Vacation Rentals By Owner In Sherwood, OR

Plan your escape to Harmony Estate for an unforgettable experience in Oregon Wine Country. This remarkable property offers peace, privacy, and breathtaking natural beauty, creating a tranquil retreat where every moment feels restorative. Set among rolling pastures with sweeping views of Mount Hood, this custom home invites you to slow down, savor, and reconnect with the simple pleasures of country living.brbrStep inside and you are welcomed by a warm and inviting family room featuring a shuffleboard table, cozy fireplace, and comfortable seating for morning coffee or an evening glass of wine.brbrThis spacious four bedroom, three and a half bath home blends elegance and ease through its open concept design. The professional kitchen is a chef's dream, complete with a large pantry that includes a coffee bar and sink, a food warmer, microwave, and oven. While preparing meals, enjoy spectacular views of Mount Hood through the large picture windows, then dine while overlooking the serene pasture where five beautiful horses graze.brbrThe primary suite, located at the end of the hallway, is a peaceful sanctuary with a king bed, vaulted ceiling, and a private deck that overlooks the garden, perfect for dining outside or relaxing in the quiet of the evening. The elegant ensuite bathroom features luxurious finishes and thoughtful details. A second suite offers another king bed, walk in closet, and a private bathroom, ideal for couples or close friends traveling together. The third bedroom provides flexible sleeping arrangements with a bed that can be set up as a king or two twins. Upstairs, the loft area includes a trundle bed, small desk, and cozy seating, an ideal spot for reading, games, or planning the day's adventures.brbrStep outside to explore the charm of Harmony Estate's lush surroundings. Behind the historic barn, you will find a chicken coop and peaceful forested green space, perfect for a morning stroll or quiet reflection. The expansive grounds invite gathering, exploring, and creating memories that will last a lifetime.brPerfectly situated in the heart of the Willamette Valley, Harmony Estate is surrounded by exceptional wineries, including Beckham Estate Vineyards, J Rallison Cellars, and Parrett Mountain Cellars, all just moments from your door. For a truly immersive experience, join one of our Pinot Car Wine Tours, where our knowledgeable guides curate personalized tastings and vineyard visits across Oregon's celebrated wine country. For evenings out, our dinner shuttle service is available Thursday through Sunday. Head into town to enjoy local favorites like Rosmarino, Trellis Wine Bar, and The Newbergundian Bistro. With its serene setting, and close proximity to First Street's boutique shops, and easy access to the surrounding vineyards, Harmony Estate provides the perfect blend of relaxation, refinement, and convenience for your Willamette Valley getaway.brbrTraveling with little ones Family items such as baby gates, high chairs, and pack n plays are available to rent for a small one-time fee. Additional items, including yoga mats, air mattresses, and outdoor games such as bocce ball, croquet, and ladder toss, can also be arranged upon request. If you have a special need, our concierge team will be happy to help make it happen.brbrAt Lifestyle Properties, our mission is to provide high-quality hospitality to Willamette Valley travelers through partnerships with the region's best local businesses. We specialize in luxury short-term lodging with a focus on comfort, cleanliness, and personalized service so that every guest feels at home from the moment they arrive.brbrImportant Things to Note:br• We welcome up to two (2) dogs, with a non-refundable fee of $100 per dog.br• Dogs are the only pets permitted unless otherwise approved. If you would like to bring a cat, you must receive prior approval from both the homeowner and property manager. If approved, a $300 non-refundable fee plus taxes and fees will apply.br• VRBO will collect the guest service fee first, and the remaining reservation payment will be processed separately by our property management team.

Country House

Harmony Estate: Spacious Home with Mt Hood Views

Sherwood, Oregon, United States

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$216.73

Our beautiful guesthouse, is located on 3 wooded acres with wonderful country views, in the hills above Sherwood. The home's bright, open space, is the perfect location for your Wine Tasting Trip, a Romantic Getaway, or a Relaxing Family Vacation. Our Casita is just minutes from local wineries, restaurants and coffee shops and is completely separate from our main home. brbrThe private deck with gas BBQ, is a great place to relax with a cup of coffee or tea in the morning, or a glass of wine in the evening, all while enjoying the lovely country views. brbrLIVING AREA:br- Relaxing Open Space w/ Lots of Natural Lightbr- Cozy & Comfortable Sofa and Loveseatbr- New 55” Sony Flat Screen TVbr- Black-Out Curtains and Black-Out Window Blinds br- Queen Size Murphy Bed – Creating a Great 2nd Sleeping Area brbrKITCHEN & DINING:br- Open Kitchen w/Granite Countersbr- Full Size Refrigerator w/ Automatic Ice Makerbr- Microwave and Bosch Dishwasherbr- Fully Stocked w/Cookware and Bakewarebr- All Utensils and Small Appliancesbr- Large Dining Table w/ Cushioned Chairsbr- Leather Bar Stools for Casual Dining at the Counter BarbrbrBEDROOM:br- Comfortable Queen Size Mattressbr- Premium Linens and Comfy Pillowsbr- Black-Out Curtainsbr- Ceiling Fan w/ Adjustable SpeedsbrbrBATHROOM:br- Large Corner Shower w/ Adjustable Rain Headbr- Marble Counter Vanity w/ Extra StoragebrbrLAUNDRY:br- Large Washer & Dryer SetbrbrOUTDOOR SPACE:br- Partially Covered Deck with a great view br- Comfortable Chairsbr- Gas BBQ w/Cooking Utensilsbr- Plenty of Parking on the Propertybr

