Holiday houses in Oak Grove

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Top-rated holiday rentals in Oak Grove

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

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Top Guest favourite
A bright living area is showcased, featuring a dining table with six white chairs and a spacious sofa set. Natural light filters through the windows, illuminating an artwork on the wall. A ceiling fan and a cozy area rug contribute to the welcoming atmosphere.
Townhouse in Clarksville
4.95 out of 5 average rating, 286 reviews

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.

Top Guest favourite
A studio loft features charming brick walls and bright windows that allow natural light to fill the space. A spacious bed is positioned beside a comfortable sectional sofa. A media console and decorative accents enhance the cozy atmosphere, creating a welcoming environment.
Loft in Clarksville
4.97 out of 5 average rating, 177 reviews

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.

Guest favourite
An outdoor seating area features a comfortable light-colored sofa adorned with a decorative pillow. A dark tabletop with a circular opening is positioned in the center. Two wooden rocking chairs are visible in the background, set against a brick wall.
Home in Clarksville
4.93 out of 5 average rating, 182 reviews

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.

Guest favourite
The front exterior of the home features a welcoming covered porch with a bench and decorative pillows. A flag is displayed prominently beside the entrance, and colorful rose bushes line the walkway, which leads to the door. The siding is light-colored, complemented by dark shutters.
Home in Clarksville
4.92 out of 5 average rating, 360 reviews

Fort Campbell Retreat w/ Tesla Charger

3 bedrooms and 1.5 bathrooms. Master has king size bed, walk-in closet and own half bath. Spare room has double bed and walk-in closet. Minutes from Fort Campbell, Downtown Clarksville and Governor's Square Mall. 45 Min from Nashville Airport. Neighborhood Walmart Marketplace within walking distance. Brand new washer, dryer and refrigerator. High-speed Wi-Fi, big screen TVs w/ Roku and Nespresso coffee. Relaxing patio deck backing up to a woodland paradise! 50amp Tesla Wall Charger.

Guest favourite
The living room features a comfortable tan sectional sofa adorned with blue accent pillows. A wooden coffee table sits at the center, complemented by a decorative plant. Natural light filters through sheer curtains above two windows, enhancing the inviting atmosphere.
Home in Oak Grove
4.83 out of 5 average rating, 161 reviews

Happy Hidaway! Pets Welcome~Fenced Yard.

Welcome to our home! Less than 5 minutes from Ft Campbell gate 4, which offers convenience for military personnel. Just 10-mile distance to Austin Peay State University and 4 miles from I-24, our house provides easy access to Kentucky, Alabama, or Georgia. We are walking distance to the casino, and 2.2-mile from Walmart and various dining options. For those looking to explore Nashville, we are just an hour away. Please take note of our pet fee and additional guest fee detailed below.

Superhost
Home in Clarksville
4.96 out of 5 average rating, 210 reviews

The PINK HOUSE in Downtown Clarksville

The Pink House Clarksville is located in downtown Clarksville 5 minutes to Austin Peay and F&M Bank ARENA and downtown restaurants. It is 20 minutes to Fort Campbell area, 45 minutes to Nashville, and 20 min to most of Clarksville areas. Cottage includes fully stocked kitchen, relaxing seating areas in backyard and SUNROOM, and on premise parking. There is also a SPEAKEASY themed airbnb NEXT DOOR you can rent as well! Be sure to bring your best camera for all the photo opportunities!

Top Guest favourite
A cozy cabin is nestled among lush greenery, partially obscured by mature trees. A gravel path leads to the entrance, which is flanked by wooden accents. A small outdoor seating area is visible, enhancing the connection to the serene natural surroundings.
Cabin in Chapmansboro
4.96 out of 5 average rating, 363 reviews

White Duck

Keep it simple at this peaceful and centrally-located cabin minutes from Interstate 24. Twenty minutes from Clarksville, APSU and nearby Fort Campbell KY to the north and thirty minutes from downtown Nashville and all it has to offer to the south. The quiet woodsy setting and comfortable interior of White Duck provide a restful transition from a day of sightseeing or an exciting football or hockey game. **There is a $50 pet fee** Please include your pet during the booking process.

Guest favourite
The living room features a light blue wall, two comfortable sofas, and a patterned area rug. A coffee table sits center, with a ceiling fan above providing airflow. A window allows natural light, while a dining area is visible through the open doorway.
Home in Oak Grove
4.95 out of 5 average rating, 143 reviews

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.

Guest favourite
A spacious sleeping area features a large bed adorned with decorative pillows. The headboard is complemented by a green floral wall, while warm lamp lighting creates a calming ambiance. A cozy seating area and an intricately designed cabinet are also visible, adding a touch of charm.
Barn in Clarksville
4.89 out of 5 average rating, 397 reviews

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.

Top Guest favourite
The exterior of the house is illuminated by soft lighting along the pathway, enhancing the welcoming entrance. An American flag is displayed, and the covered porch features a welcoming door. The well-maintained lawn is bordered by neatly arranged flowers.
Home in Oak Grove
4.89 out of 5 average rating, 122 reviews

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.

Top Guest favourite
A spacious bedroom features large glass doors, offering views of the surrounding nature. Soft natural light fills the room, highlighting a comfortable queen bed with crisp linens. Nearby, a cozy seating area and a small workspace complement the inviting atmosphere.
Tiny home in Hopkinsville
5 out of 5 average rating, 143 reviews

Romantic, Peaceful Getaway in Nature

Enjoy beautiful views of nature when you stay in this unique place! Large windows on two sides of the home make it a truly serene space. Whether you are looking to walk trails on the property or enjoy the scenery in the comfort of home, you will find serenity during your stay here. If you'd like to bring a well-behaved dog, check out our other very similar rental! www.airbnb.com/h/3907witty

Top Guest favourite
The cabin features a welcoming front porch with wooden railings and steps leading up to a central door with a rustic design. Natural wood elements complement the structure, blending with the surrounding greenery for an inviting appearance.
Cabin in Hopkinsville
4.94 out of 5 average rating, 286 reviews

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.

Popular amenities for Oak Grove holiday rentals

When is the best time to visit Oak Grove?

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Avg. price$170 NZD$170 NZD$175 NZD$186 NZD$189 NZD$175 NZD$198 NZD$198 NZD$198 NZD$189 NZD$179 NZD$188 NZD
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Frequently Asked Questions

  • How much does it cost to stay in house rentals in Oak Grove?

    Experience the best of Oak Grove with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Oak Grove have a kitchen?

    Absolutely! We offer over 20 house rentals with a kitchen in Oak Grove. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Oak Grove?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with a kitchen, over 20 homes with wifi, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Oak Grove have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Oak Grove. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oak Grove have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Oak Grove. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oak Grove have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Oak Grove. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Oak Grove?

    Four-legged friends are welcome in Oak Grove. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Oak Grove?

    Yes! Work meets play with ease at over 10 vacation rentals in Oak Grove featuring dedicated workspaces. Stay connected and productive in your home away from home.

Quick stats about holiday rentals in Oak Grove

  • Total holiday rentals

    Explore 20 holiday rentals in Oak Grove

  • Nightly prices starting at

    Oak Grove holiday rentals start at $87 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,110 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Oak Grove holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Oak Grove rentals

  • 4.8 Average rating

    Oak Grove stays are highly rated by guests—averaging 4.8 out of 5!

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