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Vacation rentals in Montgomery

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Top-rated vacation rentals in Montgomery

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Cabin in Winslow

4.9 out of 5 average rating, 252 reviews

Primitive Historical Escape with Modern Amenities

If you desire an escape from the bigger city life and want to slow things down a bit with a place that makes you feel like you have went back in time to a simpler time, while still being close to it all, then this cabin getaway is your destination. Our cabin is perfect for a family weekend retreat, anniversary celebrations, and hunters. We are excited to be able to continue to maintain this historical building and still be able to offer it as a place for people to enjoy and stay in to this day.

Jun 22 – 29

G$29,095 GYD per night

Loft in Huntingburg

4.93 out of 5 average rating, 122 reviews

Lovely Country Loft Lake, Hiking, Woods, Relaxing

Take it easy at this unique and tranquil getaway. This loft was made from wood sawn and milled on this farm. Enjoy Indiana hardwoods as they surround you in this space. Centrally located, you are not far from Holiday World, Jasper, Lincoln City, Patoka Lake and Historic Huntingburg. The Master Bedroom boasts a king-size bed. The living area has two twin beds, TV, WiFi and Kitchen. This space is perfect for singles, couples, or small families. Most love the spiral staircase and large deck.

Jan 24 – 31

G$18,313 GYD per night

Guesthouse in Hardinsburg

4.96 out of 5 average rating, 179 reviews

Once Upon a Time little Cabin in the Woods

Welcome to Always Ranch where this unique tiny cabin offers you a tranquil spot to relax. You will be surrounded by nature and off the beaten path. The cabin may look like a lean to but the inside is rustic and warming. We are located 20 minutes form Salem, 20 minutes from Paoli and Paoli Peak, and 35 minutes from Frenchlick Casino The kitchenette includes mini fridge, microwave, double hot plate and, grill on the outdoor firepit or grill. Boats are NOT available for guests at this time

Oct 28 – Nov 4

G$23,943 GYD per night

Dome in Loogootee

5.0 out of 5 average rating, 15 reviews

Birdhouse Paradise

Welcome to Birdhouse Paradise - an enchanting dome house with a whimsical birdhouse theme in memory of Bill Larkin! Completely remodeled with 2 Baths, 3 Queen Beds, 1 Sofa Bed, and a Jacuzzi Tub. Nestled in a lush forest, it's a cozy retreat with modern amenities and rustic charm. Relax in the Jacuzzi Tub, gather around the Fire Pit, or explore nearby trails at West Boggs lake. Experience the magic of this unique sanctuary and make cherished memories in the midst of nature's embrace.

Nov 25 – Dec 2

G$42,098 GYD per night

Cabin in Loogootee

4.81 out of 5 average rating, 21 reviews

Truelove Chalet - Rustic, Glam Cabin Retreat!

A great opportunity to unplug in the great outdoors, with all the comforts you need to feel like you're NOT camping! Welcome to Truelove Chalet! This hilltop 1 bed/1 bath cabin with a bunkbed loft and optional airbed mattresses has rolling hills & green, lush grass for miles. Our cabin has everything you need! Call it #glamping! Campfires, incredible views, walk in the woods, hiking, birdwatching & star gazing! 10-15 minutes to Jasper and Loogootee. There is now wifi at the cabin!

Sep 19 – 26

G$25,400 GYD per night

Guesthouse in Dubois

4.82 out of 5 average rating, 49 reviews

Rural Studio Guest-house Overlooking Corn Fields

Relax with the family on this peaceful country-side hill in Dubois, Indiana. 17 minutes to Jasper and 17 minutes to French Lick. Patoka Lake is nearby, as well as attractions like Holiday World in Santa Claus, West Baden Casino & Resort, Big Splash, indoor karting, mini-golf, horseback riding, and small-town restaurants. You'll find necessities nearby, including a Walmart. We always have fresh, multicolored eggs to sell from our free-ranging chickens who are also fed organically.

Jun 8 – 15

G$14,099 GYD per night

Cabin in Columbus

4.92 out of 5 average rating, 370 reviews

Getaway Brown County - Indianapolis

An easy drive from the city, Getaway is a new way to experience the great outdoors. Nestled across dozens of acres of private woodlands, our modern, tiny cabins have everything you need (comfy bed, bathroom, fresh linens) and nothing you don’t. Featuring a private outdoor area (hello, fire pit), each cabin is designed to help you relax, unwind and disconnect from the everyday. Plus, as part of your stay, you'll receive firewood, a s'mores kit, coffee and bottled water*.

