155+ Private Villas and Holiday Rentals in Shepardsville |
Shepardsville Holiday Rentals
Apartment
10.0Exceptional
(188 Reviews)
1 Bedroom
1 Bath
3 Guests
550 ft²
Hot Tub
Fireplace/Heating
Balcony/Terrace
Kitchen
US $227/Night
7 Nights - US $1,590
Resort
- Indiana
- ·
- Terre Haute
- 4.22 mi to center
9.0Exceptional
(473 Reviews)
7 Baths
18 Guests
691.96 ft²
Oceanfront- Fireplace/Heating
Pool
Ocean View
US $276/Night
7 Nights - US $1,930
Hotel
- Indiana
- ·
- Terre Haute
- 2.28 mi to center
9.6Exceptional
(1183 Reviews)
1 Bath
- Hot Tub
- Pool
Breakfast- Kitchen
US $118/Night
7 Nights - US $829
House
- Indiana
- ·
- Terre Haute
- 2.37 mi to center
10.0Exceptional
(27 Reviews)
1 Bedroom
1 Bath
4 Guests
Child Friendly
US $115/Night
7 Nights - US $805
House
- Indiana
- ·
- North Terre Haute
- 3.05 mi to center
3 Bedrooms
2 Baths
8 Guests
1356.25 ft²
- Fireplace/Heating
Parking
Internet- Child Friendly
US $202/Night
7 Nights - US $1,412
House
- Indiana
- ·
- Terre Haute
- 1.78 mi to center
10.0Exceptional
(15 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
US $351/Night
7 Nights - US $2,459
House
- Indiana
- ·
- Terre Haute
- 1.89 mi to center
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
4 Guests
893 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $220/Night
7 Nights - US $1,542
House
- Indiana
- ·
- Terre Haute
- 1.57 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
Air Conditioner
US $194/Night
7 Nights - US $1,360
Apartment
- Indiana
- ·
- Terre Haute
- 1.48 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $310/Night
7 Nights - US $2,173
Luxury Holiday Rentals in Shepardsville
Over 146+ Luxury Holiday Rentals in or Near Shepardsville
House
- Indiana
- ·
- North Terre Haute
- 3.15 mi to center
9.0Exceptional
(6 Reviews)
7 Bedrooms
3 Baths
30 Guests
5500 ft²
Private Pool- Hot Tub
- Fireplace/Heating
- Pool
US $1,491/Night
7 Nights - US $10,437
House
- Indiana
- ·
- North Terre Haute
- 4.76 mi to center
6 Bedrooms
4 Baths
16 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $1,093/Night
7 Nights - US $7,648
New
House
- Indiana
- ·
- Terre Haute
- 3.84 mi to center
5 Bedrooms
4 Baths
20 Guests
- Private Pool
- Hot Tub
Spa- Fireplace/Heating
US $924/Night
7 Nights - US $6,468
Villa
- Indiana
- ·
- Terre Haute
- 3.59 mi to center
5 Bedrooms
3 Baths
20 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Pet Friendly
US $749/Night
7 Nights - US $5,244
House
- Indiana
- ·
- Terre Haute
- 2.78 mi to center
10.0Exceptional
(14 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $495/Night
7 Nights - US $3,467
House
- Indiana
- ·
- Terre Haute
- 3.89 mi to center
9.8Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
6 Guests
2900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $454/Night
7 Nights - US $3,180
House
- Indiana
- ·
- Terre Haute
- 2.43 mi to center
8.6Fabulous
(4 Reviews)
4 Bedrooms
2 Baths
7 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $345/Night
7 Nights - US $2,416
New
House
- Indiana
- ·
- Terre Haute
- 1.3 mi to center
3 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $326/Night
7 Nights - US $2,279
House
- Indiana
- ·
- Terre Haute
- 2.57 mi to center
9.8Exceptional
(31 Reviews)
4 Bedrooms
2 Baths
8 Guests
1864 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $309/Night
7 Nights - US $2,165
Top-Rated Holiday Rentals with a Pool in Shepardsville
Over 16+ The Best Private Villas and Holiday Rentals in Shepardsville with a Pool
Resort
- Indiana
- ·
- Terre Haute
- 4.16 mi to center
9.2Exceptional
(922 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $154/Night
7 Nights - US $1,080
Hotel
- Indiana
- ·
- Terre Haute
- 2.25 mi to center
9.0Exceptional
(1186 Reviews)
6 Baths
310.36 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Pet Friendly
US $162/Night
7 Nights - US $1,132
Hotel
- Indiana
- ·
- Terre Haute
- 2.22 mi to center
9.0Exceptional
(1027 Reviews)
1 Bath
- Pool
- Breakfast
- Pet Friendly
- Kitchen
US $135/Night
7 Nights - US $942
Hotel
