Cumberland, MD vacation rentalscozycozy

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Best Vacation rentals and Airbnb offers in Cumberland, MD

Rails And Trails Retreat ~ Historic Home W. Yard - Cumberland, MD
9.9 168 reviews
Cumberland, MD
1 4
$317/nightfor 1 night

Rails And Trails Retreat ~ Historic Home W. Yard

apartment - Cumberland
This Cumberland apartment is located just 100 feet from the GAP and C&O trails and a short walk from the historic downtown area, making it a great choice for travelers who want to be close to the action. It has received excellent ratings for location, cleanliness, and overall experience.
The rental offers a comfortable and spacious living space for up to 8 guests. It features a fully equipped kitchen, laundry facilities, excellent broadband, and covered bike storage, along with three porches and a fenced-in yard for outdoor enjoyment.
Hillside Family Retreat - Cumberland, MD
10 5 reviews
Cumberland, MD
1 6
$421/nightfor 1 night

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 Suite On Smallwood * I 68* Gap Trail* Sleep 6 - Cumberland, MD
10 12 reviews
Cumberland, MD
1 2
$199/nightfor 1 night

The Suite On Smallwood * I 68* Gap Trail* Sleep 6

apartment - Cumberland
This luxury second-floor apartment offers a unique retreat in a peaceful district of Cumberland, conveniently located above a full-service salon and spa for on-site pampering. This renovated suite features two bedrooms accommodating up to six guests, with amenities including a full kitchen, in-unit laundry, a dedicated workspace, and the option to book spa services without leaving the building.
Jacob's Cottage - Cumberland, MD
9.8 289 reviews
Cumberland, MD
1 3
$137/nightfor 1 night

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.
Queen City Quarters- Cozy, Historic, 1920s Home - Cumberland, MD
9.8 160 reviews
Cumberland, MD
1 3
$190/nightfor 1 night

Queen City Quarters- Cozy, Historic, 1920s Home

apartment - Cumberland
This apartment is located in a peaceful residential area of Cumberland, within walking distance of the historic downtown and railroad station, and minutes away from the C&O Canal Towpath and the Cumberland Gap Trail. The apartment has received excellent ratings for its cleanliness, location, and overall experience.
The apartment has three bedrooms and two bathrooms, comfortably accommodating up to five guests. It features a well-equipped kitchen, air conditioning, a garden, parking, internet access, and a dedicated workspace, making it a perfect home base for exploring Cumberland and the surrounding area.
Lovely 1bed Unit In The Hills Of Western Maryland - Cumberland, MD
9.7 19 reviews
Cumberland, MD
1 1
$131/nightfor 1 night

Lovely 1bed Unit In The Hills Of Western Maryland

apartment - Cumberland
This apartment is located just 10 miles from downtown Cumberland, the scenic railroad, and the Rocky Gap Casino and state park, offering a peaceful retreat in the hills of Western Maryland. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The apartment is a one-bedroom unit with one bathroom and can comfortably sleep up to four guests. It includes amenities like a kitchen with a fridge and microwave, air conditioning, a garden, and parking, making it a perfect choice for families or groups looking for a comfortable and convenient stay.
Relaxing Rustic Oasis Ii -  6 Min Walk To Downtown! Cyclist Welcomed! - Cumberland, MD
10 8 reviews
Cumberland, MD
1 1
$188/nightfor 1 night

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
Cumberland, MD
1 3
$257/nightfor 1 night

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.
Polk-a-dot #2 - Walk To Downtown & Pets Welcome - Cumberland, MD
9.7 18 reviews
Cumberland, MD
1 2
$195/nightfor 1 night

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

apartment - Cumberland
This 2-bedroom rental in Cumberland offers prime walkability to downtown attractions, including shops, dining, the Western Maryland Scenic Railroad, and direct access to the C&O Canal trail, all within a few blocks. This pet-friendly apartment sleeps 6 guests and features air conditioning, internet, a fully equipped kitchen, and parking, making it ideal for outdoor enthusiasts and those exploring the historic district.
Serenity In The South End - Cumberland, MD
10 3 reviews
Cumberland, MD
1 3
$191/nightfor 1 night

Serenity In The South End

apartment - Cumberland
This two-story apartment is situated in historic Cumberland, Maryland, offering convenient access to the Cumberland Historic District and nearby landmarks.
This residence accommodates up to six guests with three bedrooms, one bathroom, a full kitchen, and shared backyard access with barbecue facilities.
Elegant Family Retreat Near - Cumberland, MD
9.0 2 reviews
Cumberland, MD
1 5
$329/nightfor 1 night

Elegant Family Retreat Near

apartment - Cumberland
This renovated historic apartment is located in Cumberland, offering convenient access to downtown restaurants, shops, and local attractions, situated just 0.5 miles away.
This pet-friendly five-bedroom, two-bathroom residence accommodates up to 14 guests with a fully equipped kitchen and air conditioning, and is suitable for events with host approval.
The Whistle Stop In Cumberland, Maryland - Cumberland, MD
9.4 7 reviews
Cumberland, MD
1 4
$315/nightfor 1 night

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.

