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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Top guest favorite
A gravel parking area is surrounded by lush trees, with a cabin visible in the background. Adirondack chairs are arranged around a fire pit in the foreground, creating a space for gathering. Bright blue skies with scattered clouds enhance the serene atmosphere.
Cabin in French Lick Township
4.99 out of 5 average rating, 239 reviews

Serenity Acres

Over 5 acres of pure serenity, just the sound of nature all around you! Beautiful Tucker Lake with hiking trail all around it just a mile away. This park like atmosphere has room for tents, RVs , boats, 4 wheelers and more. Just under 5 miles from the Fabulous French Lick and West Baden Resort town, but totally secluded.Cabin has two porches with rocker gliders and heavenly views. Cedar swing ,picnic table, fire pit with adirondack chairs for late night BBQs. Water park and boat rental, nearby

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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
4.86 out of 5 average rating, 29 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

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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, 177 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.

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Top guest favorite
A kidney-shaped in-ground pool is surrounded by a textured concrete deck, with built-in stairs leading into the shallow end. A slide stands nearby, and a white fence borders the yard. Lush greenery and a swing seat are visible in the background.
Home in Odon
4.97 out of 5 average rating, 36 reviews

Adorable Farmhouse in Odon

Bring the whole family to this great place with lots of room for fun. This newly remodeled house features 3 bedrooms, 2 full bathrooms, living room with a pull-out couch, a huge great room with a 75” TV, and a in-ground pool for fun and relaxation (pool open between Memorial Day and Labor Day). Walk across the street to the park for a nice stroll or let the kids play on the playground. Located in the heart of Amish country with great little shops. Crane Navel Base is only 10 minutes away

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Top guest favorite
A spacious game room features a red pool table alongside a round dining table. Bright lights illuminate the area, while a textured wall adds an element of depth. The room includes a seating area with benches and a few pieces of wall art, creating a relaxed atmosphere.
Home in Montgomery
5 out of 5 average rating, 25 reviews

Country escape with game room!

Very spacious with lots of space for the whole family to come and spend time together. Enjoy time by the fire in the unique patio grain bin, or in the basement game room playing board games, pool, or darts. Enjoy a meal in the large spacious kitchen with ample seating space for the whole family, 3 separate living areas with smart tvs. 4 full baths, Bedrooms include 2 king beds, 3 queens and possibly 3 or 4 twin beds in the basement game room storage area.

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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
4.94 out of 5 average rating, 47 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. Additional parking spot behind house (17’x48’) large enough for a small boat. The public ramp in Shoals and West Boggs Lake are only a short drive away.

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Guest favorite
Home in Elnora
4.85 out of 5 average rating, 62 reviews

The Manse: Family Friendly Home

Built as a parsonage next to an early 1900s Methodist church, this recently renovated house is an ideal family getaway. Plenty of space for meals, socializing, and resting. Individual temperature control (heating and cooling) in most of the rooms. • Close to I-69 • 20 minutes from Goose Pond Fish and Wildlife • 20 minutes from Crane Naval Base • 30 minutes from Green Sullivan State Forest • Just a few blocks from the White River Valley Antique Association

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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, 38 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!

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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, 124 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.

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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
4.76 out of 5 average rating, 153 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.

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Guest favorite
Home in Loogootee
5 out of 5 average rating, 7 reviews

Country Acres Retreat

Relax with the whole family at this beautiful, country setting. Located approximately 13 minutes from Loogootee & 14 minutes from West Boggs Lake. This house is nestled on a portion of the farm but has its own driveway and yard. Enjoy the farm activities in the surrounding area. There is NO TV, but rather are some games to enjoy.

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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
4.86 out of 5 average rating, 219 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.

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