Vacation rentals in Underwood

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Top-rated vacation rentals in Underwood

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Top guest favourite
The A-Frame home's exterior showcases a unique architectural design with a stone façade and a contrasting modern section. Large windows flank the entrance, allowing natural light to illuminate the interior. Lush greenery surrounds the property, enhancing its serene setting.
Home in Madison
4.99 out of 5 average rating, 562 reviews

The Artist’s A-Frame

Get away and enjoy the comfort and convenience of this unique, newly remodeled A-Frame home nestled in a quiet, safe, upscale neighborhood, minutes from Clifty Falls State Park (10 min. drive), Historic Downtown (5 min. drive), hilltop shopping (5 min. drive): Hanover College (15 min. drive) •Fast Wi-Fi •Electric Fireplace .Two 55” Roku TVs, Complimentary YouTube TV for local and cable stations •Keurig & Drip Coffee, K-cups, local coffee, tea, bottled water .Paved driveway parking .Gas BBQ grill

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Cottage in Salem
4.8 out of 5 average rating, 128 reviews

Canton Cottage- Modern Farmhouse 2 Bedroom

The Canton Cottage Built in 1901, this freshly remodeled two bedroom home is the perfect place to lay your head down after a long day. Located only 4 minutes from wal-mart and the rest of amenities that Salem has to offer. This home features new appliances, a workspace, two full beds, one queen bed, a sectional couch, and a quiet country setting to relax in. We have ordered new windows and are waiting on them to be installed. In the mean time 2 of our windows are cracked but sealed off.

Top guest favourite
Guesthouse in Hardinsburg
4.96 out of 5 average rating, 334 reviews

Once Upon a Time little Cabin in the Woods

Welcome to Always Ranch where this unique tiny cabin offers you a tranquil spot to relax. You will be surrounded by nature and off the beaten path. The cabin may look like a lean to but the inside is rustic and warming. We are located 20 minutes form Salem, 20 minutes from Paoli and Paoli Peak, and 35 minutes from Frenchlick Casino The kitchenette includes mini fridge, microwave, double hot plate and, grill on the outdoor firepit or grill. Boats are NOT available for guests at this time

Top guest favourite
The exterior of the estate features a charming porch adorned with potted plants and a flag. Sunlight filters through the surrounding trees, illuminating the stone and wood structure. A stone pathway leads through the lush green lawn, enhancing the inviting outdoor space.
Cabin in Henryville
4.97 out of 5 average rating, 358 reviews

Close to Louisville~Hot Tub~Fire Pit~Game Room

Welcome to Stone Creek, a private 3 acre estate conveniently located minutes to Louisville, KY. This is the Ultimate Getaway! Upon entering the premises, you will find a custom iron security gate requiring coded access. Stone Creek boasts 2500+ sq ft of luxury living space complete with a full kitchen, laundry, and office. Guests will have full use of the grounds including the hot tub, fire pit, and the numerous covered decks & patios. Perfect romantic getaway or multi person retreat.

Guest favourite
The exterior of a charming single-story house is shown, featuring a covered porch and stone columns. Lush green bushes frame the entrance, and two seats are visible on the porch. A modest yard surrounds the house, with a clear sky above.
Home in Clifton Heights
4.91 out of 5 average rating, 310 reviews

Quiet Neighborhood Home With Outstanding Location

Situated on a quiet hilltop neighborhood in Clifton Heights, this is the perfect location for a professional or personal visit to Louisville and very animal friendly. It is within 10 minutes of Downtown, Waterfront Park, Nulu, Frankfort Avenue, the Highlands, the Convention Center, and just 15 minutes from historic Churchill Downs. These neighborhoods feature the best dining and entertainment in the city. Just a block away is the Mellwood Arts Center complex with shops and dining.

