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)

$922.14 USD total for 3 nights

Oct 28 – 31, 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 total for 3 nights

Oct 19 – 22, 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)
Living Room
Living Room
Dining Area
Kitchen
Coffee Station

Offshore Tails

2 bedrooms·2 baths
Ocean Pines • Maryland
4.92(24 reviews)

$1,111.48 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)

$693.68 USD total for 3 nights

Oct 19 – 22, 2026

Historic Condo Near Antietam and Whitetail Ski
Historic Condo Near Antietam and Whitetail Ski
Historic Condo Near Antietam and Whitetail Ski
Historic Condo Near Antietam and Whitetail Ski
Historic Condo Near Antietam and Whitetail Ski

Historic Condo Near Antietam and Whitetail Ski

2 bedrooms·1 bath
Hagerstown • Maryland
4.82(282 reviews)

$808.81 USD total for 3 nights

Jan 1 – 4, 2027

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)

$1,109.04 USD total for 3 nights

Oct 19 – 22, 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!
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

Oct 19 – 22, 2026

Front of condo
Living Room
Living Room
Living Room
Living Room

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

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 Views-Newly Renovated
Beachfront-Panoramic Ocean Views-Newly Renovated
Beachfront-Panoramic Ocean Views-Newly Renovated
Beachfront-Panoramic Ocean Views-Newly Renovated
Beachfront-Panoramic Ocean Views-Newly Renovated

Beachfront-Panoramic Ocean Views-Newly Renovated

2 bedrooms·1 bath
Ocean City • Maryland
5(17 reviews)

$4,009.77 USD total for 7 nights

Oct 19 – 26, 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

Oct 19 – 22, 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

$902.88 USD total for 3 nights

Oct 19 – 22, 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

Oct 19 – 22, 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 total for 3 nights

Oct 19 – 22, 2026

Bahia Vista II
Bahia Vista II
Bahia Vista II
Bahia Vista II
Bahia Vista II

Bahia Vista II

3 bedrooms·2 baths
Ocean City • Maryland
4.95(21 reviews)

$750.00 USD total for 3 nights

Oct 19 – 22, 2026

Living room
Stylish retreat steps to beach with all amenities!
Bright and beautiful kitchen!
Dining room table and view of second set of patio doors
Living room with doors to the deck.

Stylish retreat steps to beach with all amenities!

2 bedrooms·2 baths
Ocean City • Maryland
5(3 reviews)
$150 – $450/ night(excl. fees & taxes)
Sunset Overlook
Sunset Overlook
Sunset Overlook
Sunset Overlook
Sunset Overlook

Sunset Overlook

3 bedrooms·2 baths
Ocean City • Maryland

$781.44 USD total for 3 nights

Oct 19 – 22, 2026

Oasis at Charity’s Hope Farm Resort image 1
Fun with inflatables on the beautiful salt water pool with whirlpool jets.
Oasis at Charity’s Hope Farm Resort image 3
Horse trainer works with our miniature horse and pony.
Oasis at Charity’s Hope Farm Resort image 5

Oasis at Charity’s Hope Farm Resort

5 bedrooms·3 baths
La Plata • Maryland
4.94(36 reviews)

$2,240.00 USD $1,424.00 USD total for 3 nights

Oct 19 – 22, 2026

The Shellback: Annapolis, MD
The Shellback: Annapolis, MD
The Shellback: Annapolis, MD
The Shellback: Annapolis, MD
The Shellback: Annapolis, MD

The Shellback: Annapolis, MD

3 bedrooms·2 baths
Anne Arundel County • Maryland
5(15 reviews)

$1,347.56 USD total for 3 nights

Oct 25 – 28, 2026

Bracken Lodge - 30 acres of private luxury & fun!
Bracken Lodge - 30 acres of private luxury & fun!
Bracken Lodge - 30 acres of private luxury & fun!
Bracken Lodge - 30 acres of private luxury & fun!
Bracken Lodge - 30 acres of private luxury & fun!

Bracken Lodge - 30 acres of private luxury & fun!

5 bedrooms·5½ baths
Garrett County • Maryland

$3,050.00 USD total for 3 nights

Oct 20 – 23, 2026

Large Family Room
Large new comfortable sectional sofa
Freshly renovated ! Steps to outdoor pool & beach
Private patio with large sectional sofa furniture
Freshly renovated ! Steps to outdoor pool & beach

Freshly renovated ! Steps to outdoor pool & beach

2 bedrooms·2 baths
Ocean City • Maryland
4.97(187 reviews)

$532.80 USD total for 3 nights

Oct 19 – 22, 2026

Cozy Cottage By The Beach-Pet Friendly
Cozy Cottage By The Beach-Pet Friendly
Main living space.
Kitchen
Cozy Cottage By The Beach-Pet Friendly

Cozy Cottage By The Beach-Pet Friendly

3 bedrooms·2 baths
North Beach • Maryland
4.96(26 reviews)

$964.05 USD total for 3 nights

Oct 19 – 22, 2026

Your Home Away From Home 3br, SF Summer Retreat
Your Home Away From Home 3br, SF Summer Retreat
Your Home Away From Home 3br, SF Summer Retreat
Your Home Away From Home 3br, SF Summer Retreat
Your Home Away From Home 3br, SF Summer Retreat

Your Home Away From Home 3br, SF Summer Retreat

3 bedrooms·2 baths
Hagerstown • Maryland
5(19 reviews)

$750.00 USD total for 3 nights

Oct 19 – 22, 2026