Vacation Rentals in Cumberland, MD

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Cumberland, MD holiday rentals
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107 Holiday rentals and Airbnb in Cumberland, MD

Recommended Family-Friendly Holiday Rentals in Cumberland, MD, United States

Find family holiday rentals in Cumberland, MD, United States with space and comfort for the whole crew.

Private 2 Bedroom Apt With Bike Storage 1 Mile To The Gap And C&o Canal / - Cumberland, MD
10 60 reviews

Private 2 Bedroom Apt With Bike Storage 1 Mile To The Gap And C&o Canal /

apartment, Cumberland
This two-bedroom apartment is situated in Cumberland's city centre, less than a mile from the downtown area, the GAP trail, the C&O Canal, and a variety of restaurants. Guests have consistently rated this property as excellent, praising its convenient location and comfortable amenities.
The self-catering apartment comfortably accommodates up to five guests and features a fully equipped kitchen, a living area, and a private porch. Guests can enjoy a range of amenities including air conditioning, a garden, secure bike storage, and a 40-inch TV with access to streaming services.
The Cottage On The Hill - Cumberland, MD
10 204 reviews

The Cottage On The Hill

apartment, Cumberland
This charming cottage is located on a hillside in Cumberland, just a short walk from the historic town centre. It has consistently received excellent ratings for its cleanliness, location, and overall experience, making it a popular choice for travellers.
The property can accommodate up to 11 guests and features three bedrooms and two bathrooms. Guests can enjoy a fully equipped kitchen, a spacious garden, a private patio with a fire pit, and a vintage game room with a pool table and games for all ages.
The Hillside Hideaway - Cumberland, MD
10 80 reviews

The Hillside Hideaway

apartment, Cumberland
This charming cottage is situated on a hillside in Cumberland, just a short walk from the historic district, offering a peaceful retreat with easy access to local attractions. The property consistently receives excellent ratings for its cleanliness, location, and overall experience.
The cottage provides comfortable accommodation for up to nine guests with three bedrooms and two bathrooms. Enjoy a fully equipped kitchen, air conditioning, a private garden with a fire pit and grill, plus the chance to spot local wildlife in the nearby wooded area.
Mountain View Escape | Great Allegheny Passage - Cumberland, MD
9.8 9 reviews

Mountain View Escape | Great Allegheny Passage

apartment, Corriganville
This three-bedroom Corriganville apartment, perfect for families or groups of up to eight, offers a peaceful mountain setting with access to beautifully tended gardens and parking.
The property features a fully renovated kitchen with modern appliances, two bathrooms with rainfall showers, and ample natural light throughout its spacious living areas; nearby landmarks' precise distances are unavailable.

Best Cumberland, MD holiday rentals with parking

Knit Inn.. - Cumberland, MD
9.6 8 reviews

Knit Inn..

apartment, Frostburg
The Knit Inn is situated on Main Street in Frostburg, Maryland, within walking distance of the Palace Theatre and the trail, and less than 1.6 kilometres from the ice cream shop on the outskirts of town. This charming town offers a variety of local businesses and attractions, making it an ideal destination for a relaxing getaway.
The property features four bedrooms with seven beds, comfortably accommodating up to 14 guests. The Knit Inn provides two kitchens, two full bathrooms, and ample living space, perfect for families or groups of friends looking for a craft-focused escape.
Hillside Family Retreat - Cumberland, MD
10 5 reviews

Hillside Family Retreat

apartment, Cumberland
This Cumberland property, comprising The Cottage on the Hill and The Hillside Hideaway, is situated near a wooded area, offering privacy yet convenient access to local attractions (distances unspecified).
Sleeping up to 16 guests across 6 bedrooms and 4 bathrooms, this large holiday home boasts extensive grounds with fire pits, two game rooms featuring pool tables, and private parking for 6-8 cars, plus options for larger vehicles.
Urban Nest On Race Street - Cumberland, MD
8.0 6 reviews

Urban Nest On Race Street

apartment, Cumberland
This quiet one-bedroom flat in the South End of Cumberland, Maryland, offers a peaceful base just 1 kilometre from downtown Cumberland's restaurants, shops, and attractions.
This comfortable abode accommodates two guests and features a fully equipped kitchen, air conditioning, and internet, making it ideal for couples or solo travellers seeking a self-catering stay.
Hila's House - Cumberland, MD
9.9 159 reviews

Hila's House

apartment, La Vale
This peaceful home is located in La Vale, just a short drive from the historic downtown area and within easy reach of the scenic Casselman River. Guests consistently rate the property excellent for its cleanliness, location, and overall experience.
The house has two bedrooms and one and a half bathrooms, comfortably accommodating up to four guests. Enjoy modern amenities like internet access and a TV, as well as the opportunity to relax outdoors on the porch or explore the surrounding nature.

Frequently asked questions about holiday rentals in Cumberland, MD

  • Which neighborhood in Cumberland, MD should you consider for a vacation rental?

    The historic district is a great choice for a vacation rental. You'll be within walking distance of many attractions, restaurants, and shops. The area around the Canal is also a good option, offering a peaceful atmosphere and beautiful views.
  • What are the best Airbnb and holiday rentals in Cumberland, MD?

  • What are the top family-friendly attractions in Cumberland, MD?

    The Western Maryland Scenic Railroad is a great option for a family day out. They offer various train rides, including a trip to Frostburg. The Cumberland Heritage Village is another popular choice, with historical buildings and exhibits that are sure to fascinate children.
  • What are the most popular Airbnbs in Cumberland, MD?

  • When is the best time to book a vacation rental in Cumberland, MD?

