Location

Dates

Guests

Vacation rentals in Maryland

Back of building, right on the beach!

Front of building from Coastal Highway

View from one of two 15-ft balconies

Atlantis 410 Oceanfront

3 bedrooms·2½ baths

Ocean City • Maryland

$550 – $900/ night(excl. fees & taxes)

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(4 reviews)

$6,562.00 USD total for 3 nights

Oct 19 – 22, 2026

Constellation House North 105

2 bedrooms·2 baths

Ocean City • Maryland

5(2 reviews)

$215/ night(excl. fees & taxes)

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)

$1,423.92 USD total for 3 nights

Sep 24 – 27, 2026

Winter looks good at Slippery Slope Cabin! Some snow, a huge hot tub and a fire pit! Inside you can get cozy by the fireplace and have a mug of your favorite warm beverage.

Grab something to drink and relax on in the hot tub or in the rocking chairs of this amazing cabin!

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

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!

Perfect view of Wisp Resort from the oversized, new hot tub!

Slippery Slope Cabin! #1 in DCL! Walk to Wisp!

3 bedrooms·3 baths

McHenry • Maryland

5(177 reviews)

$1,531.20 USD total for 3 nights

Sep 24 – 27, 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)

$832.24 USD total for 3 nights

Sep 28 – Oct 1, 2026

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)

$1,380.00 USD total for 3 nights

Sep 24 – 27, 2026

Welcome to Mulligan Manor - The lake's best cabin vacation rental. Home is less than 5 minutes to skiing, lake and more! The home has a game room, hot tub, fire pit and fireplace! Everything needed

Wintertime is magical at Mulligan Manor. The large yard and golf course behind the home provide tons and tons of space for sledding, tubing and snow fun!

The fire pit overlooking the gorgeous views of Lodestone golf course and wooded area is perfect for evening s'mores!

Clean and ready for relaxing, the hot tub at Mulligan Manor is located outside the patio door on a private and secluded deck overlooking the gorgeous views of the woods and golf course.

The s'mores station provides everything you need to enjoy s'mores by the fire!

Mulligan Manor on WISP Mountain & Lodestone Golf!

3 bedrooms·2½ baths

McHenry • Maryland

5(88 reviews)

$1,212.14 USD total for 3 nights

Sep 27 – 30, 2026

Ivy Cove

3 bedrooms·2 baths

Lusby • Maryland

4.99(128 reviews)

$1,123.60 USD total for 3 nights

Sep 24 – 27, 2026

Master bedroom overlooking park with California king bed.

Parkfront Hot Tub Haven for Families & Pets image 2

Lovely park views from the small living room.

The dining table easily accommodates 6 guests, with wooden stools for up to 4 additional guests willing to squeeze.

Parkfront Hot Tub Haven for Families & Pets image 5

Parkfront Hot Tub Haven for Families & Pets

2 bedrooms·2 baths

Baltimore • Maryland

4.96(543 reviews)

$628.00 USD total for 3 nights

Sep 24 – 27, 2026

Sit back and relax as you watch the waves roll in or all of the local wildlife around this luxurious lakefront appropriately named - Off the Hook!

Gorgeous lakefront home for all of your vacation memories!

Enjoy your favorite food & beverages on the oversized deck looking over gorgeous Deep Creek Lake!

Oversized hot tub ready for you to relax after a day on the lake or at the ski resort. Enjoy it in any season!

Game room complete with a pool table, arcade games, second fridge/freeezer & a huge TV lounging area. Fun can be found for the whole group!

New Lakefront~4/5 BR! Hot Tub~Game Rom & Firepit!

5 bedrooms·3 baths

McHenry • Maryland

4.97(32 reviews)

$2,665.13 USD total for 3 nights

Sep 24 – 27, 2026

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

3 bedrooms·2 baths

North Beach • Maryland

5(250 reviews)

$736.50 USD $631.72 USD total for 3 nights

Sep 26 – 29, 2026

Welcome to beautiful North Beach!

Cozy fire pit patio with stylish seating and outdoor dining

Cozy fire pit patio with private fenced yard and stylish outdoor seating

Palm Haven in North Beach, MD

One of two bedrooms on the ground floor, this bedroom has a queen sized bed and en-suite bathroom.

Palm Haven in North Beach, MD

4 bedrooms·3 baths

North Beach • Maryland

5(198 reviews)

$821.97 USD $711.19 USD total for 3 nights

Sep 27 – 30, 2026

Experience the enchanting charm of the log cabin, illuminating brightly under the night sky. The warm glow of The Big Dipper invites you to unwind and soak in the wooded and peaceful surroundings. Perfect for cozy summer and winter memories!

