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
The single-story home features a charming yellow exterior, complemented by well-maintained grassy areas and large trees providing shade. A spacious driveway leads to a garage, while large windows allow natural light to enter the inviting interior.
Home in Huntingburg
4.99 out of 5 average rating, 153 reviews

Chestnut Street Retreat

A quaint and friendly neighborhood, with large backyard for kids playing, relaxing in the breeze way with morning coffee, or fun by the fire pit. Biking or walking around the neighborhood is safe and fun on a sunny day. Though you may feel in the country you are very close to downtown Huntingburg, 8 miles to Downtown Jasper. House is cozy and relaxing for a weekend away or if you're looking for activities Holiday World (18 Miles), Patoka Lake, French Lick Casino & West Baden Hotel (27 Miles).

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, 204 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 fireplace with a decorative screen is centered against a white brick wall, complemented by a large wall clock above. Two small windows on either side allow natural light to fill the space. A cozy seating area and television are positioned nearby.
Home in Washington
4.91 out of 5 average rating, 104 reviews

Cozy, 2 bdrm home. Weekly and monthly rates avail.

Our sparkling clean home is located in a great neighborhood in the heart of Washington, IN. Our small town boasts of 1) Multiple dining options, 2) Coffee shops, 3) Shopping and entertainment. Or if you are wanting something a little quieter and at home you will find a host of 4) Outdoor games, 5) Bikes, and more in the storage building out back. So whether you are here on vacation or business our goal is to make you comfortable and at home while you are in our area.

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, 18 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
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.

Top guest favorite
An outdoor deck features a rectangular table with a central hole for an umbrella, surrounded by four wicker chairs. Lush greenery and trees provide a natural backdrop, with a peaceful lake visible in the distance.
Cottage in Huntingburg
4.87 out of 5 average rating, 261 reviews

Lakeside Cottage Getaway Fishing, Hiking, Relaxing

Enjoy the lovely setting of this romantic spot in nature. This quiet getaway comes with a full kitchen, two bedrooms, access to a lovely lake, and an outdoor deck for enjoying the view. The master bedroom has a queen size bed and a crib. The second bedroom has a twin bed and a bunk bed [twin over full]. This space is perfect for singles, couples, or even large families. Close to Patoka Lake and Holiday World. No smoking/not handicap accessible

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, 188 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, 33 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, 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 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, 118 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 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, 189 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
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, 109 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.

Popular amenities for Montgomery vacation rentals

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  4. Daviess County
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