Vacation rentals in Montgomery

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Top-rated vacation rentals in Montgomery

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Guest favorite

A spacious basement recreation area is showcased, featuring a ping pong table, pool table, and air hockey table. The flooring is wood-like, and walls are adorned with framed photos. Soft lighting enhances the inviting atmosphere, while stairs lead up to the main level.

Home in Newberry

4.93 out of 5 average rating, 14 reviews

Bear Hollow

Visiting NSA CRANE or Westgate for work? Traveling Nurse? Family time? Escape to our country getaway near Crane, Indiana on a beautiful rolling alfalfa field and woods. Enjoy stunning views from the walkout deck with a fire pit, fast internet, and dedicated telework desks throughout the house. Basement features an air hockey, ping pong, pool table, and a retro game room with basketball arcade. Relax with 65 inch TVs or unwind at the coffee bar. Serene surroundings make this the perfect retreat!

Top guest favorite

A wooden cabin is showcased with a welcoming front porch featuring railing and seating. The entrance is accessible by steps, and a mountain-themed sign is displayed above the door. Natural surroundings enhance the rustic charm of the structure.

Cabin in French Lick Township

4.99 out of 5 average rating, 147 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 serene view of a pond surrounded by lush greenery and tall trees. A gentle slope leads to the water’s edge, where a boat is anchored. The sky captures shades of pink and blue as the sun sets, providing a peaceful atmosphere.

Loft in Huntingburg

4.92 out of 5 average rating, 192 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.

Guest favorite

Yurt in French Lick

4.93 out of 5 average rating, 123 reviews

Luxury Glamping - Waterfront Yurt with WiFi

Retreat to the hills of French Lick in The Lazy Creek Yurt. Inside the front door you will find modern amenities including full bathroom, full kitchen, and satellite TV. You're sure to stay warm with radiant floor heating and full hvac system. Start your day off with a warm beverage or breakfast overlooking the private pond. Located in a secluded setting yet only 5 miles from downtown French Lick, winery, restaurants, and casino. Please note the yurt does not have Wifi.

Guest favorite

A dining area features a rectangular wooden table surrounded by six black chairs. A modern chandelier hangs above the table, while a brick fireplace is set against a dark mantel. Light-colored walls and warm wooden flooring contribute to the space's inviting atmosphere.

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.

Guest favorite

Two egg cartons rest on a wooden surface, each containing a variety of eggs in different shades. One carton features beige, brown, and green eggs, while the other is filled primarily with lighter blue and tan eggs, reflecting the organic nature of the surroundings.

Guesthouse in Dubois

4.84 out of 5 average rating, 89 reviews

Rural Studio Guest-house Overlooking Corn Fields

Relax with the family on this peaceful country-side hill in Dubois, Indiana. 17 minutes to Jasper and 17 minutes to French Lick. Patoka Lake is nearby, as well as attractions like Holiday World in Santa Claus, West Baden Casino & Resort, Big Splash, indoor karting, mini-golf, and small-town restaurants. You'll find necessities nearby, including a Walmart. We always have fresh, multicolored eggs to sell from our chickens who are also fed organically.

Guest favorite

A serene view of Lake Harvey is presented, with calm water reflecting the surrounding lush greenery. Trees border the lake, creating a natural frame. The scene captures a peaceful atmosphere, ideal for nature enthusiasts seeking tranquility.

Bungalow in Linton

4.9 out of 5 average rating, 157 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

A spacious garage features two large white doors, providing ample room for parking vehicles. The floor is smooth and concrete, and a doorway is visible in the background, leading to the exterior of the home. The space is well-lit, enhancing visibility.

Home in Loogootee

4.86 out of 5 average rating, 141 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

A bathroom featuring a freestanding clawfoot tub positioned against a neutral wall. Elegant white towels are neatly arranged nearby. Above, a decorative chandelier hangs gracefully, complemented by a framed floral artwork. A small metal stand holds rolled towels, enhancing the space's classic appeal.

Guest suite in Montgomery

4.93 out of 5 average rating, 15 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, 114 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.

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Other great vacation rentals in Montgomery

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, 4 reviews

Country escape with game room!

