Holiday rentals in Montgomery

Guest suite in Saint Charles

4.85 out of 5 average rating, 137 reviews

Cozy, Comfy, Close to Downtown

CarolRating, 5 stars3 days ago

I needed a place to recuperate from sinus surgery, peaceful, comfortable and pet friendly. My husband and I could prepare meals, go for walks or bike along the River. There are ducks in the back yard that are cute and like veggies. Our hosts made us feel very welcome. I would go back again without a second thought. The area is safe and friendly with lovely old homes. Downtown is easy to get to and Geneva is nearby with many enchanting shops and restaurants. Many located in old homes. They is also laundry access in the apartment which is very handy since we were there about a week and a half.

4.94 out of 5 average rating, 177 reviews

Flat in West Lake View

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

DianeRating, 5 starstoday

Sam’s place was beautiful! We felt right at home. The furniture was comfortable and the kitchen had everything we needed. The location was great. We got a free parking spot right outside of the door. Super convenient. We brought our dogs and it was perfect for them. Lots of places to walk and lots of things to do. It was just a short walk to the train. Sam was very easy to get ahold of and was a great host. I definitely recommend and we will be staying here again.

4.9 out of 5 average rating, 105 reviews

Guest house in Oswego

The Loft-Rustic Retreat and Sauna

TaraRating, 5 stars1 month ago

Sara’s place was exactly as described! It was clean and comfortable- very private. The sauna was such a nice luxury! We appreciated all of the little niceties - like coffee , candles, and beach towels for the sauna. It was near everything, but still on a quiet street. Sara was very responsive and friendly. She had great suggestions for breakfast and really made us feel at home. We’d definitely go back!

4.91 out of 5 average rating, 123 reviews

Home in Homewood

Peaceful & Private Hot Tub Vacation Home Getaway

YoshiRating, 5 stars1 month ago

This small quaint home packs a HUGE punch when it comes to amenities and that home away from home feel. We couldn't have asked for more in an airbnb during our stay in the Chicago area. From the kuerig, to the decor, to the hot tub to the amazing bathroom and shower, this Airbnb had everything we needed and everything we didn't even know we wanted. I would HIGHLY recommend this airbnb along with the amazing and attentive hosts to anyone traveling through the area.

5 out of 5 average rating, 11 reviews

Home in Avondale

Alluring Avondale Abode

MichaelRating, 5 stars2 weeks ago

Beth’s home was perfect for our group trip, which centered around cooking together for a Passover Seder! The kitchen had great appliances and equipment, with the space for many of us to cook at once. The house had everything we needed and we were all comfortable.

Guest suite in Naperville

4.95 out of 5 average rating, 414 reviews

Cozy Lakeview Studio with Private Access

YuRating, 5 stars4 days ago

Thank you so much for the wonderful stay! I was so glad to have chosen your place! Also, it was wonderful meeting you all! I had a nice time chatting with you! I hope to be back with my husband next! Happy Spring! Thanks, again!

4.95 out of 5 average rating, 104 reviews

Guest house in Oak Park

O'Malley Oasis!

AndreaRating, 5 stars3 months ago

Clean, beautiful space. Has everything needed and the most comfortable seating space to relax. Clear instructions, easy parking. Be aware that there are several stairs to enter as seen in the pictures. They are well maintained with a handrail. This was not an issue at all for us but could be for someone with mobility limitations. Otherwise one of the best places I have stayed in Oak Park. Hope it is available when I come back.

4.96 out of 5 average rating, 280 reviews

Flat in Irving Park

Spacious 1BR apartment in a central location

GilRating, 5 stars1 month ago

I have stayed in a number of AirBnB‘s throughout the years, this may have been my favorite stay. There is absolutely everything you would need for a comfortable stay. Everything is clean. Alex is a five-star communicator. It is a busy little neighborhood, but the bedroom is toward the back of the apartment. I heard nothing but dead silence at night.

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Popular amenities for Montgomery holiday rentals

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Free parking on premises

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Stay near Montgomery's top sights

Meijer5 locals recommend

GQT Kendall 11 GDX4 locals recommend

Fox Bend Golf Course3 locals recommend

Other great holiday rentals in Montgomery

4.92 out of 5 average rating, 39 reviews

Home in West Lawn

Family Friendly Duplex/9 min from MDW/Free Parking

JoannaRating, 5 stars2 weeks ago

Came for c2e2 with my friends and it was perfect for all of us! Would recommend 💗💗

Guest suite in Plainfield

4.86 out of 5 average rating, 78 reviews

Relaxing Suite with Independent Entrance

CindyRating, 5 stars1 week ago

Maria’s place was great! Easy access to the Airbnb & the yard was a bonus for our two dogs. Lots of little touches that made the stay pleasant; coffee, water, snacks were all appreciated. The bed was very comfortable too! I would definitely stay again when in the area.

4.86 out of 5 average rating, 42 reviews

Flat in Albany Park

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars2 months ago

Wonderful stay as always, thank you so much!

4.63 out of 5 average rating, 24 reviews

Flat in Jefferson Park

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars1 month ago

Peaceful, felt like home, very spacious and comfortable

5 out of 5 average rating, 22 reviews

Home in Elgin

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.