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Discover Your Ideal Rental by Owner in Cumberland, Maryland for a Comfortable Stay
Discover Your Perfect Cumberland Rentals by Owner
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Cumberland Rentals by Owner
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Security/Safety
- Parking
- View
- Sports/Activities
- Air Conditioner
- Parking
- Security/Safety
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- Balcony/Terrace
- Accessibility
- 2187 ft² House
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pool
- 796 ft² House
- Parking
- Pet Friendly
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Security/Safety
Why Choose Rent By Owner for your Cumberland vacation rental?
What makes our Rentals by Owner special?
Popular Areas for Cumberland Rentals by Owner
Where are the best neighborhoods to stay in Cumberland?
When choosing a place to stay in Cumberland, Maryland, exploring the different neighborhoods can enhance your visit. Whether you prefer the historic charm of downtown Cumberland or the quiet serenity of surrounding residential areas, each neighborhood offers unique amenities and a welcoming atmosphere. By selecting a rental by owner through Rent By Owner, you can enjoy a personalized experience in this scenic city, ensuring comfort and convenience during your stay in Cumberland, Maryland. Discover the perfect neighborhood that aligns with your travel needs and makes your trip truly memorable.
Sky Valley
Nestled near the scenic region surrounding Cumberland, Sky Valley offers a tranquil retreat with easy access to outdoor activities. Here, you can enjoy peaceful surroundings while remaining close to the area's natural beauty.
View 37+ Rentals in Sky ValleyWaterfront Greens
Located along the waterways near this region, Waterfront Greens provides a serene setting perfect for relaxation and outdoor pursuits. Its proximity to water-based attractions makes it an ideal choice for nature enthusiasts seeking convenience and comfort.
View 64+ Rentals in Waterfront GreensBlakeslee
Situated within Oakland's charming surroundings, Blakeslee offers a welcoming environment with quick access to the area's popular spots. It’s well-suited for travelers looking to explore the region from a comfortable base.
View 52+ Rentals in BlakesleeParadise Point
Overlooking the scenic vistas of the area, Paradise Point provides a peaceful escape just moments from Oakland’s attractions. Its idyllic setting makes it perfect for relaxing getaways in this part of Maryland.
View 30+ Rentals in Paradise PointMountainside
Perched amid the rolling hills and mountains here, Mountainside offers stunning views and a quiet atmosphere. It’s an excellent choice for those seeking a retreat surrounded by natural beauty.
View 67+ Rentals in MountainsideThe View
This neighborhood is renowned for its picturesque panoramas of the region, making it a favorite among visitors wanting memorable scenery. Staying here means enjoying breathtaking sights within easy reach of local attractions.
View 1734+ Rentals in The ViewNorth Glade Hills
Set in a peaceful hillside area, North Glade Hills provides a quiet and scenic setting close to this destination's outdoor recreation options. It’s perfect for travelers seeking a combination of serenity and natural exploration.
View 49+ Rentals in North Glade HillsTurkey Neck
Known for its rural charm, Turkey Neck offers a laid-back atmosphere with convenient access to the region’s scenic landscapes. It’s an ideal spot for those wanting to experience the countryside while staying near the area's main attractions.
View 1023+ Rentals in Turkey NeckBest Times to Visit Cumberland
When should you plan your Rentals by Owner stay?
Choosing the right time to vacation in Cumberland, Maryland allows you to enjoy the region's natural beauty and local events at their best, ensuring a memorable stay when booking your rental by owner through Rent By Owner.
Peak Season Highlights
Summer (June to August)
During the summer months, the area experiences warm weather ideal for outdoor activities and exploring scenic landscapes.
Fall (September to November)
Autumn brings vibrant foliage and pleasant temperatures, making it a popular time for enjoying the natural beauty here.
Off-Season Highlights
Winter (December to February)
The winter season offers a quieter atmosphere, with cooler temperatures perfect for cozy stays and off-season exploration.
Spring (March to May)
Spring features milder weather and blooming scenery, providing a peaceful setting before the busy summer months.
