House vacation rentals in Chesterton

Blue Birdhouse - Indiana Dunes

Welcome to The Birdhouse - Your Perfect Getaway! 🐦🌿 Nestled near the Indiana Dunes National Lakeshore, our cozy 2-bedroom, 1-bathroom home is perfect for families, couples, and nature lovers. Enjoy a pet-friendly, fully fenced yard, free parking for 2 vehicles, a fully equipped kitchen, laundry, and a BBQ grill with patio for outdoor dining. Minutes from Lake Michigan beaches, hiking trails, and local dining, it’s the ideal spot for beachgoers and adventurers. Book your stay today! 🌞🏖️🌳

Value · Location · Sleep quality

South Shore Studio Apartment {National Park}

I have to warn you definitely not a hook up spot or party house!!! typically rise with rooster on this 5 acre country setting with a small fishing pond. 420 friendly .. Quiet hours are 11 -8 generally some music playing, musicians are welcome !! if you happen to book on a Sunday i host an Open Mic in my Barn every Sunday ..... pretty relaxed. Upon arriving, turn into the driveway, and then right into the yard. Apartment is upstairs, the door is open with the keys inside. ✌️

Value · Location · Bathroom

UncleLarrysLakePlace HotTubKayaksPingPong

A tribute to our favorite world traveler-he's the first to stay at our properties and give us the good, bad and ugly so we can fine-tune the ultimate experience for YOU. This newly remodeled lake home boasts 4 sleeping areas, year-round hot tub, game room with a ping pong table and large screen TV, large gathering spaces in and out, new kitchen and your own kayaks to explore the area. Enjoy sunsets and lake views from the hot tub on the expansive deck or while grilling on the Weber gas grill.

Family · Location · Nearby

Downtown Chesterton "Grant-Cottage"

Charming downtown house with a front porch, back deck & covered patio. Beautifully decorated with a small fenced in backyard. Minutes from the Indiana Dunes National Park and beaches. Near the South Shore Commuter train if you wish to visit Chicago without the drive and expense of parking. We are across from an active train track so if you like trains you can watch them from the front porch. Walk to restaurants, wineries and beer pubs. European market on Saturdays from May to end of October.

Family · Value · Outdoor spaces

Lake Trail Cottage

Located just 1 mile from Lake Michigan. Lake Trail Cottage is the closest home in Pines and just minutes from Beverly Shores beaches! The cottage has two bedrooms one bath. With basement Rec room. Home sleeps 7. The primary bedroom features a Queen bed, 42in Smart TV. The second room has a full size bed. Pullout couch/ living room. Calumet Trail and South Shore Train (Chicago)is located directly behind home. South Shore train to Chicago is 1 mile from house. Bikes & beach supplies included.

Location · Value · Access

Michigan City Indiana Dunes Beach National Park

Escape to our cozy home just minutes from the stunning Indiana Dunes National Park! Located in the heart of Michigan City, this charming retreat offers a relaxing getaway Enjoy a well-furnished living area, a fully equipped kitchen, and 2 comfortable bedrooms. Outdoor Bliss: Relax on the private deck or explore our beautiful garden—ideal for unwinding. Adventure Awaits: Only a short drive from the park's sandy shores, hiking trails, Lake Michigan. **CONTACT US FOR SEASONAL DISCOUNTS**

Value · Location · Cleanliness

TRYON FARM MID-MODERN SPA IN THE WOODS

Come, enjoy our Tryon Farm modern spa. A Sustainable luxurious open concept tree-house in the woods. Minutes from the beach with an outdoor sauna, Hottub, shower, and Mr. Steam. Perfect for two or a family/group adventure. A true destination with Yoga studio, Mirror by LuLu lemon and wellness elements. The house is a perfect balance of art and nature and luxury and spiritual. Treat yourself to a farm to table, hand made, locally sourced chef services for an extra special experience.

Value · Location · Check-in

Roomy Retreat–Family&Friends|2 King Beds|Game Room

🏡Welcome to Your No-Train-Noise, Pet-Friendly Stay in Chesterton! Property Highlights: 🛏️4 Bedrooms | 🛁 3 Bathrooms | 🛋️ 3 Living Areas with Smart TVs 🍸Bar in the Basement 🍽️Outdoor Dining 🚶‍♂️Minutes from historic Chesterton Downtown 🌲 4 miles to Indiana Dunes National Park & the beach 🍳 Fully Stocked Kitchen 👶 High Chair & Crib included Get ready for endless adventures along the sandy shores and tree-lined trails of Indiana Dunes. Enjoy every moment of your stay

Family · Location · Bathroom

New Dunes Escape

Your family will be close to everything when you stay at this centrally-located place. Located just 3 minutes from the entrance of the Indiana Dunes National Park, 45 minutes from Chicago, 45 minutes from New Buffalo, MI , and 3 minutes from the Dunes Park South Shore Station, this completely remodeled home is the perfect place for a get-away. With free wifi, firepit with firewood, and a 4-seasons room, this house is the perfect place to relax after a great day swimming or hiking.

Location · Family · Access

Visit Lake Michigan | Perfect Couple's Retreat

Explore the beautiful Indiana Dunes National and State Parks. Book your stay at this cozy, newly renovated 2 bedroom home centrally-located for all your adventures. Within 2 miles of beach, restaurants, brewery, winery, casino, concert venue, spa, botanical garden, boat tours, kayak rental. Bonus trip: take the Southshore commuter train to Chicago for the day. Here, you can explore all the south shore of Lake Michigan has to offer then kick back at your home away from home. 💙

Family · Value · Outdoor spaces

The Dune Den! Huge Yard/Firepit/Near Town+Dunes

Right in-between The Dunes National Park and downtown Chesterton, you will be close to everything when you stay at this centrally-located home. Things to look forward to: Less than 10 minutes to the Dunes and beaches or head 3 minutes the other way to downtown for food, drinks and plenty of small town fun. This charismatic home greets you with all new furniture, front porch, HUGE fenced yard, and local decor. You will fall in love with this family town so bring the kids!

Location · Family · Parks

Secluded Modern Retreat Near Beach - "Sandlot"

Stunning modern home overlooks private sand dunes on 5 wooded acres just a mile away from beautiful Lake Michigan beaches and surrounded by the Indiana Dunes National Park. Relax in our updated open-concept unique home nestled in the dunes. Enjoy the trails in the backyard, the friendly community, and local attractions near by. Just an hour to Chicago by car or the South Shore train is 1/2 mile from the house, with easy rides to Chicago and South Bend.

Family · Location · Bathroom