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

Cumberland County Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Our top choices for Cumberland County vacation rentals

A wooden cabin entrance with a welcome sign, a small table with a lamp and flowers, and a woven mat on the floor.

1. Vintage Charmer on Main Street

Vintage Charmer on Main Street
Greenup
10.0 out of 10, Exceptional, (79 reviews)
"Great stay !"
United States
chris H.
The price is CA $123
CA $197 total
includes taxes & fees
Nov 2 - Nov 3
Vintage Charmer on Main Street
A small, rustic building with a metal roof, a porch with two chairs, and a gravel driveway.

2. Family Friendly Cottage in the Countryside

Family Friendly Cottage in the Countryside
Toledo
10.0 out of 10, Exceptional, (3 reviews)
"Super clean and quiet was a great place to get away while visiting family and friends."
United States
Richard
The price is CA $394
CA $596 total
includes taxes & fees
Nov 30 - Dec 1
Family Friendly Cottage in the Countryside
A reception area with a wooden counter, a chair, a television, and a clock on the wall.

3. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Effingham
10.0 out of 10, Exceptional, (4 reviews)
"Lobby had clear signs and felt straightforward on arrival."
United States
Anonymous traveller
The price is CA $82
CA $92 total
includes taxes & fees
Nov 8 - Nov 9
1 King Bed | Non-Smoking, Micfridge
An open-plan office with exposed brick walls, wooden floors, and large windows.

4. The Exchange. Cozy Studio., XCHNG Studio

The Exchange. Cozy Studio., XCHNG Studio
Effingham
10.0 out of 10, Exceptional, (36 reviews)
"Wonderful place, love the location. "
United States
Dawn K.
The price is CA $141
CA $237 total
includes taxes & fees
Nov 8 - Nov 9
The Exchange. Cozy Studio., XCHNG Studio
A brick house with a white door, a mailbox, and a wooden porch.

5. Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (53 reviews)
"Great place for a stay. Nice amenities and very clean. Would absolutely stay again"
United States
Kevin F.
The price is CA $154
CA $252 total
includes taxes & fees
Nov 1 - Nov 2
Brickway Retreat
A cozy living room with a dark green wall, a wooden chair with a white macrame throw, a potted plant, and a framed picture.

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

Luxury 1BR/BA Loft in the Heart of Downtown Marshall
Marshall
9.8 out of 10, Exceptional, (17 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 CA $196
CA $305 total
includes taxes & fees
Nov 5 - Nov 6
Luxury 1BR/BA Loft in the Heart of Downtown Marshall
A modern kitchen with dark cabinets, stainless steel appliances, and a granite countertop.

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, (10 reviews)
"Simple easy quite in the woods brand new clean nice fire pit perfect for a short stay would be awesome to rent for hunting season"
United States
J M.
The price is CA $266
CA $321 total
includes taxes & fees
Nov 7 - Nov 8
Built 2025-"OUR NECK OF THE WOODS" close to all the BIG THINGS in Casey, IL
A modern kitchen with a brick wall, a bar area with stools, and a large island.

8. 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, (14 reviews)
"Loved the atmosphere very unique and comfortable. Would highly recommend and will definitely stay the next time we travel this way"
United States
Roger
The price is CA $164
CA $281 total
includes taxes & fees
Nov 15 - Nov 16
The Exchange. Downtown Luxury for Two, XCHNG. Industrial Executive Loft w/ King Bed
A hotel room with a bed, a desk, a chair, a mirror, and a kitchenette.

9. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Effingham
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $93
CA $104 total
includes taxes & fees
Nov 8 - Nov 9
1 Queen Bed | Non-Smoking, Kitchen
A modern living room with a flat-screen TV, a sofa, a coffee table, and a ceiling fan.

10. Prairieview Cabin - with Hot Tub

Prairieview Cabin - with Hot Tub
Sullivan
10.0 out of 10, Exceptional, (47 reviews)
"Very nice place to stay!"
United States
Brandon R.
The price is CA $218
CA $352 total
includes taxes & fees
Nov 30 - Dec 1
Prairieview Cabin - with Hot Tub
Living area

11. Perfect little home

Perfect little home
Marshall
10.0 out of 10, Exceptional, (1 review)
"Beautiful home easy check-in process would definitely recommend to friends"
United States
Charles M.
The price is CA $349
CA $424 total
includes taxes & fees
Nov 22 - Nov 23
Perfect little home
Three beverage vending machines with various drink options.

