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
Cabin in Linton
5.0 out of 5 average rating, 68 reviews

The Handcrafted Hideaway

Take the back road and come stay at The Handcrafted Hideaway. Our cabin is surrounded by woods,lakes,and wild pampas grass. We are located 1.5 mile from Red Bird Off-roading State recreation area and 5 miles from Green Sullivan State Forest. Spend your day relaxing on the front porch, fishing from one of the 2 docks on the property, or bring your off-road vehicle along and head for adventure at Red Bird! We have a fire ring in the backyard-ready for relaxing evening campfires and story telling

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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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Guest favorite
Guesthouse in Newberry
4.92 out of 5 average rating, 26 reviews

Spring Haven Farm

Come to the country and enjoy a peaceful setting at this guest house. Located approximately •10 minutes from I-69, •15-20 minutes from Odon, Crane & Bloomfield. On the farm are some friendly Jersey cows, which you may get a chance to pet. A few lawn chairs are provided to enjoy the deck outside. There is no TV, but rather some card and board games inside for a great family night together! We strive to keep it a clean and happy place, and if there is anything we missed, Contact us!

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Guest favorite
A spacious basement recreation area is showcased, featuring a ping pong table, pool table, and air hockey table. The flooring is wood-like, and walls are adorned with framed photos. Soft lighting enhances the inviting atmosphere, while stairs lead up to the main level.
Home in Newberry
4.89 out of 5 average rating, 44 reviews

Bear Hollow

Traveling for work? Traveling Nurse? Family time? Escape to our country getaway near Crane, Indiana on a beautiful rolling alfalfa field and woods. Enjoy stunning views from the walkout deck with a fire pit, fast internet, and dedicated telework desks throughout the house. Basement features an air hockey, ping pong, pool table, and a retro game room with basketball arcade. Relax with 65 inch TVs or unwind at the coffee bar. Serene surroundings make this the perfect retreat!

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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
5.0 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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Top guest favorite
Home in Shoals
4.97 out of 5 average rating, 37 reviews

Lakefront Cabin - Hot Tub, Cold Plunge, & Sauna

Emerge Cabin at Atlas Views Resort: a newly built lakefront wellness cabin designed for a private reset in nature. Features 2 king beds, a private hot tub, a fire pit, a grill, a shared sauna, and pond access. Enjoy serene water views from floor-to-ceiling windows. Comfortably fits 4 guests. Minutes from Patoka Lake, Hoosier National Forest, and French Lick. Perfect for slow mornings & quiet evenings in a secluded, modern retreat.

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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
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, 218 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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Guest favorite
An open living space features exposed brick walls and hardwood flooring, creating a warm aesthetic. A comfortable sectional sofa is arranged around a dark coffee table, while a modern kitchen with granite countertops and stainless steel appliances is visible in the background.
Apartment in Washington
4.98 out of 5 average rating, 59 reviews

Livery Lofts Downtown 1BR w/sleep sofa 406-2

Completely renovated luxury apartment in downtown Washington. Heated bathroom floor, Bluetooth Shower with body jets, granite countertops, Casper mattress and washer/dryer. Steps away from all downtown amenities.

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