Pet-friendly vacation rentals in Montgomery

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Montgomery pet-friendly home rentals

Pet-friendly house rentals

Guest favorite
Home in North Park
4.96 out of 5 average rating, 169 reviews

Chicago River House -BBQ Oasis now open!

LuaRating, 5 stars1 week ago
We had our mini wedding at this home and it was perfect for us! Everything was great and the host was very communicative and understanding.
Guest favorite
Home in Naperville
4.87 out of 5 average rating, 130 reviews

Home away from home

JordanRating, 5 stars1 month ago
We couldn’t have asked for a better home for our Spring Break. We last minute booked this home, and checked in 45 later but you would have never known by how welcoming Vytauta made it. Beds were very comfortable, backyard was great, we felt right at home.
Top guest favorite
Home in DeKalb
4.94 out of 5 average rating, 271 reviews

Cozy home in front of the park and close to NIU

CristiRating, 5 stars2 months ago
The house was perfect for what we needed for a quick weekend visit.
Guest favorite
Home in Naperville
4.89 out of 5 average rating, 125 reviews

California King Bed | Fast Wi-Fi | 75" Smart TV

NathanRating, 5 stars3 weeks ago
It was a comfortable stay. Tons to do in the area. Can’t go wrong!
Superhost
Home in Bolingbrook
4.92 out of 5 average rating, 130 reviews

The Sunshine Spot

SavahannahRating, 5 stars3 weeks ago
We stayed for a week. The house was spacious and clean, and the neighborhood felt very safe. It was close to the mall and any store you'd ever need. Richard was very responsive and helpful! Washer & dryer were great to have for a longer stay. Wifi and smart tv were great. Also was glad there was even a lead in the backyard for our dog!
Top guest favorite
Home in Chicago Ridge
4.92 out of 5 average rating, 126 reviews

Quiet cul-de-sac with huge fenced in backyard

CandaceRating, 5 stars1 week ago
Tom’s place felt right at home! Spacious backyard, quiet neighborhood, and he’s very friendly. Responded right away with any questions or comments we had! 10/10 recommend anyone to stay here if available!
Top guest favorite
Home in Ottawa
4.98 out of 5 average rating, 186 reviews

Starved Rock - Fun Escape 2- Game Rooms-Art Studio

KammieRating, 5 stars5 days ago
We had an absolutely wonderful stay here. There was so much to do and this was the perfect meeting place for three couples from different states to have a reunion! We had two small children, ages 4 and 6 and there was so much for them to do. Theresa was so thoughtful in the details for this place. From the art studio to the snacks to coffee, we felt right at home! Thank you for a wonderful stay, we can’t wait to come back!!
Superhost
Home in Wood Dale
4.76 out of 5 average rating, 160 reviews

Excellent Location for Vacation or Business Stays.

JamesRating, 5 stars3 months ago
This was our second stay at Rita’s and we found it very accommodating and great of an experience as our last visit. The neighborhood is in a great location and it is cozy and quiet. The property was extremely clean. We would be happy with staying here again in the future.

Pet-friendly home rentals with a pool

Superhost
Home in Ottawa
5 out of 5 average rating, 13 reviews

Harbor Inn - Bow Wow on The River

JaclynRating, 5 stars6 months ago
Beautiful views, great layout, and extremely dog friendly with nice touches make this place stand out! Very close to all the state parks in the area, but there’s plenty to do on site as well. Check in was seamless, we had clear instructions throughout, and the place was perfect!
Guest favorite
Home in Ottawa
4.94 out of 5 average rating, 66 reviews

Ottawa Oasis. Billiards. Pool. King Bed!

BobRating, 5 stars1 week ago
It was a great stay for me and my son and his wife and my two grandsons. The boys loved all the games and us adults really liked the pool table. Didn't get to enjoy the pool while we were there cause it was too early in the season, but all in all a really nice place to relax. It's got everything you need there minus the food of course.Give it a shot you won't be disappointed.
Apartment in Logan Square
4.7 out of 5 average rating, 118 reviews

Play in the Windy City and rest by the “606”

RichardRating, 5 stars3 months ago
This airbnb would be good for 2 couplesnorna family of 4. The kitchen is verynfuntional, and the living space is open and quite large. Check in/out instructions are clear. Beau was very responsive.
Home in Schaumburg
4.78 out of 5 average rating, 9 reviews

