Friendsgiving is all about gathering your favorite people, sharing good food and making time for each other. This year, skip the stress of hosting at home and turn the celebration into a weekend getaway in Southwest Michigan.
Harbor Country is an easy place to settle in for a few days together. With spacious vacation homes, charming downtowns, local wineries and plenty to explore, you can make dinner the centerpiece of the weekend without making it the only thing on the itinerary.
Just 90 minutes from Chicago, Harbor Country is close enough for an easy weekend escape and far enough away to make it feel like a real getaway.
When to Plan Your Friendsgiving Getaway
Thanksgiving falls on Thursday, November 26 in 2026, making the weekend before, November 20–22, a great time to plan your Friendsgiving getaway. Or, turn Thanksgiving weekend itself into the trip.
If you're bringing a bigger group, booking early gives you the best selection of larger vacation homes and plenty of time to get everyone on the same page.
Find a Vacation Home With Room for Everyone
When you're bringing the whole crew, the right home makes a difference. Look for a vacation rental that gives everyone enough space to gather, cook, eat and relax together.
When choosing your Friendsgiving home, look for:
- Enough bedrooms and bathrooms for your group
- A dining table with room for everyone
- A well-equipped kitchen for cooking Friendsgiving dinner
- Cozy extras like a fireplace, hot tub or game room
We've gathered our 4+ bedroom Friendsgiving vacation rentals in Harbor Country in one place, with homes for groups of all sizes, including options that sleep up to 26 guests.
Make a Weekend of It
Before the cooking starts, get out and explore. Take a fall walk along Lake Michigan in New Buffalo, browse the shops and galleries in Three Oaks or spend a quiet afternoon exploring Lakeside and Union Pier.
If your group wants to see more of Southwest Michigan, hop in the car for a fall color drive through Harbor Country. Red Arrow Highway makes an easy scenic route through Union Pier, Lakeside, Harbert and Sawyer, with plenty of places to stop along the way.
Our Harbor Country fall itineraries are full of ideas for exploring the area, whether your group wants a laid-back weekend or a packed itinerary.
Bring Southwest Michigan to the Table
Add a little local flavor to your Friendsgiving dinner while you're here. Stop at St. Julian Winery & Distillery Tasting Room in Union Pier for a bottle of Michigan wine or cider, or head to Round Barn's Union Pier tasting room to find something local to pour with dinner. For something to add to the table, Farmette in New Buffalo combines a small farm and marketplace with a bakery and café, making it an easy stop for locally inspired treats.
Want to make an afternoon of it? Check out our guide to wineries, cider and orchards near New Buffalo for more local stops.
Tips for Hosting Friendsgiving in a Vacation Rental
A little planning before your trip makes Friendsgiving dinner a lot easier once everyone arrives.
- Check your vacation home's kitchen and cookware details before you arrive.
- Assign dishes ahead of time so you don't end up with three pies and no mashed potatoes.
- Bring any specialty items you know you'll need, like a roasting pan, meat thermometer or favorite spices.
- Pick up groceries on the way, or order from a local restaurant if your group would rather spend less time cooking.
Then turn on the music, start cooking and settle in for the reason you came in the first place: time together.
Whether your Friendsgiving means a traditional turkey dinner, takeout from a local favorite or snacks and games around the table, make a weekend of it in Southwest Michigan.
Friendsgiving Getaway FAQs
When is Friendsgiving 2026?
Friendsgiving doesn't have an official date, so you can celebrate whenever it works for your group. Many groups choose the weekend before Thanksgiving, which falls on November 20–22 in 2026.
Where can a large group stay for Friendsgiving near Chicago?
Harbor Country in Southwest Michigan is about 90 minutes from Chicago and offers spacious vacation homes designed for groups, including 4+ bedroom properties and homes that sleep 15 or more guests.
What is there to do in Harbor Country in November?
November is a great time to slow down in Harbor Country. Explore local wineries and tasting rooms, browse shops in towns like New Buffalo and Three Oaks, take a quiet walk along Lake Michigan or spend an afternoon driving through Southwest Michigan's countryside
Are your vacation homes good for holiday dinners?
Many Third Coast Vacations homes offer full kitchens, dining spaces and plenty of room for groups to gather, making them a comfortable home base for Friendsgiving and other holiday celebrations. Browse our Friendsgiving vacation rentals to find a home that fits your group.
Gather your people, pick your weekend and find a Harbor Country vacation home with room for everyone.