An aerial view of a city with a river, historic buildings, and a prominent church spire.

Montgomery Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Montgomery vacation rentals

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a stove.

1. Family-Friendly 3BR Home • Sleeps 6 • 2.5 Bath

Family-Friendly 3BR Home • Sleeps 6 • 2.5 Bath
Aurora
7.0 out of 10, Good, (2 reviews)
"Overall good I would stay there again if I was to travel to Chicago again"
United States
Avo H.
The price is ￥20,090
￥56,357 total
includes taxes & fees
Nov 2 - Nov 3
Family-Friendly 3BR Home • Sleeps 6 • 2.5 Bath
A living room with a gray sofa, a blue chair, a fireplace, and a ceiling fan.

2. PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!

PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!
Aurora
9.2 out of 10, Wonderful, (15 reviews)
"The beds were super comfortable and the location for Naperville/Aurora/Wheaton activities was ideal--about 10 minutes or so for everything."
United States
Scott D.
PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!
A patio area with outdoor furniture, a gazebo, and a barbecue grill.

3. Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.

Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.
Aurora
10.0 out of 10, Exceptional, (35 reviews)
"The property was perfect for our family! There was plenty of room, indoors and out, for us, our kids, and our grandkids. The house was spotless and the kitchen was extensively stocked with dishes, cookware, etc. We also appreciated the numerous comfy places to gather."
United States
Mila M.
The price is ￥78,997
￥181,870 total
includes taxes & fees
Oct 12 - Oct 13
Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island with seating.

4. PROMO 15% MONTHLY DISCOUNT! California King Bed, Fast Wi-Fi and 75" Smart TV

PROMO 15% MONTHLY DISCOUNT! California King Bed, Fast Wi-Fi and 75" Smart TV
Naperville
9.4 out of 10, Exceptional, (32 reviews)
"It was a great stay. You will not be disappointed all our needs for a meet"
United States
Kathy R.
The price is ￥33,578
￥74,175 total
includes taxes & fees
Oct 14 - Oct 15
PROMO 15% MONTHLY DISCOUNT! California King Bed, Fast Wi-Fi and 75" Smart TV
Walk score 55: (nearby are Ridge Park, Crescent Park & Cumberland Park)

5. 65" TV|Electric Fireplace|W/D|Grill|Parking

65" TV|Electric Fireplace|W/D|Grill|Parking
Naperville
65" TV|Electric Fireplace|W/D|Grill|Parking
A modern kitchen with white cabinetry, a dining area with a wooden table and chairs, and a large island with a stove.

6. River Access•Game room•Backyard•King•W/D•Parking

River Access•Game room•Backyard•King•W/D•Parking
Yorkville
10.0 out of 10, Exceptional, (4 reviews)
"Absolutely loved this place. The backyard was amazing and the house was clean and had everything we needed."
United States
Daniela M.
The price is ￥22,274
￥59,846 total
includes taxes & fees
Oct 12 - Oct 13
River Access•Game room•Backyard•King•W/D•Parking
A modern living room with a sofa, coffee table, and a desk with a chair. There is a painting on the wall and a view of the outdoors through a glass door.

7. Relaxing 2BR Riverfront Townhome

Relaxing 2BR Riverfront Townhome
Yorkville
9.6 out of 10, Exceptional, (4 reviews)
"Matched the photos - was a decent place to spend a night on our road trip. Yorkville seems like a nice area too - stores and restaurants nearby"
United States
Tora U.
The price is ￥21,530
￥49,494 total
includes taxes & fees
Oct 13 - Oct 14
Relaxing 2BR Riverfront Townhome
A modern living room with a wooden dining table, two brown leather chairs, a green sofa, and a coffee table. A flat-screen TV is mounted on the wall, and a forest mural is visible.

8. Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain

Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
Geneva
9.4 out of 10, Exceptional, (38 reviews)
"This is our second time at this property and we will be back. Cita the host is top notch and bent over backwards for every request. lovely neighborhood for walking and quiet. The space is perfect for a quiet dinner with our grown kids. Thank you Cita and the cleaning crew who made it beautiful!"
United States
Gail F.
The price is ￥20,897
￥52,950 total
includes taxes & fees
Oct 12 - Oct 13
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
Immediately feel at home when you step into the grand entryway.

9. 2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!

2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!
Plano
9.8 out of 10, Exceptional, (16 reviews)
"This is our second year in a row for our annual Friendsgiving. We love the place and plan to make it our annual house for our group! "
United States
Aaron P.
The price is ￥94,986
￥233,585 total
includes taxes & fees
Oct 13 - Oct 14
2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!
A spacious living room with a fireplace, a large sofa, a coffee table, and a TV.

10. 4BR Tudor • Wooded Lot • 10 Min to Downtown

4BR Tudor • Wooded Lot • 10 Min to Downtown
Naperville
9.6 out of 10, Exceptional, (5 reviews)
"This is a spacious house in a very nice, quiet neighborhood. The backyard is a perfect spot to relax and soak in the sun/play games. This is a great house for families. We had a nearby wedding and this was a wonderful house to get ready at. The hosts are extremely welcoming and communicate wonderfully. "
United States
Alicia F.
The price is ￥36,411
￥100,834 total
includes taxes & fees
Oct 12 - Oct 13
4BR Tudor • Wooded Lot • 10 Min to Downtown
A living room with a large window, a sofa, a chair, and a desk with a vase of flowers.

11. Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong

Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong
Naperville
The price is ￥33,061
￥87,385 total
includes taxes & fees
Oct 13 - Oct 14
Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong
A wooden interior hallway with a staircase, a wooden wardrobe, and a cabinet with glass doors.

12. River Park Paradise w/ Fire Pit & Chef's Kitchen

River Park Paradise w/ Fire Pit & Chef's Kitchen
Bolingbrook
10.0 out of 10, Exceptional, (15 reviews)
"Excellent just what we were looking for"
United States
Sue B.
The price is ￥66,490
￥132,375 total
includes taxes & fees
Oct 13 - Oct 14
River Park Paradise w/ Fire Pit & Chef's Kitchen
(OUTDOOR SPACE) Where comfort and charm come together. Unwind in the outdoor lounge set under an inviting gazebo with twinkling lights. Stay fresh with a gentle breeze from the fan as you relax.

13. 30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious

30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious
Plainfield
9.4 out of 10, Exceptional, (18 reviews)
"Great place to stay."
United States
Taylor E.
30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious
A pathway flanked by stone arches, surrounded by lush green grass and trees.

14. Spacious 5-bedroom house in perfect Plano with AC for relaxing stays

Spacious 5-bedroom house in perfect Plano with AC for relaxing stays
Plano
The price is ￥79,155
￥99,661 total
includes taxes & fees
Oct 12 - Oct 13
Spacious 5-bedroom house in perfect Plano with AC for relaxing stays
A covered outdoor deck with wicker furniture, a glass-top table, and a potted plant.

15. - Beautiful Condo - King Bed - Free Waffle Breakfast -

- Beautiful Condo - King Bed - Free Waffle Breakfast -
Geneva
9.8 out of 10, Exceptional, (30 reviews)
"Best hosts on VRBO. They were so fast to address questions, and put in so many thoughtful touches. I wish all hosts were like them!!!!!"
United States
Nikki G.
The price is ￥24,221
￥51,843 total
includes taxes & fees
Oct 14 - Oct 15
- Beautiful Condo - King Bed - Free Waffle Breakfast -
A modern living room with a sofa, coffee table, and bar stools. There is a kitchen area with cabinets and a countertop.

16. Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry

Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
Geneva
9.6 out of 10, Exceptional, (28 reviews)
"The location is amazing! What a cute place. Just right for two people."
United States
Shara B.
The price is ￥21,119
￥51,271 total
includes taxes & fees
Oct 26 - Oct 27
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
A covered porch with wicker furniture, a coffee table, and a potted plant.

17. - Fully-Equipped Condo - King Bed - Massive yard -

- Fully-Equipped Condo - King Bed - Massive yard -
Geneva
10.0 out of 10, Exceptional, (47 reviews)
"We had everything we needed, the host was very responsive and we would stay there again."
United States
Mike A.
The price is ￥29,778
￥58,570 total
includes taxes & fees
Oct 20 - Oct 21
- Fully-Equipped Condo - King Bed - Massive yard -
Two twin beds in a hotel room with a green accent wall, a framed picture, and a nightstand with a lamp.

18. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Chicago
9.2 out of 10, Wonderful, (30 reviews)
"Nice people,nice rooms!"
United States
Anonymous traveler
The price is ￥11,130
￥12,314 total
includes taxes & fees
Oct 30 - Oct 31
2 Full Beds | Non-Smoking, Kitchen
Dining

19. 4 BR 3 BATH Naperville Downtown with Wi-fi Desk, Near HighwayTrainStation

4 BR 3 BATH Naperville Downtown with Wi-fi Desk, Near HighwayTrainStation
Naperville
5.0 out of 10, (2 reviews)
"It was a great functional atmosphere. I would definitely stay again. "
United States
colin m.
The price is ￥54,142
￥93,620 total
includes taxes & fees
Oct 12 - Oct 13
4 BR 3 BATH Naperville Downtown with Wi-fi Desk, Near HighwayTrainStation
A modern living room with a sofa set, a coffee table, and a rug.

20. Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield

Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield
Plainfield
10.0 out of 10, Exceptional, (3 reviews)
"Great host and the home location is awesome for hosting family. "
United States
Yolanda P.
The price is ￥30,775
￥74,728 total
includes taxes & fees
Oct 14 - Oct 15
Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Montgomery Hotel Reviews

SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

10/10 Excellent
"Good when you want a reasonable clean hotel within 25 minutes of MDW."
alan 1-night trip
Posted 7 hours ago
SureStay Plus Hotel by Best Western Chicago Lombard

Find out more about Montgomery

Search for holiday rentals in Montgomery on Expedia! You can easily find your home rentals, villas, holiday apartments in Montgomery using one of the methods below:

  • View our selection of featured holiday rentals in Montgomery
  • Use the map to find apartments and other holiday homes in the Montgomery neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Montgomery while they last

Look no further and take a look at our great range of rental properties in Montgomery!

Frequently asked questions

Can I find vacation rentals in Montgomery?

Yes, you can find vacation rentals near the most popular points of interest in Montgomery, or you can go with a more secluded option if you'd like a relaxing place to stay. Montgomery is known for its breweries and riverfront. Make sure you have time to check out the shopping and restaurants during your trip.

What's the top vacation rental in Montgomery?

Spacious3BR 1.5 bath Retreat/Game Room/Fenced Yard/No Stairs!/Garage/Dogfriendly: Visitors like this Montgomery vacation home rental. It offers a patio, an arcade game room, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Our travelers also rate 3bd/1.5bath entire home/Game room/Office/extended stays/FREE Wifi & Parking as a favorite home for rent in Montgomery.

How many vacation rentals are there in Montgomery?

Expedia has 5 vacation rentals for your stay in Montgomery.

What can I see and do in Montgomery?

Explore the area and family-friendly sights such as Aurora Skate Center, or get out into nature at a spot like Fabyan Villa Museum & Japanese Garden. In the larger area, you’ll find Aurora University and Waubonsee Community College.

What are vacation rentals like in Montgomery?

Vacation rentals are private accommodations you can stay in for a short or long stay in Montgomery. Vacation rentals provide amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for family trips or small group gatherings.