Vacation rentals in Monroe County

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Top-rated vacation rentals in Monroe County

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Top guest favorite

A two-story farmhouse is set against a twilight sky, featuring a modern gray exterior with a metal roof. The front door is framed by large windows, and expansive greenery adds to the peaceful scenery, highlighting the spacious environment around the property.

Home in Tompkinsville

4.96 out of 5 average rating, 69 reviews

The Crossing

The newly renovated two bedroom farmhouse is located less than 2 miles from the city limits of Tompkinsville, KY and 3 miles from the Tompkinsville airport. Local attractions include the Old Mulkey Meeting House, restaurants, and a short drive to Dale Hollow Lake. The Crossing was built in the late 1890’s in the shape of a cross. The original house has stunning 9 foot ceilings and beautiful fireplaces in the four original rooms. Includes new appliances, Wi-Fi and outdoor space for dining.

Top guest favorite

A spacious outdoor deck features several red chairs facing a green metal barn exterior. The deck overlooks fields and trees in the distance, with two access doors leading into the apartment. The setting offers a glimpse of the rural landscape surrounding the farm.

Barn in Austin

4.98 out of 5 average rating, 403 reviews

Unique & Authentic Farm Experience

A truly one of a kind farmstead experience -stay in a newly constructed barn apartment on our 500 acre dairy farm. The Mattingly farm is home to Kenny's Cheese - farmstead cheese made right here onsite. This is a unique opportunity to stay in the heart of the action, in our modern apartments directly above the dairy barn. You will be welcomed by our friendly dairy cows and possibly a new baby calf or two. Simply because our cheese is AMAZING, we will leave some in the fridge for you to try!

Superhost

A spacious modern home features dark metal siding and multiple large windows. A covered porch is present at the front, with several chairs arranged for outdoor seating. The surrounding landscape includes grassy areas and trees, contributing to a rural charm.

Farm stay in Monroe County

4.83 out of 5 average rating, 35 reviews

New cozy home, real working farm

Beautiful brand new home on 93 acres allows breathtaking views of sunrises and sunsets across the pond and around the fire while allowing you to get away to country life. 40 minutes from Dale Hollow Lake, 35 minutes from Barren River Lake, 75 minutes from Lake Cumberland and 90 minutes from Nashville, this is the perfect location for your country getaway. Note: this is a real operating farm so please be cautious. Also, we welcome hunters but staying in our home does not grant access to hunt

Top guest favorite

A rustic cabin is framed by lush greenery, featuring a welcoming porch adorned with hanging plants. The green metal roof complements the warm wood exterior, while a meticulously landscaped garden with vibrant flowers enhances the inviting atmosphere.

Cabin in Tompkinsville

5 out of 5 average rating, 30 reviews

Pine Grove BNB

Located minutes from the heart of Tompkinsville, experience the charm of our renovated, early 1900's cabin that is professionally landscaped with ambient outdoor lighting. You'll feel miles away nestled among a historic pine grove overlooking more than 100 acres. A respite for those looking for adventure and R&R alike, we welcome anyone in search of a creative getaway, restorative time for themselves, & those wanting to escape to a curated & welcoming space to find a little peace & clarity.

Top guest favorite

A shallow creek flows gently through a wooded area, lined with trees. Smooth stones and pebbles are visible along the water's edge. A person stands mid-stream, with water reflecting the surrounding greenery. Soft light filters through the leaves, creating a peaceful ambiance.

Home in Summer Shade

4.99 out of 5 average rating, 74 reviews

Quiet country farmhouse near creek

Make some memories at this unique and family-friendly place. Located on our family farm and on Skaggs Creek. Enjoy country living and the beauty the creek has to offer. During the late summer you can enjoy the bounty of our family garden. From any direction you are about 45 mins from Bowling Green, Barren River lake, Dale Hollow Lake, and Mammoth Cave; and about 1.5hrs from Nashville. Or choose to stay close and enjoy the local arts and theater! This home is located on a family farm.

Superhost

A charming country tiny house is presented with a welcoming porch, adorned with string lights and surrounded by greenery. A well-maintained gravel path leads to the entrance, while a small fire pit and a grill are visible in the front yard.

Tiny home in Fountain Run

4.89 out of 5 average rating, 64 reviews

Tiny House Country Cabin, Private, Clean, Cozy!

Country Tiny House with a complete mini kitchen and full-size fridge, full bathroom with shower, and double sleeper sofa downstairs. Upstairs is a loft with a big king bed, a single daybed with a trundle bed. Can sleep up to 6. electric fireplace, air, and heat. All linens and bedding included. Full-size fridge, microwave, kuirig coffee maker, and toaster, cookware, charcoal grill. Free Wifi. Parking close to cabin. Complimentary homemade cinnamon rolls on your first morning!

