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
  • Be picky

    Search almost a million properties worldwide

Find holiday rentals that suit your style

Check prices for these dates

Our top choices for Cumberland holiday homes

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 €167
includes taxes & fees
22 Nov - 23 Nov
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi

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 €227
includes taxes & fees
7 Dec - 8 Dec
Newly renovated 1905 house, within walking distance to all downtown attractions!

3. Mid Century-Modern Retreat Great Allegheny Passage

Mid Century-Modern Retreat Great Allegheny Passage
Cresaptown, MD
The price is €300
includes taxes & fees
11 Dec - 12 Dec
Mid Century-Modern Retreat Great Allegheny Passage

4. 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 €193
includes taxes & fees
11 Dec - 12 Dec
Oldtown Guesthouse

5. 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
9.0 out of 10, Wonderful, (11 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 €186
includes taxes & fees
11 Nov - 12 Nov
Gorgeous, fully renovated 3-bedroom house with AC in tranquil La Vale

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 €213
includes taxes & fees
11 Nov - 12 Nov
Peaceful and relaxing three bedroom home with hot tub, right beside I-68

7. Private, clean mountain home near Rocky Gap!

Private, clean mountain home near Rocky Gap!
Cumberland
9.4 out of 10, Exceptional, (19 reviews)
"Clean and comfy cabin. Great wi-fi and everything we needed in the kitchen and bathrooms!"
United States
Alisa S.
The price is €325
includes taxes & fees
15 Nov - 16 Nov
Private, clean mountain home near Rocky Gap!

8. 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 €351
includes taxes & fees
23 Nov - 24 Nov
Rustic Oasis for the Family - 6 min walk to Downtown

9. 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 €566
includes taxes & fees
22 Nov - 23 Nov
Knit Inn..

10. 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 €380
includes taxes & fees
24 Nov - 25 Nov
Luxury Nomadic Yurt Romantic Getaway with Sauna and Hot Tub on private 8 acres

11. 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 €696
includes taxes & fees
30 Nov - 1 Dec
Splash Mountain 6 bedrooms with indoor pool & mountain and filtered lake view

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

New Private 2bd 1 ba, Hot tub, Trails, Waterfront!
Friendsville
The price is €415
includes taxes & fees
9 Dec - 10 Dec
New Private 2bd 1 ba, Hot tub, Trails, Waterfront!

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

Renovated 2bd 1ba Waterfront, Hottub, Trails!
Friendsville
The price is €412
includes taxes & fees
11 Nov - 12 Nov
Renovated 2bd 1ba Waterfront, Hottub, Trails!

14. #1 Cabin~Walk to WISP! Lake access & dock! HOT Tub~Game room~Fire Pit & DOGS OK!

#1 Cabin~Walk to WISP! Lake access & dock! HOT Tub~Game room~Fire Pit & DOGS OK!
McHenry
9.8 out of 10, Exceptional, (39 reviews)
"Our family of 4 stayed for 4 nights and we were very impressed with how clean the home was. Communication with the host was easy and quick. Would stay with this host again!"
United States
John K.
The price is €616
includes taxes & fees
22 Nov - 23 Nov
#1 Cabin~Walk to WISP! Lake access & dock! HOT Tub~Game room~Fire Pit & DOGS OK!

15. Dar's Deep Creek Log Cabin Timber Hideaway

Dar's Deep Creek Log Cabin Timber Hideaway
Oakland
The price is €396
includes taxes & fees
19 Nov - 20 Nov
Dar's Deep Creek Log Cabin Timber Hideaway

16. 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 €406
includes taxes & fees
11 Nov - 12 Nov
Cozy Lake Access Home with Hot Tub

17. Hot Tub • Near Wisp & Lake • Private • Fire Pit • Pets & Kids

Hot Tub • 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 €362
includes taxes & fees
12 Nov - 13 Nov
Hot Tub • Near Wisp & Lake • Private • Fire Pit • Pets & Kids

18. Wisp View Retreat, Hot tub

Wisp View Retreat, Hot tub
Accident
The price is €590
includes taxes & fees
12 Nov - 13 Nov
Wisp View Retreat, Hot tub

19. 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 €617
includes taxes & fees
30 Nov - 1 Dec
Lake Access, Hot Tub, Sleeps 12

20. Pine Trees, Hot Tub & Game Room

Pine Trees, Hot Tub & Game Room
Oakland
10.0 out of 10, Exceptional, (49 reviews)
"My family loved the cabin! Perfect setting for a family weekend."
United States
Michael D.
The price is €435
includes taxes & fees
19 Nov - 20 Nov
Pine Trees, Hot Tub & 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.

Cumberland and related destinations

Ride the scenic Western Maryland Railway through mountain valleys where the historic C&O Canal once transported coal and goods. Explore downtown's vibrant arts district and hike parts of the Great Allegheny Passage trail when locals have it mostly to themselves in early morning.

A calm river with dense trees on both sides, a clear sky, and a pathway along the riverbank.

Top reviews in Cumberland