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.

Rails And Trails Retreat ~ Historic Home W. Yard - Cumberland, MD
9.9 169 reviews

Rails And Trails Retreat ~ Historic Home W. Yard

apartment, Cumberland
This charming apartment is situated in a peaceful, family-friendly neighbourhood in Cumberland, just a stone's throw from the Great Allegheny Passage and C&O Canal trails and a short walk from the historic downtown area. It boasts excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
This spacious home, ideal for families, offers a comfortable living space for up to eight guests. It features a fully equipped kitchen, laundry facilities, a private garden, and off-street parking, ensuring a relaxing and enjoyable stay.
5 Minute Walk To Downtown. Cozy Family Sized Home With Everything You Need. - Cumberland, MD
9.4 32 reviews

5 Minute Walk To Downtown. Cozy Family Sized Home With Everything You Need.

apartment, Frostburg
This three-bedroom, two-bathroom flat in Frostburg's city centre offers a clubhouse atmosphere and is conveniently located 1.5 kilometres from Maplehurst Country Club, 3 kilometres from Wills Mountain State Park, and 4 kilometres from Dan's Mountain State Park, with easy access to Frostburg State University Arboretum and the Western Maryland Scenic Railroad. This family-friendly accommodation for up to 15 guests includes a kitchen with a fridge, microwave, and dishwasher, air conditioning, garden, and parking, making it suitable for both solo travellers and larger groups seeking a communal experience.
The Whistle Stop In Cumberland, Maryland - Cumberland, MD
9.6 9 reviews

The Whistle Stop In Cumberland, Maryland

apartment, Cumberland
This restored historic farmhouse in Cumberland, Maryland, offers family-friendly accommodation with four bedrooms and two bathrooms, sleeping up to eight guests, and is conveniently located for exploring local attractions. This property features a fully equipped kitchen, on-site laundry, WiFi, and air conditioning, providing a comfortable and connected stay for those visiting Cumberland.

Best Cumberland, MD holiday rentals with parking

5 Minute Walk To Downtown. Cozy Family Sized Home With Everything You Need. - Cumberland, MD
9.4 32 reviews

5 Minute Walk To Downtown. Cozy Family Sized Home With Everything You Need.

apartment, Frostburg
This three-bedroom, two-bathroom flat in Frostburg's city centre offers a clubhouse atmosphere and is conveniently located 1.5 kilometres from Maplehurst Country Club, 3 kilometres from Wills Mountain State Park, and 4 kilometres from Dan's Mountain State Park, with easy access to Frostburg State University Arboretum and the Western Maryland Scenic Railroad. This family-friendly accommodation for up to 15 guests includes a kitchen with a fridge, microwave, and dishwasher, air conditioning, garden, and parking, making it suitable for both solo travellers and larger groups seeking a communal experience.
Elegant Family Retreat Near - Cumberland, MD
9.5 4 reviews

Elegant Family Retreat Near

apartment, Cumberland
This renovated historic five-bedroom, two-bathroom house for 14 guests is situated close to downtown Cumberland, offering convenient access to local restaurants, shops, and attractions within 1 kilometre.
This pet-friendly property boasts a fully equipped kitchen, air conditioning, and internet, with an extra floor mattress available, and accommodates events and filming with prior host approval.
Rocky Gap Casino & Resort - Cumberland, MD
9.0 1756 reviews

Rocky Gap Casino & Resort

resort, Pleasant Grove
Rocky Gap Casino & Resort is located near the beach in Pleasant Grove, just a short distance from Rocky Gap State Park and Rocky Gap Casino and Golf Course. The resort has received very good ratings for its location, cleanliness and overall user experience.
The hotel has a range of facilities, including a swimming pool, a jacuzzi, a spa, a restaurant, a bar, a fitness centre and room service. Guests can enjoy the on-site casino, play a round of golf, or explore the nearby state park.
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.

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.

Elegant Family Retreat Near - Cumberland, MD
9.5 4 reviews

Elegant Family Retreat Near

apartment, Cumberland
This renovated historic five-bedroom, two-bathroom house for 14 guests is situated close to downtown Cumberland, offering convenient access to local restaurants, shops, and attractions within 1 kilometre.
This pet-friendly property boasts a fully equipped kitchen, air conditioning, and internet, with an extra floor mattress available, and accommodates events and filming with prior host approval.

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.

Elegant Family Retreat Near - Cumberland, MD
9.5 4 reviews

Elegant Family Retreat Near

apartment, Cumberland
This renovated historic five-bedroom, two-bathroom house for 14 guests is situated close to downtown Cumberland, offering convenient access to local restaurants, shops, and attractions within 1 kilometre.
This pet-friendly property boasts a fully equipped kitchen, air conditioning, and internet, with an extra floor mattress available, and accommodates events and filming with prior host approval.
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