A cabin exterior is displayed, featuring a simple log railing at the entrance. The metal siding has a muted tone, and a small air conditioning unit is visible. Sunlight brightens the area, highlighting the grassy surroundings and the welcoming front door.

Cabin in Tompkinsville

5 out of 5 average rating, 3 reviews

Wild West Cabin

Relax with the whole family at this peaceful cabin next to our lake! Sleeping 5-6, enjoy the multiple fishing ponds, paddle boats, kayaks and side by sides! All Included in this package deal! In this cabin, there is 3 beds, 1 bath and a futon! You will have full access to the cabin, pond and other areas while staying in your location. There is multiple cabins/houses at this location, be aware some places are shared with other guests. Fishing is catch and release!

Top guest favorite

A charming farmhouse is presented with a classic design and a metal roof. The front porch features seating arrangements, surrounded by neatly landscaped greenery. Large windows allow natural light to enter, while a swing chair invites relaxation. A peaceful setting is emphasized by the surrounding landscape.

Home in Monroe County

4.96 out of 5 average rating, 24 reviews

The Howard House at Miller Farms

This adorable farmhouse is for those seeking a quiet spot to unplug and rejuvenate on a beautiful farm in Southern Kentucky. There is a gorgeous farm view from the porch swing. This is the perfect place to enjoy the sound of crickets and the night starlight. An ideal retreat for families, individuals, couples, or friends. We can’t wait to share our corner of the world with you. *This is a working farm so please be cautious with animals and moving equipment.*

Top guest favorite

An open concept living space showcases a cozy seating area with a beige couch and stone fireplace. A large area rug adds warmth to the wooden floor, while a wooden dining table with chairs can be seen in the background, adjacent to the well-equipped kitchen.

Home in Fountain Run

5 out of 5 average rating, 41 reviews

Charming Cabin in the Hollow

Come stay in our peaceful setting located between a creek and a spring, down in the holler! Once inside, enjoy the space we have worked hard to create. The main floor is open concept through from the living room to dining and kitchen. The master bedroom is complete with its own bathroom and tile shower! A unique floating staircase reaches up to the loft area where a large sitting room and dorm style sleeping area combine. Lots of room to play games!

Guest favorite

The historic two-story brick house is framed by a well-maintained lawn featuring a variety of shrubs and flowers. A covered porch extends across the front, marked by white rocking chairs and supported by large columns, inviting relaxation in the shade.

Home in Tompkinsville

4.89 out of 5 average rating, 82 reviews

Unique 1805 Historical House

The Old Brick House is located within minutes of Tompkinsville. It is situated on 3 acres of land where you can hear the sound of tree frogs at night and the creek running across the road. This property is well shaded with lots of outdoor space perfect for a quiet get a way for couples or families. This home can sleep six individuals comfortably. So if you are looking to relax & enjoy some history, please come stay at The Old Brick House.

Top guest favorite

The exterior of a Victorian-style house is showcased, featuring intricate architectural details and a blue facade. The home is surrounded by a manicured lawn and small shrubs, with a welcoming porch and decorative gables highlighted above the entrances.

Home in Gamaliel

4.98 out of 5 average rating, 101 reviews

The Jackson House of Gamaliel

Stay at The Jackson House of Gamaliel. The Victorian style house was originally built in 1904 and underwent a total remodel in 2017. You will be the only guests in the house. One King bed, two Queen beds and a sofa sleeper. Kitchen with all cooking utensils, a laundry room and a large living area. Convenient to Dale Hollow Lake and Barren River Lake, (Approx 30-45 minutes). Near Old Mulkey Meeting House State Park.

Top guest favorite

The exterior of the lakehouse is displayed, featuring a two-story structure with a brown roof and light-colored siding. A spacious front porch is highlighted by wooden beams, while surrounding trees showcase autumn foliage. The driveway is lined with large rocks, enhancing the natural setting.

Home in Tompkinsville

5 out of 5 average rating, 8 reviews

Limestone Lakehouse at the Cove

Relax with the whole family at this peaceful place to stay. This Lakehouse has a beautiful view of the lake from the back porch with a primitive firepit in the woods. The house will sleep 14 (2 full size beds in the finished basement, two king and one full bedroom). The loft is perfect for children with 4 twin beds. The lake offers great fishing and kayaking and there is an abundance of wildlife.