Oversized pool is heated to 84 degrees year-round in a temperature controlled pool room. Lounge chairs and sitting areas, along with the ROKU smart tv, provide lots of space and entertainment for your group!

Gather around the outdoor fire-pit, where you can enjoy seasonal lake views amidst a backdrop of lush wooded areas with wildlife. Roast your s’mores as deer gracefully pass by & if you are lucky, catch a glimpse of a bear exploring the nearby woods.

Challenge friends and family to a nostalgic match of Pac-Man or feel the thrill of speed with Ridge Racer. Enjoy friendly competition at the shuffleboard table or showcase your skills on the pool table. Perfect for all ages, let the games begin!

Indoor Pool Cabin! Brand New~Game Room~EV Charger

5 bedrooms·5 baths

McHenry • Maryland

4.93(27 reviews)

$4,173.10 USD $3,809.43 USD total for 4 nights

Sep 24 – 28, 2026

The living room features a warm and cozy gas fireplace, spacious sectional, lounger chair, DVD player and streaming TV.

Game room includes pool table, ping pong table, shuffleboard, dart board, and poker table. Area includes bar top seating. Perfect area for a game night or football Sunday!

Spacious eating space with gas grill and beautiful Mountain View’s. Grilling utensils are located in the kitchen.

Downstairs includes cozy wood burning fireplace, beautifully updated epoxy flooring, Roku TV, gaming console, comfortable seating. Perfect for a movie night!

Beautiful fire pit and comfortable Adirondack chairs. Additional chairs are available on the property. Includes grill top, skewers, fire wood and starter logs.

Mountain Escape! Deep Creek Lake, MD

3 bedrooms·2½ baths

Oakland • Maryland

4.84(228 reviews)

$677.88 USD total for 3 nights

Sep 28 – Oct 1, 2026

Sun deck overlooking the bay

Jacuzzi in Master Bath

Seas the Day

3 bedrooms·3 baths

Ocean City • Maryland

5(15 reviews)

$200 – $500/ night(excl. fees & taxes)

Backyard, fire pit, playground

Front, driveway

Absolutely Shore

4 bedrooms·3½ baths

Garrett County • Maryland

5(179 reviews)

$1,177.62 USD total for 3 nights

Sep 27 – 30, 2026

Enjoy the backyard!

Deck overlooking the backyard

Living room with Smart TV and electric fireplace

Mountain Air

4 bedrooms·2½ baths

Garrett County • Maryland

4.95(123 reviews)

$824.22 USD total for 3 nights

Sep 24 – 27, 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)

$1,552.89 USD total for 3 nights

Sep 27 – 30, 2026

Bright vaulted living room with stone fireplace and stylish leather seating

Cozy fire pit deck with string lights in a peaceful wooded setting

Bright modern lounge with soaring ceilings and a stunning stone fireplace

Visit all year round and see the very best of nature!

Bright open living room with vaulted ceilings and sleek modern kitchen

Mountain Haven in Harpers Ferry, WV

4 bedrooms·3½ baths

Knoxville • Maryland

5(95 reviews)

$1,050.36 USD $787.41 USD total for 3 nights

Oct 12 – 15, 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

Stepping into our family room feels like entering a cozy art gallery! The antique pieces tell stories of the past, and the velvet sofa is so inviting. Curl up here for movie nights on the large screen TV. It's the perfect blend of modern and cosy.

Bedrooms with king bed.

Living room with view to private brick patio.

Large entry/ dining room with gas fireplace.

Well equipped kitchen.

Gorgeous home in town center & short walk to WAC

5 bedrooms·3 baths

Chestertown • Maryland

5(227 reviews)

$1,113.00 USD total for 3 nights

Sep 27 – 30, 2026

Black Eyed Susan

Black Eyed Susan

Black Eyed Susan

Black Eyed Susan

Black Eyed Susan

Black Eyed Susan

3 bedrooms·2½ baths

Garrett County • Maryland

5(128 reviews)

$554.04 USD total for 3 nights

Sep 24 – 27, 2026

Off The Chart Stays Cottage

living room at entrance with gas fireplace and smart tv

Kitchen and Living room

Off The Chart Stays

2 bedrooms·2 baths

Stevensville • Maryland

5(8 reviews)

$1,742.70 USD total for 3 nights

Sep 24 – 27, 2026