3034+ Vacation Rentals Near Assawoman Bay |
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Campus Legends - Vacation Rentals in Assawoman Bay

Charming canal front home, quiet neighborhood, one mile from ocean, Prof. Clean. From US $260
         

10.0 (113 Reviews)
House
Charming canal front home, quiet neighborhood, one mile from ocean, Prof. Clean.
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Capri From US $87
         

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6.1 (13 Reviews)
Apartment
The Capri
  • Air Conditioner
  • Parking
  • Pool

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2 Mi to Beach: Gem w/Enclosed Patio in Selbyville From US $306
         

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10.0 (3 Reviews)
Apartment
2 Mi to Beach: Gem w/Enclosed Patio in Selbyville
  • Air Conditioner
  • Parking
  • Pool

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Newly Updated Large 3br Bayside Townhome Perfect for Families! From US $460
         

9.6 (48 Reviews)
House
Newly Updated Large 3br Bayside Townhome Perfect for Families!
  • Air Conditioner
  • Parking
  • TV

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Lighthouse Condos From US $61
         

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7.4 (15 Reviews)
House
Lighthouse Condos
  • Air Conditioner
  • Parking
  • Child Friendly

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Saint Tropez From US $787
         

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9.2 (151 Reviews)
Apartment
Saint Tropez
  • Air Conditioner
  • Parking
  • Pet Friendly

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Dog-Friendly house. Luxury 2-story, 3 bedrooms plus den house with free WiFi, linen included, backyard for pet friendly, located in a family-friendly neighborhood on the bayside just a few blocks from the beach! From US $524
         

8.6 (22 Reviews)
House
Dog-Friendly house. Luxury 2-story, 3 bedrooms plus den house with free WiFi, linen included, backyard for pet friendly, located in a family-friendly neighborhood on the bayside just a few blocks from the beach!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Seawood From US $90
         

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4.9 (7 Reviews)
House
Seawood
  • Child Friendly
  • Internet

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Walk to the Beach Ocean Views 3BR Home Sleeps 8 w/Parking From US $646
         

8.8 (31 Reviews)
House
Walk to the Beach Ocean Views 3BR Home Sleeps 8 w/Parking
  • Parking
  • TV
  • View

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Brand New! 4-Br Bayside Townhome, Water and Pool View, Beach 1 block, Free WiFi From US $925
         

10.0 (82 Reviews)
House
Brand New! 4-Br Bayside Townhome, Water and Pool View, Beach 1 block, Free WiFi
  • Air Conditioner
  • Parking
  • Pool

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Fenwick Island Home w/Ocean Views Sleeps 11 From US $581
         

9.2 (27 Reviews)
House
Fenwick Island Home w/Ocean Views Sleeps 11
  • Air Conditioner
  • Parking
  • TV

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Ocean Block with short walk to Beach From US $402
         

9.4 (71 Reviews)
House
Ocean Block with short walk to Beach
  • Air Conditioner
  • Parking
  • TV

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7 (40133) South Carolina Avenue From US $878
         

9.6 (18 Reviews)
House
7 (40133) South Carolina Avenue
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Charming luxury 5 Bd townhouse located in the gated community with indoor and outdoor pool, private beach, and free internet From US $811
         

9.2 (11 Reviews)
House
Charming luxury 5 Bd townhouse located in the gated community with indoor and outdoor pool, private beach, and free internet
  • Air Conditioner
  • Parking
  • Pool

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Harbour Bay 23-Baywater 116th St, Pool, W/D, AC. From US $234
         

9.0 (12 Reviews)
House
Harbour Bay 23-Baywater 116th St, Pool, W/D, AC.
  • Air Conditioner
  • Parking
  • Pool

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Splendid Luxury 5 Bedroom Townhouse with WiFi In Gated Community On Bayside With Indoor/Outdoor Pools, Private Beaches, Restaurant, And More Just Ten Minutes From Beach! From US $763
         

9.0 (2 Reviews)
House
Splendid Luxury 5 Bedroom Townhouse with WiFi In Gated Community On Bayside With Indoor/Outdoor Pools, Private Beaches, Restaurant, And More Just Ten Minutes From Beach!
  • Air Conditioner
  • Parking
  • Pool

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Restful Luxury 6 Bedroom House with WiFi In Gated Community On Bayside With Indoor/Outdoor Pools, Private Beaches, Restaurant, And More Just Ten Minutes From Beach! From US $910
         

