Holiday houses in Montgomery

4.93 out of 5 average rating, 42 reviews

Home in Aurora

Spacious family friendly home away from home

This spacious suburban home offers 2 bedrooms with 2.5 bathrooms and a loft with a dedicated workspace. Front living room also has a sleeper couch. There is a full kitchen for your daily meals. The property can host up to 8 people, making it a great option for families. Ample parking space with a 2 car garage. Bring the whole family to this great place with lots of room for fun; additionally there is park close by for the kids. Close to shopping options, outlet malls, restaurants and casino.

4.99 out of 5 average rating, 659 reviews

Guest suite in Geneva

A Suite within a Cozy cottage in Geneva Illinois.

Cozy private suite in the lower level. Guests have the suite to themselves. The bathroom is adjacent to the room and is private. There is a small fridge, a coffee maker, and a microwave oven. We are in Geneva, Illinois. We are LGBTQ+friendly. Our space is ideal for shorter stays and visitors on the go . Not suitable for staycations. Quiet area. Hosts live on the upper level and guests pass through our space to get to the suite. In a bind we can accommodate a 3rd guest and a pet. Welcome.

4.87 out of 5 average rating, 140 reviews

Home in Montgomery

Nice, Private Ranch Home

Nice private ranch home in a quiet neighborhood. Fox River and the river bike trail are only 3 minutes away, Rush Copley Medical Center, lots of shopping and dining options within minutes, Phillips park zoo, and water park very close, major roadways to Chicago. 10 min, from downtown Aurora where you can find the Hollywood Casino, Paramount theatre, many shopping stores and you can enjoy a walk along the Fox river, Fox valley mall and the Chicago premium outlets mall are only 20min away.

4.99 out of 5 average rating, 155 reviews

Apartment in Aurora

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

4.79 out of 5 average rating, 14 reviews

Apartment in Aurora

Aurora Gem: Cozy Studio, near Downtown Aurora

Experience the best of both worlds in our cozy studio apartment – hotel-like comfort meets a fully-equipped kitchen. Ideal for two guests and perfect for extended stays, our pet-friendly policies are detailed in our rules. The kitchen is fully stocked for your culinary adventures, and the building features a shared laundry room with coin-operated machines. We offer free Wi-Fi and complimentary parking for one vehicle. Conveniently located on the peaceful 2nd floor for a tranquil stay.

4.9 out of 5 average rating, 127 reviews

Home in Oswego

Cozy 4-bedroom ranch - minutes from everything

Relax and have fun with the whole family at this peaceful place to stay. It is located within walking distance from US Route 34 in the middle of shopping centers such as Meijer, Jewels, Target, Walmart, great restaurants, bars, entertainment, hair and nail salons, gas stations, etc. There are 5 beds (1 king and 4 queens plus a queen-size air mattress and a twin pull-out bed) and 3 couches waiting for their guests. The house is cleaned and sanitized before every reservation.

4.71 out of 5 average rating, 7 reviews

Home in Aurora

Showstopper: 5BR+, 3.5BA

Welcome to your home away from home! This expansive 5-bedroom, 3.5-bathroom home in Aurora, IL offers over 4,600 sq. ft. of living space, making it the ideal getaway for families, groups, or sports teams visiting the area. Enjoy a fully stocked kitchen, modern amenities, and cozy living areas. Located in a quiet neighborhood, you'll be close to local attractions and dining. Whether you're here for a weekend getaway or a longer stay, this home provides everything you need.

4.92 out of 5 average rating, 48 reviews

Apartment in Warrenville

“The remote retreat”

We have a cozy one bedroom apartment that is available on the top floor of the home and has its own independent and separate entrance! Comes with free parking on premises; recently renovated; neighborhood is safe and quiet. Shopping center with grocery store, laundry mat and restaurant is available within walking distance! We are only 5 minutes from the expressway I-88 and 10 minutes from Naperville and the outlet mall in Aurora!

4.95 out of 5 average rating, 62 reviews

Guest suite in Oswego

1 Bed w/ Full Kitchen A Mile From Downtown Oswego

Enjoy a stay within walking distance of 3 parks and about a mile from downtown Oswego and its quaint shopping area. Nestled in the middle of a great neighborhood, you'll feel safe and be able to enjoy a quick getaway or an extended stay. If you're interested in visiting Chicago, we're close enough for day trips to the city (about 45 miles) but far enough to save some money. You'll definitely have a great time here!

