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

Browse Vacation Rentals in the Historic District of Cumberland, MD

From vibrant downtown areas to historic streets, these Cumberland, MD vacation rentals put you close to everything worth seeing.

The Whistle Stop In Cumberland, Maryland - Cumberland, MD
9.4 7 reviews

The Whistle Stop In Cumberland, Maryland

apartment, Cumberland
This family-friendly apartment is located in Cumberland, Maryland, within a restored historic home offering proximity to local attractions.
This residence provides accommodation for up to 8 guests with 4 bedrooms, 2 bathrooms, a fully equipped kitchen, and on-site laundry, featuring air conditioning and WiFi.
Downtown Cumberland Jewel - Cumberland, MD
10 34 reviews

Downtown Cumberland Jewel

apartment, Cumberland
This craftsman apartment in downtown Cumberland is just steps away from restaurants, coffee shops, and other attractions. It consistently receives excellent ratings for its location, cleanliness, and overall experience.
The spacious home features three bedrooms and two full bathrooms, comfortably accommodating up to seven guests. Amenities include a full kitchen with a fridge, freezer, microwave, and dishwasher, a washer and dryer, air conditioning, parking, and internet access.
Relaxing Rustic Oasis Ii -  6 Min Walk To Downtown! Cyclist Welcomed! - Cumberland, MD
10 8 reviews

Relaxing Rustic Oasis Ii - 6 Min Walk To Downtown! Cyclist Welcomed!

apartment, Cumberland
This Cumberland apartment rental is centrally located, a 10-minute walk from the Downtown Cumberland Historic District, Windsor Hall, Allegany Museum, Emmanuel Episcopal Church, Western Maryland Scenic Railroad, and Cumberland Station.
The one-bedroom, one-bathroom unit sleeps four guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, in-unit laundry, free Wi-Fi, and on-site parking.
Lock#7four - Cumberland, MD
10 17 reviews

Lock#7four

apartment, Cumberland
This historic 3-bedroom family home is located downtown Cumberland, Maryland, offering immediate access to city attractions and amenities, steps from local art and history, and serving as an ideal base for exploring the mountains and Cumberland's biking trails. The two-story residence features 2 bathrooms, accommodates up to 6 guests, and includes a fully equipped kitchen, in-unit laundry, and full guest access to the entire property.

Best Cumberland, MD vacation rentals with air conditioning

Hillside Family Retreat - Cumberland, MD
10 5 reviews

Hillside Family Retreat

apartment, Cumberland
This Cumberland, Maryland rental, The Cottage on the Hill and The Hillside Hideaway, offers two adjacent houses perfect for large groups, situated near a wooded area providing privacy yet convenient access to Cumberland's attractions (exact distances unspecified).
This 6-bedroom, 4-bathroom vacation home sleeps up to 16 guests, boasting amenities including two game rooms with pool tables, extensive grounds with fire pits, and private parking for 6-8 cars, plus flexible check-in/check-out times.
The Lookout At 301 - Cumberland, MD
10 1 review

The Lookout At 301

apartment, Cumberland
This one-bedroom, one-bathroom rental unit is located in Cumberland's historic district, offering convenient access to the Great Allegheny Passage (GAP) trail and Western Maryland attractions.
This pet-friendly apartment accommodates up to three guests and features a full kitchen, air conditioning, and internet service, serving as a comfortable base for exploring the Alleghenies.
Jacob's Cottage - Cumberland, MD
9.8 289 reviews

Jacob's Cottage

apartment, Bowmans Addition
This charming Cape Cod-style cottage is located six miles from downtown Cumberland, offering easy access to attractions like Canal Place and the Western Maryland Historic Train Rides. The property has received excellent ratings for location, cleanliness, and overall user experience.
The cottage has three bedrooms and one bathroom, comfortably accommodating up to eight guests. The property offers a spacious yard, a secluded mountain setting, and access to nearby hiking, biking, and skiing opportunities.
Historic Eden Ranch, Built 1837 - Cumberland, MD
9.8 76 reviews

Historic Eden Ranch, Built 1837

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.

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.

Popular destinations

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
9.8 136 reviews

The Dacha. Cumberland Vacation

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.

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.

