Holiday rentals in Olmstead

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!

Historic Log Cabin, Dreamy Loft Suite, Stone Frpl.

Historic Log Cabin built from reclaimed Civil War era logs, it’s recent extensive renovation revealed county doc’s showing it was developed by architect to the stars, Braxton Dixon forJohnny Cash. Perfect for artists or musicians retreat. Full kitchen, bath, loft honeymoon suite w/half bath, king bed, living/dining room, Stone fireplace & laundry. Sleeps 3 max. Deck overlooking treed acreage. Just 30 mins to Nashville attractions, Grand Ol Opry & airport, a quick drive to local restaurants etc

Treetop Views *Trails, Fishing *No Cleaning Fee

Amazing two-story house nestled high up in the trees. A true treehouse! This treehouse sits amongst a forest of poplar trees and feels very secluded and private. It has spectacular views of Kentucky’s rolling hills as it looks out across the valley. This treehouse was hand built and handcrafted with love and attention to detail. Located just off of I65 outside the historical little town of Franklin, KY. We are located between Nashville (45min), Bowling Green (35min) and Mammoth Cave (55 min).

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.

Cozy Cabin with Private Walking Trail

Relax and retreat to this peaceful rural cabin with modern amenities and charming outdoor spaces situated on a working farm. Enjoy the walking trail through 10 acres of woods or swing while enjoying beautiful country views. Experience the best of both worlds in the historic 19th century cabin with a modern addition. A short drive to quaint downtown Russellville, Auburn, or Franklin KY each with plenty of shopping. The nearby Red River provides opportunities for kayaking, tubing or fishing.

Treehouse with HOT TUB!(Lake Malone)

Prepare to be taken to new heights as you enjoy this beautiful, private treehouse located on Lake Malone. It features an absolutely stunning view of the lake through an 8x14 glass door that opens up to allow the cool lake breezes to waft your cares away as you relax in the recliner. It also features a hot tub, large deck, full kitchen, Jacuzzi tub, rainfall shower, beautiful woodwork, two complimentary kayaks, and many other unique features that will make your stay unforgettable.

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.

Cozy Cottage Wooded Retreat

Our cottage is cozy, private, and safe! It is fully equipped to make your stay as enjoyable and carefree as possible. We have WIFI, 2 TV's Roku on both TVs, a Bose Radio with CD's, a DVD player with movies. We have a Coffee Station with Keurig & pods, a Mr Coffee with a coffee grinder. Completely equipped Kitchen. Tub/shower combo. Lots of privacy on your own back deck. You may see deer and wild turkey . Gas Grill provided. plenty of parking. NO PETS ALLOWED.

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.

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!

“Updated Historic Farmhouse, Incredible Views!

"Historic farmhouse getaway with spectacular views" Great getaway for couples and families! Hi speed fiber internet! New stainless appliances Updated bath / whirlpool tub Lg updated kitchen w island Original 150 yr old floor 10’ ceilings 2 porches Fire pit Lg screen led tvs with roku controllers, netflix, etc 360º 1000 acre view Soy, corn, cow pasture, tobacco barns Lg telescope, no ambient city light!