Holiday rentals with a pool in Michigan Township

Pool House near the Indiana Dunes

Open-concept home with a private heated pool May - October. Take a hike, climb a dune & run back down to the lakeshore in downtown Chesterton, a perfect getaway weekend at the Indiana Dunes. Fenced yard, grill, and cozy fire pit. Local markets, festivals, orchards, and farms. Just a few miles from the beach and national park. Saturday's European Market offers a wonderful healthy, fun, entertaining shopping & dining experience for all. Fresh produce, food trucks, mimosa brunches, and candy shops.

“Treetops” Charming Country Coach House

Second-floor comfortably furnished coach house. Stylish and airy space with full kitchen. Great views. Private in-ground 20' x 40' swimming pool reserved exclusively for you and your guests. Basketball half-court. Softball diamond. Bocce court. Great for bicyclists. 20 acres of woods. Hiking trails on property and pond with wildlife. Centrally located between New Buffalo, MI, and Michigan City, IN. Close to the Indiana Dunes, and Lake Michigan. 70 minutes to Chicago, 45 minutes to South Bend.

Designer Cottage - walking distance to downtown

Dream cottage getaway just over an hour from downtown Chicago. Walking distance from the beach, restaurants and all of downtown New Buffalo. Close to the casino, wineries and breweries. Whether driving in or taking the train, The Bradford is a relaxing yet sophisticated getaway. Eat, drink, and enjoy the beach, the pool, the shops and incredible summer sunsets, all within walking distance! Please note pool/bathhouse open late May - September and is shared with our association.Permit C22-0051

Gray Haven: Stunning Woodland Retreat w/ Pool

Set on a 1.25-acre wooded lot less than two miles from Townline Beach, this luxurious home is a vacation dream! The open design of the living room, dining room, and kitchen, high ceilings, majestic stone fireplace, and natural light draw you in. Elegant furnishings and stylish decor, plus a pool, huge deck, and screened gazebo invite you to relax. Gather around the kitchen’s large center island or breakfast nook for coffee. Relax by the outdoor fireplace and count the stars. Boom.

'Pool Barn' w/Games & Hot Tub near Indiana Dunes

The Pool Barn offers a great location & unique experience. 1 hour from Chicago & less than 10 minutes from large sand beaches & hiking trails of Indiana Dunes National Park & Indiana Dunes State Park. pool, hot tub, grill, firepit, playground, & we are on hike/bike trail. Inside is ping pong, air hockey, darts, popashot, foosball, board games, large smart tv, 6 beds, couch, & full kitchen. *pool table is currently broken due to guests attempting attempting to move it*

Poolside Oasis - Private Heated Pool + Fun Games

Escape to our stunning 4-bed, 1.5-bath home with a private in-ground pool! Bright living spaces, a fully equipped kitchen, cozy bedrooms, and an amazing heated pool await. Conveniently located near charming Saint Joseph, Michigan, with Lake Michigan's sandy shores and vibrant downtown nearby. Indulge in local cuisine, explore nature trails, then return to the comfort of our inviting home. Your ultimate vacation experience awaits! Book now for an unforgettable getaway!

Designer Cottage Relax Beach Pool & Spa—Windjammer

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, pool, hot tub, fire pit, indoor fireplace, and loft for the kids! Take advantage of the beach and explore beautiful Harbor Country. Relax and unwind in this luxurious updated getaway with plenty of sun filled space for all to enjoy year-round. Professional Wolf stove for the chefs. Book your stay today and create lasting memories!

Cabin w/heated pool, near beach

Relax with the whole family at this peaceful place to stay. Come enjoy a day at the beach and after dinner go for a dip in the heated pool. Centrally located in Lakeside, MI close to Union Pier, New Buffalo, Bridgman and St. Joseph. Take the family to pick fruit or go for a tour of the many local wineries. We are also close to Notre Dame University if you are in town for games or to tour the campus.

New Buffalo Pool/Hot-tub/Firepit

Your family will be close to everything when you stay at this centrally-located place. This five bedroom 3 bath home has it all including pool, hot-tub, firepit, fenced yard. Steps from a the association beach (small beach currently) walking distance to the large public beach, town, and marina. Renovated in 2023.