12. 1 Queen Bed | Smoking, Micfridge

1 Queen Bed | Smoking, Micfridge
Effingham
10.0 out of 10, Exceptional, (4 reviews)
"A calm spot ideal for a quick stopover."
United States
Anonymous traveller
The price is CA $96
CA $108 total
includes taxes & fees
Nov 8 - Nov 9
1 Queen Bed | Smoking, Micfridge
A house with a porch supported by white columns, a black door with a wreath, and two white rocking chairs.

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

Cozy 1-bedroom with AC and WiFi in charming Shelbyville
Shelbyville
8.4 out of 10, Very good, (19 reviews)
"Place was great!"
United States
Robyn J.
The price is CA $116
CA $180 total
includes taxes & fees
Nov 1 - Nov 2
Cozy 1-bedroom with AC and WiFi in charming Shelbyville
A bar area with a wooden ceiling and bar stools.

14. 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 CA $172
CA $288 total
includes taxes & fees
Nov 2 - Nov 3
The Exchange. Loft Living.
A residential street with a house featuring a front porch, outdoor seating, and string lights.

15. Cozy, and private apartment near Lake Shelbyville

Cozy, and private apartment near Lake Shelbyville
Shelbyville
9.8 out of 10, Exceptional, (24 reviews)
"Excellent stay. Very nice accommodations. Will absolutely be staying there again the next time we are in town. "
United States
Brandon S.
The price is CA $112
CA $178 total
includes taxes & fees
Nov 1 - Nov 2
Cozy, and private apartment near Lake Shelbyville
A modern living room with two leather sofas, a dining area, and a kitchen in the background.

16. 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, (69 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 CA $238
CA $355 total
includes taxes & fees
Nov 23 - Nov 24
Cottage By The Park Home of The Big Things
A modern kitchen with a round dining table, chairs, a potted orchid, and a stainless steel refrigerator.

17. Cozy 2BR Loft in Downtown Charleston, IL

Cozy 2BR Loft in Downtown Charleston, IL
Charleston
10.0 out of 10, Exceptional, (15 reviews)
"Very cool space in a great location "
United States
Stewart T.
The price is CA $210
CA $275 total
includes taxes & fees
Nov 4 - Nov 5
Cozy 2BR Loft in Downtown Charleston, IL
An aerial view of Lake Shelbyville with RVs, a large building, and a bridge in the background.

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

Fish, boat, grill, chill, pets, relax
Sullivan
9.4 out of 10, Exceptional, (72 reviews)
"The house was clean. Beds and couches were very comfortable. Great for our dogs."
United States
Vince S.
The price is CA $214
CA $403 total
includes taxes & fees
Nov 1 - Nov 2
Fish, boat, grill, chill, pets, relax
A kitchen with a marble countertop, stainless steel refrigerator, and wooden cabinets.

19. Eagle's Nest near Eagle Creek State Park

Eagle's Nest near Eagle Creek State Park
Findlay
9.6 out of 10, Exceptional, (26 reviews)
"Me and my family loved this place. Very clean. We enjoyed our stay and would stay again."
United States
terri m.
The price is CA $233
CA $367 total
includes taxes & fees
Nov 1 - Nov 2
Eagle's Nest near Eagle Creek State Park
A compact kitchen with wooden cabinets, a refrigerator, a stove, and two bar stools.

20. Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds

Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds
Sullivan
9.4 out of 10, Exceptional, (3 reviews)
"We enjoyed our stay. It was close proximity to the beach on Lake Shelbyville and the property was clean."
United States
aubrey m.
The price is CA $279
CA $424 total
includes taxes & fees
Nov 23 - Nov 24
Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cumberland County Hotel Reviews

Comfort Suites Mattoon East

Comfort Suites Mattoon East

10/10 Excellent
"Wonderful room. Very comfortable and spacious. Would definitely stay here again"
cathy 1-night trip
Posted 12 hours ago
Comfort Suites Mattoon East

Find out more about Cumberland County

Everything you need to know about Cumberland County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cumberland County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cumberland County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cumberland County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cumberland County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cumberland County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cumberland County vacation rentals we have selected for you start as low as CA $197 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cumberland County rentals

At Expedia, we put the best Cumberland County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cumberland County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cumberland County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cumberland County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.