A river flowing through a town with a bridge and a large building with a sign.

Cumberland Holiday Rentals

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Our top choices for Cumberland holiday rentals

1. Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /

Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /
Cumberland
10.0 out of 10, Exceptional, (63 reviews)
"Host was very polite and helpful!"
United States
Quintin
The price is NZ$295
includes taxes & fees
22 Sept - 23 Sept
Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /

2. Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi

Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
Cumberland
9.8 out of 10, Exceptional, (50 reviews)
"The house was very clean and the view from the deck was spectacular."
United States
Toni R.
The price is NZ$326
includes taxes & fees
22 Sept - 23 Sept
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi

3. The Suite On Smallwood

The Suite On Smallwood
Cumberland
9.8 out of 10, Exceptional, (9 reviews)
"Perfect accommodation for our party. Great coffee bar and television selection. Very clean."
United States
Thomas
The price is NZ$333
includes taxes & fees
19 Oct - 20 Oct
The Suite On Smallwood

4. Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!

Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!
Cumberland
10.0 out of 10, Exceptional, (11 reviews)
"Easy walk into town and the train station."
United States
Kathy M.
The price is NZ$346
includes taxes & fees
4 Oct - 5 Oct
Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!

5. Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!

Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!
Cumberland
9.8 out of 10, Exceptional, (17 reviews)
"Lovely place! "
United States
Courtney N.
The price is NZ$336
includes taxes & fees
22 Sept - 23 Sept
Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!

6. 5 minute walk to downtown. Cozy family sized home with everything you need.

5 minute walk to downtown. Cozy family sized home with everything you need.
Frostburg
9.4 out of 10, Exceptional, (33 reviews)
"Lovely place, had all we needed for a comfortable stay. Thanks!"
United States
Molly M.
The price is NZ$401
includes taxes & fees
22 Sept - 23 Sept
5 minute walk to downtown. Cozy family sized home with everything you need.

7. Abrams Creek Center

Abrams Creek Center
2.0 star property
Elk Garden
7.6 out of 10, Good, (48 reviews)
"Did not stay no bath house just a porta john"
United States
Bill
The price is NZ$161
includes taxes & fees
23 Sept - 24 Sept
Abrams Creek Center

8. Oldtown Guesthouse

Oldtown Guesthouse
Oldtown
10.0 out of 10, Exceptional, (35 reviews)
"Beautiful property and house. Very clean and comfortable."
United States
Don B.
The price is NZ$363
includes taxes & fees
22 Sept - 23 Sept
Oldtown Guesthouse

9. Secluded, romantic cabin with hot tub on 12 acres of woodland.

Secluded, romantic cabin with hot tub on 12 acres of woodland.
Cumberland
10.0 out of 10, Exceptional, (121 reviews)
"Everything we expected and more. Visited relatively early in the Spring so we're coming back in June to make better use of outdoor dining, etc. The cabin was super cozy and we made full use of the hot tub and fireplace. We really enjoyed our stay."
United States
Steven H.
The price is NZ$673
includes taxes & fees
12 Oct - 13 Oct
Secluded, romantic cabin with hot tub on 12 acres of woodland.

10. Private cabin with two full beds. ADA accessible.

Private cabin with two full beds. ADA accessible.
Flintstone
10.0 out of 10, Exceptional, (7 reviews)
"This cabin has all the necessities, is in a great location and is clean and well maintained. Absolutely perfect for a couple and close to lots of outdoor activities! Will absolutely stay here in the future."
United States
Leah I.
The price is NZ$277
includes taxes & fees
22 Sept - 23 Sept
Private cabin with two full beds. ADA accessible.

11. Loft two story with first floor workout room, WIFI, complete cottage to yourself

Loft two story with first floor workout room, WIFI, complete cottage to yourself
Grantsville
9.8 out of 10, Exceptional, (43 reviews)
"Everything was lovely! The loft was stocked with everything we needed, it was spotlessly clean, and very comfortable."
United States
Leanna B.
The price is NZ$357
includes taxes & fees
22 Sept - 23 Sept
Loft two story with first floor workout room, WIFI, complete cottage to yourself

12. Spacious riverfront cottage with full kitchen, cozy charm, and Casselman views.

Spacious riverfront cottage with full kitchen, cozy charm, and Casselman views.
Grantsville
10.0 out of 10, Exceptional, (6 reviews)
"Great place to stay!! Very clean and extremely close to local attractions. "
United States
Mitchum
The price is NZ$385
includes taxes & fees
27 Sept - 28 Sept
Spacious riverfront cottage with full kitchen, cozy charm, and Casselman views.