Guest House

Lovely Wine Country Casita - Private Guesthouse, Beautiful Views

Sherwood, Oregon, United States

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Exceptional(2)

$433.13

Hoodview | Mt. Hood Views | 4 King Beds | Wine Country Retreat | Pet FriendlybrbrWake up to sweeping vineyard views and distant Mt. Hood at this peaceful wine country retreat, set on a working vineyard in the heart of Oregon’s Willamette Valley. Perfectly located just minutes from Newberg and Sherwood, Hoodview offers a serene setting with easy access to some of the region’s best wineries and tasting rooms.brbrStart your morning with coffee on the spacious front porch overlooking the vines, then spend your day exploring nearby estate wineries and tasting rooms. In the evening, gather with friends and family for a sunset BBQ, pour a glass of local Pinot Noir, and unwind as the vineyard comes to life around you.brbrInside, the home is designed for comfort, space, and connection. Each of the four bedrooms features a king bed, making it ideal for couples, families, or groups traveling together. You’ll also enjoy a fully equipped kitchen, inviting living areas, and plenty of room to relax after a day of wine tasting and exploration.brbrHighlightsbr• Located on a working vineyard with Mt. Hood viewsbr• 4 bedrooms, each with a king bedbr• Expansive front porch for outdoor dining and sunset viewsbr• Fully equipped kitchen and comfortable living spacebr• Minutes from wineries, tasting rooms, and downtown NewbergbrbrTraveling with pets They’re welcome for a $50 pet fee.brbrGuests will also find a complimentary bottle of Stoller Family Estate wine upon arrival.brbrNEW: Ask us about additional amenities! From pre-stocked provisions to curated wine selections and special requests, we’re happy to help personalize your stay. Complimentary on-site tastings of our estate wines are also available by appointment for your group—just send us a message.brbrWhether you're planning a wine country weekend, family getaway, or trip with friends, Hoodview is the perfect place to relax, reconnect, and experience the beauty of Oregon’s Willamette Valley.brbrWe look forward to hosting you at Hoodview!

Private Vacation Home

Pet Friendly Vineyard Home with Mountain Views

Sherwood, Oregon, United States

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Exceptional(2)

$563.55

Vineyard Views | Mt. Hood Views | Private Wine Country Retreat Near NewbergbrbrEscape to Bell Rd Farmhouse, a peaceful wine country retreat set on a working vineyard in the heart of the Willamette Valley, just minutes from Newberg and surrounded by some of Oregon’s most celebrated wineries.brbrWake up to vineyard views and distant Mt. Hood, and spend your days immersed in the beauty, flavor, and slow rhythm of wine country living. This is a place designed for connection—whether that’s with family, friends, or the landscape itself.brbrWith 5 spacious bedrooms, the home comfortably accommodates groups while still feeling warm and inviting:br• Primary king suite with soaking tub for relaxing eveningsbr• Three queen bedrooms for restful comfortbr• One twin/trundle room ideal for kids or extra guestsbrbrGather together in expansive shared spaces designed for memory-making:br• Two dining areas perfect for shared meals and celebrationsbr• Comfortable living spaces for conversation, games, and downtimebr• A fully equipped kitchen for cooking—or hosting a private chef experiencebrbrOutside, the property truly shines. Step into your own private vineyard setting:br• Sunset patio seating overlooking the vinesbr• BBQ grill for long, relaxed outdoor mealsbr• Wide open lawn for lawn games and gatheringbr• Quiet countryside views in every directionbrbrThis is more than a stay—it’s a wine country experience. Spend your days exploring nearby wineries, then return home to golden-hour vineyard views and peaceful evenings under the stars.brbrTo welcome you, a complimentary bottle of Stoller Family Estate wine awaits upon arrival.brbrElevate your stay:brAsk about private chefs, curated wine experiences, pre-stocked groceries, and personalized touches. We also offer complimentary on-site estate tastings by appointment for your group.brbrBell Rd Farmhouse is where wine country memories are made—we look forward to hosting you.

