Cottage vacation rentals in Sherwood

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Top-rated cottage rentals in Sherwood

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Guest favorite

A charming yellow cottage with a white picket fence is showcased. A stylish mailboxes stands prominently, featuring a heart-shaped accent. The entrance is marked by a white door and steps leading up to the porch, surrounded by neatly arranged rose bushes.

Cottage in Newberg

4.95 out of 5 average rating, 150 reviews

The Valley Wine Cottage - Walk to Tasting Rooms

A cozy cottage in the heart of wine country. Walk to restaurants and tasting rooms and then relax on your own front porch or private back deck. The cottage has two bedrooms, both with Christopher Knight (tm) queen-sized beds for a great night's sleep and you can rent it as a one or two bedroom. Although we're walkable to many attractions, our street is tranquil and you'll enjoy sitting in a porch rocker with a glass of wine (in our varietal-correct Riedel glasses), or relaxing in the hammock.

Top guest favorite

A serene outdoor seating area is positioned by a tranquil lake, featuring two wooden chairs and a small round table. A large, leafy tree offers shade, while lush greenery surrounds the scene, enhancing the peaceful atmosphere of the property.

Cottage in Newberg

4.97 out of 5 average rating, 155 reviews

Oxberg Lake Retreat, lake & farm view in wine ctry

A storybook oasis with lake/farm views. Enjoy your morning coffee or evening wine while listening to the sheep and chickens. One loft bedroom, one full bath with large living room/kitchen. Hosts live in attached home, but you have full privacy. * 5 min to George Fox University * 2 min to The Allison Inn & Spa * 50+ wineries within 10 min drive *Walk to Farm Craft brews at Wolves and People on Benjamin *Enjoy canoeing, feeding the sheep, or reading a book by the fire pit. roll-away bed available

Top guest favorite

A private hot tub sits on a deck, surrounded by a tranquil landscape. A gentle flow of water can be seen in the nearby river, framed by lush greenery and a wooden fence that enhances the serene outdoor setting.

Cottage in Molalla

5 out of 5 average rating, 250 reviews

Charlies Riverfront Cottage - Hot tub & Fireplace

Romantic getaway or Family retreat - We have everything you need to relax. Private Hot Tub overlooking the Molalla river, Classic Arcade cocktail table, Gas Fireplace, Fire pit, BBQ, The best swimming hole. We decorate for every season and most holidays. Covered porch with heater to enjoy your coffee and birdwatch. Stroll through the park next-door, take a ride on a mini-train or buy farm fresh eggs from our neighbor. Visit Silverfalls, Oregon coast or Mt. Hood. Fresh air and comfort awaits!

Superhost

An outdoor deck features a wooden structure with a partially transparent roof, providing filtered sunlight. A round table with four chairs is positioned on the deck, surrounded by verdant foliage. The cottage's entrance can be seen through the glass doors in the background.

Cottage in West Linn

4.88 out of 5 average rating, 185 reviews

The Bee Cottage

Welcome to The Bee Cottage! This cozy cottage is nestled in the woods overlooking a beautiful sun-filled meadow situated on 5 private acres adjacent to Mary S. Young Park. In this quiet and pastoral setting you'll see deer wandering in the orchard and on the other side of the meadow are honeybee hives tended to by the host. It’s a separate home with a fully stocked kitchen, an outdoor deck and barbecue great for entertaining just 3 blocks from Cedar Oaks Park/Boat Ramp on the Willamette River.

Guest favorite

A contemporary outdoor fire pit is featured on a wooden deck, with a warm flame visible through the metal mesh. Surrounding trees add to the natural ambiance, while a glimpse of the river can be seen in the background, providing a serene setting.

Cottage in Yacolt

4.97 out of 5 average rating, 268 reviews

Wooded, Private River Front Cottage with hot tub!

The River Cottage has a treehouse vibe, nestled into the privacy and serenity of the trees! Fishing, kayaking, swimming or relaxing in your private hot tub, right on the Lewis River. This is the place to make memories and enjoy time with family and friends. Swim from your private beach, roast marshmallows, vist nearby falls, enjoy a bottle of wine and relax with the comforts of home! Can't book now? Wishlist us for later! See also our listing for River Haven! Winery tours also available!

Top guest favorite

An outdoor fire pit is surrounded by natural stone seating arranged in a circular pattern. Wooden benches provide seating for guests, and a scenic view of trees and greenery is visible in the background under a cloudy sky.

Cottage in Washougal

5 out of 5 average rating, 213 reviews

Little Creek Cottage- Alpaca Farm

Experience a peaceful way of life by taking in the natural beauty of Little Creek Cottage. It's an ideal setting to create cherished memories in the countryside while admiring the alpacas, sheep, and other wildlife. Nestled in the heart of the breathtaking Columbia River Gorge, just a short 25-minute drive from Portland Airport, Little Ceek Cottage perfectly balances nature and modern amenities. Enjoy the serenity of the countryside while still having access to all the nearby conveniences.

