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.

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.
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 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.
Johnson Heights Getaway - Cumberland, MD
9.8 49 reviews

Johnson Heights Getaway

apartment, Cumberland
This three-bedroom apartment is situated in a convenient neighbourhood just 5km from downtown Cumberland, close to UPMC and Constitution Park. It has received excellent ratings for location, cleanliness, and overall user experience.
The property offers ample space for families with a finished attic that can be used as a games room or hangout area, accommodating up to six guests. Amenities include a fully equipped kitchen, air conditioning, a patio, a sun porch, and parking.

Best Cumberland, MD holiday rentals with parking

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.
Kat's Place - Cumberland, MD
9.7 40 reviews

Kat's Place

apartment, Cumberland
This two-bedroom Cumberland apartment, ideally located near the Cumberland Casino, the Chesapeake & Ohio Canal, and the downtown mall, offers easy access to restaurants and shops.
The self-contained flat sleeps four guests and boasts amenities including air conditioning, parking, and internet access, all within a secure building with excellent guest reviews.
809- Lovely 1 Bed/1 Bath Unit W/ Free Parking - Cumberland, MD
10 8 reviews

809- Lovely 1 Bed/1 Bath Unit W/ Free Parking

apartment, Cumberland
This one-bedroom apartment is conveniently located in central Cumberland, just a short drive from the town centre and the Cumberland Infirmary.
The self-catering flat is newly renovated, sleeps up to four guests and offers free Wi-Fi, off-street parking and a modern kitchen with a fridge, freezer and microwave.
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.

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.

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.

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.

Historic Eden Ranch, Built 1837 - Cumberland, MD
9.8 78 reviews

Historic Eden Ranch, Built 1837

farm, Ellerslie
This charming farmhouse, situated on a 110-acre property in Allegany County, Maryland, is just a short distance from the base of Wills Knob and Wills Mountain, offering a tranquil escape in a rural setting. It has been awarded excellent ratings for its location, cleanliness, and overall experience.
The three-bedroom farmhouse can comfortably accommodate up to six guests and features a sitting room upstairs, a living room with a large TV, and a fully equipped kitchen. Guests have access to the entire property, including walking trails, a BBQ grill, and the opportunity to experience life on a working cattle ranch.
Polk-a-dot #2 - Walk To Downtown & Pets Welcome - Cumberland, MD
9.6 21 reviews

Polk-a-dot #2 - Walk To Downtown & Pets Welcome

apartment, Cumberland
This two-bedroom flat in Cumberland offers direct access to the C&O Canal trail, is within 500 meters of the town centre's shops and restaurants, and is a short walk from the Western Maryland Scenic Railroad.
This pet-friendly accommodation accommodates up to six guests with two bedrooms, one bathroom, a fully equipped kitchen, air conditioning, and parking, providing a convenient base for exploring Cumberland.
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