    The best time to book a vacation rental in Cumberland is during the shoulder seasons, April-May and September-October. You'll enjoy pleasant weather and fewer crowds. The summer months can get busy, especially during the annual Allegany County Fair.
  • What are the best holiday rentals with a pool in Cumberland, MD?

    The Dacha - Cumberland Vacation, Quiet One Bedroom Apartment and The Dacha - Cumberland Vacation are the best holiday rentals with a pool in Cumberland, MD.

  • What are the best budget-friendly activities in Cumberland, MD?

    Take a walk or bike ride along the C&O Canal Towpath. It's a beautiful and scenic way to spend a few hours. You can also visit the free exhibits at the Allegany Museum or enjoy a picnic at the scenic Rocky Gap State Park.
  • What are the best rentals for families and kids in Cumberland, MD?

  • What are the best restaurants with local dishes in Cumberland, MD?

    For local dishes, try the Chesapeake Inn, known for its Maryland crab cakes. The Old Italy Restaurant serves traditional Italian dishes, and the Blue Moon Cafe is a great spot for a casual meal.
  • What are the best rentals or Airbnbs with a jacuzzi in Cumberland, MD?

    The best holiday rentals or Airbnb with a jacuzzi in Cumberland, MD are No Cleaning Fees - The Dove’s Nest, The Dacha - Cumberland Vacation and The Hidden Tree.

  • What are the best walking or cycling routes in Cumberland, MD?

    The C&O Canal Towpath is a great option for both walking and cycling, offering scenic views and a flat, easy route. The Great Allegheny Passage is another popular choice for cyclists, offering a longer, more challenging ride.
  • Are there pet-friendly attractions in Cumberland, MD?

    Yes, many attractions in Cumberland are pet-friendly. The C&O Canal Towpath is a great place to take your dog for a walk, and the Rocky Gap State Park also welcomes dogs on leash. The Allegany Museum has a designated pet-friendly entrance.
  • What are the benefits of choosing a vacation rental in Cumberland, MD?

    Vacation rentals offer more space and privacy than hotels, and you can often find rentals with unique features like hot tubs or fireplaces. They also allow you to cook your own meals and enjoy a more home-like experience.
  • What are the top sports attractions and facilities in Cumberland, MD?

    Cumberland is home to the Rocky Gap State Park, which offers various recreational activities like hiking, fishing, and boating. The city also has a few golf courses, including the Rocky Gap Golf Resort.

Popular destinations

Holiday Rentals with a Balcony in Cumberland, MD, United States

Watch the local morning bustle with a fresh breeze at holiday rentals featuring an outdoor balcony in Cumberland, MD, United States.

Tranquil 2-bedroom Retreat: Modern Comfort, Fast Wi-fi & Near Gap Trail - Cumberland, MD
9.2 5 reviews

Tranquil 2-bedroom Retreat: Modern Comfort, Fast Wi-fi & Near Gap Trail

apartment, Cumberland
This two-bedroom flat in Cumberland offers direct access to the GAP Trail, ideal for cyclists, and is situated close to the historic downtown area for exploration.
This accommodation for four guests includes air conditioning, parking, and a kitchen with a microwave, providing a convenient base for enjoying nearby attractions such as the Western Maryland Scenic Railroad and the Allegany Museum.

Premier Pet-Friendly Holiday Rentals in Cumberland, MD, United States

Let your dog stretch their legs and explore a new neighborhood alongside you at pet-friendly holiday rentals in Cumberland, MD, United States.

Studio Appearances - Cumberland, MD
No reviews

Studio Appearances

apartment, Cumberland
This ground-level studio flat is located uphill from downtown Cumberland, within 1 kilometre of local shops, the scenic railway, and biking trails.
This pet-friendly accommodation sleeps two guests and offers a kitchen with a fridge, on-site coin-operated laundry, and convenient access to outdoor activities.
Awesome New Property/ Canal River Retreat - Cumberland, MD
9.8 130 reviews

Awesome New Property/ Canal River Retreat

apartment, Cumberland
This five-bedroom house is located in the mountains of Cumberland, just 1.6km from the Chesapeake and Ohio Canal and National Historic Park and 3.2km from the Western Maryland Railroad Station. The property has received excellent user ratings, making it a popular choice for travellers.
The 228 square metre house comfortably accommodates up to eight guests and features a fully equipped kitchen, a garden, a terrace, and parking. Guests can enjoy free Wi-Fi, air conditioning, and a DVD player, as well as access to ski-in/ski-out slopes.
Cozy Country Charm  Mins To Cumberland & Trails - Cumberland, MD
9.9 14 reviews

Cozy Country Charm Mins To Cumberland & Trails

apartment, Wiley Ford
This apartment in Wiley Ford, West Virginia, is situated 1.1 kilometres from downtown Cumberland and offers immediate access to the Great Allegheny Passage, C&O Canal Towpath, and the Potomac River for outdoor pursuits.
This pet-friendly, single-level cottage accommodates up to six guests with one bedroom, one bathroom, a full kitchen including a fridge, freezer, microwave, and dishwasher, air conditioning, a garden with a picnic area and fire pit, and on-site parking.
Lavernes Lodge - Cumberland, MD
9.7 73 reviews

Lavernes Lodge

apartment, Cumberland
This Victorian flat is located just 1.6km from Cumberland's town centre, close to the C&O Canal and the Western MD railway, offering a peaceful setting within easy reach of local attractions. It has consistently received excellent ratings for location, cleanliness, and overall experience.
The flat has three bedrooms, a master with a king-size bed, a queen-size bedroom, and a TV room with a king-size daybed, comfortably accommodating up to six guests. It is fully equipped with a kitchen, air conditioning, a garden, and parking, making it a convenient and comfortable home away from home.
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