Montgomery Holiday Rentals

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Holiday Rentals in Montgomery

Enchanting Montgomery Escape w/ Private Hot Tub!
10.0 out of 10, Exceptional, (3)
"the property provided everything we asked of it. great memories were made."
Enchanting Montgomery Escape w/ Private Hot Tub!
Enchanting Montgomery Escape w/ Private Hot Tub!
3.0 star property
Enchanting Montgomery Escape w/ Private Hot Tub!
Sweet Spot in the City
The price is NZ$566
per night
7 Jun - 8 Jun
Sweet Spot in the City
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Scenic Escape: River Paradise
8.0 out of 10, Very good, (1)
"Isolated as I wanted. Wi Fi was hit and miss and so was cell service but that was okay. Wish I received check out instructions before we arrived. Did not receive them until we left since Wi Fi was spotty. Overall a good stay."
The price is NZ$492
per night
23 Jun - 24 Jun
Scenic Escape: River Paradise
Peaceful Lake House Cabin 2, Kayaks Provided Free, Direct Water Access!
9.6 out of 10, Exceptional, (108)
"Great little fishing cabin on the lake we stay here every year and love it!"
Peaceful Lake House Cabin 2, Kayaks Provided Free, Direct Water Access!
Lakehouse with Game Room, Direct Water Access, and Kayaks Included!
10.0 out of 10, Exceptional, (23)
"The cottage was very clean and cozy! The beds were comfortable. We all enjoyed the game room that was awesome! The fire pit with the wood and fire starters provided we enjoyed that a lot. Went fishing at the dock was fun with the kids! Place had everything you needed and more! Very fun family weekend games at the table, watched movies, relaxed by fire made s'mores, fishing and game room! Host responded quickly with questions. The book of everything to do and what is around very handy! Would...
Lakehouse with Game Room, Direct Water Access, and Kayaks Included!
Cozy East Side Condo in Washington close to City Park and Hospital
10.0 out of 10, Exceptional, (1)
"This was our place to stay on a family trip for the total eclipse in April 2024. Washington, Indiana, was perfect for the eclipse, just about in the center of the strip of totality. This listing seemed perfect for our needs - 3 bedrooms, 2 baths, nicely decorated with WiFi and smart TVs, and a full kitchen. I was so pleased that it was available. This property was better than we expected. Absolutely perfectly set up, with linens and towels and kitchen wares ready for our stay. We were literally...
Cozy East Side Condo in Washington close to City Park and Hospital
Truelove Chalet- A Relaxed, Rustic, Glam Cabin!
10.0 out of 10, Exceptional, (1)
"Delightful old cabin, recently updated very nicely. The layout makes a great use of the small space, and the outside spaces are PHENOMENAL! We rented this property as a place to watch the eclipse with family, and really loved the quiet location and comfortable accommodations. We're glad we were there for 3 days to really soak it up. We hope to be back!"
Truelove Chalet- A Relaxed, Rustic, Glam Cabin!
Hilltop Getaway on 140+ private wooded acres with trails, pond, beautiful view!!
10.0 out of 10, Exceptional, (14)
"Very nice"
The price is NZ$736
per night
5 Jul - 6 Jul
Hilltop Getaway on 140+ private wooded acres with trails, pond, beautiful view!!
Lake Themed Cabin - Direct Water Access - Free Kayaks
9.0 out of 10, Wonderful, (2)
"Our stay was primarily to see the newest addition to our family, a grandson that was a week old.. Since there was no room in my sons house this made a great home away feom home."
Lake Themed Cabin - Direct Water Access - Free Kayaks
Peaceful Lake House Cabin 1, Kayaks Provided Free, Direct Water Access!
9.8 out of 10, Exceptional, (10)
"We had amazing time! We loved the property and the lake."
Peaceful Lake House Cabin 1, Kayaks Provided Free, Direct Water Access!
2 Bedroom Pure Stone Delight! Close to historic downtown Jasper
10.0 out of 10, Exceptional, (13)
"Super clean home that looks even better in person. On a corner lot and directly across the street from the hospital, but still felt quiet. Great communication and instructions from host. There’s actually a second toilet in the laundry room in the basement, with a sink right outside outside the door."
2 Bedroom Pure Stone Delight! Close to historic downtown Jasper
Historic home by Dogwood Lake/Glendale
Historic home by Dogwood Lake/Glendale
Birdhouse Paradise
9.6 out of 10, Exceptional, (5)
"We had a wonderful time. Frisbee golf was a bit of a bust but we loved the location, the amenities, and the house. The fire pit was perfect for cooking a nice steak on. The jetted tub was relaxing on a cold night. We plan to be back!"
Birdhouse Paradise
Historic Home by Dogwood Lake/Glendale
10.0 out of 10, Exceptional, (1)
"Nice place wish fishing had been better and weather would have cooperated, may rent it again in the fall"
Historic Home by Dogwood Lake/Glendale
Whole house w/ full basement 3 bdrms 2.5 baths 5 recliners + air mattress space
10.0 out of 10, Exceptional, (10)
"We had a wonderful and comfortable stay with family while visiting family. Much nicer than a hotel and allowed for room to catch up and socialize."
Whole house w/ full basement 3 bdrms 2.5 baths 5 recliners + air mattress space
Green Gables 2 Bedroom Basement aprtmt, sleeps 8, ktchn, lvng rm, private ent.
10.0 out of 10, Exceptional, (2)
"Good-sized apartment in lovely rural area. Gracious hosts."
Green Gables 2 Bedroom Basement aprtmt, sleeps 8, ktchn, lvng rm, private ent.
Loft Apartment
The price is NZ$187
per night
30 Jun - 1 Jul
Loft Apartment
Cozy secluded cabin, close to Sultan's Run Golf Course and Holiday World!
Cozy secluded cabin, close to Sultan's Run Golf Course and Holiday World!
Charming Cannelburg Cottage: Beautiful New Home!
Charming Cannelburg Cottage: Beautiful New Home!
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See all available properties in Montgomery
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.

Other types of properties in Montgomery you may be interested in

Enchanting Montgomery Escape w/ Private Hot Tub!
10.0 out of 10, Exceptional, (3)
"the property provided everything we asked of it. great memories were made."
Enchanting Montgomery Escape w/ Private Hot Tub!
Enchanting Montgomery Escape w/ Private Hot Tub!
3.0 star property
Enchanting Montgomery Escape w/ Private Hot Tub!
SureStay Plus Hotel by Best Western Jasper
2.5 star property
8.0 out of 10, Very good, (498)
"The tub was clogged and the breakasft was limited. No beverages to but coffee. No meat protein available. They can really use a step up on breakfast area. However the beds were extremely comfortable. The pool area was decent with a nice warm jacuzzi."
The price is NZ$183
per night
9 Jun - 10 Jun
SureStay Plus Hotel by Best Western Jasper
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Montgomery holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Montgomery. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Montgomery. Seeing all the best attractions is bound to make you fall in love with Montgomery. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Montgomery short-term rentals, that won’t be hard to do.

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. Montgomery is known for its shopping.

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

Enchanting Montgomery Escape w/ Private Hot Tub!: This highly rated holiday home rental in Montgomery offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in Montgomery?

Visit the sights while you're exploring the area such as Dubois County Visitors Center and Dubois County Museum.

What are holiday rentals like in Montgomery?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Montgomery. Holiday rentals offer amenities like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for families.

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