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

Holiday Homes in Montgomery

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 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 €329
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 €349
includes taxes & fees
28 Oct - 29 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.

3. 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 €363
includes taxes & fees
28 Oct - 29 Oct
PROMO 15% MONTHLY DISCOUNT! California King Bed, Fast Wi-Fi and 75" Smart TV
A patio area with outdoor furniture, a gazebo, and a barbecue grill.

4. 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, (36 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 €1,021
includes taxes & fees
8 Nov - 9 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.

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

- Fully-Equipped Condo - King Bed - Massive yard -
Geneva
10.0 out of 10, Exceptional, (49 reviews)
"We had everything we needed, the host was very responsive and we would stay there again."
United States
Mike A.
The price is €268
includes taxes & fees
2 Nov - 3 Nov
- Fully-Equipped Condo - King Bed - Massive yard -
A covered outdoor seating area with wicker furniture, a sign reading 'Our Happy Place,' and a view of trees through large windows.

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

Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong
Naperville
The price is €487
includes taxes & fees
12 Nov - 13 Nov
Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong
A spacious living room with a fireplace, a large sofa, a coffee table, and a TV.

7. 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 €565
includes taxes & fees
28 Oct - 29 Oct
4BR Tudor • Wooded Lot • 10 Min to Downtown
Immediately feel at home when you step into the grand entryway.

8. 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)
"Great location, great place...perfect!"
United States
David Z.
The price is €1,064
includes taxes & fees
28 Oct - 29 Oct
2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!
A modern kitchen with a central island, bar stools, and pendant lighting.

9. 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 €1,001
includes taxes & fees
28 Oct - 29 Oct
Spacious 7-bedroom house with AC in wonderful Naperville
A modern living room with a sofa set, a coffee table, and a rug.

10. 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 €443
includes taxes & fees
2 Nov - 3 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.

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 €603
includes taxes & fees
28 Oct - 29 Oct
30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious
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, (16 reviews)
"Excellent just what we were looking for"
United States
Sue B.
The price is €791
includes taxes & fees
28 Oct - 29 Oct
River Park Paradise w/ Fire Pit & Chef's Kitchen
A pathway flanked by stone arches, surrounded by lush green grass and trees.

13. 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 €579
includes taxes & fees
28 Oct - 29 Oct
Spacious 5-bedroom house in perfect Plano with AC for relaxing stays
A backyard with a barbecue grill, a dining table with chairs, and a fire pit.

14. 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.
The price is €277
includes taxes & fees
29 Oct - 30 Oct
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
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 €429
includes taxes & fees
28 Oct - 29 Oct
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Exterior detail

16. 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 €730
includes taxes & fees
28 Oct - 29 Oct
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.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is €285
includes taxes & fees
2 Nov - 3 Nov
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A modern living room with a flat-screen TV, a grey sofa, a round ottoman, and a large window with curtains.

18. Spacious 5BR Home with Game Room and Free Parking

Spacious 5BR Home with Game Room and Free Parking
Joliet
10.0 out of 10, Exceptional, (1 review)
"The host provided everything I needdd for a comfortable stay."
United States
john g.
The price is €578
includes taxes & fees
29 Oct - 30 Oct
Spacious 5BR Home with Game Room and Free Parking
A staircase with a wooden handrail and black metal railings, leading to an upper floor.

19. 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 €236
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.

20. 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.
Travelers Retreat/King Beds/Game Room/Play House
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

Sybaris Pool Suites

Sybaris Pool Suites

10/10 Excellent
"Clean room I love the hot tub fireplace the style of room TVs everywhere the receiver acts like Bluetooth you can play music great place great time."
Angel 2-night trip
Posted 2 hours ago
Sybaris Pool Suites

Find out more about Montgomery

Montgomery Holiday Homes information

Number of reviews
235
Accommodation
154 Holiday Homes
Lowest Price
€236
Highest Price
€1,064