Pet-friendly holiday rentals in Chesterton

Find and book unique pet-friendly homes on Airbnb

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 favourite

Home in Michigan City

4.91 out of 5 average rating, 138 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!

21–28 Mar

$224 SGD per night

Guest favourite

Guest suite in Gary

4.95 out of 5 average rating, 286 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)

23 Feb – 2 Mar

$259 SGD per night

Guest favourite

Home in Michigan City

4.98 out of 5 average rating, 230 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 the week prior if we have a couple open days.

3–10 Sep

$261 SGD per night

Guest favourite

Flat in La Porte

4.93 out of 5 average rating, 452 reviews

Second Floor Apartment sitting on Pine Lake

My Airbnb is close to parks, restaurant and Sand Dunes. The apartment is in the house on beautiful Pine lake. Please note that the balcony in the picture is not part of the apartment. the pictures are to show the patio of which you have full access. Pets are welcome but there is a $15 charge per pet per night. The fee should be made in advance through the send money. We live in a area that pets must be walked to do bathroom duties. They are NOT allowed on my grass or in flower beds.

27 Jan – 3 Feb

$219 SGD per night

Guest favourite

Home in Michigan City

4.95 out of 5 average rating, 248 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.

29 Jan – 5 Feb

$636 SGD per night

Guest favourite

Home in Chesterton

4.86 out of 5 average rating, 148 reviews

Sweet Home in Chesterton

This home is nestled in a private wooded corner of Coffee Creek and rests in the heart of a bustling downtown. Stroll a block to shops, restaurants, bars, winery, DIY art studio, European market, and see one of the many trains gliding on the close-by tracks. Enjoy the many amenities: Roku TV, WIFI, printer, loaded kitchen, 4 miles to Indiana Dunes beaches, National Park, Outlet Mall, Valparaiso University, Albanese candy, casino or train/drive 50 miles to Notre Dame & Chicago.

11–18 May

$201 SGD per night

Guest favourite

Cabin in Michiana

4.97 out of 5 average rating, 112 reviews

Steps to the beach at luxury cabin 1hr to Chicago

Book an escape to our designer log cabin on Lake Michigan! Just steps from the beach and nestled in a peaceful forest, it's the perfect retreat one hour from Chicago. Built in 1932, our charming cabin sleeps 8 guests in 4 bedrooms. Enjoy 2 living areas, a stone fireplace, fire pit with games, puzzles & books. Featured in Country Living and the New York Times, it's perfect for families, friends, or solo retreats. Book now and create lasting memories in this hidden gem!

6–13 Apr

$198 SGD per night

Guest favourite

Home in Michigan City

4.96 out of 5 average rating, 108 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

27 Sep – 4 Oct

$217 SGD per night

Guest favourite

Guest house in Sawyer

4.92 out of 5 average rating, 151 reviews

Heron's Rest hideaway close to beaches, breweries

Privacy on 11 acres of conservancy-protected land including woods, two ponds, and a river. Minutes from Michigan’s most popular beach, breweries, wineries, antique malls, farm-to-table restaurants. Fully equipped kitchen, gas fireplace. Private fire pit, deck, and gas grill. Fish on site. Kayak, bike, hike nearby. Ideal for nature lovers. Separated from our home by breezeway. Private entrance, quiet road, dark nights. Daytime woodworking noise possible.

29 May – 5 Jun

$158 SGD per night

Guest favourite

Guest house in Valparaiso

4.95 out of 5 average rating, 371 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.

25 Sep – 2 Oct

$167 SGD per night

Guest favourite

Home in Chesterton

4.98 out of 5 average rating, 126 reviews

Hotel Whiskey

Fully remodeled and tastefully decorated two bedroom home for short or long term stays. Office space for work travelers. Pet friendly with secure fenced in back yard. Walking distance from downtown with quaint shops, wine bar, craft beer bar, restaurants and bike trails. Whether you're in town for work, visiting family or just looking for a weekend getaway, this house and location are perfect for short or long term stays.

5–12 Feb

$243 SGD per night

Guest favourite

Guest house in New Buffalo

4.99 out of 5 average rating, 273 reviews

Rainbows End 🌈 Bourgeois

Escape to a pet-friendly cottage in the Midwest. Nestled amidst scenic trails, with access to the South Branch of Galien River. Relax in the whirlpool tub, explore nature, and create cherished memories. Fully equipped kitchen, washer/dryer, and inviting ambiance. 10 mins from Lake Michigan, 3 miles from Fourwinds Casino. Experience rural bliss in this delightful cottage.

3–10 Oct

$205 SGD per night