Location

Dates

Guests

Vacation rentals in Anne Arundel County, Maryland, United States

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 totaal voor 3 nachten

25–28 okt 2026

Off The Chart Stays Cottage

living room at entrance with gas fireplace and smart tv

Kitchen and Living room

Off The Chart Stays

2 bedrooms·2 baths

Stevensville • Maryland

5(8 reviews)

$ 1.676,10 USD totaal voor 3 nachten

19–22 okt 2026

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

3 bedrooms·2 baths

North Beach • Maryland

5(250 reviews)

$ 594,42 USD $ 518,05 USD totaal voor 3 nachten

19–22 okt 2026

Majestic Murphy Point

Back yard launch

Front facing the bay

Kitchen/Dining open floor plan

Murphy Point on the Chesapeake Vacation Rental

3 bedrooms·1 bath

North Beach • Maryland

4.8(114 reviews)

$ 1.380,00 USD totaal voor 3 nachten

19–22 okt 2026

Welcome to beautiful North Beach!

Cozy fire pit patio with stylish seating and outdoor dining

Cozy fire pit patio with private fenced yard and stylish outdoor seating

Palm Haven in North Beach, MD

One of two bedrooms on the ground floor, this bedroom has a queen sized bed and en-suite bathroom.

Palm Haven in North Beach, MD

4 bedrooms·3 baths

North Beach • Maryland

5(198 reviews)

$ 1.106,13 USD $ 938,52 USD totaal voor 3 nachten

25–28 okt 2026

Cozy Cottage By The Beach-Pet Friendly

Cozy Cottage By The Beach-Pet Friendly

Main living space.

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 totaal voor 3 nachten

19–22 okt 2026

Stunning 9 Bedroom Villa on the Chesapeake Bay image 1

Stunning 9 Bedroom Villa on the Chesapeake Bay image 2

Stunning 9 Bedroom Villa on the Chesapeake Bay image 3

Stunning 9 Bedroom Villa on the Chesapeake Bay image 4

Stunning 9 Bedroom Villa on the Chesapeake Bay image 5

Stunning 9 Bedroom Villa on the Chesapeake Bay

9 bedrooms·6½ baths

Rock Hall • Maryland

5(4 reviews)

$ 6.917,00 USD totaal voor 3 nachten

19–22 okt 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 totaal voor 3 nachten

20–23 okt 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 totaal voor 7 nachten

19–26 okt 2026

Black Walnut Cove

Outdoor Seating

La Casita at Black Walnut-Waterfront Escape near Saint Michaels

3 bedrooms·1½ baths

Tilghman Island • Maryland

$ 1.063,75 USD totaal voor 3 nachten

19–22 okt 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)

$260/ nacht(excl. kosten & belastingen)

Master bedroom overlooking park with California king bed.

Parkfront Hot Tub Haven for Families & Pets image 2

Lovely park views from the small living room.

The dining table easily accommodates 6 guests, with wooden stools for up to 4 additional guests willing to squeeze.

Parkfront Hot Tub Haven for Families & Pets image 5

Parkfront Hot Tub Haven for Families & Pets

2 bedrooms·2 baths

Baltimore • Maryland

4.96(543 reviews)

$ 504,00 USD totaal voor 3 nachten

19–22 okt 2026

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 totaal voor 3 nachten

19–22 okt 2026

Furnished 4BR Home | Workspace & Extended Stays image 1

Furnished 4BR Home | Workspace & Extended Stays image 2

Furnished 4BR Home | Workspace & Extended Stays image 3

Furnished 4BR Home | Workspace & Extended Stays image 4

Furnished 4BR Home | Workspace & Extended Stays image 5

Furnished 4BR Home | Workspace & Extended Stays

4 bedrooms·2 baths

Silver Spring • Maryland

5(2 reviews)

$ 916,00 USD totaal voor 4 nachten

25–29 okt 2026

Private kitchen

3-bedroom house near DC

3 bedrooms·1 bath

Oxon Hill • Maryland

$ 750,00 USD totaal voor 3 nachten

19–22 okt 2026

The Green Hideaway room is a bright, cozy space with soft green accents, a comfy daybed, and plenty of natural light. Simple décor and plants make it a peaceful spot to unwind.

The Iris room features soft green tones, warm wood accents, and a cozy queen bed for a calm, relaxing stay.

The Green Hideaway room highlights the lounge chair, mirror, lamps, and hangers — thoughtful touches that keep the space comfortable and easy to settle into.

This cozy corner of the Green Hideaway includes chairs, a table, lamps, a plant, and the fireplace for a warm, inviting feel.

Bright, simple, and fully equipped — a kitchen that keeps things effortless.

Cozy Winter 2BR Gem Near DC, Fire Pit, Cocoa Bar

2 bedrooms·1 bath

Waldorf • Maryland

Cozy Winter 4BR Gem Near DC, Fire Pit, Cocoa Bar

Covered Deck Lounge with Cozy Seating & Hanging Chair

Cozy Winter 4BR Gem Near DC, Fire Pit, Cocoa Bar

Cozy Winter 4BR Gem Near DC, Fire Pit, Cocoa Bar

cozy Fire-Lit Lounge Under the String Lights

Cozy Winter 4BR Gem Near DC, Fire Pit, Cocoa Bar

4 bedrooms·2 baths

Waldorf • Maryland

4.9(73 reviews)

$ 1.196,74 USD totaal voor 3 nachten

19–22 okt 2026