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 $124
CA $198 total
includes taxes & fees
Oct 26 - Oct 27
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 $362
CA $593 total
includes taxes & fees
Oct 26 - Oct 27
Family Friendly Cottage in the Countryside
A modern kitchen with dark cabinets, stainless steel appliances, and a granite countertop.

3. 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 $318 total
includes taxes & fees
Oct 28 - Oct 29
Built 2025-"OUR NECK OF THE WOODS" close to all the BIG THINGS in Casey, IL
A modern living room with two leather sofas, a dining area, and a kitchen in the background.

4. 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 $356 total
includes taxes & fees
Oct 30 - Oct 31
Cottage By The Park Home of The Big Things
A cozy living room with a sofa, a small side table, and a dining area with a table and chairs. A kitchen is visible in the background.

5. 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, (45 reviews)
"Cozy and clean. Enjoyed our stay. Kids loved that the park was so close!"
United States
Angie R.
The price is CA $210
CA $331 total
includes taxes & fees
Oct 30 - Oct 31
Park View Place 4 Blocks From the World's Biggest
An open-plan office with exposed brick walls, wooden floors, and large windows.

6. 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 $250 total
includes taxes & fees
Nov 1 - Nov 2
The Exchange. Cozy Studio., XCHNG Studio
A spacious kitchen with a large island, exposed brick walls, and large windows offering views of the city.

7. The Exchange. Big Luxury Loft, XCHNG. Modern Loft in the heart of Effingham.

The Exchange. Big Luxury Loft, XCHNG. Modern Loft in the heart of Effingham.
Effingham
10.0 out of 10, Exceptional, (28 reviews)
"Amazing location and the property was perfect! Great communication with our host."
United States
Lynn M.
The price is CA $274
CA $482 total
includes taxes & fees
Nov 18 - Nov 19
The Exchange. Big Luxury Loft, XCHNG. Modern Loft in the heart of Effingham.
A brick house with a white door, a mailbox, and a wooden porch.

8. 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
Oct 26 - Oct 27
Brickway Retreat
A modern living room with a flat-screen TV, a sofa, a coffee table, and a ceiling fan.

9. Prairieview Cabin - with Hot Tub

Prairieview Cabin - with Hot Tub
Sullivan
10.0 out of 10, Exceptional, (45 reviews)
"Very nice place to stay!"
United States
Brandon R.
The price is CA $221
CA $375 total
includes taxes & fees
Nov 17 - Nov 18
Prairieview Cabin - with Hot Tub
A modern kitchen with a round dining table, chairs, a potted orchid, and a stainless steel refrigerator.

10. 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 $281 total
includes taxes & fees
Nov 2 - Nov 3
Cozy 2BR Loft in Downtown Charleston, IL
A spacious kitchen with wooden cabinets, a dishwasher, and a dining area with a table and chairs.

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

Fish, boat, grill, chill, pets, relax
Sullivan
9.4 out of 10, Exceptional, (72 reviews)
"It was excellent!"
United States
Samuel D S.
The price is CA $214
CA $399 total
includes taxes & fees
Oct 26 - Oct 27
Fish, boat, grill, chill, pets, relax
A compact kitchen with wooden cabinets, a refrigerator, a stove, and two bar stools.

12. 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 $252
CA $390 total
includes taxes & fees
Oct 26 - Oct 27
Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds
A building with a garage door, a driveway, and a parked car.

13. Prairieview Cottage Retreat - Hot Tub Sunsets

Prairieview Cottage Retreat - Hot Tub Sunsets
Sullivan
10.0 out of 10, Exceptional, (62 reviews)
"Very nice everything was perfect couldn't have asked for a better time recommend very much"
United States
Ben D.
The price is CA $285
CA $529 total
includes taxes & fees
Nov 17 - Nov 18
Prairieview Cottage Retreat - Hot Tub Sunsets
A cozy living room with a dark green wall, a wooden chair with a white macrame throw, a potted plant, and a framed picture.

14. 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, (16 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 $321 total
includes taxes & fees
Oct 30 - Oct 31
Luxury 1BR/BA Loft in the Heart of Downtown Marshall
A building entrance with a wooden door, a mailbox, and a bench outside.

15. 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 $188
CA $321 total
includes taxes & fees
Nov 18 - Nov 19
The Exchange. Loft Living.
A cozy cabin interior with a wooden staircase, a fireplace, a Christmas tree, and a leather sofa.

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

Luxury Log Retreat with Hot Tub, Near Homestead & Winery
Paris
9.8 out of 10, Exceptional, (16 reviews)
"Knowing we were checking in to a log cabin, we were not expecting it to be so clean and nice! The cabin is spacious, with plenty of comfortable seating, as well as lots of work space and storage, especially in the kitchen. The place seems to be new and is well cared for. Loved the setting! It is a beautiful, wooded property with plenty of privacy, but yet only 15-20 minutes from town. We enjoyed our stay very much!"
United States
Barbara A.
The price is CA $378
CA $671 total
includes taxes & fees
Oct 26 - Oct 27
Luxury Log Retreat with Hot Tub, Near Homestead & Winery
A rustic cabin with a porch, surrounded by a well-maintained lawn and trees.

17. Binion Lodge: Wooded Privacy Near Lake Shelbyville

Binion Lodge: Wooded Privacy Near Lake Shelbyville
Sullivan Township
10.0 out of 10, Exceptional, (20 reviews)
"Very nice and secluded property! Hosts are outstanding as well!"
United States
John
The price is CA $322
CA $615 total
includes taxes & fees
Nov 23 - Nov 24
Binion Lodge: Wooded Privacy Near Lake Shelbyville
A kitchen with a marble countertop, stainless steel refrigerator, and wooden cabinets.

18. 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
Oct 26 - Oct 27
Eagle's Nest near Eagle Creek State Park
Living area

19. 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 $350
CA $424 total
includes taxes & fees
Nov 20 - Nov 21
Perfect little home
A reception area with a wooden counter, a clock, and a television.

20. 3 Queen Beds | Non-Smoking, Kitchen

3 Queen Beds | Non-Smoking, Kitchen
Effingham
10.0 out of 10, Exceptional, (4 reviews)
The price is CA $135
CA $151 total
includes taxes & fees
Oct 30 - Oct 31
3 Queen Beds | Non-Smoking, Kitchen
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

Days Inn & Suites by Wyndham Casey

Days Inn & Suites by Wyndham Casey

10/10 Excellent
"It was clean and had friendly staff"
David 2-night trip
Posted less than an hour ago
Days Inn & Suites by Wyndham Casey

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 $198 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.