Holiday houses in Portland

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Top-rated holiday rentals in Portland

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Guest favourite

Guesthouse in Portland

4.98 out of 5 average rating, 112 reviews

Spacious, bright garden studio on Peninsula Park

Explore the world-class restaurants, coffee shops and bars in the nearby Williams and Mississippi districts. Take a stroll around the award winning (and oldest) rose garden in the City of Roses across the street in Peninsula Park. At home, this second story studio has extra space in the meditation loft, a full kitchen, fast internet, and projector for streaming. Enjoy your private deck over the shared garden with hammock and H/C outdoor shower. Bus and train nearby with ample on-street parking.

13–20 Oct

$225 NZD per night

Guest favourite

Guesthouse in Portland

4.97 out of 5 average rating, 541 reviews

The Westmoreland Lighthouse - Private studio in SE

We've dubbed this stunning, newly constructed detached studio the "Lighthouse" because of the way natural light pours through the 550-square-foot studio's many windows and dances off its walls and vaulted ceilings. An open loft offers soothing views. We are tucked into the Westmoreland neighborhood's quiet residential area, but are only a five minute walk from more than 20 restaurants and entertainment features. Westmoreland Park, Reed College and downtown Portland are just minutes away by car.

11–18 Dec

$233 NZD per night

Guest favourite

Home in Portland

4.91 out of 5 average rating, 123 reviews

Richmond Garden House

Enjoy a bottle of local wine on the house when check-in to the incredible Richmond Garden House. You'll get the entire house's finished space, large backyard w/ deck, grill & fire pit in this extremely clean, private space. Close to PDX’s most famous eateries in an awesome walkable neighborhood with easy parking, plenty of stores, conveniences & urban shopping. The home is full of comforts: premium bedding, stocked kitchen, high speed internet, gas fireplace, and great entertainment options.

14–21 Apr

$170 NZD per night

Guest favourite

Campervan/RV in Portland

5.0 out of 5 average rating, 138 reviews

Warm & cozy vintage camper in the woods of PDX.

Warm & cozy vintage trailer nestled next to Forest Park. Enjoy a fire pit, covered patio, uninterrupted woodland view, and hot, dreamy outdoor bath, all minutes to the center of PDX. Creature comforts all provided for a whimsical glamping experience. Forest Park Trailhead is steps away, Sauvie Island and the historic Cathedral Bridge are 5 minutes by car, and 10 minutes to Slab Town and Alphabet District. The beauty and privacy of this spot may make it hard to venture out. IG: @lilpoppypdx

22–29 Oct

$185 NZD per night

Guest favourite

Guest suite in Portland

4.97 out of 5 average rating, 212 reviews

“Nos Sueños” Modern Private Forest Retreat

Exclusive guest suite in striking new modern home tucked into the forested ridgelines of the Tualatin Mountains north of Portland. Floor to ceiling windows frame private views of the natural forest landscape, and offer plenty of natural light. Private guest entry, covered patio with fire-pit and architectural style featured in the 2020 Portland Modern Homes Tour delight. It's just a short walk to our Nos Suenos Farm property and vineyard valley views. Perfect single or couple getaway retreat!

24–31 Jul

$215 NZD per night

Guest favourite

Guesthouse in Beavercreek

5.0 out of 5 average rating, 142 reviews

Muse Cabin in old growth forest w/cedar hot tub

Enjoy our beautifully remodeled cabin that is heated exclusively by the wood stove, on the edge of an old growth cedar forest on our 11 acre farm/vineyard. Relax on the deck built into the trees, and sleep in the cozy loft with ladder, as you soak in the nature around you. The cabin has a mini kitchen for cooking. The cute out house is just across the path, and is seasonally shared with other hip campers. We have a hot/cold shower at the hot tub. The cedar hot tub is next to the garden.

22–29 Sep

$209 NZD per night

Guest favourite

Guest suite in Portland

4.95 out of 5 average rating, 318 reviews

Private Greenhouse Suite for 1 or 2 Guests

Elegant, private king bedroom suite with magical private greenhouse, private entrance, desk and ensuite bathroom. Enjoy radiant tile floor heat, charming greenhouse seating nook, spacious 2-person shower and an amenities cabinet with microwave, mini-fridge, teakettle & flatware - ideal for simple breakfasts or reheated leftovers. This spacious room is ideal for 1 or 2 guests who want an entirely separate private space and charming "interior garden" porch, but who don't need a full kitchen.

15–22 Nov

$231 NZD per night

Guest favourite

Guesthouse in Portland

4.99 out of 5 average rating, 153 reviews

Grant Park Guest House

Newly built guesthouse in highly desirable Grant Park. Beautiful and relaxing one level space with vaulted ceilings, exposed beams, skylights and lots of natural light. All amenities: high speed internet, washer & dryer, full kitchen, memory foam mattress, TV, and private entrance with patio and cafe set. Easy check out! Location is close to everything: great restaurants, food cart pod, Whole Foods, Trader Joe's, Grant park, airport, and more! Walk score of 94. Great space for a get away!

8–15 Sep

$306 NZD per night

Guest favourite

Guesthouse in Northeast Portland

4.95 out of 5 average rating, 281 reviews

Cozy Alley Cottage, Concordia/Alberta Arts, NE PDX

Come enjoy our beautiful detached cottage, in a Concordia alley 5 blocks from Alberta Street. French doors lead onto your own private patio. It has a fully stocked kitchen, with everything you need. The cottage is designed to be self sufficient, and full of natural light. We are a 10 minute walk to the Alberta Arts District. You can wander the alleys and visit the famous Concordia chicken coup, wander through Alberta park, to the vibrant Alberta Arts district.

2–9 Sep

$218 NZD per night

Guest favourite

Guesthouse in Portland

4.97 out of 5 average rating, 387 reviews

Moss Rock Retreat - Near Leach Botanical Garden!

Moss Rock Retreat is a peaceful tiny home surrounded by an acre of hillside gardens. Tucked behind the magical Leach Botanical Garden in a forested neighborhood, Moss Rock has the serenity of a mountain retreat - but is only 20 minutes from downtown and PDX. Come for respite from the busy world, a quiet workspace, a creative getaway, a romantic weekend, or to explore the natural beauty of Oregon - all are possible in the comfortable intimacy of Moss Rock Retreat.

5–12 Sep

$175 NZD per night

Guest favourite

Guesthouse in Central Northeast Portland

4.99 out of 5 average rating, 383 reviews

Beautiful, Contemporary Farmhouse

Modern farmhouse-style guest home with a private entry in a quiet and convenient Portland neighborhood. This home was built in 2017 with simplicity and style in mind. 5 minutes to Wilshire Park. 5 minutes to the vibrant Alberta Arts district. 5 minutes to charming and friendly Beaumont Village. 5 minutes to up-and coming restaurants on 42nd Avenue. 15 minutes to the airport. 15 minutes to downtown. A pleasant and peaceful hub for all of your Portland adventures.

21–28 Oct

$254 NZD per night

Guest favourite

Guesthouse in Portland

4.97 out of 5 average rating, 131 reviews

The Perch PDX - Modern Studio on Division

A guesthouse in the SE Division/Hawthorne neighborhood that will make you feel right at home. The Perch PDX is light and bright. It's a short walk away from locally roasted coffee, farm-to-table fine dining, endless brunch options, a hip brewery and beer garden, bagels made fresh daily, authentic Mexican street tacos, a neighborhood wine bar, a fiercely independent movie theater, groceries, and some of the best Thai food in Portland.

13–20 Nov

$188 NZD per night