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

Holiday Homes in Cumberland

  • 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

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Cumberland holiday homes

A garden with a variety of flowers and plants, a wooden structure, and a white fence.

1. 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, (57 reviews)
"comfortable cottage. In between most activity areas."
United States
WILSON
The price is AU$279
includes taxes & fees
2 Nov - 3 Nov
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
A kitchen with a central island, bar stools, a refrigerator, and a window with blinds.

2. Newly renovated 1905 house, within walking distance to all downtown attractions!

Newly renovated 1905 house, within walking distance to all downtown attractions!
Cumberland
10.0 out of 10, Exceptional, (2 reviews)
"The property, the price, the location, the host...all were perfect for or GAP bike trip!!!"
United States
Mark M.
The price is AU$382
includes taxes & fees
2 Nov - 3 Nov
Newly renovated 1905 house, within walking distance to all downtown attractions!
A deck with a white railing, a table, and a view of a forested landscape.

3. Gorgeous, fully renovated 3-bedroom house with AC in tranquil La Vale

Gorgeous, fully renovated 3-bedroom house with AC in tranquil La Vale
La Vale
8.8 out of 10, Excellent, (10 reviews)
"The host was very responsive and accessible. The house is freshly updated and uncluttered. The beds and pillows are comfortable. The view is lovely. The showers are small but manageable and there is no washing machine or dryer at this property. Overall it is a nice place and met our need for sleeping and making breakfast. We will very likely stay here again when we are in the area visiting family."
United States
TRINA P.
The price is AU$310
includes taxes & fees
9 Nov - 10 Nov
Gorgeous, fully renovated 3-bedroom house with AC in tranquil La Vale
A single-story house with a covered porch and a chimney, surrounded by trees and a view of a forested hill.

4. Private, clean mountain home near Rocky Gap!

Private, clean mountain home near Rocky Gap!
Cumberland
9.8 out of 10, Exceptional, (18 reviews)
"Clean and comfy cabin. Great wi-fi and everything we needed in the kitchen and bathrooms!"
United States
Alisa S.
The price is AU$535
includes taxes & fees
5 Nov - 6 Nov
Private, clean mountain home near Rocky Gap!
A modern kitchen with stainless steel appliances, white cabinetry, and a window with a view of the outdoors.

5. Oldtown Guesthouse

Oldtown Guesthouse
Oldtown
10.0 out of 10, Exceptional, (37 reviews)
"Wonderful property, comfy and perfect for a getaway. Definitely need to come back."
United States
Stephanie R.
The price is AU$301
includes taxes & fees
1 Nov - 2 Nov
Oldtown Guesthouse
A cozy living room with a fireplace, a sofa with decorative pillows, a coffee table, and a window with curtains.

6. Peaceful and relaxing three bedroom home with hot tub, right beside I-68

Peaceful and relaxing three bedroom home with hot tub, right beside I-68
La Vale
The price is AU$319
includes taxes & fees
2 Nov - 3 Nov
Peaceful and relaxing three bedroom home with hot tub, right beside I-68
A kitchen with wooden cabinets, a refrigerator, a sink, and a glass-top island with a stool.

7. Rustic Oasis for the Family - 6 min walk to Downtown

Rustic Oasis for the Family - 6 min walk to Downtown
Cumberland
9.4 out of 10, Exceptional, (3 reviews)
"Place was clean, reasonable and we could walk everywhere!"
United States
Sharon D.
The price is AU$526
includes taxes & fees
2 Nov - 3 Nov
Rustic Oasis for the Family - 6 min walk to Downtown
A room with a long wooden desk, four chairs, a woven rug, a ceiling fan, and a mural of flowers on the wall.

8. Knit Inn..

Knit Inn..
Frostburg
9.6 out of 10, Exceptional, (8 reviews)
"Great location! The host was very nice and easy to get a hold of for questions. Would definitely stay here every trip to Frostburg!"
United States
Lori F.
The price is AU$962
includes taxes & fees
3 Nov - 4 Nov
Knit Inn..
An outdoor hot tub with a fire, a wicker basket with bread, and a bottle of wine.

9. Luxury Nomadic Yurt Romantic Getaway with Sauna and Hot Tub on private 8 acres

Luxury Nomadic Yurt Romantic Getaway with Sauna and Hot Tub on private 8 acres
Keyser
10.0 out of 10, Exceptional, (1 review)
"My wife and I had a great stay at this property, we would happily visit again!"
United States
Cole D.
The price is AU$563
includes taxes & fees
3 Nov - 4 Nov
Luxury Nomadic Yurt Romantic Getaway with Sauna and Hot Tub on private 8 acres
A kitchen with a central island, a dining table, and a refrigerator.

10. Glendale Getaway: Nostalgic not Fancy

Glendale Getaway: Nostalgic not Fancy
Swanton
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive. The property was very clean and was in a great location. I would definitely recommend this property. The description of the property was spot on as well."
United States
Jason M.
The price is AU$346
includes taxes & fees
8 Nov - 9 Nov
Glendale Getaway: Nostalgic not Fancy
A wooden deck with railings and string lights, leading to a house with a porch and a window.

