Guesthouse vacation rentals in Kentucky

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Kentucky

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

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Guest favorite

Guesthouse in Nicholasville

4.98 out of 5 average rating, 323 reviews

Cottage Retreat - Wine, Horses, Convenient

Just south of Lexington KY. Cottage Retreat - nestled between horse farms & open land this 25 acre farm is a unique & convenient location to relax and spend time unwinding. 7.8 miles from the Bluegrass Airport, 10.8 miles from Rupp Arena, 8.4 miles from Keeneland - you're close to numerous items of interest. Enjoy the fully remodeled private cottage, stroll down the lane, enjoy the close proximity of horses, and perhaps buy a bottle of wine on site. No pets and no smoking. Thank you.

Guest favorite

Guesthouse in Stanton

4.98 out of 5 average rating, 266 reviews

Robbie’s Rest: Amazing Mountaintop Sunrises

2020 new unit with nice deck, wonderful mountain scape with amazing sunrises from your deck or the deck of the main house where host lives. 8 acres that sit where the rolling hills meet the mountains overlooking the Daniel Boone Forest. 35 miles from Lexington, you will enjoy the peace & quiet of the beautiful mountains. Minutes away from the trails, waterfalls & attractions of Natural Bridge State Park & the Red River Gorge! We hope you will visit us soon! *Sunrise is not always visible

Guest favorite

Guesthouse in Scottsville

4.99 out of 5 average rating, 183 reviews

Adorable Guesthouse #2 Close to Barren River Lake

We are excited to present our tiny guest home #2. Perfect for the fisherman or couple wanting to stay close to Barren River Lake or Mammoth Cave. This unit is centrally located between several towns and less that four miles from Port Oliver Boat Ramp and Dam. It is close to the main house so we will be available if you need anything. Peaceful surroundings, comfortable queen bed, refrigerator, microwave and coffee bar. 55" smart tv to kick back & relax with. Exterior outlet for boat.

Guest favorite

Guesthouse in Winchester

4.93 out of 5 average rating, 184 reviews

Carriage House on the Park

Enjoy the tranquility of this Upstairs Apartment (over 400 sq ft) suite, located across from Winchester's College Park. Executive amenities include heated bathroom floor tile, additional sink and vanity and large flat screen Roku Smart TV. Carriage house is located just steps from public gym and recreational center and historic downtown Winchester. Centrally located with easy access to Lexington, Paris, Versailles, Georgetown, Kentucky Horse Park, Natural Bridge and Red River Gorge.

Superhost

Guesthouse in Manchester

4.92 out of 5 average rating, 212 reviews

Sycamore Hollow Guest House

Cute cabin in Danial Boone National Forest. 1 BR, LR, kitchen, loft, bath. Sleeps 6. Hot tub on site, Charcoal grill. WIFI, smart TV. Pets allowed. Pet fee of $75 will be charged. Pet damage will add charges. No smoking, parties, events. Currently WiFi is spotty. working to resolve. No meals provided. Gas oven is broken. Use toaster oven instead. Manually light gas burners. Door will be open for your arrival. Only 8 miles from Manchester & 20 miles from interstate 75 at London.

Guest favorite

Guesthouse in Lexington

4.96 out of 5 average rating, 595 reviews

My Old Kentucky Home-Downtown LEX's Premier Stay!

Welcome to My Old Kentucky Home downtowns premier Kentucky themed Air B&B. The best Airbnb in Lexington for a romantic or relaxing getaway! No detail or amenity was spared; private hot tub, plush bath robes, back deck, fire pit, patio and garden with views of the city. Full bourbon bar mixers provided to make your cocktails! ( no alcohol ) Central downtown-1 block from Rupp arena and 3 blocks from UK campus! For a video tour visit the last picture to see the link !

Guest favorite

Guesthouse in Lexington

4.93 out of 5 average rating, 182 reviews

Cozy studio with private pool and firepit

Welcome to our charming studio apartment located above our detached garage with a private pool. Whether you're looking for a relaxing getaway or a convenient base to explore the city, our cozy studio has everything you need. Close to the following locations: Fayette mall 1.9 miles Bluegrass airport 4.5 miles University of Kentucky 4.6 miles Keeneland 5.1 miles Manchester Music Hall 5.7 miles Rupp Arena 6.4 miles Lexington Opera House 6.5 Please no smoking in the room.

Guest favorite

Guesthouse in Lancaster

4.98 out of 5 average rating, 193 reviews

Wishing Well Guesthouse On The Lake

A peaceful, waterfront guesthouse in a serene quiet neighborhood. On 2 acres of rolling hills, this choice location will be a peaceful getaway. Updated furnishings and appliances in this beautiful, open concept living space with a gas fireplace inside or a rustic fire pit outside. Close to lake marina rentals. #Center College #Pioneer Playhouse #Brass Band Festival #Pasture at Marksbury Farm #KY BBQ Festival #Bourbon Trail #Norton Center For The Arts #127 yard sale

Guest favorite

Guesthouse in Shelbyville

4.97 out of 5 average rating, 100 reviews

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Listen to the birds sing as the walkway guides you to your quaint cottage getaway. Take in nature, as you’re surrounded by trees, near our sweet chicken coop and a creek that flows down from the deck - all while only 10min from town. Special touches were added of Kentucky Derby photos, books, kitchenware, Bourbon Trail glasses and bourbon barrel heads with local distilleries. The dining table top is even made of wood from Shelby County’s own Bulleit Distilling Company.

Guest favorite

Guesthouse in Winchester

4.98 out of 5 average rating, 205 reviews

Escape and unwind in the country

Relax and unwind in the country! Close to Lexington, Red River Gorge, Pilot Knob and Natural Bridge with easy access to the Mountain Parkway. We do have Wi-Fi. Pets are welcome but we request that dogs are either crated or not left unattended. There is a $25 pet cleaning fee. Our guest house has a fully equipped kitchen, washer/dryer, queen size Sleep Number Bed, queen size sleeper sofa, and patio with gas grill. An air mattress is available by request.

Guest favorite

Guesthouse in Somerset

4.98 out of 5 average rating, 163 reviews

Elegant Modern Holiday Rustic Retreat w/ Hot Tub

A steel framed industrial warehouse converted into an upscale two bedroom rustic-chic living space located within 8 miles of beautiful Lake Cumberland and within 5 minutes of Downtown, Somerset. The city is yours to explore from your own private 2 bed, 1 bath modern rustic retreat. Picture comfy beds, full bathroom, a kitchen built for entertaining, all under a metal tin roof for those rainy days when you just want to curl up and relax.

Guest favorite

Guesthouse in Petersburg

5 out of 5 average rating, 291 reviews

Stones Throw Country Inn - includes breakfast!

Beautiful country setting 3 minutes from the Creation Museum! Breakfast included! Hosts live on property should you need anything during your stay. Gorgeous sunset views! Easy access to I-275 at exit 11 and about 40 min. to Ark Encounter. For winter fun, Perfect North Slopes is only 15 minutes down the road. Downtown Cincinnati - 30 min.; Dayton, OH, Lexington, KY, and Louisville, KY - All approx. 1.5 hour drive.