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)

5.915,00 $ USD gesamt für 3 Nächte

12.–15. Nov. 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)

1.404,48 $ USD gesamt für 3 Nächte

12.–15. Nov. 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)

1.313,84 $ USD gesamt für 3 Nächte

11.–14. März 2027

Majestic Murphy Point
Back yard launch
Front facing the bay
Kitchen/Dining open floor plan
Kitchen

Murphy Point on the Chesapeake Vacation Rental

3 bedrooms·1 bath
North Beach • Maryland
4.8(114 reviews)

1.320,00 $ USD gesamt für 3 Nächte

31. März – 3. Apr. 2027

Ivy Cove
Ivy Cove
Ivy Cove
Ivy Cove
Ivy Cove

Ivy Cove

3 bedrooms·2 baths
Lusby • Maryland
4.99(131 reviews)

1.176,60 $ USD gesamt für 3 Nächte

12.–15. Nov. 2026

Backyard
Private dock
Backyard, fire pit, playground
Backyard
Front, driveway

Absolutely Shore

4 bedrooms·3½ baths
Garrett County • Maryland
5(181 reviews)

978,12 $ USD gesamt für 3 Nächte

15.–18. Nov. 2026

Early morning on the tip of the Chesapeake
Waldins Chesapeake
Front Deck
Waldins Chesapeake
Waldins Chesapeake

Waldins Chesapeake

3 bedrooms·2 baths
Perryville • Maryland
4.93(54 reviews)

1.734,90 $ USD gesamt für 3 Nächte

12.–15. Nov. 2026

Makai Condominiums
Areal photo of the Makai
Kitchen Area
Dining Area Table set for Six
Living Area

Makai Unit #314

2 bedrooms·2 baths
Ocean City • Maryland
4.96(187 reviews)

444,00 $ USD gesamt für 3 Nächte

17.–20. Nov. 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 gesamt für 3 Nächte

12.–15. Nov. 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
Kitchen Area

Makai Unit #411

2 bedrooms·2 baths
Ocean City • Maryland
4.93(137 reviews)

444,00 $ USD gesamt für 3 Nächte

16.–19. Nov. 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/ Nacht(zzgl. Gebühren & Steuern)
*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 gesamt für 3 Nächte

12.–15. Nov. 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)

4.025,22 $ USD gesamt für 7 Nächte

12.–19. Nov. 2026

Sunset Overlook
Sunset Overlook
Sunset Overlook
Sunset Overlook
Sunset Overlook

Sunset Overlook

3 bedrooms·2 baths
Ocean City • Maryland

840,27 $ USD gesamt für 3 Nächte

12.–15. Nov. 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.
Exterior view.
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)

2.017,10 $ USD gesamt für 3 Nächte

26. Feb. – 1. März 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)

1.504,03 $ USD 1.384,93 $ USD gesamt für 3 Nächte

12.–15. Nov. 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 gesamt für 3 Nächte

12.–15. Nov. 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
Full Bathroom

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 gesamt für 3 Nächte

12.–15. Nov. 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

1.103,34 $ USD gesamt für 3 Nächte

12.–15. Nov. 2026

Wisp'd Away
Wisp'd Away
Wisp'd Away
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)

3.037,04 $ USD gesamt für 3 Nächte

12.–15. Nov. 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 gesamt für 3 Nächte

16.–19. Nov. 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 gesamt für 3 Nächte

15.–18. Nov. 2026

Point View 2.0
Point View 2.0
Point View 2.0
Point View 2.0
Point View 2.0

Point View 2.0

4 bedrooms·2 baths
McHenry • Maryland
5(10 reviews)

5.487,00 $ USD 4.708,95 $ USD gesamt für 7 Nächte

14.–21. Nov. 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 gesamt für 3 Nächte

15.–18. Nov. 2026