Guest favourite
An open loft space features a spacious bed with a blue accent blanket. A comfortable sofa sits opposite a stylish dining area, adorned with a round table set for six. Large windows allow natural light to brighten the wooden flooring and inviting decor.
Loft in Louisville
4.81 out of 5 average rating, 702 reviews

DerbyLoft Louisville

Enjoy the best of Louisville in our second floor loft, a studs-up renovation with modern amenities, full kitchen, and a beautiful bathroom. We're in a central location from which guests can easily tour the heart of Louisville. Private entrance Free parking on street Free Wifi 10min (0.5mi) walk to Churchill Downs 25min (1.5mi) walk to Cardinal Stadium 5min (1.8mi) drive to historic Old Louisville 6min (1.9mi) drive to KY Expo Center 12min (3.2mi) drive to Louisville Airport

Top guest favourite
Home in Deputy
4.98 out of 5 average rating, 122 reviews

The Cottage by the Woods

This small but newly renovated Cottage by the Woods offers a peaceful country alternative to an airbnb stay. The cottage is lightly decorated for seasonal transitions. It is located 15 minutes from downtown Madison, IN. A partial wrap around deck allows for a tranquil cup of coffee while bird watching. Free WiFi and Roku TV is provided along with other small amenities including various flavored coffee's for your morning cup of joe and a waffle making station.

Top guest favourite
An open-concept kitchen area showcases modern cabinetry and stainless steel appliances. A curved counter with seating for three is highlighted, alongside a stove and stylish light fixtures. The room is brightened by natural light, creating a welcoming and functional space.
Apartment in Downtown New Albany
4.99 out of 5 average rating, 119 reviews

Luxury 1BR Apt w King Bed near Louisville KY

Stylish 1BR apartment in the heart of Downtown New Albany Indiana. This apartment is centrally located to great shops and fantastic dining in downtown New Albany all within walking distance, 10 minutes to Downtown Louisville and the KFC Yum Center, and a short drive to Caesar's Casino. With a beautiful view of the downtown area from the living room, this apartment comes fully stocked with every amenity for your short or long-term stay.

Top guest favourite
The exterior of a renovated farmhouse is surrounded by lush greenery. A spacious porch with seating is visible at the front, while a gravel path leads to the inviting entrance. The structure features a metal roof and warm-colored trim that complements the natural setting.
Farm stay in Goshen
4.98 out of 5 average rating, 357 reviews

The Coop

This 2 bedroom house is a renovated old farmhouse located on the site of a small vegetable farm and native plant nursery. The back deck overlooks the woods, where you can watch the wild birds and keep an eye on the free range chickens. This is a quiet spot for a retreat, but also 25 minutes from downtown Louisville. The Coop has a fully stocked kitchen and comes with eggs right from our flock....

Top guest favourite
A cozy efficiency room features a spacious bed covered in patterned bedding and a comfortable couch. A mirror and decorative artwork adorn the walls, with bedside tables and soft lighting from lamps. The en-suite bathroom is partially visible in the background.
Guest suite in Louisville
4.96 out of 5 average rating, 174 reviews

One Room Apartment with Private Off Street Parking

Room is a stand alone efficiency with a kitchenette, blackout curtains, and reclining queen bed. It has one designated parking space and seperate entrance. Unit has private bath and walk in closet, and kitchenete. Also has refeigerator, coffee maker, work desk microwave, 42" smart tv, Ninja airfryer oven, and couch. Private porch with table and chairs. Close/secure single parking space.

Top guest favourite
A covered front porch is visible, featuring a railing and several outdoor seating options. Steps lead from the porch to a grassy area, while the white exterior of the building is complemented by a green metal roof. Natural light is evident through the large windows.
Apartment in Salem
4.98 out of 5 average rating, 123 reviews

Rural retreat apartment

This isolated, rural setting is great for a single or couple who want a quiet peaceful retreat. The apartment is located at the end of a 1/3 mile driveway on a 165 acre farm. The farm has a 40 acre crop field, 100 acres of woods and 25 acres of pasture land all full of wildlife. The northern boundary presents a challenging hike to a wide creek bed with geodes and other treasures imbedded.

Guest favourite
A white brick exterior features a light blue front door, flanked by a small tree and neatly arranged flower beds. A welcome mat is positioned in front of the door, while a grill is visible to the side, enhancing the inviting entrance.
Loft in Crestwood
4.88 out of 5 average rating, 209 reviews

Welcome to the Nest!

Welcome to THE NEST! We are located very close to great local restaurants, the best outdoor bar/venue I've seen (Third Turn - Oldham Gardens), Artisan Distillery (home of Jefferson's Ocean Bourbon), all major amenity needs, and beautiful Kentucky backroads; all while being easy to access from major highways. Your private retreat is sure to please.

Popular amenities for Underwood vacation rentals

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  2. United States
  3. Indiana
  4. Clark County
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