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Vacation rentals in Cumberland

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Top-rated vacation rentals in Cumberland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Home in Cumberland
Jacob's Cottage
Free WI-FI now available. Our place is good for couples, solo adventurers, business travelers and families (with kids). The Cottage is a quaint, Cape Cod style house built in 1950. It sits high on a hill in the heart of Maryland's Appalachian Mountains in Allegany County. It is surrounded by views of Wills Mountain and Shrivers Ridge. The Cottage sits amongst a 660 acre family managed forest. Visitors have spotted deer, turkey, rabbits, squirrels, black bear and a multitude of song birds.
Jan. 11 – 18
$153 CAD per night
Apartment in Cumberland
Quaint and comfy one bedroom apartment located just one block from historic downtown cumberland. It is in a safe and quiet neighborhood. The Cumberland Theatre & Western Maryland Scenic Railroad, the C&O Canal and GAP Trail are just around the corner. We are pet friendly (one-time per pet fee applies, billed after booking) but we do a deep clean after each guest, you’d never know that pets have ever been hosted. AT THIS TIME, WE ARE UNABLE TO ACCOMMODATE EARLY CHECK-IN/OUT DUE TO COVID.
Jun. 5 – 12
$145 CAD per night
Guest favourite
Apartment in Cumberland
Steeple View Flat in Historic District
Relax in your first level flat. Entire private efficiency suite with a secure self check in. The entrance located along side of the main house in Cumberland’s Historic District. You can safely park your car and walk to many of Cumberlands amenities. If you’re biking, they can be stored inside. Canal Place has unique shops a winery and a bike rental facility. Cumberland theater is adjacent to the property, also Baltimore St. Promenade offers a delicious choice of indoor and outdoor dining.
Feb. 12 – 19
$147 CAD per night

Popular amenities for Cumberland vacation rentals

Stay near Cumberland's top sights

Western Maryland Scenic Railroad19 locals recommend
Puccini Restaurant8 locals recommend
Crabby Pig6 locals recommend
El Jinete3 locals recommend
Cafe Mark11 locals recommend
Queen City Creamery, Cafe & Deli14 locals recommend

Other great vacation rentals in Cumberland

Guest favourite
Home in Cumberland
Cumberland Street House -GAP trail perfection!
Jan. 10 – 17
$199 CAD per night
Guest favourite
Home in Cumberland
Braddock House
Sep. 3 – 10
$173 CAD per night
Guest favourite
Cottage in Cumberland
The Cottage on the Hill
May 13 – 20
$262 CAD per night
Guest favourite
Farm stay in Romney
Potomac Hills B&B on 15 Acre Farm with a View
Mar. 17 – 24
$203 CAD per night
Guest favourite
Tiny homes in Swanton
Tiny House in the Orchard; a Romantic Stay for two
Jun. 26 – Jul. 3
$267 CAD per night
Guest favourite
Loft in Cumberland
Historical loft, 2 Blocks from Trail & Downtown
May 2 – 9
$109 CAD per night
Guest favourite
Home in Cumberland
Great Location, Spacious, Comfy 2 bdrm home
Aug. 14 – 21
$196 CAD per night
Guest favourite
Home in Cumberland
Spacious house near the Park!
Mar. 28 – Apr. 4
$175 CAD per night
Guest favourite
Home in Cumberland
Rails and Trails Retreat ~ historic home w. yard
Apr. 17 – 24
$287 CAD per night
Guest favourite
Home in Cumberland
Charming Home Near Downtown
Sep. 13 – 20
$175 CAD per night
Guest favourite
Farm stay in Ellerslie
Historic Eden Ranch, built 1837
Jun. 22 – 29
$183 CAD per night
Guest favourite
Home in Cumberland
NEW LISTING-"Cumberland Cottage"-charming,quaint
Nov. 3 – 10
$228 CAD per night

Quick stats about vacation rentals in Cumberland

Total rentals

70 properties

Rentals with dedicated workspaces

40 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

40 properties are a good fit for families

Total number of reviews

4.8K reviews

Nightly prices starting at

$54 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Allegany County
  5. Cumberland