A covered bridge with the inscription "1884 Built by Kennedy Bros."

Connersville Holiday Rentals

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Our top choices for Connersville holiday rentals

1. The Hidden Gem in downtown Connersville

The Hidden Gem in downtown Connersville
Connersville
10.0 out of 10, Exceptional, (27 reviews)
"Great place for friends to gather. "
United States
Leslie P.
The price is NZ$1,218
includes taxes & fees
27 Sept - 28 Sept
The Hidden Gem in downtown Connersville

2. Hannah's Creek Farm Cottage

Hannah's Creek Farm Cottage
Liberty
9.8 out of 10, Exceptional, (8 reviews)
"Lovely host, and beautiful location. We enjoyed the quiet away from town a lot."
United States
Melissa H.
The price is NZ$307
includes taxes & fees
27 Sept - 28 Sept
Hannah's Creek Farm Cottage

3. Charming Home! Prime Location! Dog-Friendly!

Charming Home! Prime Location! Dog-Friendly!
Richmond
9.8 out of 10, Exceptional, (20 reviews)
"Great house! Just what we needed and in an amazing Richmond neighborhood. "
United States
Jason S.
The price is NZ$565
includes taxes & fees
27 Sept - 28 Sept
Charming Home! Prime Location! Dog-Friendly!

4. Enter As Strangers Leave As Friends

Enter As Strangers Leave As Friends
Lewisville
10.0 out of 10, Exceptional, (49 reviews)
"The house was adorable with a lot of games, books and movies. The host was very friendly and helpful. "
United States
SUZANN S.
The price is NZ$504
includes taxes & fees
27 Sept - 28 Sept
Enter As Strangers Leave As Friends

5. Quaker Hill Cottage on gated estate with fire pit & hiking trails

Quaker Hill Cottage on gated estate with fire pit & hiking trails
Richmond
9.4 out of 10, Exceptional, (36 reviews)
"Very nice place to spend the night while passing through on Route 70. The Thistlethwaite Falls are only minutes away and were a perfect evening activity after driving all day."
United States
Jon and Keri C.
The price is NZ$390
includes taxes & fees
27 Sept - 28 Sept
Quaker Hill Cottage on gated estate with fire pit & hiking trails

6. Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Hagerstown
10.0 out of 10, Exceptional, (18 reviews)
"This is a darling place in a wonderful town. It met all of our needs and we'll definitely stay here again."
United States
Tamera
The price is NZ$289
includes taxes & fees
29 Sept - 30 Sept
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

7. Woodland Retreat w/ Game Room, Fire Pit & King Suite

Woodland Retreat w/ Game Room, Fire Pit & King Suite
Greens Fork
8.8 out of 10, Excellent, (18 reviews)
"Great location for Hwy 127 garage sale "
United States
Margaret G.
Woodland Retreat w/ Game Room, Fire Pit & King Suite

8. New Hagerstown Apartment - Self Check-in. Sleeps 4+

New Hagerstown Apartment - Self Check-in. Sleeps 4+
Hagerstown
9.4 out of 10, Exceptional, (27 reviews)
"Great location and just what we needed for a relaxing weekend in Hagerstown."
United States
Emily E.
The price is NZ$255
includes taxes & fees
5 Oct - 6 Oct
New Hagerstown Apartment - Self Check-in. Sleeps 4+

9. Westcott Mansion with Pickleball Court & Huge Gazebo

Westcott Mansion with Pickleball Court & Huge Gazebo
Richmond
9.8 out of 10, Exceptional, (41 reviews)
"This is a wonderful historic property if you're into a vintage stay. We were. The home is lovely. The only disadvantages are not having a host on-site and having to get luggage up the stairs without an elevator or bellhop assitance; there are no bedrooms on the ground floor. And being vintage, it takes quite a while to adjust the temperature to where you want it. Also, it would be helpful to have television instructions; we were never able to figure out how to get anything on the TV."
United States
Debbie
The price is NZ$570
includes taxes & fees
1 Oct - 2 Oct
Westcott Mansion with Pickleball Court & Huge Gazebo

