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

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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 £277
includes taxes & fees
3 Nov - 4 Nov
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.
The price is £251
includes taxes & fees
27 Oct - 28 Oct
PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!
A modern kitchen with white cabinetry, a dining area with a wooden table and chairs, and a large island with a stove.

3. 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 £292
includes taxes & fees
26 Oct - 27 Oct
River Access•Game room•Backyard•King•W/D•Parking
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, (33 reviews)
"It was a great stay. You will not be disappointed all our needs for a meet"
United States
Kathy R.
The price is £365
includes taxes & fees
28 Oct - 29 Oct
PROMO 15% MONTHLY DISCOUNT! California King Bed, Fast Wi-Fi and 75" Smart TV
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 £410
includes taxes & fees
8 Nov - 9 Nov
Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong
A covered porch with wicker furniture, a coffee table, and a potted plant.

6. - 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 £232
includes taxes & fees
27 Oct - 28 Oct
- Fully-Equipped Condo - King Bed - Massive yard -
A patio area with outdoor furniture, a gazebo, and a barbecue grill.

7. 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 £860
includes taxes & fees
25 Oct - 26 Oct
Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.
A spacious living room with a fireplace, a large sofa, a coffee table, and a TV.

8. 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 £445
includes taxes & fees
2 Nov - 3 Nov
4BR Tudor • Wooded Lot • 10 Min to Downtown
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 £882
includes taxes & fees
27 Oct - 28 Oct
2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!
A bedroom with a bed, bedside tables, a dresser, a mirror, and a hanging light fixture.

10. 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 £830
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.

11. 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 £389
includes taxes & fees
3 Nov - 4 Nov
Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield
(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.

12. 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 £548
includes taxes & fees
26 Oct - 27 Oct
30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious
A modern kitchen with dark wood cabinets, stainless steel appliances, a granite countertop, and a small island with stools.

13. 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 £357
includes taxes & fees
25 Oct - 26 Oct
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
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 £481
includes taxes & fees
25 Oct - 26 Oct
Spacious 5-bedroom house in perfect Plano with AC for relaxing stays
A dining room with a wooden table set for six, flanked by bookshelves, and a view into another room through a glass door.

15. 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 £331
includes taxes & fees
25 Oct - 26 Oct
Travelers Retreat/King Beds/Game Room/Play House
A two-story house with a garage, solar panels, and a red car parked in front.

16. Lombard 1BR & 1BH Suite Close to freeway & Mall

Lombard 1BR & 1BH Suite Close to freeway & Mall
Lombard
The price is £297
includes taxes & fees
24 Oct - 25 Oct
Lombard 1BR & 1BH Suite Close to freeway & Mall
A staircase with a wooden handrail and black metal railings, leading to an upper floor.

17. 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 £198
includes taxes & fees
1 Nov - 2 Nov
Riverfront rental
A wooden interior hallway with a staircase, a wooden wardrobe, and a cabinet with glass doors.

18. 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 £705
includes taxes & fees
24 Oct - 25 Oct
River Park Paradise w/ Fire Pit & Chef's Kitchen
A building with a sign reading 'Hale Street Cantina' and a brick facade.

19. ✽ 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 £247
includes taxes & fees
3 Nov - 4 Nov
✽ Charming Cottage ✽ close to College/Town/Station
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is £230
includes taxes & fees
28 Oct - 29 Oct
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
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

Hilton Chicago/Oak Brook Hills Resort & Conference Center

Hilton Chicago/Oak Brook Hills Resort & Conference Center

10/10 Excellent
"We had a great experience. The staff was friendly and helpful. Our room floor was upgraded and the food was delicious."
Christopher 2-night trip
Posted 3 hours ago
Hilton Chicago/Oak Brook Hills Resort & Conference Center

Find out more about Montgomery

Montgomery Holiday Homes information

Number of reviews
281
Accommodation
149 Holiday Homes
Lowest Price
£198
Highest Price
£882