A wooden covered bridge over a river surrounded by dense green trees.

Holiday Rentals in Cumberland County

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Our top choices for Cumberland County holiday rentals

Interior

1. Vintage Charmer on Main Street

Vintage Charmer on Main Street
Greenup
10.0 out of 10, Exceptional, (75 reviews)
"Great stay !"
United States
chris H.
The price is €125
includes taxes & fees
22 Aug - 23 Aug
Vintage Charmer on Main Street
TV

2. Cozy! 1-bedroom house on Lake Mattoon with dock, porch and stunning view!

Cozy! 1-bedroom house on Lake Mattoon with dock, porch and stunning view!
Neoga
The price is €233
includes taxes & fees
16 Sept - 17 Sept
Cozy! 1-bedroom house on Lake Mattoon with dock, porch and stunning view!
Outdoor spa tub

3. Bell Tent Under the Stars

Bell Tent Under the Stars
Charleston
The price is €71
includes taxes & fees
21 Aug - 22 Aug
Bell Tent Under the Stars
Exterior detail

4. Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (51 reviews)
"Place wa exactly as described and the owner was a great communicator. Highly recommend this place and when we return will see if it’s available ! "
United States
Angela C.
The price is €158
includes taxes & fees
23 Aug - 24 Aug
Brickway Retreat
Dining

5. The Exchange. Cozy Studio., XCHNG Studio

The Exchange. Cozy Studio., XCHNG Studio
Effingham
10.0 out of 10, Exceptional, (33 reviews)
"Wonderful place, love the location. "
United States
Dawn K.
The price is €158
includes taxes & fees
13 Sept - 14 Sept
The Exchange. Cozy Studio., XCHNG Studio
Interior

6. Luxury 1BR/BA Loft in the Heart of Downtown Marshall

Luxury 1BR/BA Loft in the Heart of Downtown Marshall
Marshall
10.0 out of 10, Exceptional, (12 reviews)
"It was beautifully decorated and had everything that you would need for a stay away from home. "
United States
Anonymous traveller
The price is €160
includes taxes & fees
31 Aug - 1 Sept
Luxury 1BR/BA Loft in the Heart of Downtown Marshall
Coffee/tea maker, fridge, microwave, oven

7. Built 2025-"OUR NECK OF THE WOODS" close to all the BIG THINGS in Casey, IL

Built 2025-"OUR NECK OF THE WOODS" close to all the BIG THINGS in Casey, IL
Martinsville
10.0 out of 10, Exceptional, (4 reviews)
"Great off the beat cabin. Absolutely fell in love with the cabin itself and the location!!!! Maggie was awesome to talk too. Very pleasant- we will be back!"
United States
Jeremy
The price is €186
includes taxes & fees
24 Aug - 25 Aug
Built 2025-"OUR NECK OF THE WOODS" close to all the BIG THINGS in Casey, IL
Coffee/tea maker, fridge, spices

8. 3 BR House Near Hershey/Marathon

3 BR House Near Hershey/Marathon
Robinson
The price is €183
includes taxes & fees
21 Aug - 22 Aug
3 BR House Near Hershey/Marathon
Smart TV, fireplace

9. Prairieview Cabin - with Hot Tub

Prairieview Cabin - with Hot Tub
Sullivan
10.0 out of 10, Exceptional, (42 reviews)
"Very nice place to stay!"
United States
Brandon R.
The price is €235
includes taxes & fees
25 Aug - 26 Aug
Prairieview Cabin - with Hot Tub
Smart TV

10. Park View Place 4 Blocks From the World's Biggest

Park View Place 4 Blocks From the World's Biggest
Casey
9.8 out of 10, Exceptional, (44 reviews)
"Cozy and clean. Enjoyed our stay. Kids loved that the park was so close!"
United States
Angie R.
The price is €186
includes taxes & fees
23 Aug - 24 Aug
Park View Place 4 Blocks From the World's Biggest
Smart TV, fireplace

11. Cottage By The Park Home of The Big Things

Cottage By The Park Home of The Big Things
Casey
10.0 out of 10, Exceptional, (65 reviews)
"The house is lovely and super clean. The beds were comfortable and there's lots of room to move in the bathrooms. The house is located across the street from the park, which was lovely for morning and evening walks. Casey is a cute town to visit. We enjoyed our stay!"
United States
Meg B.
The price is €205
includes taxes & fees
25 Aug - 26 Aug
Cottage By The Park Home of The Big Things
Interior

