Location

Dates

Guests

Vacation rentals in Maryland

Bring your own wood to enjoy the Solo Stove firepit.

Use caution as the metal stove gets extremely hot. A fire should never be left unattended.

Enjoy eating outside and a view of the water and sunset from the patio.

A beautiful summer evening in the yard overlooking the marina and waterfront.

This 3-season sunroom offers views of the water and community beach area.

The living room provides a gathering space to read, watch TV (Netflix, Disney+, and Hulu with live streaming), or take a nap.

The Bohemia Charmer

4 bedrooms·2 baths

Earleville • Maryland

4.96(115 reviews)

$890.00 USD total for 3 nights

Nov 16 – 19, 2026

Bahia Vista II

3 bedrooms·2 baths

Ocean City • Maryland

4.95(21 reviews)

$1,200.00 USD total for 3 nights

Nov 12 – 15, 2026

Offshore Tails

2 bedrooms·2 baths

Ocean Pines • Maryland

4.92(24 reviews)

$1,198.84 USD total for 3 nights

May 12 – 15, 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 12 – 19, 2026

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)

$725.00 USD total for 3 nights

Nov 14 – 17, 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)

$1,284.88 USD total for 3 nights

Nov 15 – 18, 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

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)

$687.00 USD total for 3 nights

Nov 12 – 15, 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 12 – 15, 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)

$507.00 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 12 – 15, 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)

$2,124.00 USD total for 3 nights

Nov 14 – 17, 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 12 – 15, 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

$1,244.88 USD total for 3 nights

Nov 12 – 15, 2026

Sunset Overlook

Sunset Overlook

Sunset Overlook

Sunset Overlook

Sunset Overlook

Sunset Overlook

3 bedrooms·2 baths

Ocean City • Maryland

$840.27 USD total for 3 nights

Nov 12 – 15, 2026

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 12 – 15, 2026

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)

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)

$4,614.00 USD $2,848.40 USD total for 3 nights

Nov 12 – 15, 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

Nov 12 – 15, 2026

Snow Escape | Walk to Wisp Lift | Hot Tub | 16+ image 1

Snow Escape | Walk to Wisp Lift | Hot Tub | 16+ image 2

Snow Escape | Walk to Wisp Lift | Hot Tub | 16+ image 3

Snow Escape | Walk to Wisp Lift | Hot Tub | 16+ image 4

Snow Escape | Walk to Wisp Lift | Hot Tub | 16+ image 5

Snow Escape: 6BR, Sleeps 16, Hot Tub, Walk to Lift

6 bedrooms·4 baths

McHenry • Maryland

4.78(58 reviews)

$2,016.00 USD total for 3 nights

Nov 12 – 15, 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)

$438.45 USD total for 3 nights

Nov 17 – 20, 2026

Private Guest Suite in Columbia image 1

Private Guest Suite in Columbia image 2

Spacious king bedroom with a Pack ’n Play available upon request, making the suite comfortable and convenient for families traveling with a little one.

Private Guest Suite in Columbia image 4

Private Guest Suite in Columbia image 5

Private Guest Suite in Columbia

1 bedroom·1 bath

Columbia • Maryland

5(41 reviews)

$671.22 USD total for 3 nights

Nov 19 – 22, 2026