Cottage holiday rentals in Sherwood

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.

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

The "Old Barn" in the woods. Peace, Romance, Ahhh

"Best Airbnb I've ever been to." Recent Guest "The location is unbelievable, like a mountain retreat in town!" Recent Guest The "Old Barn" is a gem just minutes from downtown. You will feel as if you are in a forest yet, minutes away, is the best of Portland. It's all at your fingertips. Yet, you might not want to leave the "Old Barn."

Whimsical Garden Cottage Near Sellwood

Located two blocks from the Springwater Corridor — a 21-mile paved trail for walkers and bikers — in the quiet neighborhood of Ardenwald, you’ll find The Hummingbird Cottage. This whimsical 1930s garden cottage is less than one mile from the charming streets of Sellwood, home to quaint coffee shops and restaurants, boutique shopping, and the iconic Sellwood Riverfront Park. The cottage features organic cotton sheets and goose down comforters in each room and a renovated spa-like main bathroom.

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 have access to it. Scent free. 3 beds, 2 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. Off-street parking. 950 square feet on two levels! We welcome guests of all races, faiths, genders, and sexual orientations

Figment Farmhouse

Enjoy this charming 1950's farmhouse, situated on 150 acres of countryside. Within an easy drive of Carlton, McMinnville, and Dundee—it's an ideal location for the exploring the area's many offerings. The house is well-appointed and surrounded by abundant gardens, towering cedar and fir trees—plus, a flock of chickens, three heritage sheep, and our Bengal cats add interest to the place. We live on the property (next door) with ample privacy/gardens between our place and the farmhouse.

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. Please no young children.

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.

Secret Garden Guesthouse!!

Secret garden guesthouse is located 1 mile from downtown Lake Oswego and 2 miles from Lewis and Clark. Ideal hideaway for parents weekend, visiting the college, or guest lecturers. Also great location for exploring the amazing city of Portland and its surrounds. 50 minutes to Mt Hood, 40 minutes to wine country! Located in SW Portland and just a few miles from downtown Portland food scene. 1 mile from Lake Oswego. Friendly pets are welcome with a $40 pet fee.

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!

Romantic Urban Oasis in the City-Owl Forest Studio

PORTLAND CITY PERMIT #14-248488-000-00-HO Debi's pronouns: she/her Rob's pronouns: he/him *Private Hot Tub *Separate Entrance *Private Parking *King Bed, Tuft & Needle Mattress *Large Garden *Kitchenette with Full-size Fridge and Cooking Supplies (No oven) *Gas BBQ *Good Location *Garden Hammock in good weather LGBTQ Friendly, All Races Welcome. We celebrate diversity and welcome all loving hearts, regardless of gender or race. Portland Permitted Property

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.