12. The Exchange. Downtown Luxury for Two, XCHNG. Industrial Executive Loft w/ King Bed

The Exchange. Downtown Luxury for Two, XCHNG. Industrial Executive Loft w/ King Bed
Effingham
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful, quiet, and comfortable! The hosts thought of everything you could ask for. Will definitely stay again the next time we are in town. "
United States
Amanda J.
The price is €183
includes taxes & fees
8 Sept - 9 Sept
The Exchange. Downtown Luxury for Two, XCHNG. Industrial Executive Loft w/ King Bed
Bar (on property)

13. The Exchange. Loft Living.

The Exchange. Loft Living.
Effingham
9.8 out of 10, Exceptional, (6 reviews)
"Wonderful stay! Second time we've stayed with them & it's great! "
United Kingdom
Erica C.
The price is €189
includes taxes & fees
8 Sept - 9 Sept
The Exchange. Loft Living.
Coffee/tea maker, fridge, microwave, oven

14. Cozy 2BR Loft in Downtown Charleston, IL

Cozy 2BR Loft in Downtown Charleston, IL
Charleston
10.0 out of 10, Exceptional, (12 reviews)
"Cute little loft and great location in the main square with lots of walkable restaurants."
United States
Thomas
The price is €173
includes taxes & fees
16 Sept - 17 Sept
Cozy 2BR Loft in Downtown Charleston, IL
Exterior

15. Fish, boat, grill, chill, pets, relax

Fish, boat, grill, chill, pets, relax
Sullivan
9.4 out of 10, Exceptional, (71 reviews)
"It was excellent!"
United States
Samuel D S.
The price is €258
includes taxes & fees
1 Sept - 2 Sept
Fish, boat, grill, chill, pets, relax
Exterior detail

16. Cozy 1-bedroom with AC and WiFi in charming Shelbyville

Cozy 1-bedroom with AC and WiFi in charming Shelbyville
Shelbyville
8.6 out of 10, Excellent, (16 reviews)
"It was very nice. I've stayed in both their 1st floor apartments now and have felt comfortable. "
United States
Rosanne D.
The price is €137
includes taxes & fees
23 Aug - 24 Aug
Cozy 1-bedroom with AC and WiFi in charming Shelbyville
Interior

17. Prairieview Cottage Retreat - Hot Tub Sunsets

Prairieview Cottage Retreat - Hot Tub Sunsets
Sullivan
10.0 out of 10, Exceptional, (61 reviews)
"Very clean and cute place! We enjoyed our stay very much. The hosts were wonderful, and we even got the blessing of a visit by the 2 puppies that live on the property. Definitely recommend staying here! "
United States
Lisa S.
Prairieview Cottage Retreat - Hot Tub Sunsets
Dining

18. Off grid cabin adjacent to Corp of Engineers ground. Perfect Deer Camp

Off grid cabin adjacent to Corp of Engineers ground. Perfect Deer Camp
Windsor
The price is €159
includes taxes & fees
27 Aug - 28 Aug
Off grid cabin adjacent to Corp of Engineers ground. Perfect Deer Camp
Dining

19. FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Marshall
9.8 out of 10, Exceptional, (28 reviews)
"We had a blast!!! Thank you!!!"
United States
Theresa
The price is €413
includes taxes & fees
26 Aug - 27 Aug
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Smart TV, fireplace

20. Luxury Log Retreat with Hot Tub, Near Homestead & Winery

Luxury Log Retreat with Hot Tub, Near Homestead & Winery
Paris
9.6 out of 10, Exceptional, (14 reviews)
"Great escape to get away and relax. The bird sounds were amazing! Fantastic amenities as well."
United States
Hollie D.
The price is €405
includes taxes & fees
31 Aug - 1 Sept
Luxury Log Retreat with Hot Tub, Near Homestead & Winery
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 Cumberland County Hotel Reviews

Best Western Heartland Inn

Best Western Heartland Inn

10/10 Excellent
"Very clean! Great new owners. Delicious breakfast!"
MOLLY 1-night trip
Posted 13 hours ago
Best Western Heartland Inn

Find out more about Cumberland County

Holiday Homes in Cumberland County

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