Montgomery Holiday Rentals

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Holiday Rentals in Montgomery

Lakefront Home on Crooked Lake, Beautiful Views and Plenty of Space and Hot Tub!

9.8 out of 10, Exceptional, (34)
" Hard to watch baseball playoffs when Tv is streaming.Wi-Fi was going in and out. Grandkids brought fishing poles to fish off dock and it was brought in already. Owner said it’s usually out till end of October. Hot tub was not ready for first night there, we had to turn up heat and wait till next day. Place was clean and had plenty of room. Lots of towels and rags. First VRBO that I had to make beds "
Lakefront Home on Crooked Lake, Beautiful Views and Plenty of Space and Hot Tub!

Paradise - Coldwater/North Lake Rental - Monthly/Weekly /4 day off season

10.0 out of 10, Exceptional, (92)
"The property is beautiful. Lots of space to accommodate a large party. Great big tables for gaming with some friends. "
Paradise - Coldwater/North Lake Rental - Monthly/Weekly /4 day off season

Coldwater Family Retreat w/ Boat Dock & Grill!

10.0 out of 10, Exceptional, (30)
"This property is a great destination for a lake getaway! We were in the area for my son’s wedding. And although our schedule was pretty busy. We enjoyed being able to unwind by the lake with a beautiful fire. Definitely would like to stay again. When be we have more time!"
Coldwater Family Retreat w/ Boat Dock & Grill!

Heart of Hillsdale Downtown Office / Kitchen / Two Beds / Close to Everything

8.6 out of 10, Excellent, (30)
"This place is a convenient location to the college. It’s an older home and is clean. It works just fine for my needs- a place to sleep and easy to get in and out."
The price is AU$199
includes taxes & fees
24 Dec - 25 Dec
Heart of Hillsdale Downtown Office / Kitchen / Two Beds / Close to Everything

Rest, Relax and Reboot...pet friendly

9.6 out of 10, Exceptional, (118)
"Very nice clean cottage with beautiful views. It was chilly and windy so we didn't take out the boats or kayaks so I guess we will have to come back. Rhonda stopped by to make we got checked in okay and didn't need anything. We thought that was above and beyond and it was appreciated. "
Rest, Relax and Reboot...pet friendly

HUGE 5 Bedroom Lake House Retreat On Crooked Lake

9.6 out of 10, Exceptional, (73)
"This is the second Time we have stayed at this property and we enjoyed it just as much this time as the first time. The house is perfect for a large family and the lake is beautiful and not too crowded. We will be back!!"
HUGE 5 Bedroom Lake House Retreat On Crooked Lake

Full House on the Lake with Free kayaks, paddleboats and a fishing boat.

9.6 out of 10, Exceptional, (72)
"Nice place to get away for a long weekend. "
The price is AU$427
includes taxes & fees
1 Dec - 2 Dec
Full House on the Lake with Free kayaks, paddleboats and a fishing boat.

5 Bedroom Lake Access House and Entertainment Bldg for Rent

9.6 out of 10, Exceptional, (133)
"Great place in an area with several good golfing options. The house has all the amenities that you would want for a several night stay; a lot of space, big back yard, fire pit. Grills to cook, full kitchen and several close restaurants nearby."
5 Bedroom Lake Access House and Entertainment Bldg for Rent

LAKE FRONT COTTAGE ON IYOPAWA ISLAND GOLF COURSE

9.6 out of 10, Exceptional, (39)
"What a great week away from the business of life. Great location: golf course across the street, on the lake for boating, sand bar, fishing, walking around the island, golf carting if you bring one, and great community of friendly people. We had 8 people stay comfortably, 1 restroom is a bit challenging but do able. Parking is a little struggle for day guests. Only 3 parking spots including 1 in the garage. But again all minor details that are over come by the location. Refrigerator/freezer in...
LAKE FRONT COTTAGE ON IYOPAWA ISLAND GOLF COURSE

Stunning lake front home & everything is new! Direct access to Nettle Lake!

10.0 out of 10, Exceptional, (101)
"I use to come here when I was a little girl. We stayed directly across the lake from my grandpas place.. Mike and Sue were extremely pleasant. Made us feel very comfortable. I would very much recommend this place! We are looking forward to our next vacation here"
Stunning lake front home & everything is new! Direct access to Nettle Lake!

