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

Holiday Homes in Cumberland

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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, (51 reviews)
"The house was very clean and the view from the deck was spectacular."
United States
Toni R.
The price is NZ$337
includes taxes & fees
27 Sept - 28 Sept
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
A modern kitchen with stainless steel appliances, white cabinetry, and a window with a view of the outdoors.

2. 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$378
includes taxes & fees
28 Sept - 29 Sept
Oldtown Guesthouse
A bedroom with a bed, desk, chair, and a television.

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

Newly renovated 1905 house, within walking distance to all downtown attractions!
Cumberland
The price is NZ$483
includes taxes & fees
5 Oct - 6 Oct
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.

4. 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, (3 reviews)
"This was a really lovely place to stay on a quick trip to Cumberland. It’s in a quiet neighborhood with a great Mountain View off the back deck. The property was clean and the owner was communicative. Convenient to town and the scenic railroad. The only complaint I have was the thermostat was auto set to a temp that was too high for the summer, and I had to wake up twice to make it cooler. Other than that it really is exactly as advertised and I would stay again."
United States
Kasey G.
The price is NZ$382
includes taxes & fees
28 Sept - 29 Sept
Gorgeous, fully renovated 3-bedroom house with AC in tranquil La Vale
A room with a long wooden desk, four chairs, a woven rug, a ceiling fan, and a mural of flowers on the wall.

5. 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 NZ$1,168
includes taxes & fees
27 Sept - 28 Sept
Knit Inn..
A bedroom with wooden paneling, a dresser with drawers, a mirror, and a television on a stand.

6. Glendale Getaway: Nostalgic not Fancy

Glendale Getaway: Nostalgic not Fancy
Swanton
The price is NZ$430
includes taxes & fees
27 Sept - 28 Sept
Glendale Getaway: Nostalgic not Fancy
An outdoor hot tub with a fire, a wicker basket with bread, and a bottle of wine.

7. 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 NZ$716
includes taxes & fees
29 Sept - 30 Sept
Luxury Nomadic Yurt Romantic Getaway with Sauna and Hot Tub on private 8 acres
A spacious living room with a fireplace, comfortable seating, and large windows.

8. Hot Tub Lakehouse! Game Room + Fire Pit! Walk to Lake! 5 Min to Wisp!

Hot Tub Lakehouse! Game Room + Fire Pit! Walk to Lake! 5 Min to Wisp!
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 NZ$1,240
includes taxes & fees
28 Sept - 29 Sept
Hot Tub Lakehouse! Game Room + Fire Pit! Walk to Lake! 5 Min to Wisp!
An indoor swimming pool with clear lanes, a lifeguard chair, and a high ceiling with visible structural beams.

9. Wisp View Retreat, Hot tub

Wisp View Retreat, Hot tub
Accident
The price is NZ$1,264
includes taxes & fees
4 Oct - 5 Oct
Wisp View Retreat, Hot tub
A spacious living area with a stone fireplace, wooden ceiling, and a dining table with chairs.

10. Cozy Lake Access Home with Hot Tub

Cozy Lake Access Home with Hot Tub
McHenry
10.0 out of 10, Exceptional, (20 reviews)
"Location and floorspace was perfect for our ski trip "
United States
Todd M.
The price is NZ$856
includes taxes & fees
30 Sept - 1 Oct
Cozy Lake Access Home with Hot Tub
A spacious living room with a large sectional sofa, a fireplace, and a balcony with a view of the outdoors.

11. 4BR Mountain Retreat on 2+ Private Acres • Near Lake • Hot Tub • Mountain Views

4BR Mountain Retreat on 2+ Private Acres • Near Lake • Hot Tub • Mountain Views
McHenry
8.0 out of 10, Very good, (1 review)
"Very nice and very quiet and private. Was very enjoyable. Some improvements needed are upstairs full bathroom, sink is clogged and other sink has no water. The dishwater doesn’t work real well or stove. I would recommend staying there. Also we ran out of gas for the barbecue grill"
United States
Rebekah G.
The price is NZ$1,057
includes taxes & fees
19 Oct - 20 Oct
4BR Mountain Retreat on 2+ Private Acres • Near Lake • Hot Tub • Mountain Views

12. 8BR Water View - Huge Gameroom - Hot Tub 6 acres

8BR Water View - Huge Gameroom - Hot Tub 6 acres
Waterfront Greens
9.4 out of 10, Exceptional, (3 reviews)
"What a wonderful time we had for a holiday family vacation at this home. Everything was immaculately clean and there were many things provided in the kitchen (plateware, cookware, etc.) and bathrooms (towels, shampoo, body wash). We had everything we needed and more. The rooms were each nicely decorated and cozy. We loved the open living room area and kitchen/dining space. It snowed on our last day and it truly felt magical. The host was responsive and easy to communicate with. Thank you!"
United States
Annie
The price is NZ$2,849
includes taxes & fees
27 Sept - 28 Sept
8BR Water View - Huge Gameroom - Hot Tub 6 acres
A living room with a blue sofa, red cushions, a TV, and a small staircase.

