Guesthouse holiday rentals in Portland
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Top-rated Guesthouses in Portland
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Portland guesthouses
Family-Friendly guesthouses
Guesthouse in Northeast Portland
4.95 out of 5 average rating, 279 reviewsCozy Alley Cottage, Concordia/Alberta Arts, NE PDX
18 – 25 Aug
Guesthouse in Northeast Portland
4.94 out of 5 average rating, 836 reviewsThe Hen House: Private unit in NE
30 Dec – 6 Jan
Guesthouse in North Portland
4.91 out of 5 average rating, 321 reviewsOverlook BackShack
22 – 29 Jan
Guesthouse in Northeast Portland
4.92 out of 5 average rating, 317 reviewsSmall house in a killer walkable part of town!
2 – 9 Oct
Guesthouse in Northeast Portland
4.99 out of 5 average rating, 484 reviewsSpacious Guesthouse with Creative Style and Local Charm
4 – 11 Feb
Guesthouse in Mt. Tabor
4.9 out of 5 average rating, 684 reviewsModern Garden Studio Self Check & Private Entrance
23 – 30 June
Guesthouse in Montavilla
4.95 out of 5 average rating, 391 reviewsTabor Cottage: Detached Guest House SE Portland
27 Aug – 3 Sept
Guesthouse in Northeast Portland
4.99 out of 5 average rating, 375 reviewsNE Irving Park Cottage
2 – 9 Oct
Guesthouses with a patio
Guesthouse in North Portland
4.92 out of 5 average rating, 102 reviewsLuxury Spa Retreat Studio for 1-2 Guests
8 – 15 Nov
Guesthouse in Montavilla
4.97 out of 5 average rating, 120 reviewsHotTub, Fast WiFi, cozy & convenient-Casita Morado
11 – 18 June
Guesthouse in Portland
4.97 out of 5 average rating, 228 reviewsModern Bed & Bath in Historic Sellwood
18 – 25 Feb
Guesthouse in Portland
4.99 out of 5 average rating, 119 reviewsDeluxe 2 BR Irvington Guesthouse with Hot Tub!!
20 – 27 Aug
Guesthouse in Sherwood
4.98 out of 5 average rating, 100 reviewsCozy Willamette Valley Cabin With Modern Comforts
20 – 27 Aug
Guesthouse in Northeast Portland
4.98 out of 5 average rating, 124 reviewsBeautiful Alberta Guesthouse | Full Amenities + AC
18 – 25 Apr
Guesthouse in Portland
4.99 out of 5 average rating, 180 reviewsPerfectly Portland Clinton St Guesthouse
25 July – 1 Aug
Guesthouse in Portland
4.9 out of 5 average rating, 20 reviewsFir Grove Tree House
14 – 21 Oct
Guest house rentals with a washing machine and dryer
Guesthouse in Portland
4.92 out of 5 average rating, 123 reviewsModern Luxe Loft on the Hawthorne Strip
23 – 30 Mar
Guesthouse in Portland
4.96 out of 5 average rating, 110 reviewsModern and Bright Laurelhurst Abode
4 – 11 Oct
Guesthouse in Portland
4.98 out of 5 average rating, 807 reviewsCozy Portland Studio Apartment
27 Aug – 3 Sept
Guesthouse in Central Northeast Portland
4.95 out of 5 average rating, 323 reviewsRose City Garden Retreat-Monthly rental discount!
30 May – 6 June
Guesthouse in Portland
4.91 out of 5 average rating, 486 reviewsTruly Local Experience, Steps from Restaurant Row!
29 Nov – 6 Dec
Guesthouse in Oregon City
5.0 out of 5 average rating, 518 reviewsCottage in the Country
15 – 22 Mar
Guesthouse in Portland
4.95 out of 5 average rating, 384 reviewsNewly built studio in perfect SE location
27 June – 4 July
Guesthouse in Portland
4.99 out of 5 average rating, 315 reviewsModern Hawthorne Guesthouse - Close to Everything
18 – 25 Oct
Quick stats about guesthouse rentals in Portland
Total rentals
500 properties
Wi-Fi availability
500 properties include access to Wi-Fi
Rentals with dedicated workspaces
250 properties have a dedicated workspace
Pet-friendly rentals
90 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
82K reviews
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