Short-Term Rentals in Assawoman Bay, MD: Compare 10+ Sites & Save

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7223 Best Short-Term Rentals in Assawoman Bay (Starting from $239)

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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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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⭐️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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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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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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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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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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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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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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Beautiful 3 BR 3.5 BA Town House With Open Bay Views
Beautiful 3 BR 3.5 BA Town House With Open Bay Views
Condo
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

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

3 Bedrooms7 Guests
9.6

Exceptional

4 reviews

$426
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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Harbour Bay 3
Harbour Bay 3
Condo
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

AC, Balcony, Breakfast Available, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave

2 Bedrooms5 Guests
New to Booking
$249
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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Bayfront Beauty - Shipwreck 102
Bayfront Beauty - Shipwreck 102
Condo
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$374
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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2BR 2BA Bayfront Condo- You'll Get Amazing Views & Breathtaking Sunsets Here!
2BR 2BA Bayfront Condo- You'll Get Amazing Views & Breathtaking Sunsets Here!
Condo
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

AC, Balcony, Dryer, Extra Bed, Heater, Kitchen, Laundry, Living Area, No Smoking

2 Bedrooms6 Guests
9.6

Exceptional

143 reviews

$239
Average price / night
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A Bungalow
A Bungalow
House
Ocean City, MD, USA
2.1k from Assawoman Bay center

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

2 Bedrooms6 Guests
9.2

Superb

7 reviews

$307
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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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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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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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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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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North Port-Direct Bay Front Condo iwith Spectacular Views!
North Port-Direct Bay Front Condo iwith Spectacular Views!
Condo
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$718
Average price / night
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Watergate East Unit 1 on Assawoman Bay -North Ocean City - Dog Friendly
Watergate East Unit 1 on Assawoman Bay -North Ocean City - Dog Friendly
Condo
Ocean City, MD, 21842, United States
2.1k from Assawoman Bay center

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

2 Bedrooms6 Guests
9.4

Superb

16 reviews

$272
Average price / night
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Watergate - 2 Bedroom, 3rd Floor Condo with Great VIews!
Watergate - 2 Bedroom, 3rd Floor Condo with Great VIews!
Condo
Ocean City, MD, 21842, United States
2.1k from Assawoman Bay center

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

2 Bedrooms6 Guests
5.0

Review score

2 reviews

$278
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 Short-Term Rentals in Assawoman Bay.

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Assawoman Bay Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 7223 verified short-term rentals in Assawoman Bay, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Assawoman Bay vary depending on location, property size, and travel dates. Rates typically start from around $239 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Assawoman Bay include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Assawoman Bay, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Assawoman Bay often include amenities such as Laundry, Fireplace/Heating, and Balcony/Terrace, providing a comfortable and convenient stay.

Short-term rentals in Assawoman Bay are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.