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

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

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

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

Feb 26 – Mar 1, 2027

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)

$3,008.00 USD $1,884.80 USD total for 3 nights

Nov 8 – 11, 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 8 – 11, 2026

Piney Point Harbor Haven image 1
Piney Point Harbor Haven image 2
2nd Floor Living Room area w/ large Lovesac sectional.
Piney Point Harbor Haven image 4
Piney Point Harbor Haven image 5

Piney Point Harbor Haven

3 bedrooms·3½ baths
Piney Point • Maryland
4.97(32 reviews)

$1,455.19 USD $1,340.98 USD total for 3 nights

Nov 8 – 11, 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

Nov 13 – 16, 2026

The sunsets are amazing from you own private deck!
The river is beautiful in the fall.
Beautiful Fall colors from our peer
Enjoy a cozy waterfront Christmas in front of the fireplace
Christmas Season at Serenity is so peaceful!

Breathtaking Waterfront Home/ Amazing sunsets nightly! Book Christmas now!

4 bedrooms·2 baths
Elkton • Maryland
4.84(19 reviews)

$2,012.00 USD total for 3 nights

Nov 8 – 11, 2026

Stylish brick townhome with garage and great curb appeal
Scenic view of a freight train crossing a historic stone arch bridge
Historic inn entrance with lush grounds and charming brick architecture
Bright modern living room with oversized sectional and stylish design
Bright, spacious living room with large sectional and stylish TV feature wall

Pond Views, Private Balconies & Pool Access

4 bedrooms·2½ baths
Elkridge • Maryland

$2,748.76 USD total for 7 nights

Dec 19 – 26, 2026

Bright end-unit brick townhome with curb appeal and landscaped entry
A bright and Cozy living room featuring a large sectional sofa for you to unwind after a long busy day.
A bright and Cozy living room featuring a large sectional sofa for you to unwind after a long busy day.
Bright living room with oversized sectional and open kitchen seating
Bright, spacious living room with oversized sectional and natural light

Central Elkridge Family Townhouse

4 bedrooms·3½ baths
Elkridge • Maryland

$1,189.60 USD total for 3 nights

Nov 8 – 11, 2026

Exterior
Property grounds
Dining
Private kitchen
Pool

Stylish 3BR/3BA Townhome in Crown Gaithersburg, Walk to Rio, Pool, & Restaurants

3 bedrooms·3 baths
Rockville • Maryland
5(4 reviews)

$760.00 USD total for 3 nights

Nov 8 – 11, 2026

BayAngel house Montego Bay private pier bay front
BayAngel house Montego Bay private pier bay front
BayAngel house Montego Bay private pier bay front
BayAngel house Montego Bay private pier bay front
BayAngel house Montego Bay private pier bay front

BayAngel house Montego Bay private pier bay front

3 bedrooms·2 baths
Ocean City • Maryland

$1,071.15 USD total for 3 nights

Nov 8 – 11, 2026

Wisp'd Away
Wisp'd Away
Wisp'd Away
Boat Slip and Dock - The middle boat slip is the one you can use for your boat
Main level living room

Wisp'd Away

4 bedrooms·3½ baths
Swanton • Maryland
5(10 reviews)

$2,579.12 USD total for 3 nights

Nov 8 – 11, 2026

Point View 2.0
Point View 2.0
Point View 2.0
Point View 2.0
Point View 2.0

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

Nov 14 – 21, 2026

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

$1,347.46 USD total for 3 nights

Nov 9 – 12, 2026

Waterfront Haven w/EV &Garage
Waterfront Haven w/EV &Garage
Waterfront Haven w/EV &Garage
Waterfront Haven w/EV &Garage
Waterfront Haven w/EV &Garage

Waterfront Haven w/EV &Garage

3 bedrooms·2 baths
Dundalk • Maryland
5(1 review)

$986.37 USD total for 3 nights

Nov 8 – 11, 2026

Masters Bedroom w/ Private Bath – Stylish & Comfy
Masters Bedroom w/ Private Bath – Stylish & Comfy
Masters Bedroom w/ Private Bath – Stylish & Comfy
Masters Bedroom w/ Private Bath – Stylish & Comfy
Masters Bedroom w/ Private Bath – Stylish & Comfy

Masters Bedroom w/ Private Bath – Stylish & Comfy

1 bedroom·1 bath
Frederick • Maryland
4.7(64 reviews)

$300.00 USD total for 3 nights

Nov 8 – 11, 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

$829.43 USD total for 3 nights

Nov 8 – 11, 2026