Best Fun Hotels in Portland to Explore

We checked thousands of reviews on and to find the best hotels for your stay
Go to Hotel List View map

Ila Hughes

Updated: 31 January 2024 · 3 min

Nestled in the vibrant city of Portland lies a plethora of charming and unique accommodations that promise more than just a place to rest your head – they offer an experience. When it comes to selecting a hotel, why settle for the ordinary when you can embrace the extraordinary? Portland's fun hotels cater to every traveler, from the whimsical boutique enthusiast to the trendy urban explorer seeking a touch of playfulness in their stay.

Immerse yourself in the local culture by choosing to stay at one of Portland's fun hotels, where every corner tells a story and every room exudes character. From retro-themed establishments that transport you back in time to quirky hotels brimming with artistic flair, each property is a testament to the city's eclectic spirit. Think vibrant murals, rooftop bars with stunning skyline views, and cozy common areas designed for mingling with fellow adventurers.

Whether you're drawn to the allure of live music pouring out from the hotel lounge or the prospect of exploring the city's craft breweries just steps away from your accommodation, Portland's fun hotels cater to a diverse range of preferences. Indulge in the joy of discovering a hotel that mirrors your personality and amplifies your travel experience, making your stay in the City of Roses not just memorable but unforgettable.
Show more + Show less -

Our Top 5

(Sorted by rating & number of reviews)

1. The Hoxton, Portland Hotel
2. Mcmenamins Kennedy School Hotel
3. Jupiter Hotel
4. The Society Hotel
5. The Paramount Hotel

Fun Hotels in Portland: Quirky Boutique Escapes

Check Availability

Portland
Mar 19, 2026 - Mar 20, 2026

The Hoxton, Portland Hotel

8.3

Good

(547 Reviews)

+ 57 photos
Dive into Portland's creative scene at The Hoxton, a stylish hotel that caters to those who appreciate design-forward accommodations with a playful twist. Located in the vibrant Chinatown neighborhood, this hotel features chic rooms adorned with local artwork, a vibrant lobby bar serving craft cocktails, and a lively atmosphere that embodies the essence of fun hotels in Portland. Experience the city's vibrant culture and artistic flair while enjoying the modern amenities and personalized service that The Hoxton is known for.
Address: 15 Nw 4Th Avenue
Rating: Good 8.3 (547 Reviews)
Rooms: 84
Price: From 135$

Mcmenamins Kennedy School Hotel

8.6

Good

(122 Reviews)

+ 97 photos
Experience a stay like no other at McMenamins Kennedy School, a whimsical hotel housed in a former elementary school that has been transformed into a playground for adults. This unique property features themed guestrooms, eclectic artwork adorning the hallways, and an on-site restaurant and brewery serving up local favorites. Guests can enjoy a dip in the soaking pool, catch a movie in the converted auditorium, or explore the charming courtyards that make McMenamins Kennedy School a delightful retreat for those seeking a fun-filled stay in Portland.
Address: 5736 Ne 33Rd Ave
Rating: Good 8.6 (122 Reviews)
Rooms: 49
Price: From 175$

Fun Hotels in Portland: Retro-Inspired Hideaways

Transport yourself back in time with a stay at one of Portland's retro-inspired hotels, where nostalgia meets modern comfort in a whimsical fusion. These unique accommodations perfectly capture the essence of fun and adventure, offering guests a delightful trip down memory lane with a contemporary twist. Explore the following selection of retro-inspired hideaways that promise a truly unforgettable stay in Portland.

Jupiter Hotel

7.8

Good

(326 Reviews)

+ 182 photos
As one of Portland's most iconic boutique hotels, The Jupiter Hotel marries industrial chic design with a lively atmosphere, making it a top choice for travelers seeking fun accommodations. This hip and vibrant hotel features unique art installations, a bustling courtyard, and a lively on-site bar that hosts live music events. Each room is thoughtfully designed with a blend of modern comforts and artistic flair, ensuring a memorable stay for every guest.
Address: 800 E Burnside St
Rating: Good 7.8 (326 Reviews)
Rooms: 72
Price: From 109$

The Society Hotel

8.1

Good

(1290 Reviews)

+ 116 photos
Step into the past at The Society Hotel, a historic property located in Old Town Chinatown that seamlessly blends retro aesthetics with modern conveniences. This boutique hotel boasts vintage-inspired decor, cozy communal spaces, and unique room layouts that create a sense of nostalgia and charm. From its rooftop deck with sweeping city views to its on-site cafe serving artisanal coffee, The Society Hotel offers a distinctive experience that resonates with the fun hotels in Portland theme.
Address: 203 Northwest 3Rd Avenue
Rating: Good 8.1 (1290 Reviews)
Rooms: 38
Price: From 81$

The Paramount Hotel

8.7

Good

(1066 Reviews)

+ 53 photos
Discover a touch of old-world charm at The Paramount Hotel, a historic property located in downtown Portland that exudes timeless elegance and retro allure. This boutique hotel offers a refined experience with a nod to the past, featuring classic decor, luxurious amenities, and personalized service that caters to every guest's needs. Whether relaxing in the elegant lobby lounge or unwinding in the comfort of your well-appointed room, The Paramount Hotel provides a sophisticated retreat with a hint of nostalgia that complements the fun hotels in Portland theme perfectly.
Address: 808 SW Taylor Street
Rating: Good 8.7 (1066 Reviews)
Rooms: 154
Price: From 94$