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

Vacation Rentals in Cumberland County

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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, (77 reviews)
"Great stay !"
United States
chris H.
$133 nightly
The price is $141
Oct 18 - Oct 19
Total with taxes and fees
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
$420 nightly
The price is $424
Oct 15 - Oct 16
Total with taxes and fees
Family Friendly Cottage in the Countryside
An open-plan office with exposed brick walls, wooden floors, and large windows.

3. 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.
$167 nightly
The price is $179
Oct 18 - Oct 19
Total with taxes and fees
The Exchange. Cozy Studio., XCHNG Studio
A brick house with a white door, a mailbox, and a wooden porch.

4. 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.
$170 nightly
The price is $180
Oct 18 - Oct 19
Total with taxes and fees
Brickway Retreat
A modern kitchen with a brick wall, a bar area with stools, and a large island.

5. 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.
$198 nightly
The price is $212
Oct 18 - Oct 19
Total with taxes and fees
The Exchange. Downtown Luxury for Two, XCHNG. Industrial Executive Loft w/ King Bed
A clean, well-lit kitchen area with a wooden counter, a sink, and a dining table with chairs.

6. 2 Queen Beds | Non-Smoking, Micfridge

2 Queen Beds | Non-Smoking, Micfridge
Effingham
10.0 out of 10, Exceptional, (4 reviews)
"There was ample room for our group to spread out with easy parking nearby. Location felt perfect for visiting local attractions."
United States
Anonymous traveler
$63 nightly
The price is $71
Oct 16 - Oct 17
Total with taxes and fees
2 Queen Beds | Non-Smoking, Micfridge
A cozy living room with a dark green wall, a wooden chair with a white macrame throw, a potted plant, and a framed picture.

7. 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 traveler
$215 nightly
The price is $228
Oct 26 - Oct 27
Total with taxes and fees
Luxury 1BR/BA Loft in the Heart of Downtown Marshall
A bar area with a wooden ceiling and bar stools.

8. 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.
$204 nightly
The price is $219
Nov 1 - Nov 2
Total with taxes and fees
The Exchange. Loft Living.
A modern kitchen with dark cabinets, stainless steel appliances, and a granite countertop.

9. 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, (8 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.
$215 nightly
The price is $228
Oct 18 - Oct 19
Total with taxes and fees
Built 2025-"OUR NECK OF THE WOODS" close to all the BIG THINGS in Casey, IL
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, (45 reviews)
"Very nice place to stay!"
United States
Brandon R.
$269 nightly
The price is $271
Oct 27 - Oct 28
Total with taxes and fees
Prairieview Cabin - with Hot Tub
An aerial view of Lake Shelbyville with RVs, a large building, and a bridge in the background.

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.
$269 nightly
The price is $285
Oct 18 - Oct 19
Total with taxes and fees
Fish, boat, grill, chill, pets, relax
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.

12. 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.
$215 nightly
The price is $237
Oct 19 - Oct 20
Total with taxes and fees
Park View Place 4 Blocks From the World's Biggest
A modern kitchen with a round dining table, chairs, a potted orchid, and a stainless steel refrigerator.

13. 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.
$188 nightly
The price is $199
Oct 26 - Oct 27
Total with taxes and fees
Cozy 2BR Loft in Downtown Charleston, IL
A modern living room with two leather sofas, a dining area, and a kitchen in the background.

14. 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.
$237 nightly
The price is $251
Oct 27 - Oct 28
Total with taxes and fees
Cottage By The Park Home of The Big Things
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.
$140 nightly
The price is $148
Nov 1 - Nov 2
Total with taxes and fees
Cozy, and private apartment near Lake Shelbyville
A tent set up on a wooden platform surrounded by trees.

16. Bell Tent Under the Stars

Bell Tent Under the Stars
Charleston
$74 nightly
The price is $78
Oct 15 - Oct 16
Total with taxes and fees
Bell Tent Under the Stars
A house with a porch supported by white columns, a black door with a wreath, and two white rocking chairs.

17. 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.
$145 nightly
The price is $154
Oct 18 - Oct 19
Total with taxes and fees
Cozy 1-bedroom with AC and WiFi in charming Shelbyville
A compact kitchen with a refrigerator, stove, microwave, and dining table with chairs.

18. 3 Bed/1 Bath Close to Everything in Robinson

3 Bed/1 Bath Close to Everything in Robinson
Robinson
$228 nightly
The price is $229
Oct 15 - Oct 16
Total with taxes and fees
3 Bed/1 Bath Close to Everything in Robinson
A living room with a sofa, a television, a Christmas tree, and a wall clock.

19. 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.
$385 nightly
The price is $388
Oct 27 - Oct 28
Total with taxes and fees
Prairieview Cottage Retreat - Hot Tub Sunsets
A bedroom with a bed, a TV, a dresser, and two doors.

20. 3 BR House Near Hershey/Marathon

3 BR House Near Hershey/Marathon
Robinson
$209 nightly
The price is $211
Oct 16 - Oct 17
Total with taxes and fees
3 BR House Near Hershey/Marathon
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

Quality Inn Effingham North

Quality Inn Effingham North

8/10 Good
"Clean room. Decent breakfast. Little dated but fine."
Howard 1-night trip
Posted 10 hours ago
Quality Inn Effingham North

Find out more about Cumberland County

Discover your perfect Cumberland County vacation rental with Expedia

How many vacation rentals are available in Cumberland County?


Expedia has plenty of vacation rentals to choose from in and around  Cumberland County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Cumberland County?


The selection of Cumberland County vacation rentals we have selected for you start as low as $141 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Cumberland County?


Vacation rentals in Cumberland County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Cumberland County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Cumberland County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. 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. 


How do I find the best deal on a vacation rental in Cumberland County?


Find vacation rentals in Cumberland County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Cumberland County.  


What amenities are available in a vacation rental in Cumberland County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Cumberland County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Cumberland County?   


Everytime is a great time to head to Cumberland County! Staying in a Cumberland County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Cumberland County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Cumberland County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Cumberland County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Cumberland County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.