Cumberland County Vacation Rentals

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Top cities in Cumberland County

A covered bridge with 'JACKSON, N.H.' sign, speed limit 15, and 'NO PARKING ANY TIME' sign.
Vacation Rentals

Greenup

Greenup

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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 $125
CA $187 total
includes taxes & fees
Nov 17 - Nov 18
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 $398
CA $603 total
includes taxes & fees
Dec 7 - Dec 8
Family Friendly Cottage in the Countryside
A residential street with a house featuring a front porch, outdoor seating, and string lights.

3. 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 $113
CA $168 total
includes taxes & fees
Nov 9 - Nov 10
Cozy, and private apartment near Lake Shelbyville
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.
The price is CA $155
CA $234 total
includes taxes & fees
Nov 9 - Nov 10
Brickway Retreat
An open-plan office with exposed brick walls, wooden floors, and large windows.

5. 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 $150
CA $248 total
includes taxes & fees
Nov 9 - Nov 10
The Exchange. Cozy Studio., XCHNG Studio
A modern living room with a flat-screen TV, a sofa, a coffee table, and a ceiling fan.

6. 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 $220
CA $356 total
includes taxes & fees
Nov 30 - Dec 1
Prairieview Cabin - with Hot Tub
A modern kitchen with a brick wall, a bar area with stools, and a large island.

7. 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, (15 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 $198
CA $338 total
includes taxes & fees
Nov 16 - Nov 17
The Exchange. Downtown Luxury for Two, XCHNG. Industrial Executive Loft w/ King Bed
A modern kitchen with dark cabinets, stainless steel appliances, and a granite countertop.

8. 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)
"Very nice property"
United States
Caroline G.
The price is CA $268
CA $310 total
includes taxes & fees
Nov 23 - Nov 24
Built 2025-"OUR NECK OF THE WOODS" close to all the BIG THINGS in Casey, IL
A bar area with a wooden ceiling and bar stools.

9. 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 $190
CA $327 total
includes taxes & fees
Nov 18 - Nov 19
The Exchange. Loft Living.
An aerial view of Lake Shelbyville with RVs, a large building, and a bridge in the background.

10. 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 $170
CA $334 total
includes taxes & fees
Dec 1 - Dec 2
Fish, boat, grill, chill, pets, relax
A modern kitchen with a round dining table, chairs, a potted orchid, and a stainless steel refrigerator.

11. 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 $212
CA $270 total
includes taxes & fees
Nov 18 - Nov 19
Cozy 2BR Loft in Downtown Charleston, IL
A cozy living room with a dark green wall, a wooden chair with a white macrame throw, a potted plant, and a framed picture.

12. 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 $198
CA $295 total
includes taxes & fees
Nov 9 - Nov 10
Luxury 1BR/BA Loft in the Heart of Downtown Marshall
A reception area with a wooden counter, a chair, a television, and a clock on the wall.

13. 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 13 - Nov 14
1 King Bed | Non-Smoking, Micfridge
A modern bathroom with a built-in microwave, a vanity with a mirror, and a shelf above the sink.

14. 2 Queen Beds | Suite, Nsmk, Kitchen

2 Queen Beds | Suite, Nsmk, Kitchen
Effingham
10.0 out of 10, Exceptional, (3 reviews)
"Solo trip meant I needed simple lodging close to main roads, this fit well with free parking available right there. No hassle getting checked in either."
United States
Anonymous traveller
The price is CA $109
CA $123 total
includes taxes & fees
Nov 13 - Nov 14
2 Queen Beds | Suite, Nsmk, Kitchen
A modern kitchen with a central island, dark cabinetry, and a ceiling fan.

15. Prairieview Cottage Retreat - Hot Tub Sunsets

Prairieview Cottage Retreat - Hot Tub Sunsets
Sullivan
10.0 out of 10, Exceptional, (62 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.
The price is CA $266
CA $483 total
includes taxes & fees
Dec 1 - Dec 2
Prairieview Cottage Retreat - Hot Tub Sunsets
A compact kitchen with wooden cabinets, a refrigerator, a stove, and two bar stools.

16. 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 $283
CA $407 total
includes taxes & fees
Nov 23 - Nov 24
Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds
A kitchen with a marble countertop, stainless steel refrigerator, and wooden cabinets.

17. 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 $235
CA $336 total
includes taxes & fees
Nov 9 - Nov 10
Eagle's Nest near Eagle Creek State Park
A house with a porch supported by white columns, a black door with a wreath, and two white rocking chairs.

18. 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, (20 reviews)
"Place was great!"
United States
Robyn J.
The price is CA $117
CA $170 total
includes taxes & fees
Nov 9 - Nov 10
Cozy 1-bedroom with AC and WiFi in charming Shelbyville
A rustic cabin with a porch, surrounded by a well-maintained lawn and trees.

19. 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 $325
CA $590 total
includes taxes & fees
Nov 23 - Nov 24
Binion Lodge: Wooded Privacy Near Lake Shelbyville
A compact kitchen with a gas stove, a dining table with chairs, a sink, and a window providing a view of the outdoors.

20. 3 Bed/1 Bath Close to Everything in Robinson

3 Bed/1 Bath Close to Everything in Robinson
Robinson
The price is CA $186
CA $342 total
includes taxes & fees
Nov 12 - Nov 13
3 Bed/1 Bath Close to Everything in Robinson
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

A white convertible car parked in a covered parking area at night.
Budget Host Inn Greenup

Budget Host Inn Greenup

Budget Host Inn Greenup
Greenup

10/10 Excellent

Budget friendly and not to bad for the cost. Second time staying in this motel.
Canada
Sherri
Reviewed July 28, 2026
Budget Host Inn Greenup

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 $88 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.