Calhoun Holiday Rentals

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Holiday Rentals in Calhoun

Charming Treehouse with Lake View and Access

9.6 out of 10, Exceptional, (48)
"This treehouse was a perfect little getaway for us! It was very serene and peaceful, yet exciting and fun for the kids! The house had everything we needed and the owners were easily accessible should the need occur. We loved the fishing and the boat was complimentary. It was obvious that a lot of time and attention went into ensuring that guests enjoy their stay. We will definitely be back! "
The price is AU$256
includes taxes & fees
27 Nov - 28 Nov
Charming Treehouse with Lake View and Access

Privacy and breathtaking views on the highest point in Daviess County! So cozy!!

9.8 out of 10, Exceptional, (50)
"Lovely house in a peaceful countryside setting. Really enjoyed sitting on the porch listening to all the birds singing. Everything we needed was provided. There was even an acoustic guitar that my hubby enjoyed playing. Thank you !"
Privacy and breathtaking views on the highest point in Daviess County! So cozy!!

Uniquely remodeled 3 bdrm 2 bth home in safe area! Fenced in with a large deck!

2.0 star property
10.0 out of 10, Exceptional, (6)
"Plenty of room for a large family or a ball team. Kitchen well stocked with pots pans, plates etc. Grill out back. Lots of chairs, plenty of parking. Only one bathroom but has outside shower to hose off those ball players( or before you get into the hot tub). Games for kids. Great neighborhood. Randy was super caring"
The price is AU$332
includes taxes & fees
1 Dec - 2 Dec
Uniquely remodeled 3 bdrm 2 bth home in safe area! Fenced in with a large deck!

Mary - C · Central 2bd/2ba Apt w/Pool &WiFi

10.0 out of 10, Exceptional, (3)
"The property manager was very sweet and made sure we were comfortable/had the things we needed throughout our stay. "
The price is AU$372
includes taxes & fees
1 Dec - 2 Dec
Mary - C · Central 2bd/2ba Apt w/Pool &WiFi

River View in Downtown Newburgh

9.0 out of 10, Wonderful, (2)
"The views of the Ohio River were beautiful. Lots of steps up to house but the views were worth it! House was clean and neat…gorgeous furniture. Our grandchildren especially loved the games in the library room. We also loved being able to seat the whole family at dining table for meals. Lovely home. "
River View in Downtown Newburgh

Centrally located 3 bdrm quaint house with a yard. Pet friendly, no cleaning fee

10.0 out of 10, Exceptional, (25)
"My family and I loved this place! We came in for the weekend to see some old friends and this was the perfect location for our little group! It is in a great location and we loved the bonfire pit in the backyard. "
Centrally located 3 bdrm quaint house with a yard. Pet friendly, no cleaning fee

Downtown Dream in Owensboro Ky

9.8 out of 10, Exceptional, (10)
"Our overall stay was good, we had some issues when we first checked in b/c the cleaning crew had not showed up, & the host was right on it. He had everything satisfactory within a couple hours. I would stay here again. "
The price is AU$881
includes taxes & fees
2 Dec - 3 Dec
Downtown Dream in Owensboro Ky

Enchanting historical home with River View

9.8 out of 10, Exceptional, (17)
"This home was on a very quiet street. The interior has been beautifully updated. The beds were, for the most part, comfortable. Plenty of blankets and pillows were provided. The kitchen was stocked very well for our needs. The owner reponded with any questions I had very promptly and check out was so easy! We were in town for softball so we were in and out of the house often and there was plenty of room for 3 adults and 4 kids (including an infant). Really enjoyed the comfort of this home!"
The price is AU$526
includes taxes & fees
3 Dec - 4 Dec
Enchanting historical home with River View

Blue Moon Cottage: Music Room, Inground Pool

10.0 out of 10, Exceptional, (13)
"Great house with adult children and grands. Hosts were very accommodating with need for early arrival for family wedding. "
The price is AU$612
includes taxes & fees
22 Dec - 23 Dec
Blue Moon Cottage: Music Room, Inground Pool

Heartland Hideaway in the Heart of Owensboro

10.0 out of 10, Exceptional, (11)
"We came to town for a funeral. This place was what we needed to get some much needed rest. The house was perfect for our needs. "
Heartland Hideaway in the Heart of Owensboro

Henderson Haven / KING 2BD/1BA Apartment

The price is AU$294
includes taxes & fees
1 Dec - 2 Dec
Henderson Haven / KING 2BD/1BA Apartment