The Whistle Stop In Cumberland, Maryland - Cumberland, MD
9.4 7 reviews

The Whistle Stop In Cumberland, Maryland

apartment, Cumberland
This family-friendly apartment is located in Cumberland, Maryland, within a restored historic home offering proximity to local attractions.
This residence provides accommodation for up to 8 guests with 4 bedrooms, 2 bathrooms, a fully equipped kitchen, and on-site laundry, featuring air conditioning and WiFi.
New Listing-"cumberland Cottage"-charming,quaint - Cumberland, MD
10 154 reviews

New Listing-"cumberland Cottage"-charming,quaint

apartment, Pleasant Grove
This charming renovated rancher is located just outside the city limits of Pleasant Grove, offering a peaceful setting while remaining conveniently close to local attractions and dining options. The property has received excellent ratings for its cleanliness, location, and overall experience.
The apartment features an open concept living area, creating a spacious and airy feel, and comfortably accommodates up to 5 guests. The apartment includes a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning, a garden, and on-site parking.
Hillside Family Retreat - Cumberland, MD
10 5 reviews

Hillside Family Retreat

apartment, Cumberland
This Cumberland, Maryland rental, The Cottage on the Hill and The Hillside Hideaway, offers two adjacent houses perfect for large groups, situated near a wooded area providing privacy yet convenient access to Cumberland's attractions (exact distances unspecified).
This 6-bedroom, 4-bathroom vacation home sleeps up to 16 guests, boasting amenities including two game rooms with pool tables, extensive grounds with fire pits, and private parking for 6-8 cars, plus flexible check-in/check-out times.
Private 2 Bedroom Apt With Bike Storage 1 Mile To The Gap And C&o Canal / - Cumberland, MD
10 58 reviews

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

apartment, Cumberland
This two-bedroom apartment is located less than a mile from downtown Cumberland, the GAP Trail, the C&O Canal, and restaurants in a safe, quiet neighborhood. The apartment has received excellent user ratings and is perfect for families or groups of up to five guests.
The apartment features a full kitchen, bathroom, living area, porch, and a private entrance. Guests can enjoy amenities like WiFi, a 40” TV, streaming services, a DVD player, movies, games, books, and secure bike storage.

Best Cumberland, MD vacation rentals with parking

Urban Nest On Race Street - Cumberland, MD
8.0 6 reviews

Urban Nest On Race Street

apartment, Cumberland
Lavernes Lodge - Cumberland, MD
9.7 69 reviews

Lavernes Lodge

apartment, Cumberland
Charming 2-bedroom Apartment With Equipped Kitchen And Ac, In Cumberland, Md. - Cumberland, MD
10 4 reviews

Charming 2-bedroom Apartment With Equipped Kitchen And Ac, In Cumberland, Md.

apartment, Cumberland
Queen City Quarters- Cozy, Historic, 1920s Home - Cumberland, MD
9.8 153 reviews

Queen City Quarters- Cozy, Historic, 1920s Home

apartment, Cumberland

Find the Best Luxury Vacation Rentals in Cumberland, MD

Elevate your stay in a luxury vacation rental or Airbnb in Cumberland, MD, featuring high-end finishes and a prime location.

The Place At 811 - Cumberland, MD
No reviews

The Place At 811

apartment, Cumberland

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
10 3 reviews

Cresaptown Condo On The Creek

apartment, Cresaptown
Romantic Condo With A View In Historic Cumberland - Cumberland, MD
9.3 12 reviews

Romantic Condo With A View In Historic Cumberland

apartment, Cumberland

Top-Rated Vacation Rentals with a Pool in Cumberland, MD

Dive into a refreshing stay with these Cumberland, MD rentals and Airbnbs that offer on-site swimming pool access in the heart of the city.

The Dacha. Cumberland Vacation - Cumberland, MD
9.8 136 reviews

The Dacha. Cumberland Vacation

house, Cumberland

Top Vacation Rentals with a Hot Tub in Cumberland, MD

Unwind after a day of urban exploration with a private hot tub at your own vacation rental in Cumberland, MD.

The Dacha. Cumberland Vacation - Cumberland, MD
9.8 136 reviews

The Dacha. Cumberland Vacation

house, Cumberland
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