Holiday rentals in Trenton

Private Yard: Hot Tub/B-Ball Court/X-Box/Fire Pit!

Newly Updated 3BR/1BA home that sleeps 7 people. Driveway holds 3 cars with free street parking if needed. This home comes fully equipped with wi-fi, exterior security cameras, alarm system for windows and doors for your safety & comfort, smart TVs in every room, kitchen with everyday appliances, fireplace, washer/dryer, BBQ grill, firepit w/sitting area, hot tub, & fenced in backyard. Mall 2mi, APSU 4.9mi, Oak Grove Casino 11.8mi, Fort Campbell 14mi, Vineyard/Winery 3.8mi, & Nashville 45-50min.

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.

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.

Nashville Luxury Dream Treehouse +Spa

This beautifully designed and luxurious treehouse sits on a ridge overlooking our creek. With only a 25min drive to downtown Nashville, you are tucked away amidst the towering hardwoods-away from the city noise. With careful attention to detail, the treehouse decor and design is meticulously curated to create an atmosphere of rest and beauty. This space is ideal for a couple, but can sleep four (twin beds in the loft). Parties are not permitted on the premises.

Tiny Barn on a Farm Hot Tub 45 min to Nashville

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.

Keehn Hideaway-Hot tub/King bed/Horses/Secluded!

Come relax in our brand new Amish-made mini-HIDEAWAY! (Couples, friends, mother/daughter, business, or ME-time). We built our DREAM PLACE (with a brand new hot tub, GAS grill, and GAS firepit), and we are now sharing it with you! Located on 20 acres in the beautiful hills of Kentucky, you will be AMAZED at the sunsets and quietness. There are no near neighbors except the chirping birds and our horses to pet, watch, and feed. Come be refreshed!

Beautiful 3-bedroom house

Cozy and family-friendly 3-bedroom home in Oak Grove, KY. Enjoy high-speed Wi-Fi, air conditioning, a fully equipped kitchen, laundry area, outdoor grill, and everything needed for a comfortable stay. Located less than 10 minutes from Oak Grove Racing & Gaming and Fort Campbell Military Base, 20 minutes from downtown Clarksville, TN, and under 1 hour from Nashville. Perfect for families, business travelers, and long or short stays.

Kentucky Hideaway

Take it easy at this unique and peaceful getaway. The apartment is tucked away off the main road in the lovely small town of Trenton, KY. The two story mini building sits back off the road which allows for privacy. You will especially love the large upper deck which allows you to not only look out at our beautiful town but also, enjoy the outdoors with a covered deck attached to the kitchen. Almost doubling your living space!

Beautiful & Airy Retreat with Lots of Character

Welcome to your spacious and airy retreat at Russet Ridge! Nestled in a prime location just minutes from Wilma Rudolph Boulevard, this charming three-bedroom, two-bath home offers the perfect blend of comfort, convenience, and style. Whether you’re in town for a relaxing getaway, a business trip, or just exploring the area, this home provides the ideal setting for any stay.

Tranquility Barn

Escape to the countryside and unwind in this cozy converted barn retreat. Perfect for a peaceful getaway, the space features a comfortable queen bed, relaxing soaking tub, Wi-Fi, and thoughtful essentials like Tide Pods for your convenience. Whether you’re exploring the area or simply looking to recharge, you’ll love the quiet charm and rustic atmosphere of this unique stay.

Peaceful, Romantic Getaway in Nature

Enjoy the lovely setting of this romantic spot in nature. Conveniently located less than ten minutes from downtown Hopkinsville in a private area with great views of the outdoors and wildlife. Guests can enjoy our hiking trails during their stay. Handicap accessible: walk-in shower 5x5 ft, all doorways >32 inches, no steps. Well-behaved pets allowed with pre-approval.

Elkton Family House

Relax with the whole family at this peaceful place to stay in a small town in western Kentucky Only walking distance from elkton square and it’s restaurants and gas stations, plenty of room for parking and outside activities! A few minutes from Elkton Park. 45 minutes to Ft Campbell 20 minutes to Guthrie 25 minutes to Clarksville Elkton is a true country town!