Pet-friendly vacation rentals in Chesterton

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Top-rated pet-friendly home rentals in Chesterton

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Michigan City

4.91 out of 5 average rating, 156 reviews

Historic Charmer: Walk to Casino, 2 miles to Beach

Guests will love this historic charmer! Conveniently located near the casino (1 block), beach (2 miles), & a short drive from tree-lined hiking trails in the nation's newest national park. Fully updated & stocked with new kitchenware, appliances, & beach toys/towels, king beds, & a smart TV; we've got everything you need! Enjoy wineries, boat rentals, cafes, Michigan City Zoo, splash pad & park, outlet malls, & antique shops. The perfect getaway for up to 8 people who want to relax or adventure!

Superhost

Home in Chesterton

4.8 out of 5 average rating, 255 reviews

South Shore Studio Apartment {National Park}

I have to warn u 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 11 -8 generely some music playing and musicians are welcome !! if you happen to book on a sunday i host open mic in my Barn every sunday ..... pretty relaxed. Upon arriving turn into the driveway just passed my house and then right into the yard apartment is upstairs the door is open keys inside. ✌️

Guest favorite

Guest suite in Miller

4.96 out of 5 average rating, 337 reviews

Miller Mermaid Suite-100 yds from the beach!

100 yds from the beach, the cozy MERMAID SWEET awaits you and is well suited for a young family or 2-3 adult friends. This artsy basement open studio space includes a private entrance, kitchenette, unique art & a cozy reading/sleeping nook! Enjoy beautiful sunsets from the upstairs deck or use the sun room on rainy days. BBQ on the grill. Visit local restaurants, shops & galleries. Hike wooded trails & swim by sandy, dune-grass beaches. . House-trained dogs welcome! Sorry no cats (allergies)

Guest favorite

Home in Michigan City

4.98 out of 5 average rating, 258 reviews

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, 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 during our high season (mid May-mid September), and open 2 night stays 1-2 weeks prior if we have a couple open days.

Guest favorite

Home in Michigan City

4.94 out of 5 average rating, 293 reviews

Lake Michigan Farm Retreat w/ Yoga Shed & Hot Tub

Luxury farm retreat on 7 wooded acres with hot tub, yoga shed, fire pit, fully fenced yard & pond! This home is a five minute drive to the beach, blueberry picking, Burn 'Em Brewing, Shady Creek Winery, next to Tryon Farm or 10 minute drive to downtown, the casino, and the outlet mall, but our guess is that you won't want to leave the property! This designer home has super comfy beds, 800 thread count sheets, a gourmet coffee bar, screened in porch, and even a tiny library in the laundry room

Guest favorite

Home in Chesterton

4.9 out of 5 average rating, 114 reviews

Downtown Chesterton 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.

Guest favorite

Home in Michigan City

4.95 out of 5 average rating, 267 reviews

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.

Guest favorite

Home in Michigan City

4.92 out of 5 average rating, 222 reviews

Casinos, Shopping, Pets, and Parking a Plenty!

1 mile from BLUE CHIP CASINO - with its new SPORTS BOOK and is where the away team stays for NOTRE DAME FOOTBALL, 2 miles from the outlet mall, 7 blocks to the beach, and plenty of parking! 3 bedrooms (4 beds) and 1 bathroom. This is a great place regardless of the season and though in the city; it backs up to woods with lovely walking trails. The home also has hi speed internet/WiFi and HD cable television. Simple, practical home in a safe neighborhood - and it’s a bargain!

Guest favorite

Home in Michigan City

4.96 out of 5 average rating, 127 reviews

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

Guest favorite

Barn in Stevensville

4.99 out of 5 average rating, 123 reviews

The Blue Barn - A cozy country getaway!

Welcome to “Blue Barn” vacation home, a country retreat located between beautiful St. Joseph beaches and several Baroda wineries. A welcoming, open floor plan makes it easy for your group to spend time together. Enjoy the crisp white bedding, fully stocked coffee and wine bar, and private fire pit to unwind with friends and family. Grand Mere State Park, Weko Beach, and several local breweries are all just a short drive from this ideally located property.

Guest favorite

Guesthouse in Valparaiso

4.96 out of 5 average rating, 405 reviews

Private Guest House, in Gated Nudist Resort.

Book your get away today. Make it a few days or a week. If you've ever thought of trying social nudity. This is the place to do it. Very private 200+ acre property. You can also USE GUESTHOUSE AS BASE FOR SHORT DAY TRIPS, to Indiana Dunes State Park, Michigan Wine Country, or Chicago. You won't find a more beautiful, cost effective setting for a get away. This listing is for Guest house only (see guest access below)...where NUDITY IS NOT REQUIRED.

Guest favorite

Guesthouse in New Buffalo

4.96 out of 5 average rating, 401 reviews

Rainbows End 🌈 Puryear

Discover the tranquility of a charming cottage nestled on a 20-acre farm, surrounded by nature with walking trails that end up at the South Branch of the Galien River. Unwind on the patio with a cozy fire pit and enjoy all the amenities you'll need for a perfect getaway. Just 10 minutes away from the beautiful shores of Lake Michigan and only 3 miles from Four Winds Casino. Experience the peaceful countryside retreat—book now!