- Indiana
- ·
- Terre Haute
- 4.80 mi to center
9.0Exceptional
(782 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $182/Night
7 Nights - US $1,272
Hotel
- Indiana
- ·
- Terre Haute
- 4.92 mi to center
9.0Exceptional
(529 Reviews)
1 Bath
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
US $185/Night
7 Nights - US $1,297
Hotel
- Indiana
- ·
- Terre Haute
- 4.80 mi to center
9.0Exceptional
(121 Reviews)
1 Bath
322.92 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $201/Night
7 Nights - US $1,407
Hotel
- Indiana
- ·
- Terre Haute
- 2.22 mi to center
8.8Fabulous
(748 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
US $134/Night
7 Nights - US $935
Hotel
- Indiana
- ·
- Terre Haute
- 4.90 mi to center
8.6Fabulous
(153 Reviews)
1 Bath
415.18 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $208/Night
7 Nights - US $1,458
Hotel
- Indiana
- ·
- Terre Haute
- 2.52 mi to center
8.4Excellent
(954 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $144/Night
7 Nights - US $1,007
Pet-Friendly Holiday Rentals in Shepardsville
Over 57+ Pet-Friendly Holiday Rentals in or Near Shepardsville
House
- Indiana
- ·
- Terre Haute
- 0.39 mi to center
9.8Exceptional
(12 Reviews)
2 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $198/Night
7 Nights - US $1,383
Hotel
- Terre Haute
- ·
- Downtown
- 0.14 mi to center
9.0Exceptional
(180 Reviews)
6 Baths
358.8 ft²
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Pet Friendly
US $140/Night
7 Nights - US $982
House
- Indiana
- ·
- Terre Haute
- 1.98 mi to center
1 Bedroom
1 Bath
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
US $157/Night
7 Nights - US $1,099
House
9.6Exceptional
(31 Reviews)
2 Bedrooms
1 Bath
5 Guests
980 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $216/Night
7 Nights - US $1,513
Hotel
- Indiana
- ·
- Terre Haute
- 2.33 mi to center
8.5Fabulous
(700 Reviews)
2 Baths
301.39 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $81/Night
7 Nights - US $567
House
- Indiana
- ·
- Terre Haute
- 2.36 mi to center
9.0Exceptional
(39 Reviews)
1 Bedroom
1 Bath
4 Guests
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
US $141/Night
7 Nights - US $986
House
- Indiana
- ·
- Terre Haute
- 1.11 mi to center
8.0Excellent
(1 Review)
2 Bedrooms
1 Bath
7 Guests
1750 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $248/Night
7 Nights - US $1,739
House
- Indiana
- ·
- Terre Haute
- 2.47 mi to center
6.4Good
(7 Reviews)
2 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $147/Night
7 Nights - US $1,031
Cabin
- Indiana
- ·
- Terre Haute
- 2.24 mi to center
2 Bedrooms
1 Bath
5 Guests
350 ft²
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
US $121/Night
7 Nights - US $845
Large Holiday Rentals and Private Villas in Shepardsville
Over 7+ Large Holiday Rentals and Private Villas in or Near Shepardsville
House
- Indiana
- ·
- Saint Mary Of The Woods
- 2.72 mi to center
9.8Exceptional
(8 Reviews)
2 Bedrooms
2 Baths
10 Guests
1500 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
US $278/Night
7 Nights - US $1,945
House
- Indiana
- ·
- Terre Haute
- 1.99 mi to center
4 Bedrooms
1 Bath
12 Guests
1600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $122/Night
7 Nights - US $851
House
- Indiana
- ·
- North Terre Haute
- 4.39 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
14 Guests
- Private Pool
- Spa
- Fireplace/Heating
- Pool
US $506/Night
7 Nights - US $3,539
House
- Indiana
- ·
- Terre Haute
- 3.10 mi to center
9.6Exceptional
(4 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $288/Night
7 Nights - US $2,013
House
- Indiana
- ·
- North Terre Haute
- 3.04 mi to center
5 Bedrooms
2 Baths
8 Guests
1400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $137/Night
7 Nights - US $958
House
- Indiana
- ·
- Terre Haute
- 2.10 mi to center
3 Bedrooms
1 Bath
10 Guests
2093 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $120/Night
7 Nights - US $840
House
- Indiana
- ·
- Terre Haute
- 1.44 mi to center
4.8Average
