Location

Dates

Guests

Vacation rentals in Berlin, Maryland, United States

Shire Retreat - Berlin, Assateague, Ocean City

Shire Retreat - Berlin, Assateague, Ocean City

Shire Retreat - Berlin, Assateague, Ocean City

Shire Retreat - Berlin, Assateague, Ocean City

Shire Retreat - Berlin, Assateague, Ocean City

Shire Retreat - Berlin, Assateague, Ocean City

5 bedrooms·3 baths

Berlin • Maryland

5(1 review)

$1,299.44 USD total for 3 nights

Oct 25 – 28, 2026

Offshore Tails

2 bedrooms·2 baths

Ocean Pines • Maryland

4.92(24 reviews)

$1,114.84 USD total for 3 nights

May 12 – 15, 2027

aerial of location

From kitchen to dining

Walk to Harborside & Marina|Sleeps up to 18|Boat Trailer Parking|Minutes to OC Beach

5 bedrooms·3 baths

Ocean City • Maryland

$2,231.25 USD total for 3 nights

Oct 23 – 26, 2026

Assateague House 411 | 1BR | 1.5BA | Step-Free Access | 558 Sq Ft | Elevator Access | Open Balcony / Patio | Private Entrance

Community Outdoor Pool (Open Memorial Day to Labor Day). Depth: 3 ft to 6 ft. Note: Pool access requires a small set of steps

View of the Bay at the Inlet from our balcony (overlooking the Coast Guard base)

Living Room | Smart TVs w/ Free Wi-Fi, Netflix, Hulu, and other Streaming Services | Queen Sleeper Sofa w/ Gel Memory Foam Mattress

Bedroom | King Bed | 12-Inch Medium-Firm Mattress with Eggshell Memory Foam | USB Charging Ports Embedded in Lamps | Linens & Bath Towels Included

BeachBox II • Panoramic Inlet Views • Bayside Pool • Couple's Corner • Assateague House 411

1 bedroom·1½ baths

Ocean City • Maryland

5(33 reviews)

$435.99 USD total for 3 nights

Oct 25 – 28, 2026

Assateague House 111 | 1BR | 1.5BA | Step-Free Access | 558 Sq Ft | Elevator Access | Open Balcony / Patio | Private Entrance

Community Outdoor Pool (Open Memorial Day to Labor Day). Depth: 3 ft to 6 ft. Note: Pool access requires a small set of steps

View of the Bay at the Inlet from our balcony (overlooking the Coast Guard base)

Living Room | Smart TVs w/ Free Wi-Fi, Netflix, Hulu, and other Streaming Services | Queen Sleeper Sofa w/ Gel Memory Foam Mattress

Bedroom | King Bed | 12-Inch Medium-Firm Mattress with Eggshell Memory Foam | USB Charging Ports Embedded in Lamps | Linens & Bath Towels Included

BeachBox IV • Walk to Boardwalk • Bayside Pool • Couple's Escape • Assateague House 111

1 bedroom·1½ baths

Ocean City • Maryland

5(12 reviews)

$412.91 USD total for 3 nights

Oct 26 – 29, 2026

Welcome to Harbor Breeze 54!

Spacious living area, with smart TV and wifi.

Plenty of space for everyone!

Harbor Breeze 54

Full kitchen, with dining space.

Harbor Breeze 54

1 bedroom·1 bath

Ocean City • Maryland

5(4 reviews)

$508.87 USD total for 3 nights

Feb 28 – Mar 3, 2027

Welcome to Harbor Breeze 60!

Our second floor condo is comfortable and cozy!

Plenty of space for everyone!

Full kitchen for all your dining needs!

Comfortable king sized bed.

Harbor Breeze 60

1 bedroom·1 bath

Ocean City • Maryland

5(4 reviews)

$508.87 USD total for 3 nights

Feb 28 – Mar 3, 2027

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AKTS BAY

2 bedrooms·1 bath

Ocean City • Maryland

4.76(45 reviews)

$1,725.00 USD total for 5 nights

Oct 23 – 28, 2026

Bahia Vista II

3 bedrooms·2 baths

Ocean City • Maryland

4.95(21 reviews)

$1,800.00 USD total for 3 nights

Oct 23 – 26, 2026

Oceans Edge 503 OCEANFRONT ON THE BOARDWALK FLEXIBLE STAYS

Oceans Edge 503 OCEANFRONT ON THE BOARDWALK FLEXIBLE STAYS

Oceans Edge 503 OCEANFRONT ON THE BOARDWALK FLEXIBLE STAYS

Oceans Edge 503 OCEANFRONT ON THE BOARDWALK FLEXIBLE STAYS

Oceans Edge 503 OCEANFRONT ON THE BOARDWALK FLEXIBLE STAYS

Oceans Edge 503 OCEANFRONT ON THE BOARDWALK FLEXIBLE STAYS

3 bedrooms·2 baths

Ocean City • Maryland

5(9 reviews)

$2,246.40 USD total for 3 nights

Oct 23 – 26, 2026

12th & Boardwalk Location.

