House holiday rentals in Sherwood

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Top-rated house rentals in Sherwood

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

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Top guest favourite
Home in Tigard
5 out of 5 average rating, 183 reviews

Mama J's

For whatever brings you through/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!

Superhost
The living area features a comfortable sofa and two armchairs arranged around a coffee table, with artwork displayed on the walls. Natural light enters through a window, and a dining table for four is positioned nearby, creating an inviting environment.
Home in Sherwood
4.87 out of 5 average rating, 147 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!

Top guest favourite
A tranquil outdoor space features two wooden chairs and a round table, positioned to enjoy a breathtaking sunset. The sky is adorned with vibrant purple and orange clouds, casting a serene light over the landscape below.
Home in Newberg
4.97 out of 5 average rating, 260 reviews

Luxury Wine Country Estate

Welcome to Luxury Wine Country Estate, an oasis where luxurious refinement meets the epitome of wine country indulgence. Revel in unmatched hositality, thoughtfully designed to include Tempur-Pedic suites, therapeutic hot tub, rejuvenating sauna, invigorating cold plunge, and the most stunning valley and vineyard views. Every touch is meticulously crafted, from heated stone floors and Dyson innovations to dual gourmet kitchens, Yeti picnic essentials, EV charging capabilities, and so much more.

Top guest favourite
A spacious deck features a table set with gourmet snacks, a bottle of wine, and glasses, surrounded by comfortable seating. The lush vineyards and cherry blossoms are visible in the distance, under a clear blue sky, offering a serene outdoor setting.
Home in Newberg
4.95 out of 5 average rating, 129 reviews

Vineyard and Mountain View Wine Country Retreat

Our property is available to adults looking for some peaceful time. Conveniently located, our home will be a retreat to come back to after a day of exploring gastronomy and wineries in nearby towns. Numerous vineyards are in the immediate vicinity. On clear days enjoy views from our large deck of Mt Hood, St Helens, Rainier, and local vinery. We take great pride in maintaining a quality environment to share with others. Carefully read Additional Rules to decide if our home fits your needs.

Top guest favourite
A spacious living area features a black leather sofa adorned with colorful cushions, accompanied by a glass coffee table set on a decorative area rug. Natural light filters through sheer curtains, creating a warm and inviting atmosphere, complemented by modern artwork on the walls.
Home in Beaverton
4.94 out of 5 average rating, 159 reviews

A centralized newly remodeled luxury living

Look no further if you are looking for a sparkling clean home. Minutes away from our premier Washington Square shopping mall, groceries, and restaurants. Centrally located for a day trip to the Oregon coast, wine country, beautiful Columbia Gorge, or Mount Hood National forests. WiFi download speed 400 Mbps; upload speed 10 Mbps. Smoking or vaping is strictly prohibited in property. Please consider booking some other Airbnb property if someone in your party is a smoker or vaper.

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, 173 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
A spacious outdoor deck features a white Adirondack chair overlooking a vast landscape. The view encompasses rolling hills and a horizon that fades into the distance under a clear sky. Hues of autumn are visible in the trees and ground, adding color to the scenery.
Home in Newberg
4.95 out of 5 average rating, 211 reviews

Spectacular Valley View in Wine Country

Relax and enjoy the best of what Oregon Wine country has to offer in our newly renovated country home. With a stunning view overlooking the Willamette Valley, you are close to over 300 wineries and tasting rooms, local craft beer, and a great social atmosphere in our small town. Enjoy soaking in the hot tub or having dinner outside under the gazebo. Have your pets outside, worry free with a large fenced back yard. A pellet grill is on the deck as well for outside cooking.

Top guest favourite
An aerial view captures a sprawling estate surrounded by lush greenery and mature trees. The main house stands prominently among manicured lawns, while additional outbuildings are visible nearby. A winding driveway leads to the entrance, enhancing the serene country atmosphere.
Home in Wilsonville
4.98 out of 5 average rating, 224 reviews

Beautiful Dog Friendly Cottage on a 10 Acre Estate

A little slice of heaven. Stay near the heart of wine country on a 20 acre estate and Hazelnut Orchard. Enjoy a complimentary bottle of Oregon wine and treats upon arrival. Settle in and sit on your personal porch surrounded by Hazelnuts and Dahlias. Or take a dip in the hot tub by the garden and play a little basket ball on the sports court. Close to numerous wineries, breweries, equestrian centers, just 20 miles south of Portland and 60 minutes from the beautiful coast.

Top guest favourite
A modern living area features a light grey sectional sofa and a round coffee table placed on a textured area rug. Natural light enters through large windows, illuminating the space. A wall-mounted TV and a cozy armchair complement the inviting atmosphere, with a fireplace enhancing the comfort.
Home in Newberg
4.98 out of 5 average rating, 203 reviews

Villa Fontana: Modern, Wine-Country Comfort

Welcome! Enjoy a fresh, clean, retreat while you sip your way through Oregon's Wine Country. A modern home nestled amid local historic landmarks, you will be 6 blocks from the downtown Newberg strip and within a 5 mile radius of the closest wineries, making this home the perfect choice for accessibility. Enjoy complimentary Prosecco to toast your arrival and plan to cook meals that pair with your local wine purchases using our high-end appliances!

Top guest favourite
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
4.95 out of 5 average rating, 155 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 favourite
A spacious living room is seen, featuring a comfortable seating area with two chairs and a sofa. A coffee table sits in the center, complementing the light-colored area rug. A large television and decorative items are positioned on a wooden console, with a cozy fireplace adding warmth to the ambiance.
Home in Tigard
4.96 out of 5 average rating, 138 reviews

Entire home: Charming Home with Beautiful Yard

Welcome to our spacious Airbnb! Unwind in our stunning yard with a soothing water feature. Our property offers 4 bedrooms, 2.5 baths, a well-equipped kitchen, and a large living room. Stay productive with dedicated home office spaces. Sleeps 7 comfortably with 3 queen beds and a double bed. Conveniently located near a park, Whole Foods, restaurants, bus stops, and a mall. Don't miss out - book your stay now! Sorry but no pets allowed.

Guest favourite
The exterior of a 1949 home is presented, showcasing a combination of light grey and brick walls. Large windows allow natural light in, while a spacious front porch is visible. A mature tree provides shade over a well-kept, grassy lawn.
Home in Tualatin
4.95 out of 5 average rating, 134 reviews

Outdoor Fireplace & Pup Friendly

Centrally located between Portland & Newberg Wine Country, our quaint 1949 home is walking distance to shopping, stores & food. The neighborhood is clean, friendly and safe. Public transit is close by. It is an old home but newly restored. Easy freeway access. Enjoy a glass of wine on the covered patio with a crackling fire in the outdoor fireplace. Backyard is fully fenced for pet and child safety.

Popular amenities for house rentals in Sherwood

Quick stats about house rentals in Sherwood

  • Total holiday rentals

    Explore 20 holiday rentals in Sherwood

  • Nightly prices starting at

    Sherwood holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 640 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Wifi availability

    20 of Sherwood holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Sherwood rentals

  • 4.9 Average rating

    Sherwood stays are highly rated by guests – averaging 4.9 out of 5!

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