Holiday rentals in Montgomery

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Top-rated holiday rentals in Montgomery

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
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
4.85 out of 5 average rating, 27 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 favourite
The exterior of the cabin showcases a rustic log structure with a green metal roof, surrounded by lush greenery. Two wooden rocking chairs with colorful cushions are positioned on the porch, inviting relaxation. Large windows provide a glimpse of the peaceful woodland setting.
Cabin in Nashville
4.96 out of 5 average rating, 123 reviews

Red Cedar Log Cabin | Romantic + Hot Tub

Cozy, secluded, and full of charm, Red Cedar Log Cabin is the perfect Brown County getaway for couples. Soak in the private hot tub, unwind by the wood-burning fireplace, and enjoy the peaceful wooded setting. With rustic character, modern comforts, and easy access to Nashville, trails, shops, and local dining, this cabin is made for quiet mornings, cozy nights, and unforgettable weekend escapes. Book your stay and experience Brown County at its coziest.

Top guest favourite
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, 198 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 favourite
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, 121 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 favourite
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.

Guest favourite
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
4.84 out of 5 average rating, 120 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.

Guest favourite
The interior cabin space features rustic wooden beams, a large clock on the wall, and a comfortable seating area with a view of the surrounding nature. A cozy carpet lies beneath a spacious area, providing a warm spot for relaxation.
Cabin in Paoli
4.97 out of 5 average rating, 110 reviews

Patoka River Hideaway

Take it easy at this cabin in the woods! If you are looking for a peaceful getaway nestled in the woods, you have found it! Located between Paoli and English this cabin sits back in the woods where you can see and hear the Patoka River flowing through. Sit out on the deck and enjoy our hot tub or firepit and relax! Enjoy your stay as a couple or small group to unplug and reconnect.

Top guest favourite
A secluded cabin is set against a backdrop of trees, featuring a metal roof and a covered porch with multiple seating areas. Well-maintained grass surrounds the cabin, and landscaping elements provide a welcoming appearance.
Cabin in French Lick
4.95 out of 5 average rating, 298 reviews

Wildcat Cove Lodge

Secluded on 10 acres with plenty of room for boats and turn around . Three bedroom with open living room and kitchen with Island seating . 4 TVs with satellite . Gas fireplace , Whirlpool tub in Master . Two porches with additional Shelter House . Large Laundry Room . Close to French Lick and Patoka Lake .

Top guest favourite
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, 208 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 favourite
A spacious living room showcases a large brown sectional sofa, complemented by a light wooden coffee table on an intricately patterned rug. Two lamps are placed on either side of the table, illuminating the area. Windows allow natural light to fill the room.
Home in Washington
4.93 out of 5 average rating, 110 reviews

3 bdrm, 2.5 bath, new rmdl, 7 recliners, 8 guests,

Nice 3 bedroom / full basement 2.5 bath completely remodeled home close to downtown and all area restaurants. well lit exterior and street area. Nice neighbors. Easily accessible from highway. Code lock on back door for easyheckin and entry.

Top guest favourite
A spacious barn structure features a peaked roof and large double doors, set against a backdrop of lush greenery. The area around the barn is landscaped with grass and trees, contributing to a serene rural environment.
Farm stay in Odon
4.98 out of 5 average rating, 57 reviews

The Barn

Cozy waterfront home in peaceful, scenic Amish country. Approximately two miles from Interstate 69. Visit from April through August to observe our purple Martin colony. Close to White River Valley Antique Show.

Popular amenities for Montgomery holiday rentals

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