Spacious 3 Floor Townhome

AndresRating, 5 stars5 days ago
My spouse and I couldn't of had a better weekend without Alex's listing! Everything was as Alex had described it in the post. It was close to restaurants, grocery stores and entertainment needs. Alex made it easy check in and check out. We would definitely recommend this place to any couple or small family.
Apartment in Des Plaines
4.86 out of 5 average rating, 44 reviews

Comfortable/Free Parking/Close to O'Hare & Chicago

CalebRating, 5 stars2 weeks ago
Tysha's place was perfect and had everything I needed for a great stay! I will definitely be booking again when I'm in the area!
Home in Ottawa
4.62 out of 5 average rating, 13 reviews

Casa Azul

KarlaRating, 5 stars6 months ago
We really enjoyed our stay. The house is in a quiet, pet friendly neighborhood with lovely views of the river. Everything we needed was provided and we liked the layout of the house. Regarding sleeping accommodations, there are beds for 6 people (2 queens with twin bunks above each) and additional sleeping options are provided via a pull-out sofa and 2 futons.
Place to stay in River Forest
5 out of 5 average rating, 12 reviews

Long term rental-Delightful one bdrm pool house

JenniferRating, 5 stars31 months ago
Definitely a great stay! October 1st and we were swimming! Decor is amazing! Tv was easy to figure out and had lots of options. We had a busy day before and after our stay so we used Michael’s pool house as a relaxing stay in between and it was perfect
Superhost
Apartment in Logan Square
4.8 out of 5 average rating, 65 reviews

Cozy Family 3BR Oasis: Park, Private Yard, & BBQ!

JosephRating, 5 stars1 month ago
This place is a great location for almost anything one would like to do in Chicago. Close to train lines, plenty of surrounding restaurants and grocery stores, and parking was a breeze. Also Kevin was a wonderful host and this apartment was exactly what I needed for the stay.

Private, pet-friendly home rentals

Guest favorite
Guest suite in Portage Park
4.93 out of 5 average rating, 413 reviews

Peaceful Portage Park Apartment

JenniferRating, 5 stars1 week ago
Beautiful place to stay. Beautiful decor. Host very friendly and responsive. We had a baby with us and she had lots of baby items for us. We had street parking in front of home. 🏡
Top guest favorite
Home in Elgin
5 out of 5 average rating, 22 reviews

Little Blue House

BriannaRating, 5 stars4 months ago
Alex is a great host! Dog friendly places are hard to find and his place made my dog feel super comfortable. Love this place and definitely will be back.
Top guest favorite
Home in DeKalb
5 out of 5 average rating, 34 reviews

Duplex in Dekalb, IL

JeremyRating, 5 stars2 weeks ago
Awesome location, easy to get to and quiet family neighborhood.
Top guest favorite
Apartment in Logan Square
4.98 out of 5 average rating, 131 reviews

Newly-renovated historic home in Logan Square

NatalieRating, 5 stars5 days ago
Such a beautiful home walkable to some of the best restaurants and bars in Chicago, highly highly recommend staying here! We brought our 1 year old and it was the perfect home for us to feel at home.
Guest favorite
Tiny home in Burr Ridge
4.9 out of 5 average rating, 367 reviews

Less is more! Pet friendly Tiny Home near Chicago!

EmilyRating, 5 stars3 days ago
Very cute tiny home. Had a lot of amenities including full bathroom, refrigerator/freezer, washer/dryer, and oven/stove which I haven’t seen in other tiny homes. Would recommend.
Guest favorite
Apartment in Marseilles
4.86 out of 5 average rating, 285 reviews

Dog Approved Country Suite

GusRating, 5 stars3 weeks ago
Lisa's place was nice very comfortable would definitely stay there again
Guest favorite
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 337 reviews

a SIMPLE place

KaitlinRating, 5 stars1 week ago
This is the 2nd time I've stayed here, and it is always exactly what I need. The space is great, the neighborhood is safe, and there's a Lou Malnatis and Portillos within a 15 min drive. Will definitely stay again!
Superhost
Home in Wood Dale
5 out of 5 average rating, 5 reviews

Home in the Woods!

DevynRating, 5 stars5 days ago
We stayed here for my Bachelor Party. It was a golf trip, so having the Preserve at Oak Meadows right next door was great. Jazmin was responsive when we had a small issue with the code to get in. All-in-all a great place!

Destinations to explore