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Cumberland, MD vacation rentals
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Best Vacation rentals and Airbnb offers in Cumberland, MD

Compare Vacation Rentals for Families in Cumberland, MD

These kid-friendly vacation rentals in Cumberland, MD keep you close to top city attractions for a stress-free family vacation.

Hilltop 10 Acre Cabin Retreat Getaway - Wifi! - Cumberland, MD
9.6 188 reviews
Cumberland, MD
06/23 – 06/26
$216/nighttotal: $648 (3 )

Hilltop 10 Acre Cabin Retreat Getaway - Wifi!

3 2
cabin , Fort Ashby
This family-friendly cabin is located in the mountains, within 16 miles of various attractions like Advanced Medical Care, Canal Place, and the C&O Canal National Historic Park Visitor's Center. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
This 3-bedroom, 2-bathroom cabin has a spacious 1290 square feet, comfortably accommodating up to 6 guests. Amenities include a fully equipped kitchen, a fireplace, a patio, a garden, and a barbecue grill, making it perfect for a relaxing and enjoyable stay.
The Dacha. Cumberland Vacation - Cumberland, MD
10 8 reviews
Cumberland, MD
08/17 – 08/20
$187/nighttotal: $561 (3 )

The Dacha. Cumberland Vacation

2 1
apartment , Cumberland
This Cumberland mountainside vacation home sits a 10-minute walk from the Chesapeake & Ohio Canal National Historic Park and under 3 miles from Canal Place and Advanced Medical Care.
This 1440-square-foot property boasts two bedrooms, two bathrooms, sleeps four guests, and includes a fully equipped kitchen, swimming pool, jacuzzi, and on-site hot tub and arcade/game room.
The Cottage On The Hill - Cumberland, MD
10 200 reviews
Cumberland, MD
08/12 – 08/20
$184/nighttotal: $1472 (8 )

The Cottage On The Hill

1 2
apartment , Cumberland
This charming cottage sits on a hillside just a short walk from Historic Cumberland, offering a peaceful retreat with stunning views. It consistently receives excellent ratings for location, cleanliness, and overall guest experience.
The cottage features three bedrooms and two bathrooms, comfortably accommodating up to eleven guests. Enjoy a blend of modern amenities and vintage charm, including a fully equipped kitchen, a game room, a private patio with a fire pit, and a spacious porch perfect for relaxing and enjoying the beautiful scenery.
Awesome New Property/ Canal River Retreat - Cumberland, MD
9.8 124 reviews
Cumberland, MD
08/12 – 08/20
$189/nighttotal: $1512 (8 )

Awesome New Property/ Canal River Retreat

5 2
apartment , Cumberland
This vacation home is located in the mountains of Cumberland, just a mile from the Chesapeake and Ohio Canal and National Historic Park. The house has received excellent ratings from previous guests.
This five-bedroom, four-bathroom property is perfect for families or groups of up to eight people. The house features a fully equipped kitchen, a terrace, a garden, and free WiFi, making it an excellent choice for a relaxing and enjoyable stay.

Best Cumberland, MD vacation rentals with parking

The Hillside Hideaway - Cumberland, MD
10 78 reviews
Cumberland, MD
08/12 – 08/20
$184/nighttotal: $1472 (8 )

The Hillside Hideaway

1 2
apartment , Cumberland
This charming cottage is located on a hillside in Cumberland, just a short walk from the historic district, offering easy access to local attractions, shops, and restaurants. The cottage consistently receives excellent ratings for its cleanliness, location, and overall experience.
The cottage features three bedrooms and two bathrooms, comfortably accommodating up to nine guests. Enjoy modern amenities, a private patio with a fire pit, a backyard, a garden, and a small porch, perfect for relaxing and enjoying the outdoors.
Rocky Gap Casino & Resort - Cumberland, MD
9.0 1640 reviews
Cumberland, MD
06/23 – 06/26
$122/nighttotal: $366 (3 )

Rocky Gap Casino & Resort

1 2
resort , Pleasant Grove
Rocky Gap Casino & Resort is located near the beach in Pleasant Grove, just steps from Rocky Gap State Park and Rocky Gap Casino and Golf Course. This resort has received very good ratings for location, cleanliness, and overall user experience.
The hotel features an indoor pool, fitness center, and spa. Guests can enjoy multiple dining options, including three restaurants, a bar/lounge, and a coffee shop/cafe. Free self parking and housekeeping on request are also available.
Adorable 1-bedroom Apartment With Ac In Charming Cumberland - Cumberland, MD
10 1 review
Cumberland, MD
08/12 – 08/20
$109/nighttotal: $872 (8 )

