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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Guest favorite

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

4.86 out of 5 average rating, 29 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

LocationValueCheck-in

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

4.87 out of 5 average rating, 47 reviews

Bear Hollow

Work Travel? IU Football Game? Family time? Escape to our country getaway near Crane, IN 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! 25 Minutes from Bloomington!

LocationFamilyLayout

Superhost

A kidney-shaped in-ground pool is surrounded by a textured concrete deck, with built-in stairs leading into the shallow end. A slide stands nearby, and a white fence borders the yard. Lush greenery and a swing seat are visible in the background.

Home in Odon

4.97 out of 5 average rating, 37 reviews

Adorable Farmhouse in Odon

Bring the whole family to this great place with lots of room for fun. This newly remodeled house features 3 bedrooms, 2 full bathrooms, living room with a pull-out couch, a huge great room with a 75” TV, and a in-ground pool for fun and relaxation (pool open between Memorial Day and Labor Day). Walk across the street to the park for a nice stroll or let the kids play on the playground. Located in the heart of Amish country with great little shops. Crane Navel Base is only 10 minutes away

ValueLocationBackyard

Superhost

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.

ValueLocationAir conditioning

Superhost

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

5.0 out of 5 average rating, 25 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.

LocationFamilyAccess

Guest favorite

Two blue Adirondack chairs and a small table are positioned on a brick patio, overlooking a scenic river bordered by lush greenery and trees. The peaceful waters reflect the surrounding nature, providing a tranquil outdoor setting.

Home in Shoals

4.94 out of 5 average rating, 47 reviews

Scenic Escape

Enjoy your morning coffee with a scenic river view from the front deck and listen to the peaceful sounds of nature. Spend time with your loved ones around the fire pit or challenge them to a game of bumper pool in the sunroom. Located only 5 minutes from local restaurants and 25 minutes to French Lick. Additional parking spot behind house (17’x48’) large enough for a small boat. The public ramp in Shoals and West Boggs Lake are only a short drive away.

LocationFamilySleep quality

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

4.95 out of 5 average rating, 38 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!

ValueLocationKitchen

Top guest favorite

The charming exterior of a large, two-story house is shown, featuring a classic design with a prominent gabled roof and a welcoming porch. Lush green grass surrounds the property, complemented by manicured shrubs and trees, against a backdrop of blue skies and scattered clouds.

Home in Odon

5.0 out of 5 average rating, 35 reviews

Heritage Homestead Inn

Bring the whole family to the Heritage Homestead Inn. We have plenty of space for friends and family. We have 2 large kitchens and 3 different living areas. This is a great home for family, outings, bachelorette parties, youth retreats, etc. We have 2 full kitchens and 3 separate living areas so there is room for everyone. We have enough rooms for nearly 30 people. Conveniently located in the heart of Daviess County Indiana.

LocationFamilyHospitality

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, 125 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.

LocationValueSleep quality

Superhost

A bathroom is displayed with a vintage dresser and a mirror against a light-colored wall. A shower curtain with a floral pattern is visible, along with neatly stacked towels hanging nearby. A wastebasket sits on the floor, complementing the earthy tones of the room.

Home in Loogootee

4.84 out of 5 average rating, 128 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.

LocationValueOutdoor spaces

Guest favorite

Home in Loogootee

4.88 out of 5 average rating, 8 reviews

Country Acres Retreat

Relax with the whole family at this beautiful, country setting. Located approximately 13 minutes from Loogootee & 14 minutes from West Boggs Lake. This house is nestled on a portion of the farm but has its own driveway and yard. Enjoy the farm activities in the surrounding area. There is NO TV, but rather are some games to enjoy.

LocationCleanlinessIndoor spaces

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, 219 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.

LocationFamilySleep quality