
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.
Vacation rentals for every style
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Popular amenities for Chesterton pet-friendly home rentals
Pet-friendly house rentals

South Shore Studio Apartment {National Park}
Rob was a great host & I really enjoyed my stay! The house is 5 mins from the lake & super peaceful. Robs dogs were super cute!! Would stay again if I get the chance :)

Sparkle ART House - 8 min drive to beach!
What a unique and great place to stay! The time, creativity, and love put into this art project is amazing! I would highly recommend the Sparkle House for anyone traveling in the area. Put it on your to-see list. You will not be disappointed!

Shamrock Cottage Cozy 3 bedrooms & 2 full baths
Overall great experience. The home was very clean and comfortable. Communication was great from start to finish. I would recommend and would definitely stay here again.

Renovated cozy home, short walk to Notre Dame
Peter was a great host, very responsive to all questions we had. Everything was as advertised.

Spacious Superior: The perfect relaxation getaway!
Great house and even better host. Would definitely stay again

Pet Friendly Perfect Spring Getaway with Hot Tub!
Great place and as the description suggests, it’s pup friendly! We lacked nothing during our time there and would highly recommend.

Cozy House near Beach, Casino, Outlets, & Hiking
Cozy place, friendly hosts, great communication, exactly as described.

Relax And Enjoy This Cozy Renovated Hidden Gem
Wonderful stay! Very helpful and friendly hosts. The home was clean and comfortable! Great location
Pet-friendly home rentals with a pool

Dunescape Beach Retreat, Downtown New Buffalo
Had a wonderful stay at the Townehouse in New Buffalo. Beautiful home. Loved all the outdoor patios and enclosed seating area. Spacious rooms and fully stocked bedding and linens. Perfect location right downtown. Walking distance to beach and shops and restaurants. Couldn’t ask for a better spot. Mark was very friendly and accommodating. Can’t wait to go back.

Lakeside heated pool opens May 21st! PVT beach too
Nice location, train honestly wasn’t that big of a deal as only head twice a day. Easy to find and had everything we needed.

Pool House near the Indiana Dunes
We had a great stay!! The house was perfect for the five of us and our dog, with enough space for all of us to feel comfortable. The bathrooms were clean and the kitchen was well stocked. The pool was the best part! Melissa was super prompt when it seemed like the heat to the pool wasn’t running and we were back in there in no time - the heated water was perfect for this fall weather! We also tried some of the recommended spots and overall, this was exactly the quick getaway we needed!

Pool|Games | Fire Pit | Hot Tub | Dog Friendly
I highly recommend staying at Kerilyn's farm house. My wife, a few friends and myself come to Baroda every year for my birthday to do the wine trail. This was our first time staying at Kerilyn's but definitely not the last. The home is beautiful, accommodating and located near some of the finest wineries in the area. The hot tub was fabulous and I couldn't ask for a better way to end the evening. Kerilyn was friendly, attentive and fast to respond. We're looking forward to our next visit. Thank you, Kerilyn!

Dog Friendly, hot tub, deck, play set, screened po
The house was clean, comfortable and as described in the listing. I wouldn’t hesitate to book the property again. The heated pool and hot tub were great for our group to relax.

Pool, Hot tub, Kayaks, Waterfront, SW Michigan
We met here with college friends and their families and had a wonderful time. There is a wide variety of books, games, and activities; we really didn’t need to bring our own! The hosts were very responsive and even drove out with trash bags when we messaged that we couldn’t find any. Highly recommend!

Designer Cottage Relax Beach Pool & Spa—Windjammer
Birthday brownies upon arrival! Great quiet location but very convenient for local shops and restaurants. Can walk to the beach! Can’t wait for the opportunity to visit again

Perfect Get Away - Private Hot Tub - Lots of Room
We loved staying in this adorable lake house in New Buffalo! It's a perfect location and is within walking distance of many restaurants, coffee shops, and the beach! This house was ideal for a large group and housed 10 adults and 3 children comfortably. I would definitely recommend staying here if you're planning on coming to New Buffalo!
Private, pet-friendly home rentals

Rainbows End 🌈 Plensa
My stay was everything I hoped it would be. I was looking for a peaceful getaway and found it here. The cottage is adorable and there are windows everywhere - there was nothing better than waking up surrounded by the beauty of the outdoors "right there." Bed was comfy, shower and hot water were perfect and the kitchen had everything I needed. Dennis was the perfect host. Friendly, responsive and respectful of my privacy. The property is perfect for quiet walks (my dog loved it) and there's a path along the fields out to woods and a beautiful river. Three Oaks is 15 minutes away for wandering and cute shops, and New Buffalo is 20 minutes away with the beach and fun restaurants. I'm looking forward to coming back!

Cozy "DOG friendly" cottage
This was the perfect little house and being dog friendly was a huge bonus! All the amenities to feel right at home were provided. Also, Kerri is an amazing host. She checked in with us periodically to make sure we had all we needed. I would definitely stay here again.

Steps to the beach at luxury cabin 1hr to Chicago
This is a beautiful house and Amanda has everything ready before our arrival. The house is clean and I just love the ecstatic. We have a lovely girl's night and would love to come back maybe a warmer summer time to check out the beach and outside. We were a little bit confused about the light switches though even Amanda already labeled everything.

Red Barn Lodge
We had a fantastic stay! The space was clean, spacious, and well-equipped with thoughtful extras that made traveling even easier. The host was incredibly friendly and communicative, ensuring we had everything we needed. One of the highlights was the fenced-in yard, which was perfect for our dog. We truly appreciated all the little details that made this stay comfortable and enjoyable. Highly recommend!

Log Cabin - Private - Pets Welcome
Cute log cabin, a bit rustic, but it added to the charm. Portia was very responsive to questions & helpful.

Cozy Luxe Downtown Valparaiso Stay
My partner and I had such a lovely stay! The home was beautiful and gave off such a calming atmosphere. Check in was very simple and we felt right as home as soon as we entered! Kelly and George were also very communicative, friendly, and quick to respond. We will definitely be back!!

Relaxation in the country close to everything
Great place to stay for ND Football games, we'l be back next year!

Warren Dunes State Park is Backyard- Hot Tub-WBFPL
Fantastic location right on a dunes trail! Super awesome
Quick stats about vacation rentals that are pet-friendly in Chesterton
Total rentals
20 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
1.4K 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
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- Millennium Park
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