Night Views
Pier View
Black Walnut Cove
Fire Pit
Outdoor Seating

La Casita at Black Walnut-Waterfront Escape near Saint Michaels

3 bedrooms·1½ baths
Tilghman Island • Maryland

$1,236.25 USD total for 3 nights

Oct 23 – 26, 2026

Relaxing Retreat on the Hudson image 1
Relaxing Retreat on the Hudson image 2
Relaxing Retreat on the Hudson image 3
Relaxing Retreat on the Hudson image 4
Relaxing Retreat on the Hudson image 5

Relaxing Retreat on the Hudson

5 bedrooms·2 baths
Maryland
5(34 reviews)

$950.00 USD total for 3 nights

Oct 26 – 29, 2026

Majestic Murphy Point
Back yard launch
Front facing the bay
Kitchen/Dining open floor plan
Kitchen

Murphy Point on the Chesapeake Vacation Rental

3 bedrooms·1 bath
North Beach • Maryland
4.8(114 reviews)

$1,380.00 USD total for 3 nights

Oct 23 – 26, 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)

$989.58 USD $845.28 USD total for 3 nights

Oct 25 – 28, 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)

$605.52 USD $526.93 USD total for 3 nights

Oct 27 – 30, 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 26 – 29, 2026

Off The Chart Stays Cottage
living room at entrance with gas fireplace and smart tv
Front entrance
Kitchen
Kitchen and Living room

Off The Chart Stays

2 bedrooms·2 baths
Stevensville • Maryland
5(8 reviews)

$1,676.10 USD total for 3 nights

Oct 23 – 26, 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)

$1,333.40 USD total for 3 nights

Oct 25 – 28, 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)

$687.00 USD total for 3 nights

Oct 23 – 26, 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)

$2,457.50 USD total for 3 nights

Oct 23 – 26, 2026