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Holiday houses in Olmstead

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Top-rated holiday rentals in Olmstead

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

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Top Guest favourite
Treehouse in Franklin
4.99 out of 5 average rating, 166 reviews

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).

Top Guest favourite
The exterior of a rustic cabin features a combination of log siding and a green metal roof. A spacious covered porch welcomes guests, with large columns supporting the overhang. Surrounding trees provide shade and natural beauty, enhancing the serene rural setting.
Cabin in Russellville
4.96 out of 5 average rating, 178 reviews

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.

Guest favourite
The treehouse is illuminated by soft outdoor lights, highlighting its wooden structure and welcoming design. A gently curving walkway leads to the entrance, surrounded by tall trees and a glimpse of Lake Malone visible in the background.
Treehouse in Lewisburg
4.97 out of 5 average rating, 140 reviews

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.

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, 387 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.

Top Guest favourite
A serene view of Lake Malone is captured from a wooden deck, adorned with autumn leaves. The calm water reflects the colorful foliage and the sky, contributing to a peaceful atmosphere. A hammock can be seen near the railing, inviting relaxation.
Home in Lewisburg
4.94 out of 5 average rating, 109 reviews

The FunKY Bean

Take it easy at this unique and tranquil getaway on beautiful Lake Malone. Relax in a hammock, swim off the dock , kayak , stand up paddle board, fish, or enjoy a beautiful sunrise while drinking your specialty coffee or tea! With the bean theme: There are oversized bean bags to relax on and a coffee station with LOTS of coffee options ( including Esspresso maker)! The funky bean is a real spot to get away from the hustle and bustle of everyday life and take it easy!

Top Guest favourite
The Bridge House is seen suspended over a serene creek, framed by lush greenery. A calm water surface reflects the building and surrounding foliage. A gray dog stands on a rock in the foreground, appearing to enjoy the natural setting.
Place to stay in Ashland City
4.97 out of 5 average rating, 390 reviews

Bridge House over Blue Springs Creek

Magical in all seasons! Soothe your soul with an unforgettable escape, surrounded by nature and suspended twenty feet above a babbling brook! Listen to the rushing water and the bamboo whispering in the breeze, take in a sunset, or wade in the creek below. We hope you’ll enjoy this unique covered bridge conversion, expanding from bank to bank with a 50-foot front deck. Breakfast provided the first day includes fresh fruit, a half dozen eggs, and muffins, coffee and tea.

Top Guest favourite
A charming treehouse is nestled among tall trees, featuring earthy wooden tones and a rustic design. Soft outdoor lighting creates a cozy ambiance, while a path made of stones leads to the entrance. The treehouse is elevated, providing a unique vantage point into the surrounding nature.
Treehouse in Greenbrier
4.98 out of 5 average rating, 304 reviews

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.

Top Guest favourite
A unique structure resembling a boat stands on a grassy hillside, surrounded by trees. A wooden deck encircles the building, featuring round windows along its exterior. The rustic design and red metal roof complement the natural landscape.
Boat in Springfield
4.94 out of 5 average rating, 388 reviews

Sheet

Welcome to Kelly’s Jubilee. Look us up online for a discount and more information on our romantic and birthday packages. The ark was featured in Southern Living magazine and Tennessee Crossroads. (A travel show) and recently HGTV Airbnb is having technical problems and no longer offers any kind of support for its hosts. I’m sorry if the calendar says not updated. Please try the website or contact me the number is listed on the Kelly’s Jubilee website.

Top 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
4.9 out of 5 average rating, 420 reviews

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.

Top Guest favourite
Two painted horses trot across a grassy field as the sun sets in the background, casting warm hues of orange and pink in the sky. Lush trees border the scene, enhancing a sense of tranquility in the natural landscape.
Cabin in Russellville
4.99 out of 5 average rating, 178 reviews

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!

Top Guest favourite
A log cabin exterior features a welcoming front porch with a doormat and a small bench. Flanking the entrance are decorative flower boxes beneath the windows, contributing to the natural, serene surroundings of greenery.
Guest suite in Goodlettsville
4.98 out of 5 average rating, 189 reviews

Valley View Cottage, 22 miles from Nashville

Take it easy at this unique & tranquil getaway log cabin with central air/heat & keyless entrance. The living room has a 55 in smart TV w/Roku, small fridge, microwave & keurig. It's a great place to work remote. The Queen bedroom has a Smart TV & a desk. You have a covered parking space & access to the main home front porch with a small table & 2 chairs, porch swing & rockers. No pets at all & no smoking please. We have allergies

Top Guest favourite
An open living space is depicted, featuring a white couch with decorative pillows facing a wooden dining table. A fully equipped kitchen with light wood cabinetry is visible in the background, along with a flat-screen TV on a console. Soft lighting illuminates the area.
Home in Cottontown
4.96 out of 5 average rating, 119 reviews

The Little House: Cozy Short or Extended Stays

Welcome to the Little House! Located one mile off I-65, this cozy home sits on a sleepy lane minutes from White House, TN and just 25 miles from downtown Nashville to the south and Bowling Green, KY to the north. Our 2 bedroom, 1 bath retreat has a washer and dryer for your convenience, a stocked kitchen, smart TV, extra blankets, and plenty of books for your reading pleasure. Cozy and clean is our top priority!

Popular amenities for Olmstead holiday rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. Logan County
  5. Olmstead