Location

Dates

Guests

Vacation rentals in Maryland

Point View 2.0

4 bedrooms·2 baths

McHenry • Maryland

5(10 reviews)

$5,487.00 USD $4,708.95 USD total for 7 nights

Oct 24 – 31, 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

Beach Get Away

2 bedrooms·1 bath

Ocean City • Maryland

5(1 review)

$706.00 USD total for 3 nights

Dec 21 – 24, 2026

View from Balcony

Dining/Living Room

FLEXIBLE STAY HEATED INDOOR AND OUTDOOR POOLS

FLEXIBLE STAY HEATED INDOOR AND OUTDOOR POOLS

2 bedrooms·2 baths

Ocean City • Maryland

$1,194.57 USD total for 3 nights

Oct 19 – 22, 2026

127th St | pool, short walk 2 beach & Park

127th St | pool, short walk 2 beach & Park

127th St | pool, short walk 2 beach & Park

127th St | pool, short walk 2 beach & Park

127th St | pool, short walk 2 beach & Park

127th St | pool, short walk 2 beach & Park

1 bedroom·1 bath

Ocean City • Maryland

$809.60 USD total for 3 nights

Apr 16 – 19, 2027

Escape to the Riverpoint, this unique house embodies the charm of a Swiss chalet A-Frame, complemented by a picturesque boathouse on the serene Canal of the Port Tobacco River.

The hot tub is tucked under the deck which offers privacy. End your day soaking in the hot tub that can fit up to 7 people.

The fire pit is next to the river and in the center of a sand area making it feel like a little beach.

The backyard is fully-fenced in so everyone can enjoy the backyard comfortably

Watch your favorite films on this 85” Google TV in the basement movie room.

5BR Riverfront A-Frame

5 bedrooms·4 baths

Port Tobacco • Maryland

$1,326.01 USD total for 3 nights

Oct 19 – 22, 2026

2BR Steps to Metro, 20 Min to DC

2BR Steps to Metro, 20 Min to DC

2BR Steps to Metro, 20 Min to DC

2BR Steps to Metro, 20 Min to DC

2BR Steps to Metro, 20 Min to DC

2BR Steps to Metro, 20 Min to DC

2 bedrooms·2 baths

Silver Spring • Maryland

$1,114.44 USD total for 3 nights

Oct 26 – 29, 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

Nanticoke river front Studio! Pickleball Court!

on site Pickleball Court

Nanticoke river front Studio! Pickleball Court!

Nanticoke river front Studio! Pickleball Court!

Nanticoke river front Studio! Pickleball Court!

Nanticoke river front Studio! Pickleball Court!

1 bedroom·1 bath

Mardela Springs • Maryland

$776.60 USD total for 3 nights

Oct 19 – 22, 2026

Decked-Out Sanctuary Near Loch Raven & Baltimore

Decked-Out Sanctuary Near Loch Raven & Baltimore

Decked-Out Sanctuary Near Loch Raven & Baltimore

Decked-Out Sanctuary Near Loch Raven & Baltimore

Decked-Out Sanctuary Near Loch Raven & Baltimore

Decked-Out Sanctuary Near Loch Raven & Baltimore

1 bedroom·1 bath

Cockeysville • Maryland

$2,080.16 USD total for 7 nights

Oct 19 – 26, 2026

Slippery Slope has all of the amenities for a memorable and fun vacation including LAKE ACCESS, dock (for rent), hot tub, game room, fireplace & fire pit! Book your stay today!

Slippery Slope Cabin is THE perfect location to all things in the Deep Creek Lake / Wisp area!

Cozy up to the fire pit for those summer and winter nights and roast some s'mores!

Perfect view of Wisp Resort from the oversized hot tub!

Gather round the firepit and make memories while enjoying the s'mores bar!

Slippery Slope Cabin

3 bedrooms·3 baths

McHenry • Maryland

$984.13 USD total for 3 nights

Oct 19 – 22, 2026

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 19 – 22, 2026

NEW LISTING SPECIAL 20% OFF Your Ocean City getaway -just steps from the sand.