8.6 (17 Reviews)
House
Restful Luxury 6 Bedroom House with WiFi In Gated Community On Bayside With Indoor/Outdoor Pools, Private Beaches, Restaurant, And More Just Ten Minutes From Beach!
  • Air Conditioner
  • Parking
  • Pool

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Modern, stylish 4 bedroom oceanfront end-unit townhouse with free WiFi, outdoor pool, playground, and downstairs apartment with gorgeous ocean view and only steps from beach! From US $1,120
         

8.4 (7 Reviews)
House
Modern, stylish 4 bedroom oceanfront end-unit townhouse with free WiFi, outdoor pool, playground, and downstairs apartment with gorgeous ocean view and only steps from beach!
  • Air Conditioner
  • Parking
  • Pool

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Top Reviewed 5 BD, 3 BA Spacious Canal-front Cottage with 2+ block walk to beach From US $845
         

10.0 (57 Reviews)
House
Top Reviewed 5 BD, 3 BA Spacious Canal-front Cottage with 2+ block walk to beach
  • Air Conditioner
  • Parking
  • TV

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Montego Bay - South Ocean Drive 203-Baywater 130th St, Pool, W/D, AC From US $311
         

7.0 (8 Reviews)
House
Montego Bay - South Ocean Drive 203-Baywater 130th St, Pool, W/D, AC
  • Air Conditioner
  • Parking
  • Pool

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Fabulous Luxury 5 Bedroom townhouse With WiFi In Gated Community On Bayside With Indoor/Outdoor Pools, Private Beaches, Restaurant, And More Just Ten Minutes From Beach! From US $814
         

6.8 (8 Reviews)
House
Fabulous Luxury 5 Bedroom townhouse With WiFi In Gated Community On Bayside With Indoor/Outdoor Pools, Private Beaches, Restaurant, And More Just Ten Minutes From Beach!
  • Air Conditioner
  • Parking
  • Pool

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Beach Mist, Steps to the Beach, 140th St, 3 Bedroom end unit Townhouse, Sat-Sat From US $263
         

9.8 (14 Reviews)
House
Beach Mist, Steps to the Beach, 140th St, 3 Bedroom end unit Townhouse, Sat-Sat
  • Air Conditioner
  • Parking
  • TV

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Cabin-like 2 Bedroom Oceanfront Townhouse with Free WiFi and Personal Stretch of Sand is Perfect for Kids and Located in Midtown with Beach a Few Steps Away! From US $493
         

8.8 (3 Reviews)
House
Cabin-like 2 Bedroom Oceanfront Townhouse with Free WiFi and Personal Stretch of Sand is Perfect for Kids and Located in Midtown with Beach a Few Steps Away!
  • Air Conditioner
  • Parking
  • TV

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Luxury 3 Bedroom Townhouse just steps to the beach, with free WiFi and big size living room perfect for a big family. From US $509
         

8.6 (16 Reviews)
House
Luxury 3 Bedroom Townhouse just steps to the beach, with free WiFi and big size living room perfect for a big family.
  • Air Conditioner
  • Parking
  • TV

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★ Pro Tip: Campuslegends makes it easy to compare the best listings on Campuslegends homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Campuslegends homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Assawoman Bay.

Weather in Assawoman Bay

View the weather forecast for Assawoman Bay before booking your Assawoman Bay Vacation Rentals to confirm your best time to go.

December - February
High 55°F       Low 28°F
March - May
High 72°F       Low 34°F
June - August
High 88°F       Low 63°F
September - November
High 78°F       Low 35°F

Top Attractions Around Assawoman Bay, MD

Campuslegends offers a large selection of top attractions around Assawoman Bay. Research things to do on your vacation before you visit Assawoman Bay.


Ocean City Boardwalk Ocean City Beach Jolly Roger Amusement Park Maryland Beach Bethany Beach Boardwalk Casino at Ocean Downs Roland E. Powell Convention Center Jolly Roger at the Pier Assateague State Park Carousel Ice Skating Rink Trimper's Rides Northside Park Ocean City Inlet Main Street Berlin Inlet Park Gold Coast Mall Delaware Seashore State Park Bayside Resort Golf Club Oceanic Fishing Pier Ocean City Life-Saving Station Museum

Assawoman Bay Vacation Rental Frequently Asked Questions

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:

How many vacation rentals are available in Assawoman Bay?

Currently, the total number of properties listed in 2026 is over 3034 in the Assawoman Bay area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Assawoman Bay.