Location

Dates

Guests

Vacation rentals in Maryland

Master Bedroom with a king bed and private bathroom

Master Bathroom

San Remo 210B

2 bedrooms·2 baths

Ocean City • Maryland

$784.00 USD total for 3 nights

Oct 19 – 22, 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

Oct 20 – 23, 2026

Living room complete with queen-sized sleeper sofa, TV, entertainment center, side chair, eating nook with table and chairs for two.

Living room with beachy decor and queen sleeper sofa.

Living room view facing the patio.

Dining area with table for two plus four barstools at kitchen counter.

We provide dish and dishwasher soap and starter paper towels.

33rd St, Near Attractions, Pool, 1st Fl, King Bed

1 bedroom·1 bath

Ocean City • Maryland

$564.92 USD total for 3 nights

Oct 19 – 22, 2026

Property grounds

Spacious 5-bedroom house in Silver Spring with AC Near DC & Metro

5 bedrooms·2 baths

Silver Spring • Maryland

$1,095.00 USD total for 3 nights

Oct 19 – 22, 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

$2,704.70 USD total for 7 nights

Oct 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

Oct 20 – 23, 2026

Worcester House 401 | 1 BR | 1.5BA | 634 Sq Ft | Elevator Access | Open Corner Balcony / Patio | Private Entrance

Living Room | Queen Sleeper Sofa with Upgraded 5" Thick Gel Memory Foam Mattress (No Coils)

Kitchen | Cooking Basics | Keurig Coffee Maker | Drip Coffee Pot | Dishwasher | Glass-Top Stove with Oven | Built-In Microwave | Under-Cabinet Lighting | Granite Countertops | Refrigerator with Top Freezer | Fully Equipped Kitchen

Bedroom | Queen Bed | 12-Inch Medium-Firm Mattress with Eggshell Memory Foam | USB Charging Ports Embedded in Lamps

Full Bath | Bath Towels, Toilet Paper and Hand Soap Provided | Other Personal Toiletries Not Provided

BeachBox III • Unreal Views • Oceanfront Balcony • Couple's Getaway • Worcester House 401

1 bedroom·1½ baths

Ocean City • Maryland

5(78 reviews)

$409.06 USD total for 3 nights

Oct 19 – 22, 2026

Property grounds

Private kitchen

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 6 – 9, 2026

Sunset View

3 bedrooms·2½ baths

Ocean City • Maryland

$1,358.56 USD total for 3 nights

Oct 19 – 22, 2026

Fantastic Ocean Block Condo with Ro

Fantastic Ocean Block Condo with Ro

Fantastic Ocean Block Condo with Ro

Fantastic Ocean Block Condo with Ro

Fantastic Ocean Block Condo with Ro

Fantastic Ocean Block Condo with Ro

2 bedrooms·1 bath

Ocean City • Maryland

5(16 reviews)

$1,877.01 USD total for 3 nights

May 20 – 23, 2027

East Winds 202 | 1BR | 1.5BA | 601 Sq Ft | Private Entrance | Stairs Required for Initial Check-In (2nd Floor) | Elevator Available After Check-In

Property Interior | Elevator Access Once Inside | Ocean Views

Kitchen | Cooking Basics

Bedroom | Queen Bed

BeachBox I • Oceanfront Balcony • Sunrise Views • Couple's Retreat • East Winds 202

1 bedroom·1½ baths

Ocean City • Maryland

5(50 reviews)

$409.06 USD total for 3 nights

Oct 19 – 22, 2026

Great views. Walk out and your practically stepping in the sand.

Open entertainment area. Complete with two power chaise lounge chairs that recline.

Fantastic Ocean view, newly renovated

Fantastic Ocean view, newly renovated

New sectional. Power reclining chaise lounges. Pull out Full bed

Fantastic Ocean view, newly renovated

1 bedroom·1 bath

Ocean City • Maryland

$386.00 USD total for 3 nights

Oct 19 – 22, 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

$1,026.75 USD total for 3 nights

Oct 19 – 22, 2026

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

Oct 19 – 22, 2026

Assateague House 411 | 1BR | 1.5BA | Step-Free Access | 558 Sq Ft | Elevator Access | Open Balcony / Patio | Private Entrance

Community Outdoor Pool (Open Memorial Day to Labor Day). Depth: 3 ft to 6 ft. Note: Pool access requires a small set of steps

View of the Bay at the Inlet from our balcony (overlooking the Coast Guard base)

Living Room | Smart TVs w/ Free Wi-Fi, Netflix, Hulu, and other Streaming Services | Queen Sleeper Sofa w/ Gel Memory Foam Mattress

