Cottage vacation rentals in Portland

A hot tub is situated on a wooden deck, surrounded by lush greenery. A shaded table with chairs is visible in the background. A drink is placed on the rim of the hot tub, with sunlight streaming through the trees, creating a serene outdoor atmosphere.

4.86 out of 5 average rating, 728 reviews

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."

4.91 out of 5 average rating, 154 reviews

A cozy living area features a teal sofa adorned with vibrant cushions, complemented by a wooden coffee table. Light streams in through sheer curtains, illuminating the warm wood paneling. A colorful wall hanging adds a touch of texture, while a glimpse of the kitchen can be seen in the background.

Cottage in Forest Park

Far Out Cottage, away from city riffraff

Far Out Cottage is nestled in the woods in the NW Skyline area. It’s far out like groovy and also away from the city but yet still conveniently located. This unique experience is a step back into decades past but with the convenience of fast internet, roku and a modern flatscreen TV. The highlight of all this new technology is a throw back to the 70’s with an Atari equipped with all the classics. Your stay also includes a 50’s style fully equipped kitchen, 40’s style bathroom and laundry room.

4.78 out of 5 average rating, 105 reviews

The entrance of the cottage is framed by vibrant flowers and greenery, featuring a red front door that adds a welcoming touch. A cozy lounge chair is positioned on the patio, which leads to the garden, providing a spacious area for relaxation.

Cottage in Brooklyn

Bike'N'Roll Cottage: Adventure & Relaxation

Bike 'N' Roll Cottage: Bicycle Tourism, Healing Garden See Portland by bike-Biking Score 95! GUESTS RAVE: "I can bike everywhere!" ■ Beautiful 560 sf w/the details of a 100+ year-old Craftsman ■ Bright - lots of windows - high ceilings ■ Relax & rejuvenate in a tranquil, healing garden ■ Near bus & max train - so you can bicycle even farther! ■ 100s of shops, restaurants & everything you want to see within biking distance! ■ Ranked 2nd in the CNBC's most bicycle-friendly cities in the US!

4.99 out of 5 average rating, 115 reviews

The cozy front porch features a welcoming entry with two woven chairs and decorative cushions, inviting guests to relax. The blue exterior is complemented by a white picket fence and a small garden area with greenery, enhancing the cottage home's charm.

Cottage in Ardenwald

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.

5 out of 5 average rating, 322 reviews

The kitchen area features modern appliances and wooden countertops, providing an open and functional space for cooking. Shelves above display dishes and plants, while ample natural light filters in through large windows. The stylish design balances aesthetics with practicality.

Cottage in Overlook

5* Cottage Gem | Quiet Hood | Caring Host | Min>DT

Cute, cozy cottage in a safe, quiet neighborhood. Outside, walk to nearby cafes, bars, & restaurants, or head downtown to explore the city (10 min drive or light rail 3 blocks away!). Inside, unwind on the supremely comfortable queen bed (+ queen sleeper). Enjoy the projector system, luxurious rainfall shower, or cook meals in the well-stocked kitchen. Ideal for travelers who appreciate attention to detail and a seamless experience. Attentive host ensures a polished, no-surprise stay :)

An open studio cottage interior features a cozy seating area with a light blue couch adorned with floral pillows. A vintage wooden table is positioned next to it. The sleeping area is elegantly furnished with a spacious bed, flanked by two charming white cabinets and illuminated by soft natural light.

4.99 out of 5 average rating, 560 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. Please no young children.

A charming guesthouse is nestled within a lush garden, surrounded by colorful flowering bushes and sculpted hedges. The structure features large windows that offer a glimpse of the serene interior. The path leading to the guesthouse is intertwined with greenery, enhancing the tranquil atmosphere.

4.92 out of 5 average rating, 438 reviews

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.

4.94 out of 5 average rating, 306 reviews

A comfortable sleeping area is featured, with a queen bed dressed in neutral bedding and accented by a blue throw pillow. Two bedside lamps provide soft lighting, and a dresser stands beside the bed. Natural light enters through a nearby window, with curtains partially drawn.

Cottage in Lake Oswego

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!

5 out of 5 average rating, 230 reviews

A modern kitchen features wooden cabinetry and a white subway tile backsplash. Stainless steel appliances include a refrigerator and oven. Open shelves hold glassware and kitchen essentials. A central island with seating is complemented by a fruit bowl, while natural light brightens the space.

Cottage in Kerns

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.

4.97 out of 5 average rating, 186 reviews

Several chickens are seen in a green yard, with a brown rooster prominently in the foreground. Different colored hens, including a white one, are scattered in the background. A wooden planter and a fenced area are visible beyond the chickens.

Cottage in Richmond

Tibbetts Coop - A beautiful SE Portland urban farm

Tibbetts Coop is located on a double cul-de-sac, where you will feel like you are in the country when you are really in beautiful inner SE Portland. Bring your walking shoes so you can walk through the neighborhood to SE Division to find coffee shops, cart pods, tap houses, cafes, restaurants, and bars to suit everyone, or stay at the coop to relax under a tree or on the deck. Small dogs can be approved on a case-by-case basis (fees apply).

4.96 out of 5 average rating, 120 reviews

The kitchen features light cabinetry and a white gas range, complemented by a spacious dining table with pink upholstered chairs. Large windows invite natural light, while a decorative chandelier hangs above. A pair of French doors provide access to the outdoor patio, enhancing the airy feel.

Cottage in Richmond

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.

A covered patio area is visible, featuring a small table and two chairs amidst vibrant flowers in pots. The entrance to the guest house is framed by lush greenery, complemented by a neatly trimmed lawn and stone pathway leading to the door.