We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Pet-friendly vacation 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.

0 of 0 items showing

1 of 3 pages

Home in Chesterton

4.8 out of 5 average rating, 259 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. ✌️

Chalet in La Porte

4.93 out of 5 average rating, 381 reviews

Pet friendly, cozy, lakefront home with 3 kayaks!

Looking for a relaxing lake vacation? Our studio home is directly on the water with docks to offer for guest use during warm months. Great fishing spot with included kayaks and seasonal pontoon boat to explore on the lake. Our gas fireplace on the deck provides amazing memories and relaxation. Gas grill, outdoor furniture, clean space to swim between docks, and so on! Wifi, streaming networks, and board games provided in home! Pine Lake Airbnb is the place to be for your next vacation adventure!

Guest suite in Miller

4.96 out of 5 average rating, 338 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)

Home in Michigan City

4.94 out of 5 average rating, 296 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

Home in Chesterton

4.9 out of 5 average rating, 114 reviews

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.

Serviced apartment in Michigan City

4.88 out of 5 average rating, 170 reviews

Perfect 1 Bed Penthouse Steps To Beach w/Parking!

Looking to spend some time away from the chaos of life and stay in a beautifully updated home steps from the beach on Lake Michigan? Welcome to Sheridan Beach in Michigan City! This perfect 1 bed/1 bath penthouse unit is situated within a block of the beach/water. The serenity of the neighborhood and seclusion from the outside world are its most attractive features. Located a little over an hour from Chicago, it's a quick drive to enjoy some R&R. Get ready to make some amazing memories.

Home in Michigan City

4.95 out of 5 average rating, 269 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.

Home in Sawyer

5 out of 5 average rating, 109 reviews

The treehouse at Warren Dunes

Looking for the perfect Harbor Country getaway? We've got you covered! Just 90 miles from Chicago and adjacent to Warren Dunes State Park, this beautifully remodeled home hidden in the trees is the perfect escape. With accommodations up to 6 on four levels of living space, you'll enjoy an indoor/outdoor living experience like no other. Conveniently just 200 yards from the beach with walking path access at the end of the street and easy access to all the activities this area has to offer.

Home in Michigan City

4.92 out of 5 average rating, 225 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!

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.

Guesthouse in Valparaiso

4.98 out of 5 average rating, 132 reviews

Cozy Luxe Downtown Valparaiso Stay

Welcome to “Chalet Valpo”! A historic carriage house located minutes from the heart of Valpo that we have had completely gutted and made new for you! This home is a carriage house, it is located on our personal property. You have complete privacy during your stay in a private fenced in area. Do not hesitate to reach out with any questions. Walkable to downtown Valparaiso! NO CLEANING FEE!

Home in Michigan City

4.98 out of 5 average rating, 262 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 2 night minimum stay.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodations and amenities

Popular amenities for Chesterton pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Home in Michigan City

4.91 out of 5 average rating, 157 reviews

Historic Charmer: Walk to Casino, 2 miles to Beach

Home in Chesterton

4.83 out of 5 average rating, 90 reviews

National Park Nature Lover's Paradise

Home in New Buffalo

4.95 out of 5 average rating, 228 reviews

Anna's Cottage

Home in Three Oaks

4.99 out of 5 average rating, 138 reviews

Dog Friendly Downtown Three Oaks Cottage! Fenced!

Home in New Buffalo

4.81 out of 5 average rating, 383 reviews

Sq Toe's Last Resort:Pet-Friendly*Fenced* GameRoom

Home in Walkerton

4.9 out of 5 average rating, 103 reviews

Lakefront cottage on Koontz Lake

Home in Berrien Springs

4.93 out of 5 average rating, 115 reviews

Entire House in Berrien Springs

Home in Union Pier

4.92 out of 5 average rating, 212 reviews

CASA TICA Serenity Amongst Nature Dog Friendly

Pet-friendly home rentals with a pool

Townhouse in New Buffalo

4.93 out of 5 average rating, 102 reviews

Dunescape Beach Retreat, Downtown New Buffalo

Townhouse in Chesterton

4.76 out of 5 average rating, 29 reviews

South Shore Escape

Home in Chesterton

4.98 out of 5 average rating, 40 reviews

Pool House near the Indiana Dunes

Serviced apartment in New Buffalo

4.9 out of 5 average rating, 21 reviews

Charming 2BR/2BA Cottage with Full Kitchen & Patio

Home in Michigan City

4.89 out of 5 average rating, 37 reviews

The Keystone Ranch…The only house on the block!

Villa in Niles

4.96 out of 5 average rating, 106 reviews

Pool, Hot tub, Kayaks, Waterfront, SW Michigan

Cottage in Union Pier

4.96 out of 5 average rating, 190 reviews

Designer Cottage Relax Beach Pool & Spa—Windjammer

Home in New Buffalo

4.92 out of 5 average rating, 302 reviews

New Buffalo / Farmesque with a splash of modern

Private, pet-friendly home rentals

Home in Michigan City

4.9 out of 5 average rating, 10 reviews

Fenced Yard Patio/Fire pit/8slp/1.7m to Bch/mall

Home in Porter

4.97 out of 5 average rating, 38 reviews

National Park / Lake Michigan Neighbor

Home in Chesterton

4.81 out of 5 average rating, 64 reviews

Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home

Cottage in Sawyer

4.87 out of 5 average rating, 180 reviews

Northwind Llama retreat “Loft Cottage”

Home in Porter

4.87 out of 5 average rating, 77 reviews

New Dunes Escape

Rental unit in La Porte

4.93 out of 5 average rating, 482 reviews

Second Floor Apartment sitting on Pine Lake

Cottage in New Buffalo

4.97 out of 5 average rating, 418 reviews

Twin Cottage B- Walk to Beach & Town!

Home in Valparaiso

4.92 out of 5 average rating, 51 reviews

Wooded Lake Home, 15 min. IN Dunes, 7=DT, 50=CHI.

Quick stats about vacation rentals that are pet-friendly in Chesterton

Total rentals
20 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
1.3K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi

Destinations to explore