Adorable 1-bedroom Apartment With Ac In Charming Cumberland

1 2
apartment , Cumberland
This Cumberland condo offers one bedroom and one bathroom, accommodating up to two guests, and is conveniently located near cultural sites like the Allegany Museum and Windsor Hall, as well as family attractions including the Western Maryland Scenic Railroad. Travelers seeking an apartment in Cumberland will appreciate the year-round comfort provided by heating and air conditioning, a microwave oven in the kitchen, and included parking and internet.
Gorgeous, Fully Renovated 3-bedroom House With Ac In Tranquil La Vale - Cumberland, MD
Cumberland, MD
06/23 – 06/26
$258/nighttotal: $774 (3 )

Gorgeous, Fully Renovated 3-bedroom House With Ac In Tranquil La Vale

3 2
apartment , Cumberland
This fully renovated 3-bedroom, 2-bathroom apartment on Haystack Mountain offers a secluded mountain setting overlooking National Highway, with convenient access to I68 and located just 10 minutes from downtown Cumberland's attractions.
This 1330 square foot residence accommodates up to 8 guests and features a kitchen with a fridge and microwave, air conditioning, a terrace/balcony, garden, parking, and high-speed internet, ideal for remote work and offering proximity to Allegany County Fairgrounds, Rocky Gap Casino and Golf Course, and the Western Maryland Scenic Railroad.

Frequently Asked Questions about vacation rentals in Cumberland, MD

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

    The Western Maryland Scenic Railroad is a great option for families. They have a variety of train rides throughout the year, including a Polar Express ride during the holidays. The Cumberland Railroad Station is also a great place to visit, as it's a National Historic Landmark.
  • What are the best Airbnb and vacation rentals in Cumberland, MD?

    Cumberland Street House -Gap Trail Perfection, Steeple View Flat In Historic District and Historic Downtown Cozy-modern Apt Pets Welcome are the most popular Airbnb and vacation rentals in Cumberland, MD among travelers.

  • 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, in the spring and fall. The weather is mild, and there are fewer crowds. If you're looking for a more affordable option, you can also book during the winter months. You can find some great deals on vacation rentals during this time.
  • What are the most popular Airbnbs in Cumberland, MD?

  • What events or festivals should visitors check out in and around Cumberland, MD?

    The Canal Place Festival is a great event to check out in the summer. It's a celebration of the C&O Canal, with live music, food vendors, and arts and crafts. The Allegany County Fair is another popular event, held in August. It features agricultural exhibits, livestock shows, and carnival rides.
  • What are the best vacation rentals with a pool in Cumberland, MD?

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

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

    For a taste of local flavor, check out The Old Firehouse Restaurant. They have a great menu with dishes made with fresh, local ingredients. The Chesapeake Inn is another great option, serving up classic Maryland seafood dishes.
  • What are the best rentals for families and kids in Cumberland, MD?

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

    The C&O Canal Towpath is a great option for walking or cycling. It's a paved path that follows the canal for miles, offering stunning views of the surrounding countryside. The Great Allegheny Passage is another popular route, offering a scenic ride through the mountains.
  • What are the best rentals or Airbnbs with a jacuzzi in Cumberland, MD?

    The best vacation 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.

  • Are there pet-friendly attractions in Cumberland, MD?

    The C&O Canal National Historical Park is a great place to bring your furry friend. They have a number of pet-friendly trails and picnic areas. The Western Maryland Scenic Railroad also welcomes well-behaved pets on their train rides.
  • What are the top sports attractions and facilities in Cumberland, MD?

    The city has a few sports facilities, including the Allegany County Recreation Park, which has a variety of fields and courts for different sports. The city also has a number of golf courses, including the Country Club of Cumberland. For a more unique experience, check out the Cumberland Railroad Station, which hosts the annual Cumberland Railroad Heritage Festival.

Destinations nearby

Choose the Right Vacation Rentals with a Terrace in Cumberland, MD

Enjoy your own private terrace with city skyline views at these vacation rentals in Cumberland, MD.

