Holiday houses in Oak Grove

Downtown Luxury 2Bedroom Townhome

Relax in this stylish, sun-filled Town home, just a hop, skip, and jump from everywhere you want to be. Enjoy your morning coffee on your private patio surrounded by Tennessee lush green trees. Located in the heart of downtown Clarksville, is just a short walk to shops, restaurants, live theater, Austin Peay State University, and the River Walk. 5 minute walk to Downtown Clarksville 45 minutes to Nashville 20 minutes to Fort Campbell Check out our other listings by clicking on our host profile.

Trenton Industrial Studio

Down a winding country road only 10 minutes from Interstate 24 is a clean newly renovated studio suite in a historic building. The quaint little town of Trenton, Ky a perfect get away town gives a suite with a modern industrial feel and a view of the historic town. It is located above the Traveler’s Lantern Market & Cafe, a full scale coffee and sandwich cafe with handmade farmhouse decor. Trenton also has a boutique, salon, sewing shops and antique store. And a beautiful full park to stroll in!

A cozy studio apartment downtown Clarksville

The allée des fraises loft is a studio loft inspired by my stay in Paris and London, located on the second floor of an historic 1890’s building. The charming brick walls and rustic aesthetics add character to this bright space. Perfect for a couple’s getaway or a solo traveler in town for work. Walking distance to coffee shops, restaurants, local cafes, boutiques, breweries and more. Near Austin Peay State University, Fort Campbell and less than hour from Nashville. A parking pass is provided.

Historic Downtown cottage FULL of Amenities

Take a break and unwind at this peaceful guest cottage located on historic Greenwood Ave. 1 mile from downtown and APSU, this quaint home is full of amenities and waiting for you! Enjoy cooking in the equipped kitchen,dine in front of the electric fireplace with remote settings. Plenty of games and Roku TV to pass your time. The queen bedroom is ideal for 2 adults while the living room has 2 twin ottoman beds available for kids. Full bath, laundry room, and a desk for the working professional.

TOP 1% w/ King Bed! Cozy&Luxury Downtown Townhome

"Sunjoo's Place on Cigar Hill," Hosted by Byers & Harvey is a 2 BR/2.5 BA with a big bonus room in downtown! The MB has a king bed and ensuite with double vanity and tile shower. 2nd room has a queen bed and ensuite. Downstairs, you can find designated office/perfect kids hang out bonus room with big desk and trundle bed with 2 twin size mattress. However, there is NO bathroom and NO window in the basement. Up to 6 people (max 4 adults) can stay comfortably. Inquire about long-term stays!

The Best Neighborhood Watch in the world.

Bring the whole family to this lovely 4 bedroom home and enjoy the beautiful sunsets Kentucky has to offer. This home has the best neighborhood watch with the military right down the road. The backyard will have your fur pups loving life with the amount of room they have to play. We love being pet friendly but please remember to consider future guests with possible allergies. Please make sure to keep all animals off of furniture which includes all beds. Thank you for understanding.

Paw-fect for pet lovers & thrill seekers

Whatever brings you to Oak Grove KY or Clarksville TN and surrounding areas, this renovated three bedroom house is sure to make you feel at home, away from home, in all the right ways. Paw-fect space is perfectly equipped for you to enjoy a home suitable for all groups. Book your next trip with confidence and learn why so many guests have ranked this house the premier place to stay in Oak Grove KY. Message us for more information about discounted extended stays.

Serene private new construction walk out apartment

Beautiful 1 bed 1 bath apartment tucked into the woods in Cumberland Heights. Enjoy a private getaway but still convenient access to all that Clarksville has to offer. Close to Austin Peay State University, 10 minutes from downtown and 30 minutes from Fort Campbell. The Space: Comfortable queen bed with full bath (shower only-no tub). Private entrance to walkout basement apartment. No access to main house from apartment. Full kitchen with coffee provided.

Tiny Barn Hot Tub Military Discnt 45 min2 Nashvlle

Remodeled June 2025, This a boutique style personalized romantic stay you won't find anywhere in Clarksville! Our Tiny BARN offers a romantic vibe with a private patio. The patio space is relaxing with a Hot Tub !! We have chickens, cows, a sweet pot belly pig, etc. We also grow. Only a half mile to some of our areas best local BBQ at Red Top. If you like Whiskey start at MB Rolland and try the Pink Lemonade then pop on over to Beachhaven 🍷 Winery.

Beautiful 3-bedroom house

Have fun with the whole family at this elegant venue. In this 3 bedroom house this house has Wi-Fi, air conditioning, grill, laundry and everything you need to feel at home your experience will be unforgettable. Its location stands out for being less than 10 minutes from the Oak Grove KY Casino and Racetrack, Fort Campbell Military Base, 20 minutes from downtown Clarksville TN and 50 minutes from Nashville TN.

1 Bedroom, 1 Bathroom Cozy Cabin with Hot Tub.

The Lodge is a small 2 person only cabin on 45 acres of western KY countryside with amazing sunsets included. It has a private drive and a relaxing front porch with a 2 person only hot tub. Once you walk through the cabin doors, you will be transported to the Smokey mountains without the mountains. The owners live onsite if any problems arise that need immediate attention.

Downtown Guest House

Located in Clarksville's downtown historical district. Stay in a charming 100 year old structure. You will have this little guest house all to yourself.. Located within walking distance to Austin Peay State University and downtown shopping/eating. We are about one hour from Nashville and 15 minutes from Fort Campbell.