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Holiday rentals in Allegany County

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Top-rated holiday rentals in Allegany County

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

The Hillside Hideaway
SUPERHOST
Entire cottage · 7 guests · 3 beds · 2 bathrooms
The Hillside HideawayNestled against a hillside, at the end of a small city lane, sits a charming cottage waiting your escape. Park in your private space, walk down to a unique retreat high above the city and enjoy old world charm with modern amenities. Walk to Historic Cumberland, enjoy local and regional attractions, or stay in and grill, build a fire, or play board or yard games. Small and cozy, yet well appointed, fully equipped, and with a beautiful view, come hideaway in this one of a kind location.
Efficiency Flat in Historic District
SUPERHOST
Entire guest suite · 2 guests · 1 bed · 1 bathroom
Efficiency Flat in Historic DistrictRelax in your suite with a private self check in, secure entrance located in Cumberland’s Historic District. You can safely park your car and walk to many of Cumberlands amenities. 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.
Historic 1915 home w. yard steps from bike trails
Entire residential home · 6 guests · 3 beds · 2.5 bathrooms
Historic 1915 home w. yard steps from bike trailsSpacious historic home ideal for exploring the bike trails with easy access to all Cumberland has to offer: 100 ft. from GAP and C&O trails; short walk to downtown historic Cumberland; hiking and lakes nearby; train spotting from the front porch.

Holiday rentals for every style

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Popular amenities for Allegany County holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Allegany County

SUPERHOST
  1. Entire townhouse
  2. Ridgeley
The Historic Alan Frederick Building
$296 SGD per night
  1. Entire rental unit
  2. Cumberland
Allegheny Suite in Corner Tavern Residences
$141 SGD per night
SUPERHOST
  1. Entire cabin
  2. Great Cacapon
Cacapon Heights Cabin with a gorgeous view
$255 SGD per night
SUPERHOST
  1. Entire cottage
  2. La Vale
CUTE COTTAGE at Mavi Ev
$105 SGD per night
SUPERHOST
  1. Entire rental unit
  2. Frostburg
The GreyLoo2
$101 SGD per night
SUPERHOST
  1. Private room
  2. Cumberland
The Columbia Bruce Room in the 1840 Bruce House
$66 SGD per night
SUPERHOST
  1. Entire rental unit
  2. Cumberland
The Dove's Nest - - no cleaning fees
$137 SGD per night
SUPERHOST
  1. Entire rental unit
  2. Cumberland
HISTORIC DOWNTOWN Cozy-Modern Apt PETS WELCOME!
$116 SGD per night
SUPERHOST
  1. Private room
  2. Cumberland
The D&D B&B (Basement Suite)
$60 SGD per night
SUPERHOST
  1. Entire rental unit
  2. Cumberland
Ramblewood Retreat
$158 SGD per night
SUPERHOST
  1. Entire residential home
  2. Cumberland
Cumberland Street House -GAP trail perfection!
$165 SGD per night
SUPERHOST
  1. Entire rental unit
  2. Frostburg
The GreyLoo
$108 SGD per night