The Dacha. Cumberland Vacation - Cumberland, MD
9.9 129 reviews
Cumberland, MD
08/12 – 08/20
$197/nighttotal: $1576 (8 )

The Dacha. Cumberland Vacation

2 2
house , Cumberland
The Dacha is a Cumberland vacation rental located just 14 miles from Frostburg State University and 60 miles from Altoona-Blair County Airport, making it a convenient base for exploring the area. It has received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
This 2-bedroom house comfortably sleeps 4 guests and spans 1440 square feet. Enjoy a private pool, patio, mountain views, a fully equipped kitchen, a spa with a hot tub, outdoor play equipment, casino access, continental breakfast, free Wi-Fi, and parking.
Make Memories: Mountain View Grand 6br 3ba Lavale Home, 15 Min To Rocky Gap - Cumberland, MD
9.6 7 reviews
Cumberland, MD
08/17 – 08/20
$480/nighttotal: $1440 (3 )

Make Memories: Mountain View Grand 6br 3ba Lavale Home, 15 Min To Rocky Gap

6 1
apartment , La Vale
This six-bedroom La Vale, Maryland apartment is located on National Highway, minutes from Cumberland and attractions like Rocky Gap State Park (15-minute drive) and Deep Creek Lake (45-minute drive).
This 3800-square-foot rental boasts a spacious layout, accommodating up to 15 guests with amenities including a fully equipped kitchen, a terrace, a garden, and on-site parking; board games are also available.

Discover Pet-Friendly Vacation Rentals in Cumberland, MD

Experience a pet-friendly stay in Cumberland, MD with vacation rentals located steps away from city dog parks and walking trails.

Cresaptown Condo On The Creek - Cumberland, MD
Cumberland, MD
08/12 – 08/20
$187/nighttotal: $1496 (8 )

Cresaptown Condo On The Creek

1 2
apartment , Cresaptown
This two-bedroom, one-bathroom condo in Cresaptown offers internet, air conditioning, and a full kitchen, accommodating up to four guests in a comfortable setting near local shops and dining.
This residence is conveniently located within 2 miles of Allegany County Fairgrounds and a short drive to Rocky Gap State Park, providing easy access to community amenities and outdoor recreation.
Cozy Country Charm – Mins To Cumberland & Trails - Cumberland, MD
9.3 3 reviews
Cumberland, MD
08/12 – 08/20
$138/nighttotal: $1104 (8 )

Cozy Country Charm – Mins To Cumberland & Trails

1 2
apartment , Wiley Ford
This 1-bedroom, 1-bathroom apartment in Wiley Ford, WV, is located immediately adjacent to the Great Allegheny Passage and C&O Canal Towpath, offering direct access to outdoor activities and is less than a 5-mile drive from Cumberland's dining, shopping, and historical attractions.
This pet-friendly rental accommodates up to 6 guests and features a full kitchen, air conditioning, in-unit laundry, and a private outdoor space with a grill, picnic table, and fire pit, perfect for unwinding after biking, hiking, kayaking, or fishing on the Potomac River.
Johnson Heights Getaway - Cumberland, MD
9.8 46 reviews
Cumberland, MD
08/12 – 08/20
$146/nighttotal: $1168 (8 )

Johnson Heights Getaway

1 2
apartment , Cumberland
This 3-bedroom, 2-bathroom apartment in Cumberland is close to UPMC, Constitution Park, downtown, and bike trails. It has excellent user, location, and cleanliness ratings.
The apartment can accommodate up to 6 guests and features a spacious layout, a bonus attic space, an outdoor oasis, a charming interior, modern amenities, and is pet-friendly. It also offers ample parking.
Historic Eden Ranch, Built 1837 - Cumberland, MD
9.8 72 reviews
Cumberland, MD
08/12 – 08/20
$129/nighttotal: $1032 (8 )

Historic Eden Ranch, Built 1837

1 2
gîte , Ellerslie
This historic farmhouse built in 1837 is registered in the Maryland Historic Society. It is situated on 110 acres of rolling countryside with scenic walking trails and abundant wildlife.
This gîte has excellent user, location, and cleanliness ratings. It has 3 bedrooms, 1 bathroom, and can accommodate up to 6 guests. It offers modern conveniences such as a 55-inch TV with internet streaming capabilities and Wi-Fi. Guests can enjoy a patio with a BBQ grill for outdoor dining and relaxation, and observe deer, turkey, and geese roaming freely on the property.
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