11. Near Wisp & Lake• Private • Fire Pit • Pets & Kids

Near Wisp & Lake• Private • Fire Pit • Pets & Kids
McHenry
9.8 out of 10, Exceptional, (6 reviews)
"The property was excellent. Clean and nicely decorated. Very pet-friendly. Warm and cozy "
United States
Jessica O.
The price is AU$547
includes taxes & fees
4 Nov - 5 Nov
Near Wisp & Lake• Private • Fire Pit • Pets & Kids
A riverside setting with outdoor seating and a view of a flowing river.

12. New Private 2bd 1 ba, Hot tub, Trails, Waterfront!

New Private 2bd 1 ba, Hot tub, Trails, Waterfront!
Friendsville
The price is AU$682
includes taxes & fees
1 Nov - 2 Nov
New Private 2bd 1 ba, Hot tub, Trails, Waterfront!
A riverside setting with outdoor seating and a view of a flowing river.

13. Renovated 2bd 1ba Waterfront, Hottub, Trails!

Renovated 2bd 1ba Waterfront, Hottub, Trails!
Friendsville
The price is AU$662
includes taxes & fees
1 Nov - 2 Nov
Renovated 2bd 1ba Waterfront, Hottub, Trails!
Interior

14. Captain's Quarters Deep Creek Log Cabin Oasis

Captain's Quarters Deep Creek Log Cabin Oasis
Oakland
10.0 out of 10, Exceptional, (2 reviews)
"The cabin was clean and comfortable. Keith was very responsive to messages and incredibly helpful. We especially enjoyed the massage chairs and the hot tub Looking forward to visiting again.."
United States
Brendan P.
The price is AU$638
includes taxes & fees
4 Nov - 5 Nov
Captain's Quarters Deep Creek Log Cabin Oasis
A two-story house with a stone chimney, a covered deck, and a garage.

15. Lake Access, Hot Tub, Sleeps 12

Lake Access, Hot Tub, Sleeps 12
Swanton
10.0 out of 10, Exceptional, (25 reviews)
"Very neatly kept house….beautiful and cozy place to spend the vacation…Amazing property and amazing host. "
United States
Harsh S.
The price is AU$1,008
includes taxes & fees
1 Nov - 2 Nov
Lake Access, Hot Tub, Sleeps 12
SplashMountainByJFP2025 024

16. Splash Mountain 6 bedrooms with indoor pool & mountain and filtered lake view

Splash Mountain 6 bedrooms with indoor pool & mountain and filtered lake view
Garrett County
10.0 out of 10, Exceptional, (1 review)
"The listing is accurate and complete"
United States
chuck w.
The price is AU$1,158
includes taxes & fees
4 Nov - 5 Nov
Splash Mountain 6 bedrooms with indoor pool & mountain and filtered lake view
A spacious living area with a stone fireplace, wooden ceiling, and a dining table with chairs.

17. Cozy Lake Access Home with Hot Tub

Cozy Lake Access Home with Hot Tub
McHenry
10.0 out of 10, Exceptional, (25 reviews)
"A very nice place to stay. The area is also very beautiful. Could definitely see us coming back for an extended stay."
United States
Cody S.
The price is AU$669
includes taxes & fees
9 Nov - 10 Nov
Cozy Lake Access Home with Hot Tub
A house with a fire pit and outdoor seating.

18. Wisp View Retreat, Hot tub

Wisp View Retreat, Hot tub
Accident
The price is AU$1,026
includes taxes & fees
1 Nov - 2 Nov
Wisp View Retreat, Hot tub
Outdoor dining

19. Dar's Deep Creek Log Cabin Timber Hideaway

Dar's Deep Creek Log Cabin Timber Hideaway
Oakland
The price is AU$758
includes taxes & fees
8 Nov - 9 Nov
Dar's Deep Creek Log Cabin Timber Hideaway
A covered outdoor area with wooden furniture, a stone fire pit, and a view of a forested area.

20. 5BR | Fireplace | Deck | Game Room

5BR | Fireplace | Deck | Game Room
McHenry
10.0 out of 10, Exceptional, (13 reviews)
"Excellent location and property. Had everything we needed, and the owner was more than accommodating. Thank you "
United States
Derek D.
The price is AU$987
includes taxes & fees
31 Oct - 1 Nov
5BR | Fireplace | Deck | Game Room
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 Hotel Reviews

Hampton Inn Cumberland

Hampton Inn Cumberland

10/10 Excellent
"Nice clean hotel. I bit of highway noise but it is located right at the top of a hill along the interstate. Staff was obviously new at check in but pleasant."
Lisa 1-night trip
Posted 4 hours ago
Hampton Inn Cumberland

Find out more about Cumberland

Cumberland Holiday Homes information

Number of reviews
166
Accommodation
1577 Holiday Homes
Lowest Price
AU$279
Highest Price
AU$1,158