Vacation rentals in Montgomery

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Top-rated vacation rentals in Montgomery

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A comfortable living area features a teal couch and two brown recliners, arranged around a central round coffee table. A patterned rug covers the wooden floor, while a brick fireplace and a TV are situated on the back wall. Natural light enters through the windows.
Home in Montgomery
4.85 out of 5 average rating, 27 reviews

Historic Home by Dogwood Lake/Glendale

With only a few minutes drive to Dogwood Lake and Glendale Fish & Wildlife area, this newly renovated historic 1850s home is perfect for your next getaway with friends, or that peaceful vacation. We are located 8 miles from I69 and the town of Washington. We have outfitted our home with all the amenities and comforts to make your stay as pleasant as possible! Our property provides privacy and you will enjoy listening to the sounds of nature while sitting around a campfire with a cup of coffee

Top guest favorite
A view from above captures a six-person hot tub with inviting blue water. Nearby, a circle of Adirondack chairs surrounds a fire pit, all nestled in a wooded area illuminated by warm string lights hanging overhead.
Cabin in Eckerty
4.98 out of 5 average rating, 167 reviews

Whitetail Woods cabin w/ HOT TUB and Patoka pass

Relax with the whole family at this peaceful cabin minutes from Patoka Lake entrance, winery, distillery, brewery, and dining! Perfect for family adventures, romantic getaways, ladies' weekends, and hunting trips. The cabin is located in peaceful Grant Woods surrounded by gorgeous Southern Indiana nature. You'll love relaxing in the 6-person hot tub, rocking on the covered front porch, and roasting marshmallows around the backyard fire pit. Cabin is a short drive to French Lick/West Baden.

Superhost
A cozy corner of the bedroom features a plush bed dressed in crisp white linens and decorative pillows. A small bedside table, topped with a warm lamp, stands beside the bed, with light filtering softly through a nearby window.
Home in West Baden Springs
4.9 out of 5 average rating, 197 reviews

The William: 4m drive to French Lick Hotel!

The William is a completely renovated and restored home. You will find refinished hardwood floors and new finishes; a charming fireplace and hearth (not used), and touches of old and new world throughout. This is a very functional house with a chef's kitchen and beautiful stainless steel appliances. The house offers comfy sheets, thick towels and beauty surrounding in this space to be with friends and family. There are extra spaces and nooks to take in the world or relax and breathe.

Top guest favorite
Bungalow in Shoals
5 out of 5 average rating, 30 reviews

Solo or Couples' Cabin with Hot Tub

Welcome to Stillpoint Cabin at Atlas Views Resort! Perfect for a solo or romantic wellness-focused getaway, this modern cabin blends nature, comfort, and privacy in a peaceful wooded setting. 🆕 Newly built modern cabin 🛏️ 1 King bed | Sleeps 2 💦 Private hot tub + cold plunge 🔥 Fire pit & grill 🧖‍♀️ Access to shared sauna & resort pond 🌲 Woodland views in a quiet, private setting 🥾 Near Patoka Lake & Hoosier National Forest 📍 Just 10–15 minutes from French Lick & West Baden

Guest favorite
Two blue Adirondack chairs and a small table are positioned on a brick patio, overlooking a scenic river bordered by lush greenery and trees. The peaceful waters reflect the surrounding nature, providing a tranquil outdoor setting.
Home in Shoals
4.95 out of 5 average rating, 43 reviews

Scenic Escape

Enjoy your morning coffee with a scenic river view from the front deck and listen to the peaceful sounds of nature. Spend time with your loved ones around the fire pit or challenge them to a game of bumper pool in the sunroom. Located only 5 minutes from local restaurants and 25 minutes to French Lick. Perfect for fishermen with additional parking spot (17’x48’) for a small boat. The public ramp in Shoals and West Boggs Lake are only a short drive away.

