Holiday rentals near Clint S. Bradley Park

We found 196 holiday rentals — enter your dates for availability

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November 2025

December 2025

Choose the perfect private holiday rental that's near Clint S. Bradley Park. Holiday rentals provide the amenities that you need and want for your family, friends or furry companion, such as Wi-Fi and a pool. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Clint S. Bradley Park

Showing deals for:6 Feb - 13 Feb

House and Garage as seen from above (pool on left)

Exceptional

(90 reviews)

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Royal Oak, MD

8% off

for 7 nights, 1 home

AU$3,079 per night

includes taxes & fees

Exceptional

(124 reviews)

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St. Michaels, MD

8% off

for 7 nights, 1 cottage

AU$380 per night

includes taxes & fees

Exceptional

(55 reviews)

Dollhouse in Central Historic St Michaels

St. Michaels, MD

12% off

for 7 nights, 1 home

AU$461 per night

includes taxes & fees

Front of house from St. Michaels harbor looking across Town Park

Exceptional

(122 reviews)

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

St. Michaels, MD

8% off

for 7 nights, 1 cottage

AU$571 per night

includes taxes & fees

Exceptional

(105 reviews)

Charming Waterfront Cottage Outside St. Michaels Close to the Oaks

Royal Oak, MD

8% off

for 7 nights, 1 cottage

AU$795 per night

includes taxes & fees

Baja Deck with umbrella- sit in pool on plastic adirondack chairs and read!

Exceptional

(137 reviews)

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton, MD

8% off

for 7 nights, 1 home

AU$1,719 per night

includes taxes & fees

Exceptional

(50 reviews)

Secluded Waterfront Property on 3 acres with swimming pool and dock.

Bozman, MD

5% off

for 7 nights, 1 home

AU$1,346 per night

includes taxes & fees

Exceptional

(24 reviews)

A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels

Easton, MD

8% off

for 7 nights, 1 home

AU$595 per night

includes taxes & fees

Exceptional

(23 reviews)

Family Friendly Cottage - Waterfront. Spectacular Sunsets over Chesapeake Bay

Tilghman, MD

12% off

for 7 nights, 1 cottage

AU$707 per night

includes taxes & fees

Thomas Harrison House looking from St. Michaels Town Harbor

Exceptional

(132 reviews)

Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!

St. Michaels, MD

8% off

for 7 nights, 1 home

AU$840 per night

includes taxes & fees

Charming Downtown Studio — Walk to Waterfront, Dining, and Shops

Exceptional

(29 reviews)

Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops

St. Michaels, MD

12% off

for 7 nights, 1 apartment

AU$408 per night

includes taxes & fees

Exceptional

(5 reviews)

St. Michaels Escape | Pool, Hot Tub & Fire Pit

St. Michaels, MD

11% off

for 7 nights, 1 home

AU$821 per night

includes taxes & fees

Exceptional

(137 reviews)

Charming cottage along water with private pier, near St. Michaels Winery

Bozman, MD

12% off

for 7 nights, 1 cottage

AU$451 per night

includes taxes & fees

Exceptional

(8 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman, MD

16% off

for 7 nights, 1 cottage

AU$486 per night

includes taxes & fees

Exceptional

(191 reviews)

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

St. Michaels, MD

8% off

for 7 nights, 1 cottage

AU$644 per night

includes taxes & fees

Welcome to your island escape—bright, inviting, and just steps from the water.

Exceptional

(10 reviews)

Pet-Friendly Island Getaway | Bikes & Porch

Tilghman, MD

11% off

for 7 nights, 1 home

AU$410 per night

includes taxes & fees

Private bayfront retreat just minutes from charming St. Michaels

Exceptional

(10 reviews)

Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views

Tilghman, MD

7% off

for 7 nights, 1 home

AU$610 per night

includes taxes & fees

20 x 40 Salt Water Pool - Open June- October (not heated)

Exceptional

(106 reviews)

Waterfront Cottage, Private Hot Tub, Fire Pit, Pool - perfect Romantic Getaway

Easton, MD

8% off

for 7 nights, 1 home

AU$616 per night

includes taxes & fees

Exceptional

(6 reviews)

Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels

St. Michaels, MD

17% off

for 7 nights, 1 home

AU$466 per night

includes taxes & fees

Front and side view of Blades House from Locust St.

Exceptional

(146 reviews)

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St. Michaels, MD

8% off

for 7 nights, 1 cottage

AU$578 per night

includes taxes & fees

Exceptional

(52 reviews)

Modern Flat in the Heart of St. Michaels – Walk Everywhere

St. Michaels, MD

7% off

for 7 nights, 1 apartment

AU$426 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Clint S. Bradley Park

Showing deals for: 2 Feb - 5 Feb

Premier Host

Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!

Sleeps 9 · 6 bedrooms · 3+ bathrooms

for 3 nights, 1 home

AU$808 per night

includes taxes & fees

Waterfront Property, kayaks, private dock, near town

Sleeps 6 · 3 bedrooms · 2+ bathrooms

for 3 nights, 1 home

AU$1,220 per night

includes taxes & fees

Top rated rentals - Clint S. Bradley Park

AWESOME

It by far exceeded our expectations. The home is extremely spacious AND VERY CLEAN . The property provided entertainment for all ages . We highly recommend this property.

Kenneth C.

Stayed June 2022

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Enjoy full kitchens, laundry, pools, gardens and more
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