Bedroom | King Bed | 12-Inch Medium-Firm Mattress with Eggshell Memory Foam | USB Charging Ports Embedded in Lamps | Linens & Bath Towels Included

BeachBox II • Panoramic Inlet Views • Bayside Pool • Couple's Corner • Assateague House 411

1 bedroom·1½ baths

Ocean City • Maryland

5(33 reviews)

$435.99 USD total for 3 nights

Oct 25 – 28, 2026

East Winds 502 | 1BR | 1.5BA | 601 Sq Ft | Private Entrance | Stairs Required for Initial Check-In (5th Floor) | Elevator Available After Check-In

Coastal-chic condo with bright open layout, modern kitchen & comfy seating

Fully equipped coastal kitchen with stainless appliances, quartz countertops, and glass-tiled backsplash | Dishwasher | Glass-Top Stove w/ Oven | Built-In Microwave | Refrigerator w/ Top Freezer

Sunny bedroom with 2 full/double beds, Smart TV, A/C, and beachy decor

Full bathroom w/ vessel sink, porthole mirror & butcher block vanity | Bath Towels, Toilet Paper and Hand Soap Provided | Other Personal Toiletries Not Provided

BeachBox V • 5th-Floor Oceanfront • Expansive View • Beachfront Bliss • East Winds 502

1 bedroom·1½ baths

Ocean City • Maryland

5(32 reviews)

$409.06 USD total for 3 nights

Oct 19 – 22, 2026

Modern Suite with Private Bath

Modern Suite with Private Bath

Modern Suite with Private Bath

Modern Suite with Private Bath

Modern Suite with Private Bath

Modern Suite with Private Bath

1 bedroom·1 bath

Frederick • Maryland

4.84(45 reviews)

$300.00 USD total for 3 nights

Oct 19 – 22, 2026

Oceans Edge 503 OCEANFRONT ON THE BOARDWALK FLEXIBLE STAYS

Oceans Edge 503 OCEANFRONT ON THE BOARDWALK FLEXIBLE STAYS

Oceans Edge 503 OCEANFRONT ON THE BOARDWALK FLEXIBLE STAYS

Oceans Edge 503 OCEANFRONT ON THE BOARDWALK FLEXIBLE STAYS

Oceans Edge 503 OCEANFRONT ON THE BOARDWALK FLEXIBLE STAYS

Oceans Edge 503 OCEANFRONT ON THE BOARDWALK FLEXIBLE STAYS

3 bedrooms·2 baths

Ocean City • Maryland

5(9 reviews)

$1,950.39 USD total for 3 nights

Oct 19 – 22, 2026

Captains Quarter|canal-side 2 bedroom!

Captains Quarter|canal-side 2 bedroom!

Captains Quarter|canal-side 2 bedroom!

Captains Quarter|canal-side 2 bedroom!

Captains Quarter|canal-side 2 bedroom!

Captains Quarter|canal-side 2 bedroom!

2 bedrooms·2 baths

Ocean City • Maryland

$1,164.90 USD total for 3 nights

Apr 16 – 19, 2027

127th Street| Pool, Short Walk to Beach & Park

127th Street| Pool, Short Walk to Beach & Park

127th Street| Pool, Short Walk to Beach & Park

127th Street| Pool, Short Walk to Beach & Park

127th Street| Pool, Short Walk to Beach & Park

127th Street| Pool, Short Walk to Beach & Park

1 bedroom·1 bath

Ocean City • Maryland

5(1 review)

$454.65 USD total for 3 nights

Oct 25 – 28, 2026

127th Bayside |pool-short walk 2 beach-By Park!

127th Bayside |pool-short walk 2 beach-By Park!

127th Bayside |pool-short walk 2 beach-By Park!

127th Bayside |pool-short walk 2 beach-By Park!

127th Bayside |pool-short walk 2 beach-By Park!

127th Bayside |pool-short walk 2 beach-By Park!

1 bedroom·1 bath

Ocean City • Maryland

$1,012.91 USD total for 3 nights

Apr 16 – 19, 2027

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)

$260/ night(excl. fees & taxes)

Elegant 1BR in Fells Point | Prime Location

Elegant 1BR in Fells Point | Prime Location

Elegant 1BR in Fells Point | Prime Location

Elegant 1BR in Fells Point | Prime Location

Elegant 1BR in Fells Point | Prime Location

Elegant 1BR in Fells Point | Prime Location

1 bedroom·1 bath

Baltimore • Maryland

$370.00 USD total for 3 nights

Oct 19 – 22, 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

Oct 19 – 22, 2026