13. Lake House: Lake View, Hot Tub, Dock, Wisp

Lake House: Lake View, Hot Tub, Dock, Wisp
Garrett County
The price is NZ$1,385
includes taxes & fees
29 Sept - 30 Sept
Lake House: Lake View, Hot Tub, Dock, Wisp
A modern living room with a sectional sofa, wooden coffee table, and a chandelier.

14. Heated Pool - Waterfront - 14 acre - 7bd 6ba

Heated Pool - Waterfront - 14 acre - 7bd 6ba
Friendsville
The price is NZ$1,437
includes taxes & fees
27 Sept - 28 Sept
Heated Pool - Waterfront - 14 acre - 7bd 6ba
A riverside cabin with a swimming pool, surrounded by trees and a grassy area.

15. 12 Bd! 11Ba! 18 Acres! Views! Prefect for Events!

12 Bd! 11Ba! 18 Acres! Views! Prefect for Events!
Friendsville
The price is NZ$3,744
includes taxes & fees
26 Oct - 27 Oct
12 Bd! 11Ba! 18 Acres! Views! Prefect for Events!
A spa area with a hot tub, a waterfall feature, and a stone wall with greenery.

16. New! Epic lakefront home with indoor pool!

New! Epic lakefront home with indoor pool!
McHenry
9.8 out of 10, Exceptional, (13 reviews)
"Welcoming and fantastic amenities!"
United States
Vincent M.
The price is NZ$3,308
includes taxes & fees
29 Sept - 30 Sept
New! Epic lakefront home with indoor pool!
A deck with a table and chairs, overlooking a lake and autumn foliage.

17. Private Lodge sleeps 25 guests Spectacular Views

Private Lodge sleeps 25 guests Spectacular Views
Oakland
10.0 out of 10, Exceptional, (2 reviews)
"Our group had a wonderful time - the home is beautiful and perfect for a large group. The setting and view is perfect. The home was very clean and the host was quick to get maintenance to fix the hot tub. We hope to be back!"
United States
Jocelyn M.
The price is NZ$3,284
includes taxes & fees
27 Sept - 28 Sept
Private Lodge sleeps 25 guests Spectacular Views
A bedroom with a large bed, wooden headboard, two bedside tables with lamps, a floral-patterned rug, and a window with curtains.

18. Right off the bike trail.

Right off the bike trail.
Meyersdale
9.6 out of 10, Exceptional, (118 reviews)
"We loved everything about this house: the spaciousness, cleanliness, location, quiet and comfort. It had everything we needed and Karen was a great hostess."
United States
Kathy
The price is NZ$243
includes taxes & fees
27 Sept - 28 Sept
Right off the bike trail.

19. Stone's Throw Cabin moments away from the best of the Laurel Highlands!

Stone's Throw Cabin moments away from the best of the Laurel Highlands!
Confluence
10.0 out of 10, Exceptional, (35 reviews)
"Great location and vibe!"
United States
Pedro R.
The price is NZ$272
includes taxes & fees
27 Sept - 28 Sept
Stone's Throw Cabin moments away from the best of the Laurel Highlands!
A hot tub under a covered area with string lights, surrounded by a natural landscape and a wooden structure in the background.

20. Farmhouse in the South Branch River Valley with idyllic views and country charm

Farmhouse in the South Branch River Valley with idyllic views and country charm
Romney
10.0 out of 10, Exceptional, (76 reviews)
"Beautiful house with a beautiful view of the mountains. Loved our stay "
United States
AnnaDella J.
The price is NZ$496
includes taxes & fees
27 Sept - 28 Sept
Farmhouse in the South Branch River Valley with idyllic views and country charm
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

Sleep Inn & Suites Cumberland - LaVale

Sleep Inn & Suites Cumberland - LaVale

8/10 Good
"Happy with room, price, location and so nice to have breakfast. Great selection of warm and cold food and drinks along with a make your own waffle station and pastries. Rooms and site were as pictured. McDonald's, Subway and Convenience store right next door. Enjoyed the event at the fairgrounds, seeing museum in Cumberland, little shops and the area in general. There is also a nice Moose Lodge not far away. Happy to stay again."
Patricia 2-night trip
Posted 2 hours ago
Sleep Inn & Suites Cumberland - LaVale

Find out more about Cumberland

Cumberland Holiday Homes information

Number of reviews
385
Accommodation
1597 Holiday Homes
Lowest Price
NZ$243
Highest Price
NZ$3,744