Vacation Rentals in Assawoman Bay, MD: Compare 10+ Sites & Save

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3428 Best Vacation Rentals in Assawoman Bay (Starting from $218)

309 White Heron Court
309 White Heron Court
House
Ocean City, MD, USA
1.9k from Assawoman Bay center

Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Hot tubs, Places to stay

5 Bedrooms14 Guests
New to Booking
$1503
Average price / night
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Spacious 5 bedroom, waterfront home w/grill, firepit, full kitchen & shared pool
Spacious 5 bedroom, waterfront home w/grill, firepit, full kitchen & shared pool
House
Ocean City, MD, 21842, United States
1.9k from Assawoman Bay center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Kitchen, Laundry

5 Bedrooms14 Guests
10.0

Exceptional

2 reviews

$592
Average price / night
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Stunning 2BR/2BA Bayfront Retreat
Stunning 2BR/2BA Bayfront Retreat
House
Ocean City, MD, USA
2.0k from Assawoman Bay center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$493
Average price / night
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⭐️Brand New High End Luxury Bayside Mansion Pool⭐️
⭐️Brand New High End Luxury Bayside Mansion Pool⭐️
House
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

6 Bedrooms20 Guests
9.6

Exceptional

15 reviews

$2078
Average price / night
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Bayfront Condo with Amazing Views
Bayfront Condo with Amazing Views
House
Ocean City, MD, USA
2.0k from Assawoman Bay center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Condos

2 Bedrooms6 Guests
New to Booking
$401
Average price / night
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Seas The Bay on the Waterfront!
Seas The Bay on the Waterfront!
House
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$390
Average price / night
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Bayside Beauty
Bayside Beauty
Apartment
Ocean City, USA
2.0k from Assawoman Bay center

Apartments, Accommodations, Lodgings, Places to stay, Accessible hotels

2 Bedrooms4 Guests
8.0

Good

2 reviews

$638
Average price / night
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Heron Gull Haven, a waterfront Escape from it all!
Heron Gull Haven, a waterfront Escape from it all!
House
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

AC, Arcade, Balcony, Dryer, Free Parking, Heater, Kitchen, Laundry, Microwave

6 Bedrooms14 Guests
New to Booking
$2812
Average price / night
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Shipwreck Townhome
Shipwreck Townhome
House
Ocean City, MD, USA
2.0k from Assawoman Bay center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Family

3 Bedrooms11 Guests
9.0

Fabulous

2 reviews

$620
Average price / night
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5-6BR, 5BA in Bayside Retreat with Community Pools & Boat Slip
5-6BR, 5BA in Bayside Retreat with Community Pools & Boat Slip
House
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet

6 Bedrooms18 Guests
10.0

Exceptional

198 reviews

$763
Average price / night
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Seaward Road #5 - Bay Bliss
Seaward Road #5 - Bay Bliss
House
Ocean City, MD, USA
2.1k from Assawoman Bay center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$690
Average price / night
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Luxurious Bayfront Home,  OC MD On the water, Sleeps 12 guest,  Boat access.
Luxurious Bayfront Home, OC MD On the water, Sleeps 12 guest, Boat access.
House
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater

3 Bedrooms12 Guests
10.0

Exceptional

86 reviews

$328
Average price / night
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Harbour Bay 23 Ocean City
Harbour Bay 23 Ocean City
House
Ocean City, MD, USA
2.1k from Assawoman Bay center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms8 Guests
New to Booking
$256
Average price / night
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Bayside Lighthouse Retreat w/ Private Boat Slip on Canal - Sleeps 12
Bayside Lighthouse Retreat w/ Private Boat Slip on Canal - Sleeps 12
House
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms12 Guests
9.6

Exceptional

35 reviews

$509
Average price / night
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Heron's Retreat
Heron's Retreat
House
Ocean City, MD, USA
2.1k from Assawoman Bay center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Accessible hotels

6 Bedrooms15 Guests
8.0

Good

1 reviews

$1427
Average price / night
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Waterfront townhouse w/drivate dock, bay views, outdoor shower
Waterfront townhouse w/drivate dock, bay views, outdoor shower
House
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