NEW LISTING SPECIAL 20% OFF Your Ocean City getaway -just steps from the sand.

NEW LISTING SPECIAL 20% OFF Your Ocean City getaway -just steps from the sand.

Step into comfort at OC Oasis — our bright, beach-inspired living room features plush couches, a large smart TV, and plenty of space to unwind after a day exploring Ocean City.

The dining area at OC Oasis blends coastal style with comfort — featuring a bright open layout that flows seamlessly from the kitchen to the living room.

NEW LISTING SPECIAL 20% OFF Your Ocean City getaway -just steps from the sand.

2 bedrooms·2 baths

Ocean City • Maryland

$846.46 USD total for 3 nights

Oct 19 – 22, 2026

Cozy 1 Bedroom w/pool & short walk to beach

1 bedroom·1 bath

Ocean City • Maryland

$449.40 USD total for 3 nights

Oct 19 – 22, 2026

Exterior Entrance

Living Room Pull out couch

Tiny Tides Beach House • Pool • Walk to Beach (6)

2 bedrooms·1 bath

Ocean City • Maryland

$726.08 USD total for 3 nights

Oct 19 – 22, 2026

Black Walnut Cove

Outdoor Seating

La Casita at Black Walnut-Waterfront Escape near Saint Michaels

3 bedrooms·1½ baths

Tilghman Island • Maryland

$1,063.75 USD total for 3 nights

Oct 19 – 22, 2026

Haiku River House

Haiku River House

Haiku River House

Beautiful views

Haiku River House

Haiku River House

5 bedrooms·5 baths

Fort Washington • Maryland

$2,284.79 USD total for 3 nights

Oct 29 – Nov 1, 2026

Towson Luxury Apartment

Cozy retreat with a touch of elegance – your perfect home away from home.

Towson Luxury Apartment

Towson Luxury Apartment

Towson Luxury Apartment

Towson Luxury Apartment

1 bedroom·1 bath

Towson • Maryland

$170 – $240/ night(excl. fees & taxes)

Highfield Haven Decked-Out Cockeysville Escape

Highfield Haven Decked-Out Cockeysville Escape

Highfield Haven Decked-Out Cockeysville Escape

Highfield Haven Decked-Out Cockeysville Escape

Highfield Haven Decked-Out Cockeysville Escape

Highfield Haven Decked-Out Cockeysville Escape

1 bedroom·1 bath

Cockeysville • Maryland

$1,918.46 USD total for 7 nights

Oct 19 – 26, 2026

Almost Heaven

4 bedrooms·3 baths

Swanton • Maryland

5(3 reviews)

$1,054.00 USD total for 3 nights

Oct 19 – 22, 2026

Sunset Terrace

3 bedrooms·2 baths

Ocean City • Maryland

4.95(19 reviews)

$1,067.82 USD total for 3 nights

Oct 19 – 22, 2026

Pyramid Exterior (4)

20260608_141635

20260608_141649

20260608_141730

Pyramid 2D Oceanfront Condo with Heated Outdoor Pool

1 bedroom·2 baths

Ocean City • Maryland

$787.41 USD total for 3 nights

Oct 19 – 22, 2026

Sandy Feet Retreat

2 bedrooms·1 bath

Ocean City • Maryland

5(1 review)

$574.98 USD total for 3 nights

Oct 19 – 22, 2026

Silver Spring 5BR near DC Sleeps 12

Silver Spring 5BR near DC Sleeps 12

Silver Spring 5BR near DC Sleeps 12

Silver Spring 5BR near DC Sleeps 12

Silver Spring 5BR near DC Sleeps 12

Silver Spring 5BR near DC Sleeps 12

5 bedrooms·2 baths

Silver Spring • Maryland

$1,100.00 USD total for 3 nights

Oct 19 – 22, 2026