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.

Relaxing Rustic Oasis Ii, Unit B - 6 Minute Walk To Downtown! Cyclists Welcome! - Cumberland, MD
9.2 16 reviews
Cumberland, MD
1 1
$154/nightfor 1 night

Relaxing Rustic Oasis Ii, Unit B - 6 Minute Walk To Downtown! Cyclists Welcome!

house - Cumberland
This downtown Cumberland apartment is located in Hambright's Alley, just 12 miles from Frostburg State University and within walking distance of shops, restaurants, and attractions. It has received good user ratings for its comfortable accommodations.
The apartment has one bedroom, one bathroom, and a floor area of 810 square feet, comfortably accommodating four guests. Enjoy the fresh air and city views from the private balcony, prepare meals in the fully equipped kitchen, and relax with streaming TV.
The Suite On Smallwood - Cumberland, MD
9.8 6 reviews
Cumberland, MD
1 2
$214/nightfor 1 night

The Suite On Smallwood

apartment - Cumberland
This 2-bedroom, 1-bathroom condo in Cumberland provides comfortable lodging with internet, air conditioning, and parking, located a short drive from the Allegany County Fairgrounds and Rocky Gap Casino.
This accommodation sleeps up to 6 guests and offers convenient access to attractions like the Western Maryland Scenic Railroad and Tri-State Zoological Park, ideal for exploring the Cumberland area.
Downtown Rustic Oasis Ii - Cyclists Welcome! - Cumberland, MD
9.7 63 reviews
Cumberland, MD
1 1
$146/nightfor 1 night

Downtown Rustic Oasis Ii - Cyclists Welcome!

apartment - Cumberland
This one-bedroom apartment is located just a block from downtown Cumberland, making it easy to walk to the Cumberland Theatre, Western Maryland Scenic Railroad, and the C&O Canal & GAP Trail. The quiet neighborhood provides a peaceful retreat after a day exploring the city's attractions.
The apartment comfortably sleeps up to four guests with a foldable twin bed for additional sleeping space. It offers a fully equipped kitchen, a laundry room with complimentary detergent, a TV with streaming services, and free WiFi. Guests can also enjoy access to the GAP Trail for biking or walking, and parking is available in a nearby alley.
The Downtown Railside Nook - Cumberland, MD
9.0 6 reviews
Cumberland, MD
1 3
$189/nightfor 1 night

The Downtown Railside Nook

apartment - Cumberland
This second-floor condo is located in downtown Cumberland, Maryland, approximately 5,280 feet from the shops, restaurants, art galleries, and nightlife of the downtown district, and is situated in a historic building.
This three-bedroom lodging accommodates up to four guests and includes air conditioning, parking, and a kitchen equipped with a fridge, freezer, and microwave oven.

Best Cumberland, MD vacation rentals with air conditioning

Cumberland Street House -Gap Trail Perfection! - Cumberland, MD
9.8 600 reviews
Cumberland, MD
1 3
$218/nightfor 1 night

Cumberland Street House -Gap Trail Perfection!

apartment - Cumberland
The Cumberland Street House is a charming historic property located in Cumberland's historic district, within walking distance to downtown attractions. It has excellent user, location, and cleanliness ratings.
The home has 3 bedrooms, 1 bathroom, and can accommodate up to 8 guests. It features a fully equipped kitchen, smart TV, fenced-in yard, and easy parking. Pets are welcome at no additional charge, and a private nursery is available for families with young children.
Cozy Country Charm  Mins To Cumberland & Trails - Cumberland, MD
9.8 12 reviews
Cumberland, MD
1 1
$195/nightfor 1 night

Cozy Country Charm Mins To Cumberland & Trails

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.
Hila's House - Cumberland, MD
9.9 154 reviews
Cumberland, MD
1 2
$155/nightfor 1 night

