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, 165 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

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, 121 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 modern living area features a cozy sofa and an accent chair on a patterned rug. A television sits atop a dark cabinet, with decorative artwork on the walls. Soft lighting is provided by pendant lights hanging from the ceiling.

Loft in Paoli

4.94 out of 5 average rating, 140 reviews

Aloft

Aloft is located on the edge of the Hoosier National Forest, minutes from hiking trails and Ski Paoli Peaks. Located about 20 minutes from French Lick Resort and Casino, Patoka Lake, Marengo Cave and Cave Country Canoes. You’ll love the loft because of the country setting, nestled in the trees. The loft is very comfortable and offers peace and quite with a contemporary, calming atmosphere. The loft is great for couples, solo adventurers, business travelers, and families (with kids).

Guest favorite

A modern kitchen space features natural wood cabinetry and a brick fireplace. A round dining table with black chairs is positioned centrally. A retro clock adorns the dark-painted chimney. Natural light filters through the window, accentuating the welcoming atmosphere of the area.

Home in Montgomery

4.95 out of 5 average rating, 22 reviews

Home near Dogwood lake/Glendale

Gorgeous newly-renovated property built In 1850. Legend has it, Abraham Lincoln once stayed in the home when he visited this area! With only a few minutes drive to Dogwood Lake and Glendale Fish & Wildlife area, this home is perfect for your next getaway with friends, or that peaceful vacation. You are able to utilize the entire property, there is plenty of space to park vehicles or boats. We are located 8 miles from I69 and the town of Washington.

Guest favorite

This open living space features a kitchenette with light gray cabinets and a white refrigerator. A cozy dining table sits beside a comfortable couch, while a spacious bed is positioned in the background. Warm wood flooring enhances the inviting atmosphere.

Guesthouse in Dubois

4.86 out of 5 average rating, 102 reviews

Rural Studio Guest-house Overlooking Corn Fields

Relax with the family on this peaceful country-side hill in Dubois, Indiana. 17 minutes to Jasper and 17 minutes to French Lick. Patoka Lake is nearby, as well as attractions like Holiday World in Santa Claus, West Baden Casino & Resort, Big Splash, indoor karting, mini-golf, and small-town restaurants. You'll find necessities nearby, including a Walmart. We always have fresh, multicolored eggs to sell from our chickens who are also fed organically.

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, 8 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 4 twin beds in the basement game room storage area.

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

4.85 out of 5 average rating, 156 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. PLEASE READ! Due to a recent storm, the back fence was damaged and has been removed and we are waiting for the new fence to be installed.

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, 22 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, 117 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 spacious living area features a large sectional sofa in warm brown tones, complemented by decorative throw pillows. A coffee table with a dark finish occupies the center, while natural light filters through sheer curtains, creating a bright and comfortable environment.

Home in Loogootee

4.86 out of 5 average rating, 106 reviews

Covel’s Cottage 3br easy checkin great location

Your family will be close to everything when you stay at this centrally-located place. Less than 1 mile from restaurants, gas stations, and grocery. The kitchen is fully stocked with condiments, Spices, coffee and cookware plates etc. there are two queen rooms and a room with two singles. The back yard has a charcoal grill, a large deck with table and a fun treehouse for the kids.