Location

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Vacation rentals in Maryland, United States

Stunning 9 Bedroom Villa on the Chesapeake Bay image 1

Stunning 9 Bedroom Villa on the Chesapeake Bay image 2

Stunning 9 Bedroom Villa on the Chesapeake Bay image 3

Stunning 9 Bedroom Villa on the Chesapeake Bay image 4

Stunning 9 Bedroom Villa on the Chesapeake Bay image 5

Stunning 9 Bedroom Villa on the Chesapeake Bay

9 bedrooms·6½ baths

Rock Hall • Maryland

5(6 reviews)

5915,00 $ USD total por 3 noites

12/11/2026 – 15/11/2026

Lake Front Home w/ Hot Tub & Firepit, walk to Wisp image 1

Lake Front Home w/ Hot Tub & Firepit, walk to Wisp image 2

Cozy living room with wood burning fireplace and lake views!

Relax in the hot tub, roast s'mores, grill, and more! The stunning views of Deep Creek Lake are priceless!

Stunning lake views from the primary bedroom!

Lake Front Home w/ Hot Tub & Firepit, walk to Wisp

3 bedrooms·3 baths

McHenry • Maryland

4.86(278 reviews)

1404,48 $ USD total por 3 noites

12/11/2026 – 15/11/2026

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)

1313,84 $ USD total por 3 noites

11/03/2027 – 14/03/2027

Majestic Murphy Point

Back yard launch

Front facing the bay

Kitchen/Dining open floor plan

Murphy Point on the Chesapeake Vacation Rental

3 bedrooms·1 bath

North Beach • Maryland

4.8(114 reviews)

1320,00 $ USD total por 3 noites

31/03/2027 – 03/04/2027

Ivy Cove

3 bedrooms·2 baths

Lusby • Maryland

4.99(131 reviews)

1176,60 $ USD total por 3 noites

12/11/2026 – 15/11/2026

Backyard, fire pit, playground

Front, driveway

Absolutely Shore

4 bedrooms·3½ baths

Garrett County • Maryland

5(181 reviews)

978,12 $ USD total por 3 noites

15/11/2026 – 18/11/2026

Early morning on the tip of the Chesapeake

Waldins Chesapeake

Waldins Chesapeake

Waldins Chesapeake

Waldins Chesapeake

3 bedrooms·2 baths

Perryville • Maryland

4.93(54 reviews)

1734,90 $ USD total por 3 noites

12/11/2026 – 15/11/2026

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 por 3 noites

17/11/2026 – 20/11/2026

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)

967,87 $ USD total por 3 noites

12/11/2026 – 15/11/2026

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 por 3 noites

16/11/2026 – 19/11/2026

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/ noite(excl. taxas & impostos)

*Where Eagles Soar*
Peaceful Waterfront Retreat. image 1

*Where Eagles Soar*
Peaceful Waterfront Retreat. image 2

The perfect place to unwind, share stories, and make memories!

The true heart of the home is our spacious sunken living room. Just one step down from the kitchen and dining area, this space wraps you in cozy comfort and is the ultimate spot to unwind. The water views, gorgeous sunsets, wildlife are unbeatable!

*Where Eagles Soar*
Peaceful Waterfront Retreat. image 5

Where Eagles Soar Peaceful Waterfront Retreat.

2 bedrooms·2 baths

Cobb Island • Maryland

4.97(105 reviews)

986,25 $ USD total por 3 noites

12/11/2026 – 15/11/2026

Beachfront-Panoramic Ocean and Bay Views

Beachfront-Panoramic Ocean and Bay Views

Beachfront-Panoramic Ocean and Bay Views

Beachfront-Panoramic Ocean and Bay Views

Beachfront-Panoramic Ocean and Bay Views

Beachfront-Panoramic Ocean and Bay Views

2 bedrooms·1 bath

Ocean City • Maryland

5(17 reviews)

4025,22 $ USD total por 7 noites

12/11/2026 – 19/11/2026

Sunset Overlook

Sunset Overlook

Sunset Overlook

Sunset Overlook

Sunset Overlook

Sunset Overlook

3 bedrooms·2 baths

Ocean City • Maryland

840,27 $ USD total por 3 noites

12/11/2026 – 15/11/2026

Floor-to-ceiling glass allows complete lakefront experience!