Top-Floor Condo with Unobstructed Views

Direct Ocean Front

Left-Balcony View

Center-Balcony View

Decatur House (Ocean Front)

1 bedroom·1 bath

Ocean City • Maryland

5(42 reviews)

$933.04 USD total for 3 nights

Oct 23 – 26, 2026

Beach Get Away

2 bedrooms·1 bath

Ocean City • Maryland

5(1 review)

$706.00 USD total for 3 nights

Dec 21 – 24, 2026

Living room complete with queen-sized sleeper sofa, TV, entertainment center, side chair, eating nook with table and chairs for two.

Living room with beachy decor and queen sleeper sofa.

Living room view facing the patio.

Dining area with table for two plus four barstools at kitchen counter.

We provide dish and dishwasher soap and starter paper towels.

33rd St, Near Attractions, Pool, 1st Fl, King Bed

1 bedroom·1 bath

Ocean City • Maryland

$587.32 USD total for 3 nights

Oct 23 – 26, 2026

Bayfront Sunsets, Renovated Coastal Retreat image 1

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Bayfront Sunsets, Renovated Coastal Retreat

2 bedrooms·2 baths

Ocean City • Maryland

5(3 reviews)

$1,625.00 USD total for 3 nights

Oct 23 – 26, 2026

Living Area w/ Cozy Fireplace & Big Screen LCD TV

Living Room w/ Queen Sleeper

Living Area w/ Queen Sleeper Featuring an Air Dream Mattress

Kitchen Area w/ Granite Counter Tops & Stainless Steel Appliances

Makai Unit #411

2 bedrooms·2 baths

Ocean City • Maryland

4.93(137 reviews)

$444.00 USD total for 3 nights

Oct 25 – 28, 2026

Makai Condominiums

Areal photo of the Makai

Dining Area Table set for Six

Makai Unit #314

2 bedrooms·2 baths

Ocean City • Maryland

4.96(187 reviews)

$444.00 USD total for 3 nights

Nov 1 – 4, 2026

Sunset View

3 bedrooms·2½ baths

Ocean City • Maryland

$1,400.00 USD total for 3 nights

Oct 23 – 26, 2026

Wight Bay Unit 245

Wight Bay Unit 245

Wight Bay Unit 245

Wight Bay Unit 245

Wight Bay Unit 245

Wight Bay Unit 245

2 bedrooms·2 baths

Ocean City • Maryland

4.89(204 reviews)

$350/ night(excl. fees & taxes)

Master Bedroom with a king bed and private bathroom

Master Bathroom

San Remo 210B

2 bedrooms·2 baths

Ocean City • Maryland

$784.00 USD total for 3 nights

Oct 25 – 28, 2026

Private balcony with sunrise ocean views over the dunes

The Ocean City beach at 51st Street in front of Worcester House

Cozy coastal living room with private balcony and beautiful ocean views

A moonlit night over the Atlantic Ocean

Bright coastal-style bedroom with natural light and calming decor

BeachBox VI • Direct Oceanfront • Walk to Seacrets • Couple's Dream • Worcester House 203

1 bedroom·1½ baths

Ocean City • Maryland

5(6 reviews)

$412.91 USD total for 3 nights

Oct 26 – 29, 2026

Worcester House 401 | 1 BR | 1.5BA | 634 Sq Ft | Elevator Access | Open Corner Balcony / Patio | Private Entrance

Living Room | Queen Sleeper Sofa with Upgraded 5" Thick Gel Memory Foam Mattress (No Coils)

Kitchen | Cooking Basics | Keurig Coffee Maker | Drip Coffee Pot | Dishwasher | Glass-Top Stove with Oven | Built-In Microwave | Under-Cabinet Lighting | Granite Countertops | Refrigerator with Top Freezer | Fully Equipped Kitchen

Bedroom | Queen Bed | 12-Inch Medium-Firm Mattress with Eggshell Memory Foam | USB Charging Ports Embedded in Lamps

Full Bath | Bath Towels, Toilet Paper and Hand Soap Provided | Other Personal Toiletries Not Provided

BeachBox III • Unreal Views • Oceanfront Balcony • Couple's Getaway • Worcester House 401

1 bedroom·1½ baths

Ocean City • Maryland

5(78 reviews)

$543.68 USD total for 3 nights

Oct 23 – 26, 2026

Constellation House North 105

2 bedrooms·2 baths

Ocean City • Maryland

5(2 reviews)

$1,202.40 USD total for 3 nights

Oct 23 – 26, 2026

Happy Ours on Sunset Island

Happy Ours on Sunset Island

Happy Ours on Sunset Island

Covered porch off of living room

Covered porch off of living room (bayside)

Happy Ours on Sunset Island

5 bedrooms·4½ baths

Ocean City • Maryland

5(12 reviews)

$4,663.68 USD $4,530.32 USD total for 7 nights

Jun 6 – 13, 2027

Welcome to Surf's Edge

Path to the beach

Welcome to Surf's Edge

Enjoy the views!

Ocean Front room (Queen)

Surf's Edge - Ocean front with stunning views

2 bedrooms·2 baths

Ocean City • Maryland

5(57 reviews)

$922.14 USD total for 3 nights

Oct 28 – 31, 2026