Cottage holiday rentals in Shelbyville

4.95 out of 5 average rating, 223 reviews

Luxury Retreat with Hot Tub

Welcome to Four Seasons Cottage on the Bourbon Trail! This charming property is located in a peaceful vacation community, just a short walk from the seasonal pool. Featuring 2 bedrooms, a fully equipped kitchen, and cozy living room with a fireplace, this cottage is perfect for a family getaway or a couples retreat. Enjoy the large deck with a hot tub and BBQ, as well as access to nearby hiking trails and attractions. Cottage 37 sits on a ridge that overlooks the 3,050-acre Taylorsville Lake.

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4.98 out of 5 average rating, 333 reviews

A porch overlooks the serene Kentucky River, featuring a wood breakfast bar with counter stools. Rocking chairs provide a cozy seating area, framed by lush greenery and views of the river's banks. Sunlight filters through the trees, enhancing the tranquil setting.

Cottage in Wilmore

River House - Cottage with KY River View & Access

Come relax at the peaceful river house. It feels like a retreat right on the Kentucky River with a party-sized dock for easy river access. It’s a cozy cottage on stilts with a breakfast bar on the porch and swing on the patio. Be surrounded by nature and beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 minutes or less from LEX Bluegrass Airport, Keeneland and Shaker Village. See guidebook for more info.

ValueFamilyWalkability

4.87 out of 5 average rating, 372 reviews

A bright living room is furnished with a gray sofa and two blue armchairs. A glass coffee table is centered on a colorful area rug. A flat-screen TV sits on a wooden console, and a bookshelf is visible, filled with various books. Natural light enters through multiple windows.

Cottage in Germantown

Tyler Park Cottage in the Highlands

Adorable, light-filled cottage in the beloved Highlands neighborhood. An easy ten minute walk in one direction will put you on Bardstown Road, full of dining and bars, while a 15 minute walk in the other will land you in the hip Germantown-Schnitzelburg neighborhood. A short (6 minute) drive to downtown, 11 minutes to Churchill Downs. You'll find wireless internet, clean towels and sheets, basic kitchen and bathroom amenities, coffee maker, a flat screen TV with Apple TV, and keyless entry.

ValueFamilyBathroom

4.97 out of 5 average rating, 155 reviews

A cozy living area is presented with a television mounted on the wall. A black leather sofa faces a small wooden coffee table and two armchairs. Natural light filters through the windows, complemented by patterned curtains, creating a warm atmosphere.

Cottage in Salvisa

Cottage on the Bourbon Trail

Cottage located in the country. Enjoy amazing views from a covered front porch as you rock in comfortable rocking chairs. Fully furnished and beautifully decorated to make your stay comfortable and delightful. Memory foam mattresses for wonderful sleep and a kitchen for cooking if desired. Pool is behind owners residence and is shared with owners family and possibly 2 additional people June-Sept. We have recently also installed a Tesla High Powered Wall Charger w/60amps. We’d love to have you!

FamilyValueLayout

4.97 out of 5 average rating, 209 reviews

The exterior showcases a charming white house with large windows adorned with string lights, offering a glimpse of the interior space. A wooden deck extends out front, while a covered patio area is visible to the side, surrounded by lush greenery.

Cottage in Louisville

ArTisTs CoTTaGe

Enjoy peaceful privacy with center city convenience! Bright, open ambiance. Art and music supplies, books, toys, games, CD's, movies. Two decks and a covered patio. Found art gardens and galleries. Fully equipped kitchen with granite counters. Large windows in downstairs bedroom with queen bed and gas fireplace. Ladder access to queen bed in skylit loft. A perfect getaway for artists/writers on retreat, solo adventurers, couples, business travelers and small families with well behaved kids.

ValueFamilyBathroom

4.99 out of 5 average rating, 471 reviews

The charming yellow cottage features a covered front porch with two black chairs, inviting relaxation. Neatly trimmed hedges line the walkway, leading up to the front door, which is adorned with a decorative wreath. A spacious lawn and a clear blue sky enhance the warm appearance.