Top of the line Kingston outdoor furniture - with seating for 10 on upper deck - great views of lake, lakefront and outdoor fire pit.

Main floor living area with HD TV and wood-burning fireplace - and lake views!

Main floor living area - open floor plan and independent heat/ac allows for fine-tuning your comfort.

Lakefront pup-friendly home on Deep Creek Lake!

4 bedrooms·3 baths

Swanton • Maryland

5(29 reviews)

2017,10 $ USD total por 3 noites

26/02/2027 – 01/03/2027

Piney Point Harbor Haven image 1

Piney Point Harbor Haven image 2

2nd Floor Living Room area w/ large Lovesac sectional.

Piney Point Harbor Haven image 4

Piney Point Harbor Haven image 5

Piney Point Harbor Haven

3 bedrooms·3½ baths

Piney Point • Maryland

4.97(32 reviews)

1504,03 $ USD 1384,93 $ USD total por 3 noites

12/11/2026 – 15/11/2026

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)

412,91 $ USD total por 3 noites

12/11/2026 – 15/11/2026

East Winds 202 | 1BR | 1.5BA | 601 Sq Ft | Private Entrance | Stairs Required for Initial Check-In (2nd Floor) | Elevator Available After Check-In

Property Interior | Elevator Access Once Inside | Ocean Views

Kitchen | Cooking Basics

Bedroom | Queen Bed

BeachBox I • Oceanfront Balcony • Sunrise Views • Couple's Retreat • East Winds 202

1 bedroom·1½ baths

Ocean City • Maryland

5(50 reviews)

412,91 $ USD total por 3 noites

12/11/2026 – 15/11/2026

BayAngel house Montego Bay private pier bay front

BayAngel house Montego Bay private pier bay front

BayAngel house Montego Bay private pier bay front

BayAngel house Montego Bay private pier bay front

BayAngel house Montego Bay private pier bay front

BayAngel house Montego Bay private pier bay front

3 bedrooms·2 baths

Ocean City • Maryland

1103,34 $ USD total por 3 noites

12/11/2026 – 15/11/2026

Boat Slip and Dock - The middle boat slip is the one you can use for your boat

Main level living room

Wisp'd Away

4 bedrooms·3½ baths

Swanton • Maryland

5(10 reviews)

3037,04 $ USD total por 3 noites

12/11/2026 – 15/11/2026

East Winds 502 | 1BR | 1.5BA | 601 Sq Ft | Private Entrance | Stairs Required for Initial Check-In (5th Floor) | Elevator Available After Check-In

Coastal-chic condo with bright open layout, modern kitchen & comfy seating

Fully equipped coastal kitchen with stainless appliances, quartz countertops, and glass-tiled backsplash | Dishwasher | Glass-Top Stove w/ Oven | Built-In Microwave | Refrigerator w/ Top Freezer

Sunny bedroom with 2 full/double beds, Smart TV, A/C, and beachy decor

Full bathroom w/ vessel sink, porthole mirror & butcher block vanity | Bath Towels, Toilet Paper and Hand Soap Provided | Other Personal Toiletries Not Provided

BeachBox V • 5th-Floor Oceanfront • Expansive View • Beachfront Bliss • East Winds 502

1 bedroom·1½ baths

Ocean City • Maryland

5(32 reviews)

412,91 $ USD total por 3 noites

16/11/2026 – 19/11/2026

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)

412,91 $ USD total por 3 noites

15/11/2026 – 18/11/2026

Point View 2.0

4 bedrooms·2 baths

McHenry • Maryland

5(10 reviews)

5487,00 $ USD 4708,95 $ USD total por 7 noites

14/11/2026 – 21/11/2026

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 por 3 noites

15/11/2026 – 18/11/2026