fold-down bathroom counter, secret phone shelf, under-bed luggage storage, and yes, our famous cedar loo (eco-friendly, quirky, and we’ll happily explain how it works). Step outside for the true showstopper—an outdoor shower with cedar walls and forest views that turns into a steam shower in colder months. br brBack inside, you’ll find all the comforts: a stocked kitchen (yes, real creamer, no sad powder), slippers at the door, a ‘just in case’ jar of essentials, and a WiFi hotspot phone so you can stay connected…or not. br brBest of all We’re just 15 minutes from a dozen local wineries—sip, swirl, and toast, then return to your forest hideout. br brThe Wine Wagon isn’t just a stay—it’s a story waiting to be told.brbrHuman neighbors are friendly, but enjoy the privacy that country life ensures. The numerous animal neighbors are furry, or feathered, and some are approachable; but most are pretty shy. (deer, raccoon, quail, squirrels, skunk, etc...)brbrLooking for a stress free ride Uber, Lyft, and Enterprise Rent A Car all provide easy and convenient service for My Tiny Wine Wagon.brbrPlease, please, do read the Helpful House Handbook. Tiny Houses are unique and your comfort will be GREATLY enhanced if you`re familiar with the features. br brPet and Animal Policy: brFor a harmonious coexistence in our cozy space, we kindly ask you to consider these simple guidelines to make the most of your pet-friendly stay: br1. To ensure everyone`s safety, all animals must remain leashed when outside. br2. We have a bit of a no-pets-on-the-furniture policy. That includes beds and lofts too! br3. Our general limit is two pets per stay, unless we`ve chatted and made special arrangements. br4. Cat lovers, bring your own litter box along for your feline friends. br5. We`ve got you covered with pet waste bags—please use them for clean-ups, every single time. br6. We`re all about quality time together, so no leaving furry friends solo in the homes. Even in a crate. br7. Oopsie moments happen! If they do, there are handy cleaning supplies under the sink. br8. A little daily sweep will do wonders, and is required, to keep fur from taking over. br9. The main driveway is available for walking your pet. Please be mindful of our neighbor’s desire for privacy and avoid their lawns, personal driveways, and private forest. br10. To keep things fair and square, we now require an add on to your reservation: a fully refundable $150 security deposit, due 14 days before your stay, and processed via the AirBnB Resolution Center. It`s all about trust. If we all play by the rules, your deposit will be returned to you. However, after any rule-bending (including extra laundry, cleaning, or upholstery work), it`s not gonna’ come back to you. Plus, intentional rule breakers might face extra fees. Let`s keep things snazzy! br br brCedar Loo Toilet Details: brWe want you to love your stay, and that means making sure you’re comfortable with our eco-friendly, flushless Cedar Loo style toilet. It’s simple to use and saves thousands of gallons of water each year. But let’s be real—if you’re expecting a traditional flush toilet, this might not be the right rental for you. br brHow it works Sit, do your business, toss in a handful of cedar chips, and close the lid. Once a day (or as needed), simply lift out the bag, tie it shut, and place it in the designated outdoor bin. A fresh bag will be ready to go—no extra setup needed! br brIf the idea of this type toilet makes you uneasy, we totally understand! We’d rather you book a place that meets your expectations than be surprised upon arrival.brGuests must review and reply to our Welcome Message incl intake questions ~ No SMOKING indoors or out ~ Guest’s visitors must be approved prior to their arrival ~ Pet and animal owners must review & agree to pet policy & $150 add on refundable security deposit (processed via AirBnB Resolution Center) ~ Government ID SELFIES may be required for guests ~ No 3rd Party Bookings ~ Responsible use of cedar loo toilet per instructions provided
Bath 1

Bath

Sleep 3

Sleeps

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Exceptional(3)

$258.04

/ Nightly
Cottage

Dreamy Wine Country Retreat: Sherwood 'Rose Cabin'

