
Pet-friendly holiday rentals in Montgomery
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Top-rated pet-friendly home rentals in Montgomery
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Popular amenities for Montgomery pet-friendly home rentals
Pet-friendly house rentals

Chicago River House -BBQ Oasis now open!
Even more spacious than in the photos! Well-kept place, with a fully stocked kitchen, projector, BOSE speaker, and great backyard. Double shower in the master bedroom, and strong water pressure. Entry is easy with a code. Finally, the host is VERY accommodating, flexible, and responsive. Recommended!

Bliss in Batavia near the Fox River
The house had a lot of space for our five adults and two little children, so we could give the kids space to play and sleep without being disturbed. The location was close to downtown and easy to get to. Mark was easy to communicate with and very responsive. Would stay here again.

Home away from home
Your place was perfect for my needs. It was larger than necessary for just myself but the location was perfect. My son attends BenU and I loved that I could meet up with him in minutes. Lisle and Naperville are great communities. The house was very well equipped and the yard was perfect. If you are going to have the full 6 people staying there is only one bathroom. Not a problem but if you come with a larger group I just wanted to note that as it is sometimes important. I highly recommend this place and I hope to use it again next year when my son graduates from BenU. Thanks for a great place and stay.

Perfect little paradise
My wife and I and our two dogs visit the area every year for the Chicago Drum Show and Kathleen’s home was great for the location to the fairgrounds, restaurants in Geneva. The home was very clean and had everything we needed for a long weekend. For anyone bringing pets, this is a very pet friendly listing but the access to the yard is outside of the home. This would have been a big consideration of ours prior to booking and was only made aware of the outside situation until we got the welcome info.

Little Blue House
We enjoyed our stay. Very quiet for the location. Very clean and well kept house. The Shop next door was relatively quiet, did spook our pup a couple times while being outside. Didn’t bother me or my wife and dog at all while inside the house. We will gladly stay again at this location. Thank you again alex, you are a great host!

Retro Modern Bungalow | fire pit | free parking
This exquisite MCM GEM in Berwyn was the perfect home base for us while visiting Chicago. Every corner is curated with unique and authentic MCM touches, all with the contemporary creature comforts one could want and then some. Everything was sparkling clean and April was a superb host. We hope to come again, & highly recommend!!

Chic Cottage close to Metra large enclosed yard.
The house was great for what we needed. Small house in a very quiet and neat neighborhood. Thanks for allowing us to stay.

Basement Suite
Blesson was a pleasure to meet. He was very easy to talk to and accommodating for us. The unit itself was very clean. Staying in the basement suite was not a problem. Basically it felt like an in-law apartment. The neighborhood is very nice. We have family that lives there and I am very familiar with it. It is very appealing and very safe. We were comfortable with our stay. We would stay there again if our situation needed.
Pet-friendly home rentals with a pool

2-Acre Highland Park Retreat with Heated Pool ~ 5*
We had a great stay overall. From start to finish, Kailash was extremely helpful, friendly and responsive. We needed a long-term stay with 2 big dogs, and this house worked great for us. We didn't get to use the pool much because the weather didn't cooperate, but the pool and patio area are gorgeous. The location is great, close to everything - grocery stores, restaurants, etc. There is a trail behind the house (accessible through a gate in the back yard), and it leads to a beautiful and huge forest preserve - beautiful for walks/hikes in the woods! The kitchen was a great space for us, and it had everything we might need for cooking, etc. The house was very comfortable for our family, and we would come again. Thank you, Kailash!

Ottawa Oasis. Billiards. Pool. King Bed!
Great place for multiples families with kids. The layout was perfect. Kids were happy, and parents were able to relax.

Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool
Stayed here for my girls trip and it was a super convenient location! It was our first time visiting Chicago, and it was perfect. Had the most beautiful view we loved the private patio. Beds were all comfy and the hosts were extremely communicative the entire stay. Would definitely stay again!

Harbor Inn - Zuzu's Petals
Richard's place was great and as described. We will stay there again when in the area.

South Loop | Rooftop With In & Out Parking | 1
Elegant furnishings & easy check-in & check-out. Good neighbour hood

Luxury 3 Bed w/ Gym, Pool, Parking, Game Rm & More
We had a great stay! The place was exactly as shown in the listing—clean, comfortable, and well-equipped. We had some minor issues with the digital locks, but the host was always very quick and helpful in resolving them. Overall, a very positive experience and we’d definitely recommend it!

In Ground Pool, Full Ranch Home
Great place and easy to work with.

Penthouse near Fulton Market: 3BR Luxury
The view alone is very much worth the price
Private, pet-friendly home rentals

Your Unique Stay by the Tracks | LCP Collection
We definitely enjoyed our stay. The house beautiful and lots of room! Even though it’s right next to train track we literally only heard the train one time it’s a very quiet and beautiful home inside and out. There is also a beautiful walking trail very close by the water. The beds are absolutely so comfortable! We would definitely choose to stay here again if we are in the area!!!! Thank you so much !!!!

Waterfront dog friendly 3 bedroom home w/game room
Great vacation with our dogs. Couldn’t be any more dog friendly and pretty human friendly too. Great place to relax and reset. We really enjoyed being in the treetops with all of the wild life. Can’t wait to come back in the summer to float down the river. Book today, you will not be sorry.

Charming Guest House on Farm
We had an EXCELLENT time at Marianne's home in Batavia. The home was outfitted with everything that we required and then some. The place is even bigger than it appeared in the listings. There were sectional sofas both upstairs and in the basement that we didn't recall from the listing that provided even more sitting room with family. The property is so beautiful. We had such a wonderful time watching the horses play in the pastures directly out the window. Can't recommend these hosts or their property enough! Thanks again for a wonderful home away from home this holiday season.

Game Room | Exercise Area | Firepit | Sanitized
★★★★★ We had an absolutely phenomenal stay at Nayeli’s townhouse in Hoffman Estates, and I can’t recommend it highly enough! From the moment we booked, Nayeli’s communication was top-notch—warm, welcoming, and incredibly detailed. The pre-arrival message with clear instructions for check-in, parking, and amenities made everything seamless and stress-free. The townhouse itself is a gem—spotlessly clean, stylishly decorated, and equipped with everything you could possibly need. The newly remodeled bathroom in the bedroom hallway was a delightful surprise, with modern fixtures and a fresh, spa-like feel. The master bathroom was equally impressive, and the entire home felt cozy yet spacious. The beds were super comfortable, and the futons in the basement were a great bonus for our group, ensuring everyone had a cozy spot to sleep. One of the best experiences with Airbnb I had! Thank you for the unforgettable Stay!

Full Kitchen, Near Hwy, Parking Nearby, Work Desk
Gus was extremely helpful and the place was beautiful! I would definitely stay here again!

Duplex in Dekalb, IL
Exactly as described. The home was easy to find, great instructions for checking in, and very clean.

Cozy Tiny Home, LG Fenced yard add RV Brisbon/ 80
We stayed for 6 weeks for work. Fenced in yard worked out great for our pup!

River Retreat- Studio C
We really loved Dawns cozy place along the river. Fairly priced little haven with some comforts of home. Thanks again Dawn and will see you again : )
Destinations to explore
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- Matthiessen State Park
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Wicker Park
- Willis Tower
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center
- Medinah Country Club