AC, Balcony, Barbecue, Dryer, Elevator, Fireplace, Free Parking, Heater, Internet

3 Bedrooms11 Guests
8.4

Very Good

8 reviews

$449
Average price / night
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Point Lookout
Point Lookout
House
Ocean City, MD, USA
2.1k from Assawoman Bay center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms8 Guests
New to Booking
$568
Average price / night
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New Listing!  Beautiful family home with 4 bedrooms and a game room!
New Listing! Beautiful family home with 4 bedrooms and a game room!
House
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

AC, Arcade, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking, Pool

4 Bedrooms12 Guests
9.6

Exceptional

5 reviews

$710
Average price / night
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Harbor Bay
Harbor Bay
House
Assawoman Bay, Maryland, USA
2.1k from Assawoman Bay center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms11 Guests
7.3

Good

26 reviews

$281
Average price / night
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Harbour Bay 23-Baywater 116th St, Pool, W/D, AC.
Harbour Bay 23-Baywater 116th St, Pool, W/D, AC.
House
Ocean City, MD, 21842, United States
2.1k from Assawoman Bay center

AC, Balcony, Extra Bed, Free Parking, Heater, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
9.2

Superb

11 reviews

$235
Average price / night
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Bayfront home with WiFi, fireplace, & pool
Bayfront home with WiFi, fireplace, & pool
House
Ocean City, MD, 21842, United States
2.1k from Assawoman Bay center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Kitchen, Laundry

6 Bedrooms15 Guests
9.0

Fabulous

70 reviews

$488
Average price / night
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Canalfront House w/ Private Deck, Central AC, Free WiFi, Bay Views, Washer/Dryer
Canalfront House w/ Private Deck, Central AC, Free WiFi, Bay Views, Washer/Dryer
House
Ocean City, MD, 21842, United States
2.1k from Assawoman Bay center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
9.0

Fabulous

35 reviews

$218
Average price / night
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Harbour Bay 34-Baywater 116th St, Pool, W/D, AC, Free WIFI.
Harbour Bay 34-Baywater 116th St, Pool, W/D, AC, Free WIFI.
House
Ocean City, MD, 21842, United States
2.1k from Assawoman Bay center

AC, Balcony, Dryer, Extra Bed, Free Parking, Heater, Kitchen, Laundry, Living Area

2 Bedrooms8 Guests
8.0

Good

4 reviews

$244
Average price / night
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Canal-front townhome with front/back decks, shared pool, private w/d, & WiFi
Canal-front townhome with front/back decks, shared pool, private w/d, & WiFi
House
Ocean City, MD, 21842, United States
2.1k from Assawoman Bay center

AC, Balcony, Dryer, Extra Bed, Free Parking, Heater, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
4.0

Review score

3 reviews

$252
Average price / night
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Five Bedroom Waterfront Home with Lots of Space
Five Bedroom Waterfront Home with Lots of Space
House
Ocean City, MD, 21842, United States
2.2k from Assawoman Bay center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

5 Bedrooms18 Guests
10.0

Exceptional

2 reviews

$862
Average price / night
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Bayfront townhome with 3 balconies, a shared pool & only 5 blocks to the beach
Bayfront townhome with 3 balconies, a shared pool & only 5 blocks to the beach
House
Ocean City, MD, 21842, United States
2.2k from Assawoman Bay center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area

3 Bedrooms10 Guests
9.6

Exceptional

10 reviews

$500
Average price / night
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Newly Updated Large 3br Bayside Townhome Perfect for Families!
Newly Updated Large 3br Bayside Townhome Perfect for Families!
House
Ocean City, MD, 21842, United States
2.2k from Assawoman Bay center

AC, Balcony, Crib, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
9.6

Exceptional

48 reviews

$434
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Assawoman Bay.

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Assawoman Bay Vacation Rentals on the Map

Frequently Asked Questions

You can explore 3428 verified vacation rentals in Assawoman Bay. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Assawoman Bay vary depending on the season, property size, and location. Rates typically start from around $218 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Assawoman Bay include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Assawoman Bay welcome pets. Currently, 10 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Assawoman Bay often include amenities such as Fireplace/Heating, Balcony/Terrace, and Laundry. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.