13. Private Home in Garrett County, surrounded by trees, fields and farmland.

Private Home in Garrett County, surrounded by trees, fields and farmland.
Grantsville
10.0 out of 10, Exceptional, (58 reviews)
"Awesome house. And great location "
United States
Richard M.
The price is NZ$432
includes taxes & fees
4 Oct - 5 Oct
Private Home in Garrett County, surrounded by trees, fields and farmland.

14. Private cabin with two double beds (sleep 4)

Private cabin with two double beds (sleep 4)
Flintstone
10.0 out of 10, Exceptional, (7 reviews)
"Weve stayed here before, enroute to visit family in Maryland. The cabins are very amply large, with modern ammenities. The beds were comfy, eating area was clean and spacious, with even a well thought out large front porch, with a rocking chair to enjoy the serenity of the distant mountains. We'll be back!"
Canada
Karl
The price is NZ$277
includes taxes & fees
22 Sept - 23 Sept
Private cabin with two double beds (sleep 4)

15. 1/2 of a double cabin with one king sized bed (sleeps 2)

1/2 of a double cabin with one king sized bed (sleeps 2)
Flintstone
10.0 out of 10, Exceptional, (1 review)
"If you’re looking for a quiet peaceful cabin to just go get lost in the world of your significant other, this is the place to go! They’re far enough from the everyday life but still close enough to enjoy all the beauty of their charming city!! The food is to die for and definitely a reason for us to return!! Nothing bad to say at all except they need larger hot water tanks bc when I’m enjoying my wife that includes sharing a shower that we would have preferred not to be rushed out of!! Otherwise...
United States
LaRon G.
The price is NZ$277
includes taxes & fees
22 Sept - 23 Sept
1/2 of a double cabin with one king sized bed (sleeps 2)

16. Private cabin with two double beds (sleeps 4)

Private cabin with two double beds (sleeps 4)
Flintstone
9.6 out of 10, Exceptional, (4 reviews)
"Cute, clean cabins conveniently located to highway and nearby Cumberland. Nice stay!"
United States
Amy R.
The price is NZ$277
includes taxes & fees
22 Sept - 23 Sept
Private cabin with two double beds (sleeps 4)

17. Private Pond Access! Covered Hot Tub with TV!

Private Pond Access! Covered Hot Tub with TV!
Accident
The price is NZ$733
includes taxes & fees
28 Sept - 29 Sept
Private Pond Access! Covered Hot Tub with TV!

18. 1/2 double cabin with king bed and single child sized pull-out sleep sofa (sleeps 2 adults & 1 child

1/2 double cabin with king bed and single child sized pull-out sleep sofa (sleeps 2 adults & 1 child
Flintstone
9.0 out of 10, Wonderful, (4 reviews)
"Beautiful, calming environment to relax and unwind for the weekend. Excellent communication with property owner. Couldn’t recommend more!"
United States
Drew S.
The price is NZ$277
includes taxes & fees
22 Sept - 23 Sept
1/2 double cabin with king bed and single child sized pull-out sleep sofa (sleeps 2 adults & 1 child

19. The winter is coming !!!

The winter is coming !!!
Oakland
9.8 out of 10, Exceptional, (67 reviews)
"The host was very helpful. Nice quiet property in a good location."
United States
Brandi
The price is NZ$762
includes taxes & fees
27 Sept - 28 Sept
The winter is coming !!!

20. All about the view

All about the view
McHenry
9.8 out of 10, Exceptional, (17 reviews)
"The location is awesome."
United States
Dale S.
The price is NZ$678
includes taxes & fees
22 Sept - 23 Sept
All about the view
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 Hotel Reviews

Find out more about Cumberland

Everything you need to know about Cumberland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cumberland holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cumberland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cumberland. 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cumberland holiday rentals we have selected for you start as low as NZ$161 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cumberland rentals

At Expedia, we put the best Cumberland holiday 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 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 holiday.

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. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Cumberland?

Yes, there are holiday rentals in Cumberland close to Western Maryland Scenic Railroad, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the mountain landscape and riverfront in Cumberland. Make sure you have time to check out the casinos and churches during your trip.

What are some of the best holiday rentals that Cumberland has to offer?

Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi: This highly rated holiday home rental in Cumberland is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave. Some other homes for rent in Cumberland include Make memories: Mountain view Grand 6BR 3BA LaVale Home, 15 min to Rocky Gap and Awesome New Property/ CANAL RIVER RETREAT .

How many holiday rentals will I find in Cumberland?

With 11 Expedia holiday rentals, you're guaranteed to find just the right place for your Cumberland stay.

What’s there to see and do in Cumberland?

Enjoy the outdoors at Lake Habeeb Beaches and Canal Place, or simply take in cultural attractions like Windsor Hall and Allegany Museum. Downtown Cumberland Historic District and Western Maryland Scenic Railroad are other places to visit while you're in town.

What’s a holiday rental in Cumberland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cumberland. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for small groups.