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

Holiday Homes in Montgomery

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Montgomery holiday homes

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
7.4 out of 10, Good, (3 reviews)
"Overall good I would stay there again if I was to travel to Chicago again"
United States
Avo H.
The price is NZ$644
includes taxes & fees
2 Nov - 3 Nov
Family-Friendly 3BR Home • Sleeps 6 • 2.5 Bath
A modern kitchen with white cabinetry, a dining area with a wooden table and chairs, and a large island with a stove.

2. 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 NZ$680
includes taxes & fees
26 Oct - 27 Oct
River Access•Game room•Backyard•King•W/D•Parking
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 NZ$1,971
includes taxes & fees
5 Nov - 6 Nov
Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.
A covered porch with wicker furniture, a coffee table, and a potted plant.

4. - 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 NZ$521
includes taxes & fees
28 Oct - 29 Oct
- Fully-Equipped Condo - King Bed - Massive yard -
A covered patio with a grill, outdoor seating, and a view of a house.

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

Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong
Naperville
The price is NZ$887
includes taxes & fees
27 Oct - 28 Oct
Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong
A spacious living room with a fireplace, a large sofa, a coffee table, and a TV.

6. 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 NZ$1,040
includes taxes & fees
2 Nov - 3 Nov
4BR Tudor • Wooded Lot • 10 Min to Downtown
A bedroom with a bed, bedside tables, a dresser, a mirror, and a hanging light fixture.

7. Spacious 7-bedroom house with AC in wonderful Naperville

Spacious 7-bedroom house with AC in wonderful Naperville
Naperville
8.0 out of 10, Very good, (1 review)
"Very smooth booking, checking in, and checking out process. The house was older, and it showed, but was big enough to hold my group. There were problems with the fire detectors randomly beeping, and some mold in the basement, but everything else was fine."
United States
Brett H.
The price is NZ$1,923
includes taxes & fees
26 Oct - 27 Oct
Spacious 7-bedroom house with AC in wonderful Naperville
A modern living room with a sofa set, a coffee table, and a rug.

8. 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 NZ$807
includes taxes & fees
26 Oct - 27 Oct
Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield
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 NZ$2,085
includes taxes & fees
27 Oct - 28 Oct
2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!
A wooden deck with wicker furniture and a view of a green landscape.

10. 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 NZ$1,060
includes taxes & fees
23 Oct - 24 Oct
Spacious 5-bedroom house in perfect Plano with AC for relaxing stays
(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.

11. 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.
The price is NZ$1,217
includes taxes & fees
26 Oct - 27 Oct
30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious
A backyard with a barbecue grill, a dining table with chairs, and a fire pit.

12. PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle
9.4 out of 10, Exceptional, (36 reviews)
"This property was perfect for our weekend stay in the Chicagoland area. It was conveniently located to activities, shops and restaurants. Vic is a wonderfully attentive host who responds quickly and is happy to answer any questions or concerns."
United States
Christine M.
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Dining

13. 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
6.8 out of 10, (3 reviews)
"My God the host was extremely helpful and responsive when reaching out, place was super clean, place and area was super peaceful and quiet. She over delivered guys"
United States
Marquis M.
The price is NZ$1,407
includes taxes & fees
1 Nov - 2 Nov
4 BR 3 BATH Naperville Downtown with Wi-fi Desk, Near HighwayTrainStation
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

14. Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is NZ$529
includes taxes & fees
17 Nov - 18 Nov
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A modern kitchen with dark wood cabinets, stainless steel appliances, a granite countertop, and a small island with stools.

15. Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Lockport
10.0 out of 10, Exceptional, (16 reviews)
"Perfect spot for our group of 6! More than enough dishes/silverware etc. the house was clean and comfortable. Would definitely stay again if in the area."
United States
Kathy L.
The price is NZ$878
includes taxes & fees
26 Oct - 27 Oct
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
A staircase with a wooden handrail and black metal railings, leading to an upper floor.

16. Riverfront rental

Riverfront rental
South Elgin
10.0 out of 10, Exceptional, (51 reviews)
"Incredible host and property."
United States
John V.
The price is NZ$440
includes taxes & fees
1 Nov - 2 Nov
Riverfront rental
A dining room with a wooden table set for six, flanked by bookshelves, and a view into another room through a glass door.

17. Travelers Retreat/King Beds/Game Room/Play House

Travelers Retreat/King Beds/Game Room/Play House
Joliet
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay"
United States
Ken B.
The price is NZ$812
includes taxes & fees
25 Oct - 26 Oct
Travelers Retreat/King Beds/Game Room/Play House
A white house with a garden featuring purple flowers and a birdbath.

18. ✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (74 reviews)
"This was the perfect place for our short stay!"
United States
Laurie R.
The price is NZ$561
includes taxes & fees
22 Nov - 23 Nov
✽ Charming Cottage ✽ close to College/Town/Station
A living room with a flat-screen TV, a wooden coffee table with a vase, a sofa, and a dining area with chairs and a chandelier.

19. Tranquil 3-bedroom house with AC in charming Wheaton, Illinois

Tranquil 3-bedroom house with AC in charming Wheaton, Illinois
Wheaton
The price is NZ$926
includes taxes & fees
25 Oct - 26 Oct
Tranquil 3-bedroom house with AC in charming Wheaton, Illinois
A wooden interior hallway with a staircase, a wooden wardrobe, and a cabinet with glass doors.

20. 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, (16 reviews)
"Excellent just what we were looking for"
United States
Sue B.
The price is NZ$1,691
includes taxes & fees
26 Oct - 27 Oct
River Park Paradise w/ Fire Pit & Chef's Kitchen
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montgomery Hotel Reviews

Hollywood Casino Aurora

Hollywood Casino Aurora

10/10 Excellent
"Beautiful property, casino floor exciting, loved the fire pit outside, and enjoyed the live music, the only downside was the over-fragranced air."
Annette 3-night trip
Posted 7 hours ago
Hollywood Casino Aurora

Find out more about Montgomery

Montgomery Holiday Homes information

Number of reviews
305
Accommodation
149 Holiday Homes
Lowest Price
NZ$440
Highest Price
NZ$2,085