Sep 19 – 26

G$25,369 GYD per night

Home in Washington

5.0 out of 5 average rating, 8 reviews

Road House

This cozy and clean one bedroom, one bathroom home resides on a beautiful tree lined cul-de-sac, in town. Only 1.1 miles from Daviess County Hospital and .07 miles from Eastside Park Community Building. Washer, dryer, and high speed internet are included. Living room couch has queen size pull out bed. Bedroom has comfortable queen size bed. Both living room and bedroom have smart televisions. Bathroom has walk-in shower for two. Fully stocked kitchen.

May 8 – 15

G$21,236 GYD per night

Bungalow in Linton

4.92 out of 5 average rating, 107 reviews

Lake Harvey Vacation Rentals - 2-Bedroom Bungalow

Relax in our 2-bedroom Bungalow on 15-acre Lake Harvey just south of Linton, Indiana on the edge of Goose Pond Fish & Wildlife area, and just minutes from Greene Sullivan State Forest. Perfect for your hunting/fishing trip, or to bring your family for a peaceful vacation. Our Bungalow features 2 bedrooms, one with 2 queen beds, and one with a double bed, living room, dining room, fully equipped kitchen, 2 full bathrooms, and an attached carport.

Nov 19 – 26

G$26,626 GYD per night

Home in Loogootee

4.78 out of 5 average rating, 129 reviews

Izzy’s Treasure, entire cottage, super value!

Open concept living, dining and kitchen stocked with everything you need. Just grab some eggs, and milk on your way in. The upstairs has a spacious king room. The small Bedroom with full size bed has a full mattress that slides out from underneath. The lake picture is my personal dock that is 4 miles from the house. You can access the dock if you’re boating. The house is not on the lake.

Feb 10 – 17

G$19,111 GYD per night

Loft in Washington

4.87 out of 5 average rating, 75 reviews

Lovely 3 bedroom loft apartment!

Welcome to The WrightAway! Enjoy a stylish experience at this centrally-located place. 2nd floor loft apartment. Private entrance. Close to restaurants and pubs. Nice three bedroom and two bathroom. Full kitchen. Free wifi. Off street parking available. Open concept with plenty of room for a family to gather or space out.

Sep 11 – 18

G$28,254 GYD per night

Home in Loogootee

4.87 out of 5 average rating, 67 reviews

The Getaway House

Welcome to our Get Away House. Located on the edge of Loogootee, it is a very peaceful area and yet close to the local stores and restaurants. Relax with the family and spend the evening on the back patio. With two bedrooms and one bathroom, this single level home is perfect for your night away.

Jun 26 – Jul 3

G$12,939 GYD per night

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Other great vacation rentals in Montgomery

Home in Washington

5.0 out of 5 average rating, 11 reviews

Quiet 2 bdrm beside Hospital Weekly, monthly rates

Mar 2 – 9

G$22,650 GYD per night

Cabin in Bloomfield

4.95 out of 5 average rating, 42 reviews

Peaceful, Secluded Cabin Getaway

Feb 17 – 24

G$20,023 GYD per night

Home in Vincennes

4.96 out of 5 average rating, 75 reviews

Cheerful 3-bedroom home with huge yard

Apr 21 – 28

G$21,912 GYD per night

Home in Vincennes

5.0 out of 5 average rating, 32 reviews

Ernie's Place

Mar 26 – Apr 2

G$25,870 GYD per night

Tiny home in Shoals

5.0 out of 5 average rating, 13 reviews

The Leona (Relax and unwind)

Oct 18 – 25

G$18,772 GYD per night

Cabin in Velpen

4.97 out of 5 average rating, 32 reviews

Modern cabin in a country setting

Aug 17 – 24

G$31,193 GYD per night

Cabin in Montgomery

4.97 out of 5 average rating, 61 reviews

Private Secluded 3BR 2BA Cabin/Lake on 16 acres

May 27 – Jun 3

G$42,890 GYD per night

Home in Petersburg

4.79 out of 5 average rating, 14 reviews

Hopper Hideaway

Jun 22 – 29

G$13,563 GYD per night

Destinations to explore