Location

Dates

Guests

Vacation rentals in Maryland

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)

$876.41 USD total for 3 nights

Nov 8 – 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 for 3 nights

Nov 9 – 12, 2026

Kone Oasis- hot tub, pool, theater/game rm. image 1

Kone Oasis- hot tub, pool, theater/game rm. image 2

Kone Oasis- hot tub, pool, theater/game rm. image 3

Kone Oasis- hot tub, pool, theater/game rm. image 4

Kone Oasis- hot tub, pool, theater/game rm. image 5

Kone Oasis- hot tub, pool, theater/game rm.

3 bedrooms·1 bath

Upper Marlboro • Maryland

4.94(223 reviews)

$718.00 USD total for 3 nights

Nov 9 – 12, 2026

Lazy Bear Lodge At Deep Creek Lake

Lazy Bear Lodge At Deep Creek Lake

Lazy Bear Lodge At Deep Creek Lake

Lazy Bear matching EXTERIOR 31' Stacked Stone Wood Burning Fireplace

Lazy Bear Lodge At Deep Creek Lake

Lazy Bear Lodge At Deep Creek Lake

5 bedrooms·3½ baths

Garrett County • Maryland

4.93(237 reviews)

$1,596.00 USD $1,356.60 USD total for 3 nights

Nov 8 – 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/ night(excl. fees & taxes)

Fall Fun at our close everything Lake View Condo! image 1

Fall Fun at our close everything Lake View Condo! image 5

Fall Fun at our close everything Lake View Condo!

3 bedrooms·2 baths

Oakland • Maryland

4.97(126 reviews)

$611.70 USD total for 3 nights

Nov 8 – 11, 2026

*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)

$941.85 USD total for 3 nights

Nov 9 – 12, 2026

Bahia Vista II

3 bedrooms·2 baths

Ocean City • Maryland

4.95(21 reviews)

$1,200.00 USD total for 3 nights

Nov 8 – 11, 2026

Offshore Tails

2 bedrooms·2 baths

Ocean Pines • Maryland

4.92(24 reviews)

$1,201.08 USD total for 3 nights

May 12 – 15, 2027

The Blue Sky Bungalow: A-frame/Lake Access/Firepit

The Blue Sky Bungalow: A-frame/Lake Access/Firepit

The Blue Sky Bungalow: A-frame/Lake Access/Firepit

The Blue Sky Bungalow: A-frame/Lake Access/Firepit

The Blue Sky Bungalow: A-frame/Lake Access/Firepit

The Blue Sky Bungalow: A-frame/Lake Access/Firepit

3 bedrooms·2 baths

Swanton • Maryland

5(44 reviews)

$716.36 USD total for 3 nights

Nov 14 – 17, 2026

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)

$1,214.32 USD total for 3 nights

Nov 8 – 11, 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

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 total for 7 nights

Nov 8 – 15, 2026

Hickory House on the Chesapeake Bay! image 1

Hickory House on the Chesapeake Bay! image 2

Hickory House on the Chesapeake Bay! image 4

Hickory House on the Chesapeake Bay! image 6

Bay Views, Private Beach Access and Pet Friendly!

2 bedrooms·1 bath

Saint Leonard • Maryland

4.92(88 reviews)

$647.00 USD total for 3 nights

Nov 8 – 11, 2026

Mountain Escape | Hot Tub | Game Room | 16+ Guests image 1

Mountain Escape | Hot Tub | Game Room | 16+ Guests image 2

Mountain Escape | Hot Tub | Game Room | 16+ Guests image 3

Mountain Escape | Hot Tub | Game Room | 16+ Guests image 4

Mountain Escape | Hot Tub | Game Room | 16+ Guests image 5

Mountain Escape: 6BR, Sleeps 16, Hot Tub, Wisp

6 bedrooms·4 baths

McHenry • Maryland

4.87(98 reviews)

$2,016.00 USD total for 3 nights

Nov 8 – 11, 2026

Quiet Family Getaway with Pool

2 bedrooms·2 baths

Ocean City • Maryland

4.92(61 reviews)

$910.20 USD total for 4 nights

May 21 – 25, 2027

mid century through and through.

