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  2. Maryland
  3. Waldorf
  4. Cheltenham
  5. Rentals by Owner

Discover Your Perfect Cheltenham Rentals by Owner

Cheltenham Rentals by Owner

10.0 (2 Reviews)
Apartment
Crystal Place
  • Air Conditioner
  • Parking
  • View
View Availability
|
10.0 (1 Review)
House
Luxury lifestyle
  • Air Conditioner
  • Parking
  • Pool
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|
9.2 (5 Reviews)
Apartment
Z Presidential Suite
  • Air Conditioner
  • Parking
  • Pet Friendly
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8.4 (35 Reviews)
House
The Oasis
  • Air Conditioner
  • Parking
  • TV
View Availability
More Top-Rated Rentals by Owner in Cheltenham Area

Why Choose Rent By Owner for your Cheltenham vacation rental?

What makes our Rentals by Owner special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Cheltenham

When should you plan your Rentals by Owner stay?

Choosing the ideal time to visit this destination ensures you experience its best features and enjoy a seamless stay, whether you're seeking a peaceful retreat or planning to explore the vibrant local scene in the area.

Peak Season Highlights

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Spring (March to May)

During spring, the area experiences mild temperatures and blooming landscapes, making it an ideal time for outdoor activities and exploring local attractions.

Average Temperature Daytime: 60°F to 75°F - Nighttime: 40°F to 55°F
autumn
Fall (September to November)

Autumn brings crisp weather and vibrant foliage, providing a picturesque setting for your stay in this destination's charming rentals.

Average Temperature Daytime: 65°F to 70°F - Nighttime: 45°F to 50°F

Off-Season Highlights

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Summer (June to August)

The summer months tend to be warmer and busier, with visitors enjoying longer daylight hours and outdoor leisure in the region.

Average Temperature Daytime: 80°F to 90°F - Nighttime: 60°F to 70°F
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Winter (December to February)

Winter can be colder and quieter, offering a peaceful retreat with the chance to experience cozy accommodations and fewer crowds.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F

Weekly Weather Forecast for Cheltenham

How to Book Your Cheltenham vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Cheltenham

More Top-Rated Rentals by Owner in Cheltenham Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

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 outdoor seating areas such as patios or decks to relax and take in the fresh air.
  • Take advantage of private gardens or landscaped yards perfect for outdoor activities.
  • Make use of a barbecue grill for outdoor cooking and family gatherings.
  • Benefit from access to walking trails or nature paths nearby for outdoor exploration.
  • Relax by an outdoor swimming pool if available, ideal for warm days.
  • Utilize outdoor fire pits or fireplaces for cozy evenings under the stars.
  • Experience outdoor recreational spaces like sports courts or playgrounds designed for guest enjoyment.

Top Attractions Around Cheltenham

What attractions are nearby?

During your stay, you'll find a variety of nearby activities in this region that allow you to explore the local charm and enjoy outdoor recreation, cultural experiences, and relaxing outings just moments from your rental by owner.

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Family Activities

  • Potomac Horse Center: Discover a family-friendly horseback riding experience that introduces both kids and adults to equestrian activities in the scenic surroundings of this destination.
  • Fort Washington Park: Enjoy a day outdoors with hiking, picnicking, and exploring historical sites along the Potomac River in this inviting regional park.
  • National Capital Trolley Museum: Embark on a nostalgic journey through transportation history with engaging trolley rides that are perfect for children and families alike.
  • Andrews Air Force Base Tour Center: Experience an educational and inspiring visit by touring the base, offering insight into military aviation and aircraft operations here.
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Adult Activities

  • Golf at the nearby courses: Enjoy a relaxing day on the fairways of the local golf courses, perfect for both beginners and seasoned players seeking a scenic round.
  • Visit the historic sites: Explore the area's rich history through well-preserved landmarks and museums that offer fascinating insights into the region’s past.
  • Attend local wine tastings: Discover regional wineries and indulging in tasting sessions that highlight the area’s burgeoning wine scene.
  • Enjoy outdoor recreational parks: Take advantage of the numerous parks by engaging in activities like walking, picnicking, or simply unwinding amidst nature.

Cheltenham Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local attractions and outdoor activities: Take advantage of the area's scenic parks and recreational spots to enjoy the natural beauty and relax during your stay.
  • Connect with the community: Engage with nearby events or visit local markets to immerse yourself in the authentic atmosphere of the region.
  • Plan your transportation options in advance: Consider renting a vehicle or utilizing regional transit to easily access popular destinations throughout the area.
  • Choose your rental wisely: Look for properties that offer convenient amenities and are close to key points of interest to maximize comfort and convenience.

Transportation Options

  • Washington Metro Area Transit Authority (WMATA): This regional transit option provides convenient access to the broader area, making it easy to explore nearby attractions from your rental stay.
  • Local Bus Services: The area is well-served by local bus routes that connect residential neighborhoods with key destinations, offering an affordable transportation method during your visit.
  • Rideshare Services (Uber and Lyft): These on-demand ride options are widely available here, providing flexible and reliable transportation around the region at any time.
  • Private Car Rentals: Renting a private vehicle gives you the freedom to explore the region at your own pace, ideal for visiting local sights or traveling further afield.

Local Customs Options

  • Respect for Local Traditions: When visiting the area, embracing local customs such as traditional community events is appreciated to foster a genuine connection with the region's culture.
  • Greeting Etiquette: Polite greetings like a friendly handshake or a nod are customary here and demonstrate your respect for local social norms.
  • Dining Etiquette: It’s common to observe specific manners during meals, including waiting for everyone to be served before beginning to eat, reflecting the area's dining traditions.
  • Community Engagement: Participating in neighborhood gatherings or local celebrations can enhance your experience and show appreciation for the area's communal spirit.

Frequently Asked Questions About Cheltenham Rentals by Owner

1. What are the top vacation rentals in Cheltenham?

There are a lot of options in Cheltenham. If you plan on staying in the Cheltenham area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Cheltenham:

2. How many Rentbyowner vacation rentals are available in Cheltenham?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 39 in the Cheltenham area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Cheltenham. 

3. What is the cancellation policy for a rental by owner in Cheltenham, Maryland?

The cancellation policy varies depending on the individual listing. You should review the specific rental's cancellation terms on the listing page or contact the owner directly to understand any fees or restrictions associated with cancellations.

4. How do I confirm my booking for a rental by owner in Brandywine?

Booking confirmation typically occurs after you select your dates and complete the reservation process through the rental's platform. Ensure you receive a confirmation email from the owner or the booking system, and reach out to the owner if you have any questions.

5. What amenities are usually included in rentals by owner in the local area?

Amenities vary between properties but commonly include essentials like Wi-Fi, parking, and kitchen facilities. For detailed information about what's included, refer to the listing description or contact the owner directly before confirming your stay.

6. Are there any rules or restrictions I should be aware of when staying at a rental by owner here?

Yes, each rental has its own house rules which may include policies on pets, smoking, and noise. Make sure to read these rules carefully on the listing and communicate with the owner if you have any special requirements.

7. How can I ensure a smooth check-in process at a rental in this area?

Check-in procedures are outlined by the property owner and may include details about key collection or access codes. Contact the owner beforehand to clarify any instructions and confirm your arrival time to ensure a seamless check-in experience.

More Rentals You May Like Near Cheltenham

More Top-Rated Rentals by Owner in Cheltenham Area