Townhouse holiday rentals in The Great Lakes

Summer Escape | Sip, Stroll + Stay @ Harbor Haven!

⭐️⭐️ Welcome to Harbor Haven ⭐️⭐️ Escape to this stunning townhome in Ashtabula Harbor! Enjoy a short walk to the beach, yoga, delicious restaurants, charming shops, and a brewery. This home is thoughtfully designed with all the amenities you need for a comfortable getaway. Spend your days kayaking or fishing on Lake Erie, or explore nearby wineries and covered bridges. Spire Institute is also a short drive away! The Harbor Haven offers the perfect blend of adventure, comfort, and convenience!!

Tremont Townhouse with Skyline Views

Welcome to Tremont Townhouse in Cleveland's historic Tremont. A mile from downtown, enjoy skyline views from all floors and two decks. Relax in our year-round hot tub at no extra cost. Inside, find a fully-equipped kitchen, large dining table, and a cozy fireplace. Sleep well on a King Sleep Number bed, four queen memory foam beds, a twin, and various sofas. No extra fees for additional guests, cleaning, or pets. Walk to shops, dining, and galleries like Paul Duda Gallery. Top-rated on AirDna.

Upscale Home in Lincoln Park Minutes from Downtown

Minutes outside downtown Chicago, built in 1890, this gorgeous fully-remodeled modern Victorian-era row house is located in the heart of Chicago’s historic and vibrant Lincoln Park. One of Chicago’s most affluent neighborhoods! > Walkability score of 98/100 > 4 min walk to the train station, steps to bus stops, short Uber ride to all top Chicago attractions > Across DePaul > Amazing parks & bike trails, free zoo, performing arts, shops, nightlife, spas & some of Chicago’s finest restaurants

Spacious Executive 2BR Home Near Shopping & Dining

Professionally Managed by Kevin Bush, this rental is nestled in a safe and quiet neighborhood in a desired location that is convenient to Woodman’s Center, Janesville shopping and dining destinations. Enjoy the city’s hundreds of acres of tranquil parkland, miles of peaceful trails, and beautiful downtown riverwalk. Bonus: This location is an easy drive for day trips to Madison, Milwaukee, Chicago, and surrounding. Please check out our listing on Margate Drive for more dates. Kevin, Host

Spacious TC Forest Condo w/ Porches & Brook View!

Welcome to my top-rated Traverse City condo! Nestled in The Commons on 11th Street, this second-floor haven awaits. Discover a chef-ready kitchen. Enjoy morning coffee relaxation on one of two porches overlooking a brook. Relish in spacious living with a queen pull-out sofa, work area, and a kitchen island. Entertainment awaits with a 65-inch 4K TV. Conveniently near west beaches, it's the ultimate retreat for tranquility and adventure. Experience comfort and relaxation at my esteemed abode.

Blue Mountain Gallery Getaway

Welcome to a cozy family escape featuring a stunning gallery wall showcasing scenic photography of South Georgian Bay. This peaceful retreat is just minutes from Blue Mountain Village or downtown Collingwood. Listen to the soothing sounds of the Cranberry Marsh Wetland, or walk to nearby Georgian Bay. Whether you’re hitting the slopes, the spas or the shops, unwind in a space that’s as inspiring as it is relaxing. Send us a message if you have any questions — we're always happy to help!

The Pingree of Piety Hill_Home # 1

Come stay at our preserved 1912 lower flat, furnished with Detroit-honored art & literature throughout, and enriched with craftsman character & contemporary charm. Found in the peaceful Piety Hill neighborhood, so unfortunately we do NOT allow gatherings of more than 15 persons. This is a 2-family home, but ONLY YOU will have full access to the entire 1st floor and basement level of this property. The 2nd floor home will NOT be occupied during your stay; just maintenance and cleaning staff.

Majestic & Relaxing Home w/ 3 Beds Pool Table Bar!

If your looking to relax and kick back look no further than our lovely townhome in the heart of Dubuque. Our home features 2 Bedrooms with 3 Total Beds (King, Queen, and a Full) and a 1 1/2 Bath located in a quite area. This space is perfect for hosting! We offer a fun and relaxing space. This home has a Full size pool table and dart board. We Welcome you to enjoy a nice quite evening relaxing in the living room in front of the welcoming fireplace. We offer off street parking for one car.

Historic Walker’s Point Home, Garage & Yard

Welcome to The Bentley Hotel, a luxury selection of townhouses decorated with everyone in mind. We aim to provide a quality experience and memories that will last a lifetime. This townhome is finished with top of the line amenities including a 60” smart TV, board games, organic coffee and teas, a full kitchen with Caraway non-stick pans, workout mats, dumbbells and more. This is your new home away from home and the perfect place to gather whether you are in town for business or pleasure!

1880s Midtown Victorian

Renovated 1200 ft2 historic 1880's home with plenty of charm, beautifully restored woodwork, and hardwood floors, located in the heart of Midtown. Walking distance from restaurants, independent shops, and local nightlife in the historic Willis-Canfield retail district. Our 3 bedroom listing has an additional guest fee after the first 2 guests on the reservation. This fee covers the additional housekeeping of bedrooms, linens, and towels needed for larger groups.

Cozy Downtown Walkerville Home

Welcome to your perfect home away from home in the heart of Windsor! This charming and cozy residence offers the perfect blend of comfort, style and convenience making it an ideal spot for both short and long stays. Whether you're in town for business, leisure, or a family visit, you'll find everything you need to feel right at home. Situated downtown Windsor just minutes from the VIA train station, Casino Windsor, Detroit tunnel and great popular restaurants

Historic Gem|Steps to UWM|Lake Mich|Free Parking

🔹 5-Star Rated | Superhost Quality | Fast Wi-Fi | Free Parking 🔹 🏡 Experience a Slice of Milwaukee’s History in a 100-Year-Old Home! Step inside this charming first-floor retreat—a beautifully preserved prairie-style home blending historic elegance with modern convenience. Located right across from UWM, this top-rated Airbnb is perfect for visiting students, faculty, families, and travelers looking for a relaxing, walkable neighborhood.