(34 Reviews)
2 Bedrooms
1 Bath
10 Guests
1018 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $146/Night
7 Nights - US $1,022
Wheelchair Accessible Holiday Homes in Shepardsville
Over 15+ Wheelchair Accessible Holiday Homes in or Near Shepardsville
Hotel
- Terre Haute
- ·
- Downtown
- 0.12 mi to center
8.5Fabulous
(102 Reviews)
1 Bath
301.39 ft²
- Hot Tub
- Fireplace/Heating
- Breakfast
- Pet Friendly
US $201/Night
7 Nights - US $1,409
Hotel
- Terre Haute
- ·
- Downtown
- 0.13 mi to center
9.2Exceptional
(894 Reviews)
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $136/Night
7 Nights - US $950
Hotel
- Indiana
- ·
- Terre Haute
- 2.51 mi to center
7.8Very Good
(184 Reviews)
1 Bath
352.52 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $259/Night
7 Nights - US $1,815
Hotel
- Indiana
- ·
- Terre Haute
- 2.56 mi to center
8.8Fabulous
(754 Reviews)
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Kitchen
US $154/Night
7 Nights - US $1,079
Hotel
- Indiana
- ·
- Terre Haute
- 2.28 mi to center
7.8Very Good
(105 Reviews)
8 Baths
301.39 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $230/Night
7 Nights - US $1,612
Hotel
- Terre Haute
- ·
- Downtown
- 0.14 mi to center
8.8Fabulous
(715 Reviews)
1 Bath
- Fireplace/Heating
- Breakfast
- Kitchen
- Parking
US $146/Night
7 Nights - US $1,024
Hotel
- Indiana
- ·
- Terre Haute
- 2.22 mi to center
7.3Very Good
(773 Reviews)
3 Baths
301.39 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $86/Night
7 Nights - US $602
Hotel
- Indiana
- ·
- Terre Haute
- 0.38 mi to center
6.9Good
(292 Reviews)
4 Baths
313.35 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- View
US $78/Night
7 Nights - US $546
Hotel
- Indiana
- ·
- Terre Haute
- 2.57 mi to center
6.8Good
(157 Reviews)
10 Baths
283.17 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $150/Night
7 Nights - US $1,053
Shepardsville Private Villas and Holiday Homes Under $200
Over 69+ Shepardsville Private Villas and Holiday Homes Under $200
House
- Indiana
- ·
- North Terre Haute
- 2.76 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $177/Night
7 Nights - US $1,240
House
- Indiana
- ·
- Terre Haute
- 4.04 mi to center
1 Bedroom
2 Baths
6 Guests
- View
- Parking
- Air Conditioner
- Internet
US $171/Night
7 Nights - US $1,197
Hotel
- Indiana
- ·
- Terre Haute
- 2.31 mi to center
7.8Very Good
(1006 Reviews)
1 Bath
- Breakfast
- Kitchen
- Parking
- Air Conditioner
US $75/Night
7 Nights - US $528
House
- Indiana
- ·
- Terre Haute
- 2.30 mi to center
9.8Exceptional
(49 Reviews)
2 Bedrooms
1 Bath
5 Guests
600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $121/Night
7 Nights - US $847
Apartment
- Indiana
- ·
- Terre Haute
- 2.22 mi to center
1 Bedroom
2 Baths
5 Guests
- View
- Parking
- Air Conditioner
- Internet
US $84/Night
7 Nights - US $588
House
- Indiana
- ·
- North Terre Haute
- 5.19 mi to center
9.6Exceptional
(26 Reviews)
2 Bedrooms
1 Bath
4 Guests
906 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $160/Night
7 Nights - US $1,123
House
- Indiana
- ·
- Terre Haute
- 1.86 mi to center
8.4Excellent
(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Internet
- Child Friendly
Security/Safety
US $157/Night
7 Nights - US $1,100
House
- Indiana
- ·
- Terre Haute
- 2.22 mi to center
8.0Excellent
(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $133/Night
7 Nights - US $930
Apartment
- Indiana
- ·
- Terre Haute
- 1.23 mi to center
8.0Excellent
(1 Review)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $109/Night
7 Nights - US $760
Instantly Bookable Holiday Homes in Shepardsville
Over 48+ Instantly Bookable Holiday Homes in or Near Shepardsville
Apartment
- Indiana
- ·
- Terre Haute
- 0.96 mi to center
7.4Very Good
(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $219/Night
7 Nights - US $1,530
House
- Indiana
- ·
- Terre Haute
- 0.86 mi to center
7.2Very Good
(19 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $178/Night
7 Nights - US $1,244
Apartment
- Indiana
- ·
