Holiday rentals with a pool in 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

Enchanting Pool House (2.2 miles from Notre Dame)

Relax in a private pool house located on historic Studebaker property. Pool house has a fun Key West vibe and includes one bedroom with (2) full size beds. One full bathroom with standup shower and a separate changing room with shower. The common area is spacious and can easily sleep 2 more guests. Weather permitting, enjoy our 82k gallon heated pool that was the first inground pool in South Bend. Pool area includes an outdoor gazebo and fire pit. Minutes to Notre Dame and downtown South Bend.

Large, Cozy, Theatre, Pool, Walk to ND Restaurants

Centrally located to walk & explore Notre Dame, restaurants, and all South Bend offers! Spacious 6-bedroom luxury home with open concept design, master suite w/ spa shower & jacuzzi, and balcony overlooking the pool with lounge deck. Theatre room w/ recliners, poker table & Xbox. Two large entertainment areas w/ 65” & 85” TVs, surround sound, blazing-fast WiFi, granite kitchen, large charcoal grill, fire pit, and comfy beds. Indoor & outdoor games make it perfect for families & game weekends.

Experience Fall Beauty & Harbor Country Charm!

Important notes: - Home is in HARBERT by the lakefront, NOT in Three Oaks - Hot tub open all year - Pool closes October 10, 2024 through Memorial Day 2025 After a day of exploring the waters of Lake Michigan, Warren Dunes, or nearby wineries, find your sanctuary at Mae's Place. Recharge by soaking in the inviting hot tub, sizzle up a delicious meal on the grill or in the kitchen and end the evening roasting marshmallows around the fire pit or watching an outdoor movie on the pool deck.

Luxury home with pool.

Plan your next family gathering, winery tour, football weekend, or simply hang by the pool (seasonal) in this spacious and well-appointed home. Perfectly located in the charming town of New Carlisle, approx 16 miles to New Buffalo, Michigan, and approx 17 miles to Notre Dame. This spacious, tastefully decorated home features a gourmet kitchen, private office, large family room with gas fireplace. The outdoors boasts a heated in-ground pool (seasonal), bbq, and wood-burning fireplace.

Designer Cottage Relax Pool Beach & Spa—Windjammer

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, community pool, private 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! Create lasting memories!

New Buffalo / Union Pier Pool Hot tub 6 Bedroom

Relax with the whole family at this peaceful home with Classic European style meets Lake Michigan! This astonishing turnkey home is the perfect escape from life in the busy city. The home is ideal for entertaining Famliy . 5 bed , 4 bath , hot tub and gas grille and( pool opens June 6) close to union pier beaches and wine country . Property is nestled in a quaint country road location 1/2 mile off re arrow highway. Room for 10 cars,blue stone patios,ping pong table .

Hot Tub | Backyard Oasis | Game Room | |Coffee Bar

Discover The Glendale Treasure 🏡, your perfect getaway hosted by Home Away From Home! This 4-bedroom, 2-bath home is packed with fun—swim in the heated pool 🏊, soak in the hot tub ♨️, or unwind around the firepit table 🔥. Inside, enjoy the coffee bar, the ultimate game room 🎮 with pool, air hockey, ping pong, and arcade classics. With cozy spaces and nonstop entertainment, it's ideal for families or groups. Book your stay today and make unforgettable memories!

Wabi Sabi Chic at The Flamingo Ranch in Lakeside

Autumn at Flamingo Ranch—an unforgettable retreat nestled in Harbor Country, 1/2 mile from the lake. Equal parts sanctuary and playground, this designer-owned haven offers both deep seclusion + an open-format layout that invites connection, healing + memory-making. Whether you’re gathering with family, reuniting with old friends, or seeking a rejuvenating escape, we deliver an experience that’s as comfortable + stylish as it is energetically charged.

Couples cottage with hot tub!

Come for a relaxing getaway in the country. Cook in our small kitchenette or use our Blackstone or fire pit. Located in a small hobby farm setting with sheep roaming the pasture. We also have a couple cats that claim the pool area as their own. The long driveway and gravel road are perfect for a leisurely stroll to enjoy the great outdoors. Take a swim in the pool or a soak in the hot tub and let the worries of life melt away during your stay.

Bibi's Retreat- Grand 7 Bedroom Private Escape

Bibi's Retreat-Nestled among 6,000 trees along 15 acres of secluded property. This is the ultimate private getaway. Located in Niles, MI, the home offers 7 true bedrooms with plenty of space for multi-family living. We are within 30 min of 15 wineries and breweries. We are within 20 min of 10+ golf courses and 20 min to Notre Dame. Ladies Retreat, Golf Getaway or Winery Tours, this home is perfect for large groups.

Year Round Hot Tub, Outdoor Pool, 3 Bedroom & Bar

Experience the ultimate South Bend getaway! This charming 3-bed, 1.5-bath home is just steps from Notre Dame. Enjoy a 24ft pool 🏊‍♂️, 5-person hot tub ♨️, spacious deck with outdoor dining, and a BBQ grill. Inside, relax with a full kitchen, bar area, and washer/dryer for total convenience. Perfect for game days, family trips, and summertime fun—make lasting memories at The Poolside Retreat! ☀️🏡