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, 57 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

Guest favorite
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 favorite
Bungalow in Shoals
5 out of 5 average rating, 30 reviews

Solo or Couples' Cabin with Hot Tub

Welcome to Stillpoint Cabin at Atlas Views Resort! Perfect for a solo or romantic wellness-focused getaway, this modern cabin blends nature, comfort, and privacy in a peaceful wooded setting. 🆕 Newly built modern cabin 🛏️ 1 King bed | Sleeps 2 💦 Private hot tub + cold plunge 🔥 Fire pit & grill 🧖‍♀️ Access to shared sauna & resort pond 🌲 Woodland views in a quiet, private setting 🥾 Near Patoka Lake & Hoosier National Forest 📍 Just 10–15 minutes from French Lick & West Baden

Guest favorite
The exterior view showcases a newly renovated cottage with a modern facade. A set of steps leads to the entrance, framed by landscaped gravel and low-lying plants. A decorative wheel design is mounted on the wall, adding a rustic touch.
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
A circular stone fire pit is surrounded by grass, with a crackling fire at the center. Lush trees frame the background, and the serene lake is visible beyond the fire pit, reflecting soft light from the sky.
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 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.

Guest favorite
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.

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, 18 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, 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 favorite
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.

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, 52 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.

Top guest favorite
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 vacation rentals

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