Discover Your Perfect Pomona Vacation Homes

Pomona Luxury Rentals

See More Pomona Luxury Vacation Rentals
Find More Pomona Villas, Resorts, & Rentals on BedroomVillas

Pomona Pet Friendly Vacation Rentals

See More Pet-Friendly Vacation Rentals in Pomona on PetFriendly.io

Pomona Large Vacation Homes

See More Family Vacation Rentals in Pomona on FVR

Why Choose Rent By Owner for your Pomona Vacation Rental Homes?

What makes our Vacation Rentals special?

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

Best Times to Visit Pomona

When should you plan your Vacation Rentals stay?

Choosing the right time to visit can enhance your experience and ensure you enjoy the best of what this charming area has to offer, making it an ideal destination for your next vacation rental stay in Chestertown, Maryland.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During these months, you'll experience warm weather perfect for enjoying the region's outdoor activities and scenic views.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Early Fall (September to October)

This period offers pleasant temperatures and vibrant landscapes, making it an ideal time to explore and relax in the area.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Off-Season Highlights

image
Winter (December to February)

The quiet winter months bring cooler temperatures, providing a peaceful setting perfect for cozy getaways and off-season tranquility.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 30°F to 40°F
image
Late Fall to Early Winter (November)

This shoulder season features cooler weather with fewer visitors, offering a more secluded experience before the winter crowds arrive.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 40°F to 45°F

Weekly Weather Forecast for Pomona

How to Book Your Pomona Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. 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 Pomona

More Top-Rated Vacation Rentals in Pomona Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals 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 dining areas perfect for relaxing meals beneath the open sky.
  • Take advantage of private patios or decks to unwind while soaking in scenic views.
  • Make use of spacious yards or gardens ideal for outdoor activities or gatherings.
  • Benefit from access to well-maintained grills or barbecue stations for cookouts.
  • Relax by designated fire pits, perfect for evening socializing and making memories.
  • Utilize nearby fishing or boating facilities if available on the region’s waterways.
  • Explore landscaped pathways or trails suitable for walking, jogging, or biking adventures.

Top Attractions Around Pomona

What attractions are nearby?

Within this charming region, you can enjoy a variety of outdoor activities, cultural experiences, and scenic excursions that showcase the natural beauty and local heritage of the area surrounding your vacation rental.

image
image

Family Activities

  • Chester River Maritime Museum: Explore this engaging museum to learn about the region’s maritime history, offering hands-on exhibits perfect for family learning adventures.
  • Chestertown Waterfront Park: Enjoy a relaxing day by the water at the park, where you can have picnics, rent kayaks, or simply take in scenic views along the Chester River.
  • Kent County Arts Council's Studio & Gallery: Discover local art and participate in family-friendly workshops that inspire creativity in a welcoming environment.
  • Washington College Campus Tours: Take a stroll through the historic campus, offering picturesque scenery and educational opportunities for children and adults alike.
image

Adult Activities

  • Harriet Tubman Museum and Educational Center: Explore the history of the region through engaging exhibits dedicated to the life and legacy of Harriet Tubman, offering a meaningful experience here in Chestertown.
  • Chester River: Enjoy a relaxing day of boating, kayaking, or fishing along this scenic waterway that runs through the area, providing a perfect setting for outdoor enthusiasts.
  • Chestertown Farmers' Market: Visit the lively market to sample fresh, local produce and artisanal products, immersing yourself in the local culture during your stay.
  • Historically Rich Downtown: Stroll through the charming streets lined with unique shops, galleries, and historic architecture that showcase the area's welcoming community and vibrant heritage.

Pomona Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Take advantage of the region’s fresh seafood and charming eateries to enhance your stay and experience authentic flavors.
  • Visit Nearby Waterways: Engage in water-based activities or simply enjoy picturesque views along the area’s serene rivers and lakes.
  • Plan Ahead for Seasonal Events: Check the local calendar for festivals, markets, or outdoor concerts that showcase the area's vibrant community spirit.
  • Choose a Prime Location: Select vacation rentals close to key attractions and scenic spots to maximize your comfort and convenience during your visit.

Transportation Options

  • Car Rentals: Exploring the area at your own pace is easy with local car rental services, offering convenient transportation to and from nearby attractions in Chestertown.
  • Public Transportation: Bus services operate throughout this destination, providing an affordable way to navigate the region without the need for a personal vehicle.
  • Taxi and Ride-Sharing: Taxis and ride-sharing options are readily available, ensuring reliable transportation for quick trips within the vicinity of Pomona.
  • Bike Rentals: For a more scenic experience, consider bike rentals to enjoy the charming surroundings and explore the local area at a leisurely pace.

Local Customs Options

  • Crab Feast Tradition: Celebrated locally, this region takes pride in its longstanding tradition of enjoying freshly steamed blue crabs, especially during annual festivals and seafood gatherings.
  • Barrel Rolling Events: Unique to the area are community barrel rolling competitions held during festivals, showcasing local heritage and fostering a sense of camaraderie among residents and visitors alike.
  • Historic Fishing Practices: The region honors its maritime roots through the preservation of traditional fishing methods, often demonstrated during cultural events that highlight the area's nautical history.
  • Heritage Craftsmanship: Handmade boat building and artisanal crafts are cherished here, with local artisans often sharing their skills during seasonal markets and craft fairs that reflect the area's maritime culture.

Frequently Asked Questions About Pomona?

1. What are the top vacation rentals in Pomona?

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

2. Which vacation homes in Pomona are best for families?

If you are looking for a family-friendly vacation home in Pomona, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Pomona:

3. How many Rentbyowner vacation rentals are available in Pomona?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 53 in the Pomona 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 Pomona. 

4. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary depending on the property listing. It is important to review the specific terms and conditions provided in the listing details or contact the property owner directly to understand the cancellation options available.

5. How do I find available dates and book a vacation rental here?

You can search for available dates by entering your preferred travel period into the booking platform. Once you find a suitable property, follow the booking instructions provided, or reach out to the owner if you need further assistance.

6. Are there any fees or additional costs I should be aware of when booking?

Additional fees such as cleaning fees, service charges, or local taxes may apply to certain listings. Please review the full pricing details in the listing description or contact the owner for clarification before completing your reservation.

7. What amenities are typically included in these vacation rentals in this region?

Most properties offer essential amenities like Wi-Fi, parking, and kitchen facilities. Specific features such as outdoor spaces or unique conveniences will be listed on each property page, so it’s advisable to check the listing for detailed information.

8. How do I communicate with the property owner if I have questions before booking?

You can send a message through the booking platform's messaging system to ask questions directly to the property owner. This ensures you receive accurate details about the rental and helps confirm your reservation.