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 out of 5 average rating, 62 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

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, 231 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 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, 28 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

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, 169 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.

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, 21 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.

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, 37 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, 123 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 bathroom is displayed with a vintage dresser and a mirror against a light-colored wall. A shower curtain with a floral pattern is visible, along with neatly stacked towels hanging nearby. A wastebasket sits on the floor, complementing the earthy tones of the room.
Home in Loogootee
4.84 out of 5 average rating, 123 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.

Top guest favorite
Bungalow in Shoals
5 out of 5 average rating, 33 reviews

Solo or Couple's Hot Tub Retreat

Welcome to Stillpoint Cabin at Atlas Views Resort, a newly built private couples cabin made for quiet mornings, slow evenings, and a peaceful reset in nature. Enjoy 1 king bed, a private hot tub and cold plunge, fire pit, grill, shared outdoor sauna, resort pond access, and quiet woodland views. Near Patoka Lake, Hoosier National Forest, French Lick, and West Baden.

Top guest favorite
A wood-paneled sleeping area features a spacious bed with dark bedding and decorative pillows. A compact kitchenette area is equipped with a refrigerator, microwave, and sink, complemented by wooden cabinetry. Bright lighting is provided by recessed ceiling lights, enhancing the inviting atmosphere.
Guesthouse in Jasper
5 out of 5 average rating, 20 reviews

Oliver's Oasis

Keep it simple at this peaceful and centrally located place. Only a little over 30 miles to Holiday World, 20 miles to French Lick (water park, casinos), and 35 miles to Crane Naval Center. 4 miles from grocery shopping and local restaurants. You will have access to a washer / dryer. Country setting with city amenities.

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
4.87 out of 5 average rating, 209 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.

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, 55 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.

Popular amenities for Montgomery vacation rentals

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