Pet-friendly holiday rentals in Montgomery

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Montgomery

Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Top Guest favourite

Apartment in Forest Park

4.99 out of 5 average rating, 348 reviews

Walk to Oak Park from Our Sunny Turn of the Century Apt

Soak up the vintage charm of this apartment dating back to 1908. This newly remodeled space is an elegant retreat, featuring 10-foot ceilings, local art treasures, and plush linens. A relaxing outdoor lounge area awaits after a busy day exploring. Pets are welcome on a case by case basis (contact host). The space is a charming two bedroom, one bathroom first-floor unit in a two unit historic home built in 1908. The apartment combines historic details with modern conveniences such as central heat and air, a dishwasher and washing machine and dryer access. The Monroe House is a stone’s throw from historic Oak Park and just three blocks from the CTA Blue Line making downtown Chicago a 25 minute train ride away. The condo includes additional amenities such as: •Smart TV for watching any account may you have (Netflix, Hulu etc...) •Central Air conditioning •Front and back porches for your enjoyment •Washer and dryer on site Just to the east lies historic Oak Park, and an array of attractions such as: •Brookfield Zoo •Chicago Architecture Foundation •Ernest Hemmingway Museum and Birthplace •Frank Lloyd Wright Home and Studio •Frank Llyod Wright’s Unity Temple •Oak Park Conservatory After taking in the local attractions, Chicago is only a train ride away, and it offers such noteworthy experiences as: •Shedd Aquarium •Architecture River Cruise •Skydeck Chicago •Navy Pier •The Field Museum •John Hancock Observatory •Adler Planetarium •Art Institute of Chicago •The Museum of Science and Industry You will have access to the entire unit and the basement so you can use the washing machine and dryer. We also have a back patio with a chiminea, patio table that seats 6, and a grill/smoker. You are welcome to use the backyard at anytime during your stay. We live in the top unit and are as available as you need. That being said, we very much respect your privacy and will not be checking in with you in person unless you request it. It is located in the Madison district, with acclaimed restaurants, pubs, and unique boutiques. Downtown Chicago is a 25-minute train ride away. The local brewery across the street offers delicious beers and creative meals for the whole family. We have a parking pad located behind our building. You can fit two cars on your side of the parking pad if they are parked in tandem. Some street parking is also available. We are located .4 miles from the CTA Blue Line train - Forest Park Stop. It is about a 6 - 10 minute walk from the flat. You can also take an Uber/Lyft into the city. It is about a 15 - 25 minute ride and it costs between $15 and $25. We are located about one mile from the Metra Station (Union Pacific West) and CTA Green Line - Oak Park Stop. Third bed is a queen sleeper sofa. We provide sheets and blankets for the sleeper sofa. You can smoke in the backyard. An ashtray is provided.

Guest favourite

Condo in Avondale

4.95 out of 5 average rating, 104 reviews

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE!! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops. Free parking on Lawndale Ave.

Guest favourite

Apartment in Joliet

4.95 out of 5 average rating, 203 reviews

*The Belltower Haven*Large*Family Friendly*Wi-Fi

Completely remodeled, spacious floor plan, in prime location. Everything is new. Free Wi-Fi (480Mbps) and private parking for 2 cars. Short walking distance to most anything! Near Chicago, The Rialto Theatre, Shopping Mall, Harrah's Casino, Hollywood Casino, Haley Mansion, Route 66 Raceway, Chicago Speedway, Autobahn Country Club. We have a large comfy King Size bed along with several Queen beds. Note: You must be 21 or older to book. Must provide a photo of your D.L. or State ID upon request.

Guest favourite

Guest suite in Saint Charles

4.86 out of 5 average rating, 138 reviews

Cozy, Comfy, Close to Downtown

Discover serenity in our centrally located guest apartment in our charming St. Charles cottage. The space is pet-friendly with a fenced yard, featuring a spacious kitchen, living room, bath, queen-sized bed, and in-unit laundry. The yard offers views of the Fox River, a peaceful patio, friendly ducks, with award-winning parks & biking trails at your doorstep. Note: The unit is studio style located in the lower level of a home. The space is completely private. Only outdoor spaces shared. 😊🦆🪻🏡