Guest suite in Naperville

4.95 out of 5 average rating, 433 reviews

Cozy Lakeview Studio with Private Access

Enjoy luxury and comfort in this cozy lakefront studio with a private entrance, attached to a home where the friendly hosts reside. The studio offers a plush queen bed, a kitchenette with a mini fridge, microwave, induction cooktop, and a full bathroom. Located in one of Naperville’s safest neighborhoods, it’s just moments from cafes, restaurants, markets, and a biking trail, with easy access to I-88.

4.71 out of 5 average rating, 63 reviews

Apartment in Oswego

No Stairs Rustic Farmhouse APT King Beds/Fast WIFI

Bring the whole family to this great place with lots of room for fun. • Fast, Dedicated Wifi • 2 King Size Beds • 3 Smart Tvs w/ Roku • Onsite parking • Fully equipped + stocked kitchen with Keurig coffee & Tea • Desk • Basic toiletries • Vivint security system + keypad entry • Everything is sanitized/washed/cleaned after every guest

4.83 out of 5 average rating, 294 reviews

Home in Aurora

Albor Homes #1

We welcome you to our recently renovated home! Our house features 3 bedrooms w/ all new queen beds, master bedroom includes a half bath, a cozy living room and small work desk. You'll enjoy the natural light that comes in through the kitchen and dining room. Our home is your home, we look forward to hosting you!

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Other great holiday rentals in Montgomery

Apartment in Yorkville

5 out of 5 average rating, 4 reviews

Riverfront/Fast Wi-Fi/Fishing/Extended stay/Kayak

KeithRating, 5 stars1 month ago

Nice place, definitely worth the money. Hosts instructions was easy to follow. Did not need to contact host for anything. Location great too. I would recommend this place to others

Private room in Naperville

4.98 out of 5 average rating, 65 reviews

Private spacious room w/dresser in a nice home

ContessaRating, 5 stars1 day ago

⭐️⭐️⭐️⭐️⭐️ A+ Stay! Juan’s place was one of the best I’ve ever stayed in—clean, peaceful, and incredibly comfortable. His communication was excellent from start to finish, making everything easy and stress-free. If we ever come back to the area, we’ll definitely stay here again. Highly recommend it to anyone needing a great night’s rest and a relaxing stay. Thank you, Juan!

4.75 out of 5 average rating, 157 reviews

Private room in Aurora

Cozy Room

SavRating, 5 stars2 days ago

Jude is incredibly kind and welcoming I loved his space and it was exactly what I needed for the couple days I was there. I will be back!

5 out of 5 average rating, 37 reviews

Private room in Aurora

Spacious home in beautiful quiet neighborhood

KaushikRating, 5 stars1 week ago

This is an excellent place for long term stay and Craig is extremely helpful and kind. The place is extremely beautiful and has all the modern amenities. There is enough parking and working from here was also. Breeze. Thank you for the support

4.92 out of 5 average rating, 24 reviews

Barn in Oswego

The GC Barn - Town & Country Escape

TamikaRating, 5 stars1 month ago

This place is absolutely beautiful and spacious. I was able to host family and friends in comfort. The rooms are nice and the master is what every girl would want on a room. I will rent this house again. The hosts were responsive and very accommodating.

4.87 out of 5 average rating, 86 reviews

Private room in Aurora

Enchanted Egyptian “Treehouse” with Soaking Tub

ChristopherRating, 5 stars4 weeks ago

The Treehouse was clean, cozy, & private! Phil & Sunshine were super responsive & helpful for all of our needs. They were affable and seemed always happy to help. We'd definitely stay again and felt at home there. The private balcony is a nice bonus for sure too. The mini fridge was also very much appreciated. Please check out Alice's Corner nearby for excellent steak sandwiches & empanadas of all kinds! It's less than a mile away from here. Also, check out Harner's bakery for sausage and biscuits & tons of pastries and doughnuts of all kinds. Thanks again for a tremendous stay. I hope you enjoyed hosting us too.

Private room in Woodridge

4.86 out of 5 average rating, 499 reviews

Private floor with Bedroom, bathroom, living rm

NecoleRating, 5 stars3 days ago

Taylor's place was very nice; she really thought of everything. Everything you could need was there; Taylor makes you feel right at home. The neighborhood is nice and you're close to a number of things. Oh and the shower pressure was great!