Weekly Weather Forecast for Cumberland
How to Book Your Cumberland vacation rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Cumberland
Common Rentals by Owner Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy access to a spacious outdoor patio or deck, perfect for relaxing and entertaining amidst the scenic surroundings.
- Take advantage of a private or shared backyard area for outdoor activities and gatherings.
- Look for properties with a fire pit or outdoor fireplace to enjoy cozy evenings under the stars.
- Make the most of well-maintained hiking or nature trails nearby to explore the area's natural beauty.
- Seek rentals with outdoor dining spaces, ideal for savoring meals while taking in the fresh air.
- Discover outdoor swimming pools or hot tubs available for your relaxation and enjoyment during your stay.
- Check for access to scenic overlooks or viewing platforms that showcase the region's picturesque landscapes.
Top Attractions Around Cumberland
What attractions are nearby?
Enjoy nearby outdoor adventures, cultural experiences, and scenic views that highlight the charm of Cumberland when you book a rental by owner in this welcoming destination.

Family Activities
- George's Creek Railroad Museum: Explore this engaging museum to learn about the area's rich railroad history and enjoy interactive exhibits perfect for family curiosity.
- Cumberland Historic Downtown: Take a stroll through the charming historic district, where you can discover unique shops, kid-friendly cafes, and beautiful architecture that tell the story of the region.
- Pony Express Museum & Park: Visit this outdoor park to experience educational displays about local transportation history and enjoy family-friendly picnic areas.
- Rocky Gap State Park: Spend quality time outdoors by hiking, picnicking, or participating in water activities in the natural beauty surrounding this popular destination for families here.
Adult Activities
- Cumberland Scenic Rail Trail: Discover the area's natural beauty by cycling or walking along this popular trail, offering scenic views and a peaceful escape.
- Great Allegheny Passage: Embark on a biking adventure through the region's picturesque landscapes as you follow this renowned multi-use trail from Cumberland to Pittsburgh.
- Eastern Trails Adventure: Enjoy hiking through wooded terrains and gently rolling hills that highlight this destination’s outdoor charm and tranquil environment.
- Cumberland Historic District Tour: Immerse yourself in local history by exploring beautifully preserved buildings and landmarks within the historic core of this area.
Other Places to Stay in Cumberland, MD
Cumberland Travel Tips
How Can You Make the Most of Your Stay?
- Explore local outdoor recreation: Take advantage of the region’s scenic parks and trails to enjoy outdoor activities that showcase Cumberland's natural beauty.
- Visit nearby historic sites: Immerse yourself in the area's rich history by planning visits to notable landmarks and museums close to your rental.
- Sample regional cuisine: Discover the local flavors by dining at eateries near your accommodation, offering authentic dishes unique to this destination.
- Plan ahead for convenience: Arrange your transportation and amenities early to ensure a smooth stay in this welcoming part of Maryland.
Transportation Options
- Local Bus Services: You can explore the area conveniently with local bus routes that connect key points within Cumberland, making it easy to navigate without a car.
- Amtrak Train Station: The Amtrak station in town offers reliable rail connections for travelers looking to arrive or depart via train with scenic routes through the region.
- Rental Car Agencies: Several rental car companies operate here, providing flexible transportation options for those wanting to explore beyond the city limits at your own pace.
- Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available for quick, convenient travel around the local area and nearby attractions.
Local Customs Options
- Local Craftsmanship: You might notice the region's reputation for artisan woodworking and handmade crafts, reflecting a deep appreciation for craftsmanship in this area.
- Historical Preservation: Respect for preserving historic sites and architecture is central to the community’s identity here, offering you a glimpse into the area's rich past.
- Welcoming warmth and friendliness are characteristic of the locals, ensuring your stay feels comfortable and inviting.
- Community Events: You can often partake in local festivals and gatherings that celebrate regional traditions and bring residents together in this part of Maryland.
Cumberland Rentals by Owner Frequently Asked Questions
1. How do I find detailed information about the rental's cancellation policy in Cumberland, Maryland?
2. What should I know about the check-in and check-out process for rentals here?
3. Are there any special requirements or house rules I should be aware of before booking?
4. What is the best way to inquire about amenities and property features in this destination?
5. How do I handle payments and security deposits when booking a rental here?
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