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Discover Your Perfect Assawoman Bay Rentals by Owner

Assawoman Bay Rentals by Owner

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9.2 (111 Reviews)
Apartment
Saint Tropez
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
More Top-Rated Rentals by Owner in Assawoman Bay Area

Why Choose Rent By Owner for your Assawoman Bay 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.

Popular Areas for Assawoman Bay Rentals by Owner

Where are the best neighborhoods to stay in Assawoman Bay?

When seeking the perfect place to stay in Assawoman Bay, Maryland, exploring its diverse neighborhoods can enhance your visit. Each area offers unique surroundings that cater to different preferences, whether you’re after a peaceful retreat or close proximity to local amenities. Staying in neighborhoods near Assawoman Bay provides convenient access to scenic views and outdoor activities, making your vacation both relaxing and memorable. Trust Rent By Owner to help you find a rental by owner in these welcoming communities, ensuring a seamless booking experience for your Maryland getaway.

Midtown Ocean City

This area offers convenient access to the lively entertainment and shopping options of Ocean City, making it an ideal choice for those seeking a vibrant stay close to the bustling coast. Here, you'll find comfortable rentals that put you near the heart of the region's energetic scene.

View 2647+ Rentals in Midtown Ocean City

West Ocean City

Located just west of the main boardwalk, this neighborhood provides a more relaxed atmosphere with easy access to local dining and outdoor activities. It’s perfect for travelers wanting a peaceful retreat while still being close to the attractions of the area.

View 128+ Rentals in West Ocean City

Ocean Pines

Set amidst scenic golf courses and parks, this community offers a tranquil setting where you can enjoy nature and outdoor leisure. It’s a popular choice for visitors seeking a quiet stay with convenient access to the region’s coastal beauty.

View 316+ Rentals in Ocean Pines

Bayside

Offering stunning waterfront views and serene surroundings, Bayside is a preferred destination for those who want to relax by the water. Rentals here provide a peaceful base to explore the natural charm of the coastline.

View 36+ Rentals in Bayside

Assateague Pointe

Close to protected wildlife areas, this community invites you to experience the region’s unspoiled coastal environment. It’s ideal for nature lovers looking for a stay immersed in the region’s pristine landscapes.

View 38+ Rentals in Assateague Pointe

Sunset Island

This private island offers exclusive accommodations with spectacular sunset views over the water, perfect for a memorable beachside escape. It’s a prime spot for travelers desiring privacy combined with proximity to the region’s sandy shores.

View 182+ Rentals in Sunset Island

Little Salisbury

Known for its cozy community atmosphere, Little Salisbury provides charming rental options that give you a taste of local life in the region. It’s well-suited for visitors seeking a welcoming and relaxed environment.

View 24+ Rentals in Little Salisbury

Montego Bay

Nestled within Ocean City, Montego Bay features a variety of vacation rentals that cater to families and groups looking for convenient access to the area's attractions. It combines comfort and accessibility for a seamless stay.

View 86+ Rentals in Montego Bay

Best Times to Visit Assawoman Bay

When should you plan your Rentals by Owner stay?

Knowing the optimal time to visit here can help you enjoy the region's best weather and activities, making your vacation experience more enjoyable when you choose to book a rental by owner through Rent By Owner in Assawoman Bay, Maryland.

Peak Season Highlights

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Summer (June to August)

During the summer months, this coastal destination experiences its busiest travel period, attracting visitors seeking warm weather and outdoor activities.

Average Temperature Daytime: around 85°F to 90°F - Nighttime: about 70°F to 75°F
autumn
Early Fall (September to October)

As the region transitions into fall, the pleasant weather and fewer crowds make it an ideal time for exploring the area's scenic beauty and enjoying the local ambiance.

Average Temperature Daytime: roughly 75°F to 80°F - Nighttime: approximately 60°F to 65°F

Off-Season Highlights

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Late Fall to Early Winter (November to December)

With cooler temperatures and decreasing tourist activity, this period offers a peaceful escape for those seeking quiet accommodations and serene surroundings.

Average Temperature Daytime: around 50°F to 55°F - Nighttime: about 40°F to 45°F
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Winter (January to February)

During the coldest months, tourism slows down significantly, providing an excellent opportunity to find affordable rentals and enjoy a tranquil beachfront experience.

Average Temperature Daytime: between 40°F and 50°F - Nighttime: around 30°F to 40°F

Weekly Weather Forecast for Assawoman Bay

How to Book Your Assawoman Bay 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 Assawoman Bay

More Top-Rated Rentals by Owner in Assawoman Bay 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

  • Access to private or shared outdoor patios and decks, perfect for relaxing and enjoying the scenic views
  • Outdoor dining areas to enhance your alfresco meals while soaking in the fresh bay air
  • A spacious yard or lawn area ideal for outdoor activities or just unwinding in nature
  • Boat docks or slips, providing convenient access if you're planning to explore the waterways by boat
  • Barbecue grills for outdoor cooking and gatherings with family and friends
  • Pool or hot tub options to add extra relaxation to your stay in this coastal region
  • Patio furniture and loungers designed for comfort as you enjoy the tranquil surroundings of the area

Top Attractions Around Assawoman Bay

What attractions are nearby?

