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 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.

Guest favorite
A cozy master bedroom features warm wooden walls and ceiling, enhancing the natural ambiance. A king-size bed is adorned with a patterned blanket and complemented by wooden furniture. A mirror and map artwork are visible on the walls, with a small window allowing natural light to enter.
Loft in Huntingburg
4.93 out of 5 average rating, 246 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.

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.

Top guest favorite
A living room area features a flat-screen TV positioned on a light-colored console. A comfortable armchair is situated nearby, complemented by a small side table. The room is illuminated with soft lighting, and a wooden door provides access to the exterior.
Bungalow in Linton
4.9 out of 5 average rating, 196 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.

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!

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.

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, 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.

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.

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
4.86 out of 5 average rating, 205 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.

Popular amenities for Montgomery vacation rentals

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