Country House

Vineyard Farmhouse Stay with Mt. Hood Views. Spacious and Ideal for Large Groups

Sherwood, Oregon, United States

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Exceptional(3)

$258.04

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

Cottage

Dreamy Wine Country Retreat: Sherwood 'Rose Cabin'

Sherwood, Oregon, United States

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Exceptional(2)

$1620.67

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!

Private Vacation Home

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

Sherwood, Oregon, United States

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$499.31

Welcome to Beckham Estate Vineyard Guesthouse, a serene retreat tucked away on a beautiful thirty-four-acre property in the heart of Oregon Wine Country. This private single-level home is perfect for a family vacation or a peaceful wine getaway, offering the comfort of home paired with the refined touches of a luxury stay.brbrStep inside and feel the calm of wine country living. The spacious living room invites you to sink into the soft couch or loveseat and take in the sweeping vineyard views through large picture windows. A wood-burning fireplace anchors the space, creating a warm and welcoming atmosphere ideal for conversation and a glass of Beckham Estate wine before or after dinner. Each guest receives a complimentary tasting at the estate's nearby tasting room, a perfect way to begin your stay. For a quiet moment, slip into the smaller sitting area with another cozy fireplace, an inviting spot for reading, reflection, or a relaxed movie night. No matter where you choose to unwind, every corner of this home is designed for comfort and relaxation.brbrThe open kitchen is both stylish and functional, featuring beautiful countertops, brand new appliances, and everything you need to prepare family meals or casual vineyard brunches. Enjoy breakfast in the nook overlooking the vines, or gather around the farmhouse dining table for a shared meal. The views from the kitchen may even make you volunteer to do the dishes. If you'd rather leave the cooking to someone else, our team is happy to help coordinate an in-home chef for a private dining experience.brbrEach of the three inviting bedrooms offers vineyard views and plush bedding for a peaceful night's sleep. The primary suite includes a king bed and an ensuite bathroom with a standing shower, while the additional bedrooms share a newly renovated bathroom with a shower-tub combination and modern fixtures. Soft blankets, fluffy pillows, and gentle morning light make it easy to linger in bed with a cup of coffee as you start your day.brbrOutside, a large grassy area offers plenty of room for fun and games, perfect for a round of cornhole or space for the kids to run and play. The spacious patio features comfortable seating and two BBQ grills, inviting you to relax with a drink in hand while dinner cooks on the grill and laughter fills the air.brbrEvery detail at Beckham Estate Vineyard Guesthouse has been carefully considered to create a welcoming and memorable experience. From the beautifully maintained landscaping to the ease of keyless entry, this home is designed to help you settle in and unwind.brbrSurrounded by vineyards and close to the charming small towns that define Oregon Wine Country, this location offers the perfect blend of privacy and convenience. Explore Sherwood for a night out at 503 Uncorked or brunch at Fat Milo's, or head to Newberg for an afternoon at Social Goods or The Newbergundian. Whether you're exploring nearby wineries or savoring a quiet evening at home, this is wine country living at its finest.brbrTo make your stay even more special, consider booking a private wine tour through our preferred partner, Pinot Car Wine Tours. Enjoy curated tastings, scenic drives, and an insider's look at the best of Oregon's renowned Willamette Valley vineyards.brbrFamily items such as baby gates, high chairs, and pack n plays are available upon request, along with yoga mats, additional kitchen appliances, and outdoor games.brbrImportant Things to Note:br• We welcome up to two (2) dogs, with a non-refundable fee of $100 per dog.br• VRBO will collect the guest service fee first, and the remaining reservation payment will be processed separately by our property management team.

Private Vacation Home

Stunning New Listing - Beckham Vineyard Guesthouse

Sherwood, Oregon, United States

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Most popular vacation rentals in Sherwood

$1620.67

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

Sherwood, Oregon, United States

Bed

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Sleeps

$104.74

Sweet Bamboo Room with Half-Bath in delightful Sherwood with AC, WiFi, TV

Sherwood, Oregon, United States

Bed

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Sleeps

$148.97

Cabin

Cozy Willamette Valley Cabin With Modern Comforts

Sherwood, Oregon, United States

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Sleeps

$229.24

Cottage

Oregon Wine Country Retreat: Sip & Dine Outside

Sherwood, Oregon, United States

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Sleeps

$258.04

Cottage

Dreamy Wine Country Retreat: Sherwood 'Rose Cabin'

Sherwood, Oregon, United States

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Bath

Sleeps

$433.13

Pet Friendly Vineyard Home with Mountain Views

Sherwood, Oregon, United States

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$712.17

Luxury Wine Retreat • Spa Sunroom • Walk Downtown

Sherwood, Oregon, United States

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$563.55

Country House

Vineyard Farmhouse Stay with Mt. Hood Views. Spacious and Ideal for Large Groups

Sherwood, Oregon, United States

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$1580.50

Luxury and Cozy Villa in the Vineyard (Pet Friendly!)

Sherwood, Oregon, United States

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Bath

Sleeps

$717.75