In this scenic area, you can enjoy a variety of outdoor activities such as boating, fishing, and watersports, making it an ideal destination for those seeking adventure and relaxation by the water.

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Family Activities

  • Kayaking and Paddleboarding: Explore the calm waters of Assawoman Bay by renting kayaks or paddleboards, offering a fun and active way for your family to enjoy the scenic views and wildlife.
  • Beach Activities at the Shore: Spend quality time together building sandcastles, swimming, or relaxing on the sandy beaches that surround this popular region, ideal for family outings.
  • Fishing Excursions: Experience fishing in the area’s abundant waters, providing an engaging activity for kids and adults alike, with various local charters available for family-friendly trips.
  • Wildlife Watching and Nature Tours: Discover the diverse birdlife and natural habitats through guided boat tours, giving your family an educational and memorable adventure in this region.
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Adult Activities

  • Fishing Excursions: You can enjoy guided fishing trips on the bay, offering a relaxing way to connect with the local aquatic environment.
  • Kayaking and Paddleboarding: Exploring the calm waters of the area by kayak or paddleboard provides a peaceful outdoor activity suitable for all skill levels.
  • Sailing Adventures: Take part in sailing excursions that allow you to appreciate the scenic views and expansive waterways of this coastal region.
  • Wildlife Watching: The region is ideal for observing native birds and marine life, making it an engaging activity for nature enthusiasts visiting here.

Assawoman Bay Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities Ahead: Research and schedule outdoor activities such as boating or fishing in advance to maximize your time in this scenic bay area.
  • Choose the Right Rental: Select a rental by owner that offers easy access to the water and local attractions, ensuring a convenient and enjoyable stay.
  • Respect Local Nature: Follow guidelines for preserving the region’s ecosystem by staying on designated paths and properly disposing of waste.
  • Engage with the Community: Connect with local hosts to get insider tips on hidden gems and the best ways to experience this peaceful destination.

Transportation Options

  • Driving: Renting a car is a convenient way to explore the area and access your rental property with ease, offering flexibility during your stay.
  • Public Transportation: Buses serve the region, providing an affordable and eco-friendly transportation option to navigate around the local attractions and nearby towns.
  • Taxis and Rideshare Services: Taxis or rideshare options like Uber and Lyft operate within the area, ensuring quick and reliable transit from your rental to various destinations.
  • Biking and Walking: The area features scenic bike paths and walkable routes that allow you to enjoy the natural beauty while getting around comfortably and sustainably.

Local Customs Options

  • Seafood Celebrations: Locals take pride in their fresh seafood traditions, often participating in communal gatherings centered around oyster and crab feasts.
  • Respect for the sandy shores is key, with customary practices including designated pet areas and quiet hours to preserve the area's natural beauty.
  • Boating Traditions: The community values its maritime roots, evident in the common customs of welcoming boaters and practicing responsible navigation in the waterways.
  • Festive Events: Participation in seasonal festivals and local parades reflects the area's vibrant culture and deep-rooted community spirit here.

Frequently Asked Questions About Assawoman Bay Rentals by Owner

1. What are the top vacation rentals in Assawoman Bay?

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

2. How many Rentbyowner vacation rentals are available in Assawoman Bay?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 2700 in the Assawoman Bay 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 Assawoman Bay. 

3. What is the cancellation policy for rental properties in Assawoman Bay, Maryland?

Cancellation policies vary by owner; therefore, you should review the specific listing details or contact the property owner directly to understand the terms and conditions.

4. Are there any additional fees when booking a vacation rental here?

Additional fees such as cleaning, service charges, or security deposits are typically specified in the listing. It's recommended to read the full listing description or reach out to the owner for clarification.

5. How do I ensure my reservation at a rental by owner in this region is secure?

Secure reservations are made through the booking platform, which provides protections and guarantees. Always confirm your booking through the official site and communicate directly with the owner for any questions.

6. What amenities are usually included in rental properties in the area?

Amenities vary between listings but often include essentials like Wi-Fi, kitchen facilities, parking, and outdoor spaces. For detailed information, check the property's description or contact the owner directly.

7. Is there a minimum stay requirement for rentals in this destination?

Minimum stay requirements differ depending on the property. Please refer to the specific listing details or contact the owner to confirm the length of stay needed.

More Rentals You May Like Near Assawoman Bay

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10.0 (3 Reviews)
House
Ocean Village 14
  • Air Conditioner
  • View
  • Wheelchair Accessible
View Availability
More Top-Rated Rentals by Owner in Assawoman Bay Area