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Guesthouse vacation rentals in Kentucky

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Top-rated guesthouse rentals in Kentucky

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

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Guesthouse in Manchester

4.92 out of 5 average rating, 206 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 by permission only. Pet fee of $100 will be charged. Pet damage will add charges. No smoking, parties, events. Use WIFI calling. 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. Put tissue in garbage.

Guesthouse in Nicholasville

4.98 out of 5 average rating, 314 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.

Guesthouse in Stanton

4.98 out of 5 average rating, 259 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

Guesthouse in Scottsville

4.99 out of 5 average rating, 173 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.

Guesthouse in Williamsburg

4.88 out of 5 average rating, 454 reviews

Williamsburg Poolside Homestead

Private guest house with incredible outdoor resort feel, nature, and simple homestead life. 3 miles to University of the Cumberlands. 20 min to Cumberland Falls, home of the world's only Moonbow. *NO smoking of any kind (e-cig included) permitted anywhere on the property or the entire neighborhood. Guests violating our smoking policy are subject to a minimum $400 fee for returning the house or property to smoke-free status and agree to being charged by accepting this policy.

Guesthouse in Lexington

4.93 out of 5 average rating, 158 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.

Guesthouse in Lancaster

4.98 out of 5 average rating, 188 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

Guesthouse in Winchester

4.98 out of 5 average rating, 199 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.

Guesthouse in Somerset

4.98 out of 5 average rating, 153 reviews

Elegant Modern 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.

Guesthouse in Richmond

4.97 out of 5 average rating, 292 reviews

Richmond Guesthouse

Private country apartment between Richmond and Berea. Enjoy quiet time away from the city but you are still just a short drive away from all the amenities. We have everything you could need for a one night stay or longer. There is livestock in the adjacent fields but won't be a bother to you. There is free wifi and a roku hooked up to the tv so you can access all of your streaming services.

Guesthouse in Louisville

4.93 out of 5 average rating, 880 reviews

HIghlands Modern Get Away

Ideal, quiet place in the highlands. You have the apartment over the garage. You'll have a place all to yourself with most the amenities of your own home. Studio apartment with a balcony if you decide to hang out and relax for the evening. There is a cook top, but no oven in the kitchen. Park in front of the garage. Pets are welcome, plz add them when booking.

Guesthouse in Benton

4.78 out of 5 average rating, 134 reviews

Spud A. Cabin. At my tiny house community.

Cute cozy cabin, plenty of natural light. Outside deck has a picnic table a propane grill. just a 2- 5 min. drive to nearest marinas . I live on the property in lower cabin. Upper cabin (rental) has adequate privacy from my cabin. But I am here to assist with any questions or concerns. love to socialize, but give my guest their stay space.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Kentucky guesthouse rentals

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guesthouse in Louisville

4.99 out of 5 average rating, 382 reviews

Highlands - Elegant Calm Clean & Green - Walkable

Guesthouse in Wilmore

4.96 out of 5 average rating, 146 reviews

Coach House at the 1898 Red Bud B & B

Guesthouse in Louisville

4.93 out of 5 average rating, 61 reviews

Yoga Barn with 90’s Loft Bedroom

Guesthouse in Pendleton

4.89 out of 5 average rating, 56 reviews

The Waterfall Place, Suite and Walkout!

Guesthouse in Louisville

4.83 out of 5 average rating, 483 reviews

Carriage House Loft

Guesthouse in Brooksville

4.77 out of 5 average rating, 124 reviews

Johnson Hills Farm Bed and Breakfast

Guesthouse in Louisville

4.96 out of 5 average rating, 699 reviews

Germantown Carriage House w/garage

Guesthouse in Louisville

4.88 out of 5 average rating, 117 reviews

Cottage Park Carriage House. Rest w/Hollyhock

Guest house rentals with a patio

Guesthouse in Georgetown

4.96 out of 5 average rating, 24 reviews

Cozy Cottage on Horse Farm

Guesthouse in Stanton

5 out of 5 average rating, 32 reviews

Forest Edge Retreat; Cozy Charm w Hottub Wi-Fi

Guesthouse in Rockholds

4.71 out of 5 average rating, 49 reviews

Lofty retreat

Guesthouse in Jamestown

5 out of 5 average rating, 10 reviews

The Boat Haus Guesthouse

Guesthouse in Louisville

5 out of 5 average rating, 38 reviews

2BR Sterling Springs Guest Suite

Guesthouse in Louisville

5 out of 5 average rating, 191 reviews

*BRAND NEW* Gem of Germantown Private Derby Suite

Guesthouse in Morehead

4.97 out of 5 average rating, 106 reviews

Cozy 2-bedroom guesthouse, close to MSU/hospital

Guesthouse in White Plains

4.95 out of 5 average rating, 38 reviews

Quaint cottage house, 2 bedroom 1 bath w/kitchen

Guest house rentals with a washer and dryer

Guesthouse in Pine Ridge

4.99 out of 5 average rating, 340 reviews

Family Guest House-near Red River Gorge&MuirValley

Guesthouse in Springfield

4.99 out of 5 average rating, 95 reviews

Lofty Lodge on the Bourbon Trail

Guesthouse in Glasgow

4.8 out of 5 average rating, 103 reviews

A frame in the trees

Guesthouse in Louisville

4.94 out of 5 average rating, 98 reviews

Carriage House - Crescent Hill (Frankfort Avenue)

Guesthouse in Louisville

5 out of 5 average rating, 44 reviews

New custom guesthouse | Free parking | Sleeps 4

Guesthouse in Louisville

4.97 out of 5 average rating, 120 reviews

The City Cottage…quiet, peaceful, and convenient!

Guesthouse in Pendleton

4.96 out of 5 average rating, 84 reviews

The Wooded Retreat

Guesthouse in Raywick

4.99 out of 5 average rating, 75 reviews

Peaceful Easy Feelin’

Destinations to explore