Sleeps 11 - Bar Room - Game Room - Handicap Accessible

9.8 out of 10, Exceptional, (10)
"We booked this for a long weekend with the family to watch the eclipse and celebrate my nephew's birthday. The property was just as described; secluded, spacious, and quite charming. We had 6 adults, a 7 year old, and an 80 lb Rottweiler, and there was plenty of room for everyone. Lots of space for outdoor activities and even though you're literally 10 mins from civilization and a store, you feel like you're out in the middle of nowhere. The whole group said they'd definitely come back so if...
Sleeps 11 - Bar Room - Game Room - Handicap Accessible

4 bedroom Lake James Cottage with sandy beach and fishing pier

9.8 out of 10, Exceptional, (25)
"The property and the owner/hosts were fantastic. We had a wonderful week and had everything we needed. It was very comfortable for 3 couples and a guest or 2 that stopped by for a night. "
4 bedroom Lake James Cottage with sandy beach and fishing pier

Cottage on beautiful Lake James

9.8 out of 10, Exceptional, (58)
"Great property."
Cottage on beautiful Lake James

Family-Friendly Retreat on Long Noble Lake!

10.0 out of 10, Exceptional, (9)
"Annual get together. Brothers and nephews"
Family-Friendly Retreat on Long Noble Lake!

Hillsdale County, Michigan: weddings, groups, Hillsdale College, Trine Univ.

10.0 out of 10, Exceptional, (62)
"Nick and Marisa provided a beautiful home for us. The accommodations and their graciousness exceeded our expectations. Thank you!"
Hillsdale County, Michigan: weddings, groups, Hillsdale College, Trine Univ.

NEW LISTING! Luxury Lakefront Home on Lake James

10.0 out of 10, Exceptional, (48)
"Spent a long weekend at the Lake House - a group of people in town for Trine Homecoming...house was fantastic! Great for entertaining and large groups."
NEW LISTING! Luxury Lakefront Home on Lake James

Gilead Lakefront Cottage with Large Deck and Beautiful View

9.6 out of 10, Exceptional, (35)
"Nice and quiet place"
Gilead Lakefront Cottage with Large Deck and Beautiful View

Home away from home

9.8 out of 10, Exceptional, (20)
"Have stayed a few times. Good location and clean"
The price is AU$322
includes taxes & fees
1 Dec - 2 Dec
Home away from home

Experience lakefront luxury with spectacular views on Lake James, Indiana!

10.0 out of 10, Exceptional, (4)
"We had a great time. Property was as listed. Would go back again."
Experience lakefront luxury with spectacular views on Lake James, Indiana!

Breathtaking Lakefront View - Pontoon Available! Coldwater Chain of Lakes

9.8 out of 10, Exceptional, (36)
"Property was very clean, good communication with Josh. Nice centralized location to restaraunts. Lake has options, whether wanting the peacefullness of the sunset, or chances to go tubing. It was a great place to stay. Quiet neighbors."
Breathtaking Lakefront View - Pontoon Available! Coldwater Chain of Lakes
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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Other types of properties in Montgomery you may be interested in

Days Inn by Wyndham Hillsdale

2.0 star property
7.2 out of 10, Good, (651)
"Good service, area just average."
The price is AU$128
includes taxes & fees
1 Dec - 2 Dec
Days Inn by Wyndham Hillsdale

Wingate by Wyndham Angola

3.5 star property
9.6 out of 10, Exceptional, (706)
"Clean, safe and quiet. Easy access from the Indiana Turnpike but far enough away in a quiet, safe and convenient location. Comfortable beds, great accommodations in the room and a well lit parking lot. Quick and easy checkin and checkout. Everything's we needed and were looking for in a one night stay. "
The price is AU$220
includes taxes & fees
1 Dec - 2 Dec
Wingate by Wyndham Angola

Holiday Inn Express & Suites Montpelier, an IHG Hotel

2.5 star property
8.6 out of 10, Excellent, (637)
"C"
The price is AU$172
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Express & Suites Montpelier, an IHG Hotel
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Montgomery?

Yes, there are holiday rentals close to the most popular sights in Montgomery, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Montgomery has to offer?

Paradise - Coldwater/North Lake Rental - Monthly/Weekly /4 day off season: This holiday home rental outside of Montgomery is located on a lake, and has a patio, a private garden and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

What’s there to see and do in Montgomery?

While exploring the area, visit family-friendly sights like Adventure Zone, or get outside and enjoy nature at Coldwater Lake State Park. The Outlet Shoppes at Fremont and Pokagon State Park are a couple of places you'll find in the wider area.

What’s a holiday rental in Montgomery like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montgomery. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family getaway.