10. Cozy 1 Bedroom Apartment

Cozy 1 Bedroom Apartment
New Castle
10.0 out of 10, Exceptional, (12 reviews)
"We absolutely enjoyed our stay!!"
United States
Auren
The price is NZ$347
includes taxes & fees
27 Sept - 28 Sept
Cozy 1 Bedroom Apartment

11. Boho Bungalow off Main-one block from Lovely Park

Boho Bungalow off Main-one block from Lovely Park
Richmond
9.0 out of 10, Wonderful, (19 reviews)
"The house is very clean and nicely appointed. Owner is quick to respond to messages. We would definitely stay here again."
United States
Joanne K.
Boho Bungalow off Main-one block from Lovely Park

12. 2 Queen Beds Non-Smoking

2 Queen Beds Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (116 reviews)
"Loved how cozy and inviting this place felt!"
United States
Anonymous traveller
The price is NZ$146
includes taxes & fees
27 Sept - 28 Sept
2 Queen Beds Non-Smoking

13. King Bed Non-Smoking

King Bed Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (152 reviews)
"The staff were friendly and helpful throughout our stay. It felt welcoming right away."
United States
Anonymous traveller
The price is NZ$136
includes taxes & fees
27 Sept - 28 Sept
King Bed Non-Smoking

14. Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
3.0 star property
Economy
The price is NZ$576
includes taxes & fees
27 Sept - 28 Sept
Pets Welcome! Quiet Economy Home w/ Spacious Yard

15. 1 KING BED | SUITE, NON-SMOKING, HOT TUB

1 KING BED | SUITE, NON-SMOKING, HOT TUB
Richmond IN
The price is NZ$270
includes taxes & fees
1 Oct - 2 Oct
1 KING BED | SUITE, NON-SMOKING, HOT TUB

16. Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
Economy
2.0 out of 10, (1 review)
"Bed bugs in upstairs bedroom!!!Unfortunately we had a terrible experience both during and following our stay. During the stay the air conditioning was not functioning properly and we were forced to use portable AC units that didn’t get the temperature below 78 in the house.Three people sleeping upstairs had bed bug bites and upon searching the two beds we found numerous bugs. We promptly made the property owner aware of the situation and requested our stay be refunded due to the inconvenience...
United States
Payton L.
The price is NZ$574
includes taxes & fees
27 Sept - 28 Sept
Pets Welcome! Quiet Economy Home w/ Spacious Yard

17. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Richmond IN
The price is NZ$115
includes taxes & fees
1 Oct - 2 Oct
1 King Bed | Non-Smoking

18. 1 QUEEN BED | BUSINESS, NON-SMOKING

1 QUEEN BED | BUSINESS, NON-SMOKING
Richmond IN
The price is NZ$115
includes taxes & fees
1 Oct - 2 Oct
1 QUEEN BED | BUSINESS, NON-SMOKING

19. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
Richmond IN
The price is NZ$115
includes taxes & fees
1 Oct - 2 Oct
2 Queen Beds | Non-Smoking
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Connersville Hotel Reviews

Find out more about Connersville

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Connersville holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Connersville. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Connersville. Seeing all the best attractions is bound to make you fall in love with Connersville. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Connersville short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Connersville?

Yes, there are holiday rentals in Connersville close to Whitewater Valley Railroad, or you can select a more secluded option if you're looking for a relaxing stay. Connersville is known for its shopping and museums. Make sure you have time to check out the restaurants while you're in the area.

What are some of the best holiday rentals that Connersville has to offer?

The Hidden Gem in downtown Connersville: This highly rated holiday home rental in Connersville is located in the city centre, and offers an arcade/games room, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Our travellers also rate 17 Mi to Brookville Lake: Home w/ In-Unit Laundry as a favourite home for rent in Connersville.

How many holiday rentals are there in Connersville?

Expedia has 4 holiday rentals for your stay in Connersville.

What’s there to see and do in Connersville?

While exploring the area, visit family-friendly sights like Warm Glow Candle Company, or get outside and enjoy nature at Brookville Lake. While here, Whitewater Valley Railroad and Fayette County Historic Museum are other places worth a visit.

What’s a holiday rental in Connersville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Connersville. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for families.