NEW LISTING! The Cabin | Tranquil Lakefront Retreat by RedAwning

2.0 star property
10.0 out of 10, Exceptional, (4)
"We had a lovely stay. We had coffee on the porch each morning and shared it with many hummingbirds. The property was very quiet and felt very secluded. The place was clean and the AC worked well!"
NEW LISTING! The Cabin | Tranquil Lakefront Retreat by RedAwning

Welcome to simple comfort a like new family friendly home Full of accommodation

10.0 out of 10, Exceptional, (8)
"Very clean and well organized house. Great communication with host both before and after checkout. We will stay again. "
The price is AU$362
includes taxes & fees
27 Nov - 28 Nov
Welcome to simple comfort a like new family friendly home Full of accommodation

HOME AWAY - Newly Updated 3-BR house with WiFi and AC in the heart of Beaver Dam

2.0 star property
10.0 out of 10, Exceptional, (4)
"We were there to actually deer hunt and needed a place close by to stay. I really enjoy my time away so this home worked perfect for us. It was very nice and modern. Very comfortable and has a nice home feeling. I could live there. The beds were so very comfortable. It was very well stocked up. This home is a great place to stay. It is in the heart of downtown. I would highly recommend renting this home. The host was extremely generous and quick to respond. I Will be staying there again next...
HOME AWAY - Newly Updated 3-BR house with WiFi and AC in the heart of Beaver Dam

Mary - H · Conveniently Located 2bd 2ba Apt w/ Pool & Wi-Fi

10.0 out of 10, Exceptional, (6)
"Was much better than staying in a hotel"
Mary - H · Conveniently Located 2bd 2ba Apt w/ Pool & Wi-Fi

Lakeside Log Cabin-Wedding Venue -Hunting -Fishing

10.0 out of 10, Exceptional, (24)
"Our family of nine, from IN and AZ got together for four days at the cabin. A great property for family gatherings. So tranquil and relaxing. Thoroughly enjoyed our stay."
Lakeside Log Cabin-Wedding Venue -Hunting -Fishing

Entire home Beautiful remodeled bluegrass bungalow

8.0 out of 10, Very good, (5)
"Very clean house and quiet neighborhood. Really close to everything. Beds was comfortable everything you need in the house. "
The price is AU$496
includes taxes & fees
2 Dec - 3 Dec
Entire home Beautiful remodeled bluegrass bungalow

The Robinette House: Endless view of rolling farmland

10.0 out of 10, Exceptional, (73)
"Loved this home! Very comfortable, beautifully decorated and they thought of all the small touches to make our stay comfortable."
The price is AU$701
includes taxes & fees
29 Nov - 30 Nov
The Robinette House: Endless view of rolling farmland

Quiet Farm setting surrounded hundreds of acres of fields. Workers welcome.

9.0 out of 10, Wonderful, (2)
"Welcome snacks and clean house. Had a very homey feel! Secluded enough so no traffic or neighborhood noise, but still close enough to enjoy activities with the family!"
Quiet Farm setting surrounded hundreds of acres of fields. Workers welcome.

Newly renovated- 2.5 mi to Downtown Riverfront

10.0 out of 10, Exceptional, (14)
"We had a wonderful stay the house was perfect and the owner was very responsive "
Newly renovated- 2.5 mi to Downtown Riverfront
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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Other types of properties in Calhoun you may be interested in

Wingfield Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1053)
"."
The price is AU$128
includes taxes & fees
27 Nov - 28 Nov
Wingfield Inn & Suites

Hampton Inn & Suites Downtown Owensboro/Waterfront

2.5 star property
9.4 out of 10, Exceptional, (982)
"The convention center is right next door. Very convenient. "
The price is AU$198
includes taxes & fees
15 Dec - 16 Dec
Hampton Inn & Suites Downtown Owensboro/Waterfront

Courtyard by Marriott Owensboro

3.0 star property
9.0 out of 10, Wonderful, (565)
"Updating the pool area would make this an even better place to stay. Staff was friendly, enjoyed the fire pit and lounge area. "
The price is AU$176
includes taxes & fees
26 Dec - 27 Dec
Courtyard by Marriott Owensboro
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find holiday rentals in Calhoun?

Yes, there are holiday rentals close to the most popular sights in Calhoun, or you can select a more secluded option if you're looking for a relaxing stay.

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

Privacy and breathtaking views on the highest point in Daviess County! So cozy!!: This holiday home rental outside of Calhoun offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books.

What can I see and do in Calhoun?

While exploring the area, visit family-friendly sights like International Bluegrass Music Museum, or get outside and enjoy nature at Green River. Riverfront Park and Kentucky Wesleyan College are a couple of places you'll find in the wider area.

What are holiday rentals like in Calhoun?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Calhoun. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family gatherings.