Holiday rentals in Portland

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Top-rated holiday rentals in Portland

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Guest favourite

Guest house 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.

17–24 Sep

$136 SGD per night

Guest favourite

Guest house in Portland

4.97 out of 5 average rating, 540 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 Mar

$147 SGD per night

Guest favourite

Campervan/Motorhome in Portland

4.99 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

19–26 Oct

$131 SGD per night

Guest favourite

Guest house in Beavercreek

5.0 out of 5 average rating, 141 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.

10–17 Jan

$162 SGD 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.

6–13 Jan

$152 SGD per night

Guest favourite

Guest house 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.

26 Apr – 3 May

$150 SGD per night

Guest favourite

Guest house 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.

15–22 Aug

$141 SGD per night

Guest favourite

Guest house 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.

28 Aug – 4 Sep

$123 SGD per night

Guest favourite

Guest house in Portland

4.96 out of 5 average rating, 110 reviews

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.

13–20 Oct

$177 SGD per night

Guest favourite

Guest house in Portland

4.97 out of 5 average rating, 130 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.

5–12 Nov

$117 SGD per night

Guest favourite

Guest house in Portland

4.94 out of 5 average rating, 308 reviews

The Artist’s Nest

You'll love this private and comfortable artist's studio complete with your own outdoor deck and pergola. Enjoy a King size Casper bed to relax on. You can walk to the Montavilla bars/restaurants or up to the top of Mt. Tabor and grab a city view while you picnic. Located conveniently near the airport, downtown, public transit and freeways, whatever you have planned for Portland, this is a perfect launchpad.

6–13 Oct

$145 SGD per night

Guest favourite

Guest house 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.

22–29 Mar

$86 SGD per night