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, 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.

18–25 Sep

$139 SGD per night

Guest favourite

Guest house 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.

26 Apr – 3 May

$150 SGD per night

Guest favourite

Farm stay in Hillsboro

5.0 out of 5 average rating, 363 reviews

Oakwood Gardens Studio •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.

7–14 Oct

$168 SGD per night

Guest favourite

Campervan/Motorhome 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

25 Oct – 1 Nov

$131 SGD per night

Guest favourite

Guest suite in Portland

5.0 out of 5 average rating, 282 reviews

*Walk to Alberta eats & drinks*Dog Park*Playground

Bright one-bedroom with private access and parking for 1 vehicle. Beautiful Alberta Park is just across the street and you’ll be within four blocks of Alberta Street and all the restaurants, shops, galleries, and nightlife it has to offer. Aside from the location, you’ll have a fully stocked kitchen with dishwasher, Roku TV, and washer and dryer. If you're traveling with a pup, read the full description. No cats (sorry!). Please reach out to discuss longer term stays (up to 30 days). Thanks!

18–25 Sep

$181 SGD per night

Guest favourite

Guest house in Beavercreek

5.0 out of 5 average rating, 143 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

$162 SGD per night

Guest favourite

Yurt in Portland

4.99 out of 5 average rating, 1209 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.

29 Oct – 5 Nov

$122 SGD per night

Guest favourite

Flat in Portland

4.97 out of 5 average rating, 208 reviews

Studio in Walkable Foodie Heaven

We're on a quiet side street – right around the corner from a dynamic gourmet restaurant scene. Take a short stroll to parks, live music, vintage shops, and a vintage movie theater. Walk, Lyft/Uber, bicycle, or use Portland’s amazing public transportation everywhere. Tall windows overlook greenery and a cozy front porch. Our family's 1900 house has been divided into 3 units. This unit is like an artsy hotel room (with microwave and mini fridge), but much more homey!

26 Apr – 3 May

$94 SGD per night

Guest favourite

Guest house 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

$141 SGD per night

Guest favourite

Guest house 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

$118 SGD per night

Guest favourite

Guest house in Portland

4.94 out of 5 average rating, 309 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.

13–20 Oct

$146 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.

15–22 Apr

$86 SGD per night