Discover Your Perfect Washington College Vacation Homes

Best Vacation Homes in Washington College

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9.6 (19 Reviews)
Bed & Breakfast
Brampton 1860
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability

Why Choose Rent By Owner for your Washington College Vacation Rental Homes?

What makes our Vacation Rentals 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 Washington College

When should you plan your Vacation Rentals stay?

Choosing the right time to visit is key to enjoying the best of this destination, as the region offers unique experiences and favorable weather conditions throughout different seasons.

Peak Season Highlights

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Spring (March to May)

During the spring months, you can enjoy the area's vibrant natural beauty and mild weather, making it an ideal time for outdoor activities and scenic walks.

Average Temperature Daytime: 60-75°F - Nighttime: 45-55°F
autumn
Fall (September to November)

The fall offers beautiful foliage and comfortable temperatures, perfect for exploring the region's historic charm and relaxing in your vacation rentals.

Average Temperature Daytime: 65-70°F - Nighttime: 50-55°F

Off-Season Highlights

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Summer (June to August)

Summertime is less crowded, providing a more tranquil experience while visiting here. The warm weather invites outdoor relaxation around your vacation rentals.

Average Temperature Daytime: 80-85°F - Nighttime: 65-70°F
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Winter (December to February)

Winter tends to be quieter and cooler, offering a peaceful retreat with fewer tourists. Expect the temperatures to be colder, creating cozy atmospheres in your chosen vacation rentals.

Average Temperature Daytime: 40-50°F - Nighttime: 30-40°F

Weekly Weather Forecast for Washington College

How to Book Your Washington College 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 Washington College

More Top-Rated Vacation Rentals in Washington College 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 spaces such as patios or decks for relaxed meals amid the scenic surroundings.
  • Take advantage of private gardens or yard areas perfect for outdoor activities and leisure.
  • Make use of outdoor grills or barbecues to prepare delicious meals while enjoying the fresh air.
  • Relax in a screened porch or sunroom to experience the area's tranquil atmosphere comfortably.
  • Benefit from access to nearby lakes, rivers, or beaches for water-based recreational activities.
  • Utilize patios with seating areas designed for outdoor gatherings and socializing.
  • Experience outdoor fire pits ideal for cozy evenings under the stars during your stay here.

Top Attractions Around Washington College

What attractions are nearby?

While staying here, you'll have the opportunity to explore nearby activities such as scenic waterfront walks, charming local shops, and cultural events that showcase the charm of this historic region.

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Family Activities

  • Chestertown Marina: Spend a day exploring the local waters by boat or paddleboard, perfect for family fun on the Chesapeake Bay.
  • Chester River Maritime Museum: Discover fascinating exhibits about the region's maritime history that engage visitors of all ages.
  • Washington College Arboretum: Enjoy outdoor family walks among beautiful native trees and plant collections in this scenic campus setting.
  • Downtown Chestertown Historic District: Take a leisurely stroll through charming streets filled with historic architecture, shops, and family-friendly dining options.
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Adult Activities

  • Sailing and Boating on the Chester River: You can enjoy a relaxing day exploring the scenic waters of the Chester River, which offers opportunities for sailing, kayaking, and boat tours right from this charming region.
  • Historic Downtown Chestertown: Take a leisurely stroll through downtown to experience local shops, cafes, and architecture that showcase the area's rich history and vibrant community spirit.
  • Chesapeake Bay Maritime Museum: Discover maritime history and enjoy engaging exhibits that highlight the region's connection to Chesapeake Bay's waterways and boating traditions.
  • Wander Through Local Nature Trails: Explore the area's natural beauty with tranquil hiking or biking along scenic trails that provide peaceful escapes within reach of your vacation rental.

Washington College Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Events and Markets: Take advantage of community events and farmers' markets to experience the authentic charm and vibrant culture of this region.
  • Visit Scenic Spots and Waterfronts: Discover picturesque parks and waterfront areas that showcase the natural beauty unique to this destination.
  • Plan Excursions to Nearby Attractions: Make the most of your stay by visiting nearby historical sites and noteworthy landmarks that highlight the area's rich heritage.
  • Choose a Convenient Location for Your Stay: Select vacation rentals close to central amenities and key attractions to maximize your time exploring the region.

Transportation Options

  • Car Rentals: Local car rental services offer convenient transportation options for exploring the region around Washington College in Chestertown, Maryland, making it easy to visit nearby attractions and enjoy flexible travel during your stay.
  • Taxi Services: Taxi providers in this area provide reliable and on-demand transportation, ensuring you can get to and from local destinations without hassle.
  • Public Transit: The regional bus services connect key points within the region, offering an affordable way to navigate the surroundings of Washington College and access neighboring towns.
  • Bike Rentals: For a more leisurely experience, bike rentals are available, allowing you to explore the scenic beauty of this destination at your own pace while reducing your ecological footprint.

Local Customs Options

  • Welcome Celebrations: Participating in local welcome celebrations is a cherished tradition here, where community gatherings often mark the start of seasonal festivals.
  • Crab Feast Customs: Sampling and sharing Maryland blue crabs during regional crab feasts reflect the area's deep-rooted maritime heritage that you can enjoy during your stay.
  • Historic Preservation: Respect for historic sites and architecture is a common practice, emphasizing the importance of preserving this destination’s rich cultural legacy.
  • Seasonal Festivals: Engaging in seasonal festivals showcases the area's vibrant community spirit and provides an authentic cultural experience for visitors.

Frequently Asked Questions About Washington College?

1. What are the top vacation rentals in Washington College?

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

2. How many Rentbyowner vacation rentals are available in Washington College?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 44 in the Washington College 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 Washington College. 

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

Cancellation policies vary depending on the individual property owner. You should review the specific listing details or contact the host directly for information about cancellations, refunds, and any applicable fees.

4. How do I find pet-friendly options for my stay in this destination?

Pet policies differ among vacation rentals here. To find pet-friendly accommodations, use the search filters available on the listing platform or reach out to the property owner to confirm their pet policies before booking.

5. Are linens and towels provided with the vacation rental?

Most rental owners include linens and towels in the property amenities, but it's best to verify this information on the listing description or by contacting the host directly to ensure a seamless stay.

6. What are the check-in and check-out procedures?

Check-in and check-out times are set by each host and can vary. Details are typically provided in the property listing or communicated directly by the owner. It's recommended to coordinate your arrival and departure times in advance.

7. How can I ensure my payment is secure when booking in this region?

The booking platform employs secure payment methods to protect your financial information. For additional reassurance, always book through trusted platforms that offer secure transaction processes and clear terms.

Best Vacation Homes in Washington College

5.0 (87 Reviews)
Hotel
Driftwood Inn
  • Air Conditioner
  • Parking
  • Accessibility
View Availability