- Terre Haute
- 1.03 mi to center
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $118/Night
7 Nights - US $823
Apartment
- Indiana
- ·
- Seelyville
- 0.07 mi to center
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $91/Night
7 Nights - US $637
Apartment
- Indiana
- ·
- Terre Haute
- 1.91 mi to center
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $82/Night
7 Nights - US $575
House
- Indiana
- ·
- Terre Haute
- 1.99 mi to center
10.0Exceptional
(12 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $286/Night
7 Nights - US $2,001
House
- Indiana
- ·
- Terre Haute
- 2.35 mi to center
10.0Exceptional
(11 Reviews)
3 Bedrooms
1 Bath
5 Guests
1164 ft²
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
US $190/Night
7 Nights - US $1,328
House
- Indiana
- ·
- Terre Haute
- 2.35 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Pet Friendly
- Air Conditioner
- Internet
- Child Friendly
US $141/Night
7 Nights - US $986
House
- Indiana
- ·
- North Terre Haute
- 3.05 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
8 Guests
1358 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $194/Night
7 Nights - US $1,360
Book a Last Minute Place to Stay in Shepardsville
About Casai's Private Villas and Holiday Rentals in Shepardsville
Discover more than 155 vacation rentals available in Shepardsville. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Shepardsville.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Shepardsville, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Shepardsville. On average, places to stay near Shepardsville offer 352.48 ft², with nightly prices averaging US $241.
With Casai, finding and comparing holiday rentals in Shepardsville is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Shepardsville
| Type | Count |
|---|---|
| Vacation Homes | 85 |
| Holiday Apartments | 24 |
| Cottages | 3 |
| Villas | 1 |
Use these Quick Filters to Find a Holiday Rental in Shepardsville
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Shepardsville.
Weather in Shepardsville, IN
View the weather forecast for Shepardsville before booking your Shepardsville Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Shepardsville, IN
Casai offers a large selection of top attractions around Shepardsville . Research things to do on your vacation before you visit Shepardsville.
Frequently Asked Questions About Shepardsville?
What are the top holiday rentals in Shepardsville?
With numerous options available in Shepardsville, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Shepardsville:
- Getaway in the country/Beautiful Parke County/Large hot tub and much more!
- Camp Lilybug-Calm Oasis Pet Friendly!
- Wi-Fi avail at this Beautiful 1896 Farmhouse, rural setting. Tranquil location.
- Charming Pet Friendly Bungalow
- FORT HARRISON RIVER FRONT PROPERTY
- Modern 3-bed farmhouse AC, Wifi
- You'll love your stay at the Azul Abode centrally located in Terre Haute!
- Cozy, clean, pet friendly - King bed, fenced yard
- Charming 2 bedroom home centrally located near ISU and Rose Hulman
- Charming 2-bedroom apartment close to Universities in downtown Terre Haute.
How many holiday rentals have private pools in Shepardsville?
Discover a selection of holiday rentals with private pools near Shepardsville with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Shepardsville are best for families?
If you're searching for a family-friendly holiday home in Shepardsville, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Shepardsville:
- Magic Cottage - 2 Bedrm,1 Ba, Washer&Dryer, Nice Kitchen, & Fenced Yard for Dogs
- La Quinta by Wyndham Terre Haute
- Quality Inn Terre Haute University Area
How many Casai.com holiday rentals are available in Shepardsville?
As of 2026, Casai boasts over 155 properties listed in the Shepardsville area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Shepardsville.
People Also Ask
Finding the best prices in Shepardsville
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