RobertRating, 5 stars4 days ago

It was a great stay for our large family for a wedding! Kids loved the game room and the house layout felt roomy for everyone!

Guest favorite

A wooden world map is mounted on a blue wall, showcasing detailed geographical features. The map features engraved country names and borders, with a compass rose in the corner. The natural wood finish contrasts with the wall color, adding warmth to the space.

Cabin in Shoals

4.86 out of 5 average rating, 7 reviews

Secluded Cabin w/ Hot tub near French Lick, IN

JohnRating, 5 stars5 days ago

What great place to stay! Centrally located to so many cool destinations in Southern Indiana. The home is clean, beds are comfortable, and the setting is private. Kitchen fully equipped. Enjoyed the hot tub and listening to a huge variety of birds. We would highly recommend!

Guest favorite

A compact bathroom area is featured, showcasing a clean white toilet positioned beside a wooden storage cabinet with sliding doors. The cabinet has open shelves displaying decorative items. Natural light enters through a window with vertical blinds, illuminating the neutral tones of the space.

Tiny home in Hymera

4.94 out of 5 average rating, 17 reviews

North St Retreat No Cleaning Fee

JonathanRating, 5 stars4 months ago

It was a great place with a great host

An airy loft space features a sloped wooden ceiling with natural wood paneling. A cozy area is set up with a plush covering and a twin bunk bed. Light from multiple windows illuminates the room, creating a bright and inviting atmosphere.

Cabin in Loogootee

4.77 out of 5 average rating, 53 reviews

Truelove Chalet - Rustic, Glam Cabin Retreat!

LeslieRating, 5 stars1 week ago

We had a great time! Super clean and very comfy. We absolutely loved the cabin. We saw a fox, out front, trotting down the road. We also deer and turkeys by the backyard pond. We will definitely book again!

Top guest favorite

The living area features solid wood flooring and a ceiling fan. A large smart TV is positioned opposite two comfortable sofas and a coffee table. Natural light enters through the windows, which are partially covered by blinds. A dining area is visible in the background.

Home in Vincennes

5 out of 5 average rating, 17 reviews

Home in cozy neighborhood

NinaRating, 5 stars1 week ago

Our family had a wonderful stay ❤️ this is a Beautiful home. Thank you again Carolina

Top guest favorite

Home in Washington

4.86 out of 5 average rating, 7 reviews

Sonny’s place

RoxanneRating, 5 stars1 week ago

What a thoroughly delightful home, it felt like a sweet little cocoon of comfort and rest. This charming home is cozy and comfortable, feels like a hug. The property has peaceful green space, and a delightful patio with a grill and a swing. It was exactly what we needed for a retreat! Tom and Trina were quick to respond and resolve a small problem we had with the coffee maker, and it 'saved the day' for us! I highly recommend this adorable property to anyone who needs a pleasant, 'homey' retreat!

Guest favorite

Cabin in Linton

5 out of 5 average rating, 7 reviews

The Handcrafted Hideaway

BobbiRating, 5 stars5 days ago

My husband and I enjoyed a weekend at Susannah’s with our adult children. It is spacious, clean and well stocked. Our favorite parts were the wrap around porch (with a lovely swing and nice big table for family breakfast), games and being able to fish and drop our kayaks in right there on the property. We will definitely be back!

A white picket fence encloses the pool area, prominently displaying a warning sign indicating no lifeguard on duty. The sign features bold blue and red text, contrasting against the fence's bright surface, with grass visible beyond the fence.

Home in Odon

5 out of 5 average rating, 4 reviews

Adorable Farmhouse in Odon

LeneseRating, 5 stars2 months ago

Chris' house in Odon, IN exceeded our expectations in every way! The home was immaculate, comfortable, and perfectly suited our needs. Chris was a wonderful host, and we truly appreciated his hospitality. We'd highly recommend his house to friends and family. It's a perfect getaway spot! We can't wait to return!

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Vacation rentals in Montgomery

Top-rated vacation rentals in Montgomery

Vacation rentals for every style

Popular amenities for Montgomery vacation rentals

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