Guest favorite

A two-level private cottage is surrounded by greenery and features a blue exterior. The path leading up to the cottage is bordered by fallen leaves and ornamental plants. Off-street parking with one car can be seen beside the structure.

Cottage in Portland

4.95 out of 5 average rating, 281 reviews

950 sq ft Guest House w/Gourmet Kitchen

Renovated cottage with unbelievable gourmet kitchen. Fast, high speed internet is dedicated to the Cottage - only Cottage guests will have access to it. Three beds, two smart TVs, desk, large living area. Centrally located close to Washington Square shopping mall, Trader Joe's, local restaurants; short drive to downtown Portland, Nike, Intel, Multnomah Village. Of-street parking. 950 square feet on two levels! We welcome guests of all races, faiths, genders, and sexual orientations.

Guest favorite

An illuminated patio area features a covered wooden structure with string lights providing a warm glow. Comfortable seating is arranged around a central table, and a large umbrella adds color to the outdoor space. Lush plants are visible along the perimeter, enhancing the tranquil atmosphere.

Cottage in Beaverton

4.93 out of 5 average rating, 106 reviews

Cozy Cooper Mtn Cottage

Uniquely cozy with all the amenities of home but in a cottage up on Cooper Mt. Where you are surrounded by trees , feel the breezes, sunrise and sunset in the same day, and sometimes the wonderful wildlife around us. Birds in the sky , rabbits and sometimes deer, and yes our two friendly goats. Oh yes and the expansive midnight sky with the bright stars twinkling above or the big round moon shining down on you as you sit on the patio in the evening enjoying the night air.

Top guest favorite

A sandy beach area is visible along the riverbank, with people enjoying the water in kayaks and swimming. A boat is seen cruising on the water, framed by lush green trees lining the shore under a bright blue sky.

Cottage in Lake Oswego

4.93 out of 5 average rating, 282 reviews

Peacock Grove Cottage in Lake Oswego, OR

Sunny, private one bedroom cottage in quiet, wooded neighborhood. Separate dwelling behind main house. Queen bed, sofa bed, TV, WiFi, A/C, full kitchen, washer & dryer, bathroom with shower and beautiful patio. One mile from I-5 and 8 miles to downtown Portland. Short drive to downtown Lake Oswego. Walking distance, just two blocks, to La Provence, Jefe, Zupans, Albertsons, Starbucks, Waluga Park. Perfect for families or the business traveler. Come stay!

Top guest favorite

An outdoor space features a wooden outdoor shower alongside a cedar sauna. Flagstone pathways lead through a garden area, with potted plants visible. Two blue chairs are positioned nearby, inviting relaxation in this serene setting.

Cottage in Buckman

5 out of 5 average rating, 211 reviews

Kerns Neighborhood Cottage with Sauna

Oak St. Cottage with outdoor cedar sauna is a newly renovated urban oasis centrally located in Southeast Portland just steps from Restaurant Row, Whole Foods, Tri-Met Bus and Laurelhurst Park. Set back from the main house, at the end of a quiet cul-de-sac, the modern cottage offers easy access to all Portland has to offer. When you are ready to relax, the private outdoor sauna and shower are waiting for you. We take great care to clean and sanitize the cottage.

Top guest favorite

A spacious outdoor area is surrounded by tall trees and vibrant greenery. A fire pit is located at the center, with several chairs arranged around it. A colorful playground with a slide can be seen in the background, complemented by a variety of plants and flowers.

Cottage in Portland

4.99 out of 5 average rating, 537 reviews

Cozy Vintage Cottage in the Woods

The studio cottage is located in an east Portland neighborhood bordering the city of Gresham. It is close to public transport (near a MAX light rail station), the airport and outdoor activities (the Columbia Gorge; Mt Hood) and is a 20-30 min drive to downtown. It's cozy (eclectic vintage style), a wooded 1-acre setting within the city limits, and has secure premises (electric gate). Our place is good for couples, solo adventurers, and business travelers.

Top guest favorite

A daybed is adorned with a white cover and a variety of cushions, including pink and green pillows and a fluffy pink accent pillow. A large plant can be seen in the background, complementing the natural light filtering through nearby windows.

Cottage in Portland

4.96 out of 5 average rating, 103 reviews

Luxury Richmond Rose Cottage Division & Hawthorne

Located in Richmond, one of SE Portland's most popular neighborhoods, our 700 sq. ft., custom-designed luxury cottage offers modern comfort with vintage flair. Walk to Stumptown Coffee, Good Coffee, Woodsman Tavern, Petite Provence, Hinterland Bar & Food Carts and other great restaurants, food carts and coffee shops. 90/88 Walk/Bike Score. Close to bus lines 2, 14, 71 and 0. Enjoy the private patio surrounded by nature.