Vacation rentals in Montgomery

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Top-rated vacation rentals in Montgomery

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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, 222 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

Guest favorite
A modern living space is highlighted by a dark sectional sofa and a plush armchair. Sunlight filters through large windows, brightening the wood-style flooring. A small dining area is seen in the background, featuring high-backed chairs and a countertop near the entrance to the balcony.
Apartment in French Lick
4.93 out of 5 average rating, 225 reviews

French Lick, Luxury Downtown Suite 315

This cozy, newly remodeled townhouse apartment is perfect for a family getaway, bachelorette/bachelor parties, or even your next golf trip. Centrally located in downtown in French Lick, IN. Directly across the street from the French Lick Resort & Casino! Accessible parking, within walking distance to shops, restaurants, and bars. Stay with us and receive 10% off your meal at Legendz Sports Bar & Grill, open seven days a week and features live music/karaoke and DJ every Friday & Saturday night.

Guest favorite
A living area is displayed with a comfortable sofa and patterned armchairs, offering spaces for relaxation. Natural light enters through large windows, illuminating the wood-beamed ceiling and highlighting the rustic wooden accents. A small table and television are positioned for convenience.
Bungalow in Bloomington
4.98 out of 5 average rating, 123 reviews

Cheerful two bedroom Farmhouse with free parking

Your family will be located in a lovely Bloomington rural setting that is less than 10 miles from Indiana University and less than 5 miles from beautiful 10,750 acre Lake Monroe. You will be able to unwind on the front porch swing, relax on the spacious back deck or warm your hands and feet by the fire pit provided. If you are a foody you are within 10 to 15 minutes from the many Bloomington restaurants or if you prefer the cooking option there is a full kitchen for your culinary creativity.

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, 161 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.

Guest favorite
A fire pit surrounded by gravel is lit, featuring logs crackling in the center. Two colorful Adirondack chairs in red and teal are positioned invitingly nearby, with trees and greenery visible in the background, creating a serene outdoor atmosphere.
Home in French Lick
4.96 out of 5 average rating, 318 reviews

Caddy Corner has a hot tub just outside of town

Caddy Corner is a 1920s schoolhouse converted into a modern farmhouse. Enjoy a country feel while being just over a mile from everything that French Lick and West Baden have to offer. Escape to our hot tub after a day in town, and let your cares drift away. Relax on our American-made upholstered furniture, dine at our table made by a local artisan, and find slumber on our plush euro top mattresses. If you are into cooking, our kitchen is well stocked, just like home.

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
4.94 out of 5 average rating, 36 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!

Guest favorite
A spacious living area features large windows with arches, allowing natural light to illuminate the room. A comfortable sofa and wooden coffee table are present, along with a dining table and two chairs. Decorative vines adorn the walls, enhancing the inviting atmosphere.
Apartment in Bloomfield
4.83 out of 5 average rating, 115 reviews

1 Bedroom Apartment Overlooking Courthouse Square

Cozy, downtown apartment overlooking the Courthouse on the square in Bloomfield. Located approximately 25 minutes from Crane Naval Base, this apartment is perfect for contractors or attorneys in the area on work or anyone visiting family or friends in the Bloomfield area. The Kitchen is fully functional with necessary cookware, dishes and utensils. Beautiful view of the Courthouse. Cheaper than the Hotels near Crane!

Guest favorite
A solid brick farmhouse is set on a gentle knoll, surrounded by greenery. The house features large windows and a stone chimney, complemented by a nearby garage. The gravel path leads up to the home, offering a clear view of the surrounding landscape.
Home in Bloomington
4.91 out of 5 average rating, 104 reviews

Harmony Hills 3 bedroom farm house

This 1970s brick farmhouse on 60 acres of pasture, forest, and stream offers a cozy “grandma’s house” vibe. Enjoy 3 beds, plus pullout sofa, 2 baths, and a basement with washer/dryer. Brick walls keep it quiet despite nearby highway noise. Outside, a roofed deck with grill and a campfire ring with firewood await, lit by string lights for cozy nights. Just 20 min from IU, it’s a serene escape for families or nature lovers.

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, 119 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.

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, 149 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 spacious living area features a high stone fireplace, complemented by a large television mounted above. A modern dining table with dark chairs is positioned in front, while large windows allow natural light to fill the room. The ceiling fan adds to the openness.
Home in Birdseye
4.96 out of 5 average rating, 213 reviews

Country Getaway

Relax with scenic views of the adjacent national forest, enjoy the stars near the pond at night, or explore popular nearby destinations. Nearby Attractions: - Hoosier National Forest -Hiking/Horse riding trails. (Trail Head 5 min walk) - Patoka Lake and recreational area (10 Min.) - Frenck Lick Casinos and Resorts /Winery (20 min) -Marengo Caves (20 min) -Holiday World Theme Pak (25 min)

Guest favorite
A welcoming wooden sign stands in front of a cabin surrounded by lush greenery. The cabin features a broad porch and a gabled roof, with large windows allowing for natural light. A gravel driveway leads up to the entrance, enhancing the serene forest setting.
Cabin in Birdseye
4.9 out of 5 average rating, 175 reviews

Cozy cabin close to Patoka Lake main entrance!

Inviting, private cabin close to Patoka Lake main entrance, near restaurants, boat rental and so much more! Nestled in the woods this cabin includes screened in porch, full size washer and dryer and fully equipped kitchen. Relax with the whole family at this peaceful place to stay. Including park pass available during your stay.

Popular amenities for Montgomery vacation rentals

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