Lake house holiday rentals in Chain-O-Lakes

Beach! Hot Tub! New Buffalo! Firepit! King Bed!

Highlights: ✔ 8-person Hot Tub ✔ Sleeps 12 (10 in main house + 2 in guest cabin) ✔ 1 mile to beach ✔ 6 min to Shady Creek Winery ✔ 10 min to New Buffalo + Michigan City ✔ Outdoor firepit & picnic table ✔ Gas BBQ grill ✔ Smart TVs & board games ✔ King bed in main bedroom ✔ Luxury custom-designed home ✔ Private wooded lot ✔ 2 Adult & 2 kids' bikes ✔ Beach chairs, toys, wagon and towels ✔ Pickleball paddles & nearby courts ✔ 4 vehicle parking ✔ 2-person workstation ✔ High speed wifi ✔ Fully stocked

House of Zen: Peaceful Modern Cabin on Tryon Farm

The House of Zen is an architect designed home situated in the woods, part of a sustainable farm community on 170 acres. Only an hour drive from Chicago, and close to Indiana Dunes National Park, it is the ultimate escape. The perfect getaway for couples, creatives and nature lovers who want some peace, quiet and space. Explore the farm trails & enjoy the wildlife and soothing sounds. Note: We have a 3 night minimum stay during summer, but open up 2 night stays 1-2 weeks before if possible.

Lakefront House, Pontoon, Deck, Fire Pit & More!

Pontoon INCLUDED in all rentals May 2026-Sept 2026! No extra fees for unlimited use of private pontoon, pier, paddle boards and more!! Rental price of our lakefront house includes the pontoon, deck, yard and endless activities!! Take the pontoon for a cruise, fish, swim, paddle board, kayak, watch the wildlife or have a bonfire!! Travel 15 minutes to the Indiana Dunes or 10 minutes to downtown Valpo. You will also be able to cook delicious meals on the propane grill & fully stocked kitchen

Pure Michiana - Rustic & Cozy - near the stateline

NO EVENTS. 10 person max on property at all times. It puts too much wear on the septic/well and deck. Dining table seats 8. 3- block walk to a small shared lake and near a host of lovely spots: Breweries/Wineries, Dunes, Three Oaks, Frisbee Golf, and more. A gas fireplace for cold winter nights, an outdoor firepit, a hammock, grill, and outdoor seating/camping chairs. A short walk to the Nowhere Bar & Grill for great local food! Only 1 hour 15 minutes from Chicago. Sleeps 8 comfortably.

Harbor Country Charm w Heated Pool Open Til 10/12!

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.

Steps to Beach & Starbucks! Private Yard, Firepit!

Walk to Starbucks! Walk to beach, restaurants, shops, ice cream, grocery! 2 queen bed 2 bath home is perfect to enjoy fenced yard, grill, fire pit, & yard games offered. Take a few days to explore wineries/breweries, art galleries, antique stores, kayaking, casino and more! Live bands Fridays/Saturdays until 2 am Memorial Weekend to Fall at Casey's (behind property). Noise machines in each bdrm. Pet fee $100, 2 dogs MAX. Exterior areas have video/audio cameras w/ live feeds. Wp#bcnbwmech

Midcentury marvel steps from beach! Pups

Year-round beach fun an hour from Chicago!Welcome to Barefoot Bungalow, a mid-century marvel with modern amenities. Your group will love the game room with pool table, ping pong. Private dog-friendly fenced backyard with grill, patio & firepit. Short stroll to Stop 7 to beach (Beachwalk boardwalk, wagon provided). Quiet relaxation far from the madding crowds. So many excellent restaurants, shopping, brew pubs, wineries, hiking, biking. Off-street parking, Wave bus

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!

Quiet cottage on Buck Lake, 1 bedroom

Take it easy at this unique and tranquil getaway at Hummingbird Hill Cottage!You’ll be on peaceful and beautiful, no-wake Buck lake where you can enjoy kayaking, paddleboarding, fishing, and more! Take a hike, ride bikes, or play disc golf in the beautiful Dr. Lawless International Dark Sky Park which is directly across the street! Whether you’re looking to have a couples getaway, a guys’ fishing trip or time with girlfriends, Hummingbird Hill is for you!