Cottage in Bardstown

The Cottage Circa 1898 Downtown Location

Charming 1800's cottage listed on the National Register of Historic Places in Bardstown. Voted Most Beautiful Small Town in America. Walking distance from downtown shopping, nightlife, dining, and local attractions. Located along the Kentucky Bourbon Trail. I love Bardstown and wanted my cottage to look and feel like what is best about the town- historical charm mixed with modern amenities. Clean, cozy and comfortable; it is a space that I hope you find enjoyable while visiting Bardstown.

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A two-story cottage is situated against a lush green backdrop. The exterior features light-colored siding, a covered porch, and multiple windows that allow natural light. A well-maintained lawn surrounds the home, enhancing the inviting appearance of the property.

4.94 out of 5 average rating, 189 reviews

The Gathering Place

The Gathering Place is the perfect place to get away and gather with family and friends. The resort is located conveniently between Bardstown, Louisville, and Frankfort on the Bourbon Trail. Offseason hiking, fireplace, and hot tub make a great peaceful getaway or work from "home" experience. Enjoy fishing, boating, kayaking, hiking, bird/deer watching and relaxing. The owners have been Resort guests for years and now own a cottage to enjoy and share with family, friends, and guests.

ValueLocationCheck-in

A two-story cottage with light gray siding and a symmetrical facade is shown. The front porch features wooden steps leading to an inviting entrance. Lush green hedges frame the exterior, while a gravel driveway extends to the left, emphasizing the cottage's serene setting.

4.84 out of 5 average rating, 128 reviews

Lake Livin' & Bourbon Sippin'

Edgewater Resort, 20 minutes from Louisville, is Taylorsville Lake's premier vacation spot, tucked away in a gated community with over 163 acres that overlooks the marina. Within walking distance you'll find a community pool (seasonal) with a sand volleyball court and a fire pit. This two-story cottage sleeps up to 10 guests and showcases a master suite with two private balconies and a jetted soaking tub. You can also hang out on the private deck out back equipped with a 4-person hot tub.

LocationFamilyCheck-in

A living area features comfortable seating arranged around a wooden coffee table. A stone fireplace with an electric insert is positioned beneath a flat-screen television mounted on the wall. The warm red walls create a cozy backdrop, and kitchen facilities are visible in the background.

4.99 out of 5 average rating, 153 reviews

Lakeside Cottage -upgraded hot tub- Bourbon Trail!

Welcome KY visitors, horse lovers, Bourbon Trail guests, or anyone looking for a getaway! This is a somewhat rustic, homey, comfortable 20 year old cottage. It's not perfect, but our guests find it charming and sufficient. You'll find the home exactly as described with the offerings and expectations. Rest, relax, and recharge in a gated community overlooking Taylorsville Lake. Don’t be another hotel's customer when you can stay in a spacious home with a Jacuzzi J-235 hot tub.

ValueFamilyLayout

4.99 out of 5 average rating, 169 reviews

Cottage in Louisville

Derby City

FYI : 1) I DON’T accept Louisville guests to stop large local party’s 2) 4 beds to sleep ONLY 6 people. I have a play pen/crib with sheets and mattress pad Extra guests over 4 pay $5 per guest per day. I have more laundry to do and extra supplies to replace like coffee, hot chocolate - Keurig pods, and other amenities I have for my guests. 3) I have surveillance cameras outside monitoring 24/7, Additional fees will be added for unauthorized guests not in booking.

ValueFamilyCleanliness

4.93 out of 5 average rating, 255 reviews

Cottage in Frankfort

Charming South Frankfort Cottage!

Great private guest house in the heart of South Frankfort! Only a 5-10 minute walk to all the Historic Downtown Frankfort and the Kentucky Capitol. Great location for the Bouron Trail (especially Buffalo Trace and Woodford Reserve) and the KY River. We are also close to Keeneland and the Horse Park. Come enjoy what our community has to offer! We pride ourselves in hosting families and friends who want an affordable place to stay!

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