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, 113 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.

16–23 Oct

$223 NZD per night

Guest favourite

Farm stay in Hillsboro

5.0 out of 5 average rating, 267 reviews

Oakwood Gardens Retreat •Alpaca Farm• Wine Country

Experience an immersive farm adventure on 70-acres in the quaint community of Scholls, while being close to quality markets, great restaurants and exceptional vineyards. The Willamette Valley is recognized as one of the best Pinot Noir producing regions in the world. Enjoy hand-feeding alpacas and exploring paths in enchanting gardens and natural wetlands. Located six miles from Hillsboro and 14 miles from Portland. Offering seven unique and private accommodations. Please read all information.

14–21 Aug

$224 NZD per night

Guest favourite

Campervan/RV in Portland

5.0 out of 5 average rating, 139 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

20–27 Oct

$183 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.

9–16 Nov

$232 NZD per night

Guest favourite

Yurt in Portland

4.99 out of 5 average rating, 1210 reviews

Garden Home Backyard Yurt Experience

Our cozy-comfy 4 season yurt is nestled under majestic trees on a beautifully landscaped 1/3 acre. Located in a quiet, safe SW Portland neighborhood with a park, hike/bike trail a block away. We are 6 miles from downtown, with beaches, gorge and Mt. Hood accessible for day outings. There is a full kitchen, a natural gas fireplace and complete electrical and plumbing service. The guests full bathroom is located in the home's utility room a short lighted pathway walk from the yurt.

20–27 Oct

$160 NZD per night

Guest favourite

Home in Portland

4.93 out of 5 average rating, 135 reviews

Spacious Forest Retreat w/ Hot Tub & Views

In the woods, next to a creek, but still in Portland! Forget your worries in this spacious and serene space. There is a private entrance to this large two story guest suite, which includes a family room, living area with dining area and kitchenette, bedroom and bathroom, central AC, and private balcony. Located in a quiet neighborhood, close to hiking trails in Woods Memorial Park. A 3-minute drive or 1 mile walk to popular Multnomah Village; 15 minutes from Downtown Portland.

12–19 Sep

$273 NZD per night

Guest favourite

Guest suite in Portland

4.97 out of 5 average rating, 1004 reviews

The Perch - Relax in style/Walkable Location!

An Architectural staircase leads to your private birds-eye deck as you enter your airy urban sanctuary. Bright, clean, elemental decor offer the perfect retreat - just one block off of fabulous Mississippi St. Restaurants, bars, shopping and entertainment venues at your doorstep! Fast Wi-Fi and extra cleaning protocols. Minutes from downtown via bike, bus, light rail or car. Easy access to/from the Airport too! Six years with a consistent five star rating says it all.

11–18 Nov

$227 NZD per night

Guest favourite

Guesthouse in Portland

4.96 out of 5 average rating, 405 reviews

Fresh North Portland Studio

Walk to Restaurants, Coffee Shops, Bars, Shopping, Mississippi Avenue District, MAX Yellow Line, Public Library, PCC-Cascade Campus. Beautifully furnished space with a fully stocked kitchen, high ceilings, comfy bed and custom-built features like the walk-in shower and kitchen bar. Bright and open indoor/outdoor living with French doors that open to a private patio. Great for couples, solo adventurers, and business travelers. Well-behaved dogs are permitted. No cats.

8–15 Mar

$234 NZD per night

Guest favourite

Guesthouse in 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.

11–18 Aug

$220 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.

3–10 Sep

$186 NZD per night

Guest favourite

Place to stay in Portland

4.85 out of 5 average rating, 737 reviews

The Royal Scott Double Decker Bus

Our tiny home started life as a commuter bus in Manchester, England, in 1953, then did stints in San Francisco and Mt. St. Helens before finding a home as the Grilled Cheese Grill in Portland. Now it’s been reimagined as a mid century modern-inspired tiny home, with whimsical painting details from one of its former lives and fresh new handmade details that make it a cozy, inspiring stay. Find more on IG @smore.life

30 Jul – 6 Aug

$193 NZD per night

Guest favourite

Guesthouse in Portland

4.98 out of 5 average rating, 808 reviews

Cozy Portland Studio Apartment

The space is a well appointed, comfortable studio apartment. It is an ADU at the back of the main house. All the amenities that one would desire are provided (wifi, internet, cable TV, washer & dryer, fridge, dishwasher, stove, microwave, AC, cooking utensils, etc., etc). It is also very modern and clean, with a private entrance and keyless entry. Close to many restaurants, bars and coffee shops.

11–18 Feb

$138 NZD per night