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

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

4.98 out of 5 average rating, 183 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 cozy master bedroom features warm wooden walls and ceiling, enhancing the natural ambiance. A king-size bed is adorned with a patterned blanket and complemented by wooden furniture. A mirror and map artwork are visible on the walls, with a small window allowing natural light to enter.

Loft in Huntingburg

4.93 out of 5 average rating, 223 reviews

Lovely Country Loft Lake, Hiking, Woods, Relaxing

Take it easy at this unique and tranquil getaway. This loft was made from wood sawn and milled on this farm. Enjoy Indiana hardwoods as they surround you in this space. Centrally located, you are not far from Holiday World, Jasper, Lincoln City, Patoka Lake and Historic Huntingburg. The Master Bedroom boasts a king-size bed. The living area has two twin beds, TV, WiFi and Kitchen. This space is perfect for singles, couples, or small families. Most love the spiral staircase and large deck.

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, 14 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 welcoming entryway features two white plastic chairs positioned by a small, wooden shelf. A potted plant sits atop the shelf, while a doormat with the word 'Welcome' greets guests. The floor is adorned with a blue and white chevron pattern, enhancing the airy space.

Apartment in Vincennes

4.8 out of 5 average rating, 46 reviews

1 Bedroom Apartment Unit 1

Private one bedroom one bathroom with large kitchen! Close to everything. Located 1 block from the library. 0.5 miles from Vincennes University. 0.9 miles to Good Sam. A hotel room with a full kitchen AND it’s cheaper. Fully equipped kitchen provides coffee pot, filters, paper towels, etc for easy use. Willing to accommodate pets for an additional fee of $25 for cleaning and count them as a guest ($10 per day). *Backyard is currently unavailable.

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, 169 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

4.93 out of 5 average rating, 30 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

4.81 out of 5 average rating, 118 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 bedroom features a king-size bed with light blue striped bedding and two bedside lamps. A wooden dresser and a small desk are visible. A light rug covers the hardwood floor, and artwork adorns the walls, enhancing the cozy ambiance.

Home in Bloomington

4.86 out of 5 average rating, 168 reviews

Great offer! Private entrance, Spacious, King-IU

Seasoned and experienced superhosts host this charming private suite with a private entrance. It has one bedroom with a king size bed. The house is on a very quiet street. You may not even know you're in the middle of town. You may see deer and other animals roaming around the neighborhood. The space includes private bathroom, kitchenette, and a sitting area with a loveseat and a small dining area.

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, 114 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.

Superhost

A spacious open-concept living area features a cozy seating arrangement with two plush sofas and a wooden coffee table. High ceilings are supported by exposed beams, and light fixtures provide a warm glow. The kitchen and dining area are visible in the background.

Loft in Washington

4.87 out of 5 average rating, 102 reviews

Lovely 3 bedroom loft apartment!

Welcome to The WrightAway! Enjoy a stylish experience at this centrally-located place. 2nd floor loft apartment. Private entrance. Close to restaurants and pubs. Nice three bedroom and two bathroom. Full kitchen. Free wifi. Off street parking available. Open concept with plenty of room for a family to gather or space out.

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, 107 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.