Vacation rentals in Montgomery

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Montgomery

Guests agree: these stays are highly rated for location, cleanliness, and more.

1 of 1 pages1 / 1
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, 28 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
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, 34 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

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, 20 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
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
4.95 out of 5 average rating, 44 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. Perfect for fishermen with additional parking spot (17’x48’) for a small boat. The public ramp in Shoals and West Boggs Lake are only a short drive away.

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, 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!

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 out of 5 average rating, 31 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.

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, 122 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.

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, 122 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
Bungalow in Shoals
5 out of 5 average rating, 32 reviews

Solo or Couple's Hot Tub Retreat

Welcome to Stillpoint Cabin at Atlas Views Resort, a newly built private couples cabin made for quiet mornings, slow evenings, and a peaceful reset in nature. Enjoy 1 king bed, a private hot tub and cold plunge, fire pit, grill, shared outdoor sauna, resort pond access, and quiet woodland views. Near Patoka Lake, Hoosier National Forest, French Lick, and West Baden.

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, 19 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, 209 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, 112 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

  1. Airbnb
  2. United States
  3. Indiana
  4. Daviess County
  5. Montgomery