Holiday rentals with a patio in Chesterton

Location location

Need to relax for a weekend or few days of vacation?Retreat to this 5 bedroom 3.5 bathroom estate .Plenty of space for entertaining throughout the home! The lower level ideal for related living and features 2 bedroom,kitchenette second living room. Located right on the wine trail. Surrounded by farms, apples, and peach orchards. Imagine having a glass of wine and picking fresh fruit from the trees - all walking distance from the house. Warren Dunes Park and Weko beach only short distance away!

Cheerful Stevensville cottage, GREAT LOCATION!

Right in the prettiest area of Stevensville, Glenlord Cottage is an ideal location for your Southwest Michigan stay. Down the road you will find Glenlord Beach Park, a beautiful Lake Michigan overlook. Around the corner, an award-winning bakery. In Stevensville with its variety of restaurants, beaches, and shops, Glenlord Cottage is also within easy reach of many SW Michigan attractions and is well placed for visits to wineries, golf courses, and downtown St. Joseph with its shops and festivals.

Secluded Country Cabin

Spring is just around the corner, schedule your getaway and start planning for the summer now and enjoy your stay in this 400 sf newly renovated cabin that has knotty pine interior walls throughout along with new carpet and vinyl flooring. Enjoy the peace & quiet as you sit around the fire pit or relax on the outdoor patio that's fully furnished with furniture and a charcoal grill. Come enjoy your stay as you take advantage of the local wine tours, nearby Lake MI. beaches and the county parks.

Charming 2BR/2BA Cottage with Full Kitchen & Patio

The cottages, or townhouses, are situated steps away from the main inn, providing an added sense of privacy while still feeling the vibe of the community. This cottage has two bedrooms (one with a queen bed in the downstairs bedroom + another with 2 twin beds in the upstairs bedroom). Two bathrooms (one upstairs, one downstairs) keep things fresh with a queen sleeper sofa. The upstairs loft space provides extra room for rest. An in-unit washer/dryer and high speed WiFi makes things easy.

Cozy 1 bedroom condo on Marina near Lake Michigan

Come stay at this adorable one bedroom condo on the Marina near Lake Michigan! This condo has everything you need to enjoy a special getaway from everyday life. Conveniently located near the Indiana Dunes with the South Shoreline to Chicago directly across the street. Relax on the patio and enjoy watching the boats come and go as they please. Check out the drinks and food at the Marina Shores Yacht Club just a short walk away from this unit. This condo has everything you're looking for!

Superhost, hot tub, golf cart, fire pit, large!

Newly renovated 5 bed, 2 bath home in the quaint village of Grand Beach. Golf cart included with rental (in season - May thru mid-Nov). Home is situated on a large lot, high on a sand dune that overlooks the 6th fairway and park area. Enjoy two large decks and year-round eight person hot tub. The property is very private, on secluded street and fully stocked for a great stay. It's a great place to enjoy some down time in an idyllic village in the heart of Michigan's "Harbor Country."

Couples alert! PVT beach access, hot tub, firepit!

ADORABLE HOME IN LAKESIDE WAS RECENTLY REHABBED & OFFERS A SUPER CLEAN AND MODERN FEEL IN THE HEART OF HARBOR COUNTRY. GUEST HAVE ACCESS TO PRIVATE BEACH WHICH IS A 7 MIN WALK AWAY - NO CROWDED BEACHES! YEAR ROUND HOT TUB, A SUPER COMFY KING SIZE BED AND ONE PULL-OUT COUCH FOR 4 GUEST (MAX). FIREPIT SUPPLIED WITH WOOD, AN OUTDOOR PATIO AND WEBER GRILL COMPLETE THIS LOFT LIKE HOME. FULLY STOCKED KITCHEN, HIGH DEF TV, STREAM MUSIC, ETC! YOU WILL LOVE IT!

Baroda "Wine Country" Beauty With Hot Tub!

This is a gorgeous, newly renovated home with a ton of great amenities! Everything in this house was renovated in 2022, including the floors, HVAC, kitchen, bathroom, patio, new fire pit, all appliances, and all new furniture! The house is great for anyone that wants to be close to the beach, golf course, or wineries. Located just a short 10 minute drive to Weko Beach, 5 minutes from Pebblewood golf course, and right in the middle of a TON of wineries.

Union Pier - Hot Tub/Fire Pit!

Welcome to the Cottage in Union Pier! We truly love Harbor Country and have specifically come to LOVE Union Pier for the quaint and calming vibes. Explore the great restaurants, breweries/vineyards, casinos and of course . . . BEACHES that are all right at your fingertips. Enjoy smores over the fire or relax in the Hot Tub! Walk to Timothy's Restaurant or town - about 3/4 mile and then you have your pick of beaches ( about a 3 minute drive beach).