Sherwood, Oregon, United States

Working Horse Farm Location | Scenic Views | Ideal for Corporate & Wellness Retreats | Close to Wineries & Hiking AreasbrbrWith its peaceful countryside setting and charming design, this 4-bedroom, 2-bath vacation rental hosts the perfect pairing. Scout out a spot to practice your morning flow — like the private back deck — and spend afternoons hiking (or sipping) your way through the Willamette Valley. Seeking even more adventure Visit exciting Portland, just 22 miles away.brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 twin bunk bedbr- Bedroom 3: 1 twin bunk bedbr- Bedroom 4: 1 twin bunk bedbr- Living Room: 1 queen daybedbrbrHOME FEATURESbr- Flat-screen TVbr- Dining tablebr- Remote workspacesbr- Open floor planbr- Charming cottage decorbrbrOUTDOOR SETTINGbr- Furnished deck w/ forest viewsbr- Bubble rock w/ viewing deckbr- Peaceful countryside settingbr- 12 gated acres w/ on-site animalsbrbrKITCHENbr- 2-burner induction electric cooktopbr- Microwave, toaster, toaster ovenbr- Breakfast bar w/ stools, dishwasherbr- Cooking basics, dishware/flatwarebr- Blender, air fryer, juicer, kettlebr- Drip coffee maker (starter coffee provided)brbrGENERALbr- Free WiFibr- Washer/dryerbr- Linens/towels, hair dryerbr- Complimentary toiletriesbr- Central heating & air conditioningbr- Emergency lanternsbrbrFAQbr- Homeowner on-site (separate house)br- On-site farm animalsbr- 1 exterior security camera (facing out)brbrACCESSIBILITYbr- 2-story cottage, 2 steps requiredbrbrPARKINGbr- Driveway (4 vehicles)brbr-- THE LOCATION --brbr- 2-3 miles to local wineriesbr- 4 miles to Downtown Sherwoodbr- 7 miles to Newbergbr- 8 miles to Wilsonvillebr- 22 miles to Downtown Portlandbr- 33 miles to Portland International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-story cottage requires 2 small steps for entry br- This property does not have an oven but does have a toaster ovenbr- The homeowner lives on-site, in a completely separate house, and may be present during your staybr- This property is located on a working horse farm with on-site animals and may not be suitable for young children. Guests may not touch or interact with any of the animals, including the horses. While there are roosters in proximity to the property that may be present during your stay, you must refrain from coming into contact with them and all other animals on-sitebr- Power outages are known to happen in the area. There is a tack room located 90 feet from the property that has running heated water and a toilet if neededbr- Your safety matters. This property features 1 exterior security camera located on the outside of the house facing the main entrance and yard with horses. The camera is outward facing and does not look into any interior spaces. The camera records video and sound while guests are in residence
Bed 4

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Bath 2

Bath

Sleep 10

Sleeps

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Exceptional(2)

$1620.67

/ Nightly
Private Vacation Home

NEW build! 20 acres, Sauna, Theater, Games, Sport Ct, Turf, Outdoor Kitchen, Gym

Sherwood, Oregon, United States

Brand new build! 8500 sqft on 20 acres! (Events require case-by-case approval, please visit BeyondTheAbode . org for rules, fees, & info.)brbr Bluetooth Surround Sound connects easily from your phone throughout all of the downstairs, master bedroom/bathroom, outdoor kitchen & sports court. HUGE garage door opens up indoor sports court to the huge outdoor patio. Game Room, Sauna, Theater, Backyard is turf, Playroom with endless amounts of toys, Bunk room, Gym, high end appliances, ballpit under the stairs, indoor slide sturdy enough for adults, 5 bathrooms have bathtubs, 6 showers plus an outdoor shower, master bathtub is a giant soaker tub and master shower is heaven with 4 rain showers, 3 body sprayers and a hand sprayer. So many extras!brbrThe Wall to Wall glass doors in the Great Room open up completely to the outdoors, as well do the wall to wall glass doors in the game room. Slat pool table, air hockey, pop a shot, foos ball, so many kid and adult board games..Luxury upgrades & More! brbrThis is our beautiful family dream home & we want to share it with you. Relax with family & friends at this spacious escape in nature - walking distance to so many things! brbrDeer are seen nearly daily. We currently have several families including 2 sets of twin babies. You may also spot hawks, eagles, bunnies, squirrels, and much more wildlife. The home backs up to a nature reserve, but is also close to the urban growth boundary on the other side, so you can walk to many parks, trails, or old town where you’ll find a fantastic local coffee shop, scrumptious dinner options, fun gift shops, wine bars and more! brbr*PLEASE NOTE*br* From time to time you can hear the Tualatin gun range from our property (as with most all houses in Sherwood). It never bothers us and we almost never hear it from inside but when outside IF it's extremely active it is definitely noticeable. Most of the time you will hear the sound of birds chirping and leaves rustling, but we want to be SURE this details is understood.br*The property does have poison oak out in the areas beyond our home. We take fequent walks throughout the entire 20 acres but if you'd like to do the same, please make sure you have pants and/or at least high socks, and boots if you want to be extra cautious :) br*Event permission approval is on a case by case basis & with an additional fee. Rules & restrictions apply. We are only able to accept a small number of events per year - please inquire! br*Most closets will be locked off since this is our personal home, but we will have free standing clothes hanging options and organization as well as a luggage rack, etc in each bedroom.br*Several cupboards and drawers will be locked as well. We provide everything you will need, in your own guest cabinets and cupboards. We have marked all cabinets and drawers that are open for your convenience to use and store items,br*No garage access, but plenty of parking available!br*There are cameras monitoring the exterior of the home and property as well as one camera monitoring the sports court. These will not be monitored routinely but will remain live during your stay.br*Absolutely NO SMOKING inside OR outside anywhere on the property or gravel easement leading to the property. And please do not walk up to the neighborhood and smoke on their street. $1000 fine for smoking anywhere outside and $2,500 fine for smoking inside.brThis home has our heart & soul & all we ask is you love & respect it as much as we do!
Bed 8

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Bath 7

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Sleep 24

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