Guest favorite
The exterior view showcases a two-story cottage with a symmetrical facade. A central entrance is framed by two tall support pillars. Windows with flower boxes are placed on either side, all surrounded by a well-maintained lawn and bare trees, highlighting the building's rustic charm.
Guest suite in Montgomery
4.95 out of 5 average rating, 37 reviews

Amish Country Cottage

Welcome to your serene retreat in Amish Country! Newly renovated, it offers modern comforts and rustic charm, ideal for relaxation. Enjoy the cozy living area and fully equipped kitchen. Step outside to watch horse-drawn carriages pass by and admire stunning sunset views. We can even help set-up a personal horse-drawn carriage ride for guests! Just let us know how we can help make your stay in Amish Country truly unforgettable!

Superhost
The property is surrounded by tall trees, providing a natural setting. The cabin features a unique architectural design with circular windows and a sloped roof, partially obscured by foliage. Leaves cover the ground, indicating the changing season.
Cabin in Loogootee
4.82 out of 5 average rating, 121 reviews

Peaceful Lake House Cabin 1, Direct Water Access!

This Cozy Cabin Duplex is located directly on West Boggs Lake, with a large, wrap-around, stationary dock to fish from, and multiple floating docks for your boat! Enjoy our kayaks, free with your stay, and explore all West Boggs has to offer! Cabin features 2 bedrooms with 2 Queen beds and a pull out sofa bed in the living room. Fully equipped kitchen, full bathroom, and an amazing deck for watching the sun set.

Guest favorite
A recreational area features a green indoor putting green, complemented by an American flag mounted on the wall. Nearby, a billiard table provides additional entertainment options. Natural light enters through windows, illuminating the spacious room with neutral-colored walls and a ceiling with visible metal panels.
Barn in Montgomery
5 out of 5 average rating, 6 reviews

Country Escape 2

3 bedroom, 2 bathroom pole barn home with indoor parking for your vehicle or boat. Spacious living area, bar seating and table for dining with full kitchen. Large game room with pool table, ping pong, putting green, weights, and large tv with couch. Would make a great rental for contractors or a small family. This unit could be rented separately or in addition to the other large family home on the property.

Superhost
A comfortable seating area features a large, dark fabric sofa with two decorative pillows. An armchair sits nearby. Natural light enters through a window with blinds, and a framed landscape artwork hangs on the wall, adding visual interest.
Home in Loogootee
4.77 out of 5 average rating, 150 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.

Top guest favorite
A wood-paneled sleeping area features a spacious bed with dark bedding and decorative pillows. A compact kitchenette area is equipped with a refrigerator, microwave, and sink, complemented by wooden cabinetry. Bright lighting is provided by recessed ceiling lights, enhancing the inviting atmosphere.
Guesthouse in Jasper
5 out of 5 average rating, 18 reviews

Oliver's Oasis

Keep it simple at this peaceful and centrally located place. Only a little over 30 miles to Holiday World, 20 miles to French Lick (water park, casinos), and 35 miles to Crane Naval Center. 4 miles from grocery shopping and local restaurants. You will have access to a washer / dryer. Country setting with city amenities.

Top guest favorite
A single-story house with a metallic roof is shown, featuring a two-car garage with two white doors. A small entryway is highlighted by a white door and a bench against the side, surrounded by green grass and trees in the background.
Home in Loogootee
4.87 out of 5 average rating, 208 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.

Guest favorite
A spacious living room showcases a large brown sectional sofa, complemented by a light wooden coffee table on an intricately patterned rug. Two lamps are placed on either side of the table, illuminating the area. Windows allow natural light to fill the room.
Home in Washington
4.93 out of 5 average rating, 110 reviews

3 bdrm, 2.5 bath, new rmdl, 7 recliners, 8 guests,

Nice 3 bedroom / full basement 2.5 bath completely remodeled home close to downtown and all area restaurants. well lit exterior and street area. Nice neighbors. Easily accessible from highway. Code lock on back door for easyheckin and entry.

Popular amenities for Montgomery vacation rentals

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