Hot tub for 6. 2nd heater used during winter months so the hot tub is kept 100 to 104 all year round. Jets most powerful when focused on a single row of seats at a time.

Extra large Connect Four game set up on the deck. The deck is lit and there is a seating.

MCM w/ Hottub + Firepit, mins to DC/Metro image 4

MCM w/ Hottub + Firepit, mins to DC/Metro image 5

MCM w/ Hottub + Firepit, mins to DC/Metro

4 bedrooms·1 bath

Cheverly • Maryland

4.93(168 reviews)

$488.00 USD total for 3 nights

Nov 29 – Dec 2, 2026

"Woodlore" at Deep Creek Lake MD

"Woodlore" at Deep Creek Lake MD

"Woodlore" at Deep Creek Lake MD

"Woodlore" at Deep Creek Lake MD

"Woodlore" at Deep Creek Lake MD

"Woodlore" at Deep Creek Lake MD

3 bedrooms·1½ baths

Swanton • Maryland

5(16 reviews)

$1,022.00 USD total for 3 nights

Nov 8 – 11, 2026

Cozy 5-Bed Retreat, Heated Spa

Elegant brick home with glowing entry and stunning autumn curb appeal

Convenient in-home laundry room with washer, dryer, iron, and folding space

Cozy 5-Bed Retreat, Heated Spa

this is the Blue Room. The Decour is inspired by grand millennial chinoiserie. Daylight above is a remote controlled fandelier for climate comfort.

Cozy 5-Bed Retreat, Heated Spa

5 bedrooms·3½ baths

Port Republic • Maryland

4.78(58 reviews)

$1,680.50 USD total for 3 nights

Nov 9 – 12, 2026

Bear Escape: 6BR, Sleeps 16, Hot Tub, near Wisp

Bear Escape | Hot Tub | Game Room | Fire Pit | 16+ image 2

Bear Escape: 6BR, Sleeps 16, Hot Tub, near Wisp

Bear Escape | Hot Tub | Game Room | Fire Pit | 16+ image 4

Bear Escape | Hot Tub | Game Room | Fire Pit | 16+ image 5

Bear Escape: 6BR, Sleeps 16, Hot Tub, near Wisp

6 bedrooms·4 baths

McHenry • Maryland

4.76(82 reviews)

$2,016.00 USD total for 3 nights

Nov 8 – 11, 2026

Base Camp | Dogs OK, Hot Tub, Walk to Wisp, Arcade image 1

Fully loaded with amenities, this spacious log cabin, with TWO bedroom suites (all with private bathrooms) is ready to provide your group with endless fun. Centrally located to the lake, restaurants, all local activities & walkable to Wisp Resort.

Cozy up in the living room with the sweeping views of Wisp Resort right outside the window. And, with the added warmth of the fireplace, the living area is your perfect place to relax in the cabin.

Base Camp | Dogs OK, Hot Tub, Walk to Wisp, Arcade image 4

Base Camp | Dogs OK, Hot Tub, Walk to Wisp, Arcade image 5

Base Camp | Dogs OK, Hot Tub, Walk to Wisp, Arcade

2 bedrooms·2 baths

McHenry • Maryland

$1,073.88 USD total for 3 nights

Nov 8 – 11, 2026

Sunset Overlook

Sunset Overlook

Sunset Overlook

Sunset Overlook

Sunset Overlook

Sunset Overlook

3 bedrooms·2 baths

Ocean City • Maryland

$763.68 USD total for 3 nights

Nov 8 – 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)

$2,017.10 USD total for 3 nights

Feb 26 – Mar 1, 2027

Lake Escape | Hot Tub | Game Room | Sleeps 16+ image 1

Lake Escape | Hot Tub | Game Room | Sleeps 16+ image 2

Lake Escape | Hot Tub | Game Room | Sleeps 16+ image 3

Lake Escape | Hot Tub | Game Room | Sleeps 16+ image 4

Lake Escape | Hot Tub | Game Room | Sleeps 16+ image 5

Lake Escape: 6BR, Sleeps 16, Hot Tub, Deep Creek

6 bedrooms·4 baths

McHenry • Maryland

4.75(72 reviews)

$2,016.00 USD total for 3 nights

Nov 8 – 11, 2026