Superhost

Apartment in Austin

4.82 out of 5 average rating, 179 reviews

Reno btrm; Big family escape, W/parking, love pets

This apartment is on the top floor of an owner occupied two flat. It's located in a very quiet, family friendly neighborhood. The skylights bring in a ton of natural light. There is a full kitchen available with pots, pans, flat ware and dishes. I'll supply coffee/tea and snacks! It's a great option for short and long term stays. Dog friendly with an additional fee per animal ($25/day). Laundry available for a small fee. Brand new renovated bathroom with awesome shower. Thanks! Hannah and Emma

Top Guest favourite

Home in Forest Park

4.98 out of 5 average rating, 108 reviews

NEW Gather in spacious 3 bedroom 2 bath home

CA relief: if IL is an option for temporarary housing, please reach out! I have 4 properties I will do whatever I can. Introducing Mohr Cottage in the heart of Forest Park. Spacious & recently updated 3 bedroom 2 full bath 2 story home is perfect for families or large groups looking space & comfort. Quiet residential neighborhood, blocks from restaurants, shops, coffee. Dogs welcome. Near public transportation, easy access to expressway to downtown Chicago. STRICT Non-smoking property.

Superhost

Home in Naperville

4.85 out of 5 average rating, 120 reviews

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!

Guest favourite

Home in Elmhurst

4.94 out of 5 average rating, 16 reviews

Stylish Elmhurst Ranch Home Pet-friendly Oasis

Welcome to our charming 3-bedroom ranch-style home, ideally located just 3 minutes from Elmhurst’s vibrant downtown. This cozy retreat offers easy access to a variety of shops, restaurants, and entertainment options, making it perfect for your stay. Our home features three comfortable bedrooms, each thoughtfully decorated to ensure a restful night's sleep. The open-concept living and dining area is perfect for relaxing and enjoying quality time with family and friends.

Guest favourite

Home in Elmhurst

4.96 out of 5 average rating, 110 reviews

Elmhurst NEW - Super Clean Modern Farmhouse!

Not your average Air BNB!!! 🏡 Newly renovated - CLEAN modern farmhouse in a great location! ✨ ✅Pet Friendly! 🐕 ✅15 min from O'hare. ✈ ✅25 min to Downtown Chicago 🏦 ✅Close to Grocery, restaurants, coffee, shopping, golf, expressways, down town Elmhurst ,Train and Oakbrook and Fashion Outlet Mall. ✅3 great sized bedrooms, 2 living area sofas converts into sleepers ✅Smart TV in family room and Master. ✅ Back patio with dining and seating ✅Large fenced in yard.

Guest favourite

Guest suite in Portage Park

4.94 out of 5 average rating, 157 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

Private entrance apartment on the 2nd floor of this historic bungalow. Free street parking! Medicinal & recreational smokers permitted... outdoor ONLY. This comfortably cozy quiet get-away is nestled in NW Portage Park in a family neighborhood. Dog and kids park nearby. Fenced yard for Fido. Backyard patio w/ BBQ grill. High-speed internet. Front porch swing Easy access to buses & Jefferson Park Transit train station to Downtown & Museum Campus NO PARTIES

Top Guest favourite

Condo in Logan Square

4.91 out of 5 average rating, 340 reviews

Susie's Space. 2BR easy parking & pet friendly

Sunny and spacious, 2 bedroom apartment in Avondale near the Green Exchange/ Greenhouse Loft Flexible, self check-in Easy street parking (with provided permits) Pet fee $80 per pet Bedroom 1 with a king sized bed Bedroom 2 with a full bed Air conditioning and ceiling fans Soft linens and towels Separate dining room Fully equipped kitchen Free WIFI Smart TV for streaming Garden in back with a fire pit and charcoal grill Laundry room in basement

Superhost

Apartment in Oak Park

4.75 out of 5 average rating, 151 reviews

1BR Apartment - Walk to Shops - Downtown OAK PARK

Your family will be close to everything when you stay at this centrally-located place. - 4 min drive to the train - 2 min drive to grocery stores & shopping - 20 min drive to Downtown Chicago Enjoy the historic neighborhood and see Frank Lloyd architecture nearby. ➢ Everything is sanitized/washed/cleaned after every guest ➢ Fast, Dedicated Wifi ➢ 2 Smart TVs (Living Room, Bedroom) ➢ Fully equipped + stocked kitchen / bathroom ➢ Pack 'n Play