Guest house holiday rentals in Southeast Portland

Woodstock Tiny House

Detached, very small (300 sq ft) guest house in the Southeast Portland neighborhood of Woodstock. Lots of walkable eateries as well as New Seasons and Safeway within a 5 minute walk. Close to Reed College, Woodstock Village, Springwater Trail, Southeast Portland Neighborhoods, Public Transportation. You’ll love the location, the outdoors space, and the ambiance. Good for couples, solo adventurers, and business travelers. TV (Netflix enabled!), A/C (summer months), heat, coffee, fridge/freezer.

Cozy Guest Cottage in Woodstock Neighborhood

A bright and cozy cottage located near Reed College, Woodstock's restaurants/coffeehouses, Trader Joe's and public transit. This residential neighborhood is ideal for a quiet retreat for all visitors. The private guesthouse is outfitted to make your stay comfortable including a spacious bathroom with a walk in shower and a heated floor. Plus, you may want to enjoy a cup of coffee on your own patio located behind the Airbnb. As an added bonus, breakfast items and home baked treats are provided.

Sunny, Modern Guesthouse South Tabor Neighborhood

A modern guesthouse with one bedroom, one bathroom, a living/kitchen space and a deck. The guesthouse is above our garage and was built in 2011. There's a deck off the kitchen which is a nice place for relaxing. We are about 1.5 miles from restaurants and shops at SE Division. There are several bus stops within 1-2 blocks of our house. Downtown Portland is 30 minutes by bus We've done a lot of traveling and enjoy meeting new people. We welcome folks from all backgrounds and places.

Perfectly Portland Clinton St Guesthouse

This light & airy guesthouse is a private retreat in a perfect location, steps from Division St. Walkable to Salt & Straw & local eateries, food carts, and thrift shops. Prepare meals in the fully equipped kitchen or head out by foot to Oma’s Hideaway, a 2022 James Beard Award Finalists. Bring your bicycles to enjoy Clinton St Bike Boulevard or stroll to the Clinton St Theater. The guesthouse is family friendly, having special items to accommodate the littlest of guests.

Modern and Bright Laurelhurst Abode

Our one bedroom cottage is completely private, accessible by a separate walkway, and has an outdoor patio. Extra time was spent choosing finishes and creating a modern, comfortable, and light-filled space. You’ll find everything you need for a weekend in Portland, or a long-term stay. We’ve outfitted a full kitchen, full bathroom with luxurious tub and plush towels, a bedroom with a queen mattress and soft bedding, washer and dryer, and lots of extra touches.

Award-Winning Guest House with Private Entrance

Featured in Dwell Magazine; Winner of “Best Whole House Design” by Oregon Home Magazine, this spacious urban garden retreat has one-bedroom with a luxurious king bed, full bathroom, and fully equipped kitchen. Tucked away in a tranquil urban oasis, the space is filled with natural light and boasts a private garden entrance. Wake up refreshed in the crisp, white bedroom and slide open the rustic barn door for a coffee on the patio of this zen retreat.

Charming, private 2-level guesthouse-Woodstock

**No list of chores to do at the end of your stay!** Vaulted ceilings, fully private 2 level home. Chef’s kitchen, AC, patio, designer decor and architecture. Contact-less, private self checkin. New Guest House in quiet residential area, upscale Eastmoreland-15 mins from downtown Portland. One bedroom/one bath. Within 10 minutes’ walk is Woodstock Ave-full of cafes, bars, bakeries, and shopping. Ample parking on the street.

Cozy Cottage in Mt. Scott

The cottage has everything you'll need for your Portland adventures! It comes fully equipped with a well stocked kitchen, outdoor patio, and lots of natural light. You'll have quick access to shops, restaurants and bars in the Woodstock/Mt. Scott neighborhoods. Highlights include Mt. Scott Park, Double Mountain Brewing, Bella's Italian Bakery, The Portland Mercado, Cartlandia, Cloud City Ice Cream and New Seasons Market.

Tiny House, Big Charm

This cute and comfortable studio apartment used to be our detached double car garage! We worked tirelessly to curate the perfect Portland experience to compliment your vacation. With art and photography from NW artists, to locally sourced materials and treats, we are honored to host you during your trip.