Hila's House

apartment - La Vale
This La Vale home is located just a short drive from historic Cumberland, MD, and offers easy access to the scenic Appalachian Mountains. It has received excellent ratings for cleanliness, location, and overall user experience.
The home features two bedrooms and one and a half bathrooms, accommodating up to four guests comfortably. Enjoy modern amenities like air conditioning, a fully equipped kitchen with a fridge, and free Wi-Fi, as well as a private outdoor space perfect for relaxing.
344 Cozy Cottage - Cumberland, MD
9.6 37 reviews
Cumberland, MD
1 1
$142/nightfor 1 night

344 Cozy Cottage

cabin - La Vale
This cozy cottage is conveniently located across the street from Fratelli's restaurant, putting you within easy reach of LaVale's shopping and dining options. The house is just a short drive from downtown Cumberland, allowing you to explore the historic district and enjoy the rail trails and bike paths.
The cottage offers a private bedroom, a cute living room with a pub table dining area, a kitchenette with a stove, microwave, and refrigerator, and a full bathroom with a shower. You'll also have private parking and access to amenities like air conditioning, internet, and a garden.

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.

Relaxing Rustic Oasis Ii, Unit B - 6 Minute Walk To Downtown! Cyclists Welcome! - Cumberland, MD
9.2 16 reviews
Cumberland, MD
1 1
$154/nightfor 1 night

Relaxing Rustic Oasis Ii, Unit B - 6 Minute Walk To Downtown! Cyclists Welcome!

house - Cumberland
This downtown Cumberland apartment is located in Hambright's Alley, just 12 miles from Frostburg State University and within walking distance of shops, restaurants, and attractions. It has received good user ratings for its comfortable accommodations.
The apartment has one bedroom, one bathroom, and a floor area of 810 square feet, comfortably accommodating four guests. Enjoy the fresh air and city views from the private balcony, prepare meals in the fully equipped kitchen, and relax with streaming TV.

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.

New Listing-"cumberland Cottage"-charming,quaint - Cumberland, MD
10 160 reviews
Cumberland, MD
1 3
$200/nightfor 1 night

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.
Private 2 Bedroom Apt With Bike Storage 1 Mile To The Gap And C&o Canal / - Cumberland, MD
10 59 reviews
Cumberland, MD
1 2
$175/nightfor 1 night

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.
2 Br Apt, 1 Mile To C&o & Gap Trail W/bike Storage - Cumberland, MD
9.8 104 reviews
Cumberland, MD
1 2
$167/nightfor 1 night

2 Br Apt, 1 Mile To C&o & Gap Trail W/bike Storage

apartment - Cumberland
This Cumberland apartment is located in a quiet neighborhood, less than a mile from downtown, the Great Allegheny Passage trail, the C&O Canal, and restaurants. It has earned excellent ratings for location, cleanliness, and user experience.
This two-bedroom unit can accommodate up to five guests and offers a full kitchen, bathroom, living area, and a private porch. Amenities include a 40" Roku TV, fast Wi-Fi, washer and dryer, secure bike storage, and a well-equipped kitchen.

Best Cumberland, MD vacation rentals with parking

The Bobo's - Cumberland, MD
10 12 reviews
Cumberland, MD
1 3
$203/nightfor 1 night

The Bobo's

apartment - La Vale
The Woodland Getaway - Cumberland, MD
9.8 107 reviews
Cumberland, MD
1 3
$183/nightfor 1 night

The Woodland Getaway

apartment - Corriganville
Rocky Gap Casino & Resort - Cumberland, MD
9.0 1750 reviews
Cumberland, MD
6 3
$644/nightfor 1 night

Rocky Gap Casino & Resort

resort - Pleasant Grove
Mountain Maryland Getaway - Cumberland, MD
9.9 55 reviews
Cumberland, MD
1 2
$167/nightfor 1 night

Mountain Maryland Getaway

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.

Kat's Place - Cumberland, MD
9.7 40 reviews
Cumberland, MD
1 2
$138/nightfor 1 night

Kat's Place

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
Cumberland, MD
1 2
$217/nightfor 1 night

Cresaptown Condo On The Creek

apartment - Cresaptown

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.

Rocky Gap Casino & Resort - Cumberland, MD
9.0 1750 reviews
Cumberland, MD
6 3
$644/nightfor 1 night

Rocky Gap Casino & Resort

resort - Pleasant Grove

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.

Secluded, Romantic Cabin With Hot Tub On 12 Acres Of Woodland. - Cumberland, MD
10 119 reviews
Cumberland, MD
1 1
$335/nightfor 1 night

Secluded, Romantic Cabin With Hot Tub On 12 Acres Of Woodland.

cabin - Spring Gap
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