Holiday houses in Highland Park

Historic Carriage House Queer Friendly by Midtown

Detroit 1914 carriage house in National Historic District was built as the chauffeur's residence by the VP of Studebaker Automotive. Try out Tiny House life! Updated with character: original kitchen sink, push button switches, clawfoot tub/shower. Modern USB outlets, retro blue fridge, on demand hot water, and blasting minisplit AC! Great for those comfortable in a diverse ungentrified city environment right off Woodward, antiracist only! Easy few minutes to midtown, downtown, and waterfront.

Chic and Cozy Attic Oasis

Welcome to your home away from home in Detroit! This unique attic studio apartment is a favorite among students and professionals alike. Renovated in October of 2022, our airy studio apartment offers an open floor plan which includes a private bathroom, fully stocked kitchen, work space, integrated living room, dining area and bedroom with a queen size bed. 4 skylights offer plenty of natural light. While we have AC, the system struggles to cool the large space when outside temps exceed 85.

Detroit 100

Centrally located in the historic North End neighborhood, you can relax and be surrounded by authentic Detroit history in this sunny 1500 sq. foot upper flat of a quiet 100-year old home. Whether you are traveling for work, vacation, or to visit family we offer a spacious place to unwind that has: 2 cozy bedrooms, bathroom with full bathtub + bluetooth speaker, kitchen with laundry center, dedicated office, yoga mats and weights, dedicated driveway parking space, balcony and backyard access.

Historic carriage house with gated parking & patio

Kick back and relax in this calm, stylish space. You'll have a private space in a detached historic carriage house, sharing a yard with the host. We have a large yard with a patio near the carriage house, covered porch, grill, bbq pit, bocce court, and outdoor living room (summer). We have a dog that has yard access. Private, secured parking is available for 1 car. Families are welcome, as are pets. We recommend families 3+ contact us before booking to ensure the space will work for you.

Historic Detroit Charm • 10 min Downtown

Welcome to our 100-year-old Detroit home just 10 minutes from downtown. Step into a warm, character-filled space that blends historic charm with the comforts you need for a stress-free stay. What you’ll love: Private bedroom with plush queen bed and fresh linens Fast Wi-Fi for work or streaming on the Smart TV Fully stocked kitchen—coffee, tea, and cookware ready Quiet residential block only 5 min to Motown Museum, 7 min to Henry Ford Hospital and 10 min to Little Caesars Arena

Walkable Historic Flat+Secure Parking+Laundry

Brand New listing from 5-star superhosts: + walk to top-rated restaurants, cocktail spots, coffee shops + secure parking in our gated lot + 1 block from metro line and bus + 1 mile to Midtown (4 min drive), 3 miles to downtown (10 min drive) + contactless self-check-in + responsive hosts who live nearby + mid-century modern interior inspired by D-Town Records (the 1960s soul music record label that was headquartered in the building) + 2 blocks from the Fisher Theater

The Boho Oasis: Studio Apartment

Welcome to The Boho Oasis!🪴 Our studio apartment is fully stocked with luxurious furniture, a fully-equipped kitchen, and features farmhouse, industrial, and bohemian themes. Enjoy high-speed wifi, and space for one car on the driveway with private back entrance. Located in a quiet neighborhood with easy access to local restaurants, grocery stores, parks, and the Detroit River just 10-minute walk away. Ideal for anyone seeking a trendy and comfortable stay!

Lykke House - 5min Walk to DTRO

Enjoy your visit to Royal Oak in our peaceful and centrally-located place; just a short 5 minute walk from downtown Royal Oak full of a variety of restaurants, bars, entertainment, coffee shops and more! Long stays as well as short stays are welcome! Our place is tucked into a quiet, safe, walkable neighborhood close to many parks, Royal Oak Music Theater, Beaumont Hospital, Detroit Zoo, Downtown Detroit and multiple freeways.

Modern 1BR Near Ferndale & Downtown Vibes

Modern 1BR apartment in Hazel Park, perfectly located near top golf courses, Royal Oak, and Ferndale. This cozy space offers a peaceful retreat with easy access to dining, shopping, and entertainment. Ideal for solo travelers, couples, or small groups, it features practical amenities and a relaxing vibe. Enjoy a quiet stay while staying close to vibrant urban hubs. Your ideal home base for both leisure and convenience.