Holiday rentals near Saint Marys Square Museum

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November 2025

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Take a look at holiday rentals within easy reach of Saint Marys Square Museum that provide the perfect home base for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the amenities that you need and want for your stay, which might include Wi-Fi and a hot tub. Whatever you're looking for, you'll find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Saint Marys Square Museum

Showing deals for:27 Feb - 6 Mar

Exceptional

(45 reviews)

Chesapeake Houseboat Getaway on Kent Island, Maryland

Stevensville, MD

12% off

for 7 nights, 1 houseboat

AU$469 per night

includes taxes & fees

A great spot to soak in the views of the Chesapeake Bay.

Exceptional

(18 reviews)

Modern Waterfront House with amazing views of the Chesapeake Bay and a dock!

North Beach, MD

16% off

for 7 nights, 1 home

AU$905 per night

includes taxes & fees

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$3,118 per night

includes taxes & fees

Exceptional

(15 reviews)

CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16

Cambridge, MD

8% off

for 7 nights, 1 home

AU$2,181 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$805 per night

includes taxes & fees

Our home blends into towering pines, lawns & hundreds of feet of waterfront

Exceptional

(74 reviews)

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Woolford, MD

8% off

for 7 nights, 1 home

AU$1,485 per night

includes taxes & fees

The Beachcomber's expansive backyard is on its own private beach.

Exceptional

(17 reviews)

Bayfront One-Level House with Private Beach Access & Panoramic Bridge Views

Stevensville, MD

5% off

for 7 nights, 1 home

AU$652 per night

includes taxes & fees

Cambridge Vacation Rental | 4BR | 4BA | 2,000 Sq Ft | Stairs Required

Exceptional

(6 reviews)

Walk to Dtwn: Waterfront Eastern Shore Townhome!

Cambridge, MD

7% off

for 7 nights, 1 home

AU$565 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$603 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$716 per night

includes taxes & fees

Exceptional

(25 reviews)

Spacious waterfront home with amazing views, private pier, fishing and crabbing.

Cambridge, MD

8% off

for 7 nights, 1 home

AU$1,055 per night

includes taxes & fees

Exceptional

(9 reviews)

Chessie Cottage-Chesapeake Bay Great views from easy single floor living!

Stevensville, MD

8% off

for 7 nights, 1 cottage

AU$1,009 per night

includes taxes & fees

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

Exceptional

(138 reviews)

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

Easton, MD

8% off

for 7 nights, 1 home

AU$1,420 per night

includes taxes & fees

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

Exceptional

(124 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$450 per night

includes taxes & fees

Exceptional

(125 reviews)

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

St. Michaels, MD

8% off

for 7 nights, 1 cottage

AU$386 per night

includes taxes & fees

Exceptional

(10 reviews)

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Cambridge, MD

8% off

for 7 nights, 1 apartment

AU$330 per night

includes taxes & fees

Exceptional

(202 reviews)

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Stevensville, MD

12% off

for 7 nights, 1 room

AU$724 per night

includes taxes & fees

Enjoy views of the Chesapeake Bay, pool and garden through a wall of glass!

Exceptional

(78 reviews)

Comfortable Spacious Fun! 6+Acres Pool+Bay Waterfront St Michaels-Yes Weddings!

Wittman, MD

6% off

for 7 nights, 1 room

AU$1,911 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Saint Marys Square Museum

Premier Host

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Sleeps 10 · 4 bedrooms · 3 bathrooms

Thomas Harrison House looking from St. Michaels Town Harbor

Premier Host

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

Sleeps 9 · 6 bedrooms · 3+ bathrooms

Premier Host

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

Sleeps 10 · 5 bedrooms · 3+ bathrooms

Waterfront 5+ bedroom home on the Miles River!

Premier Host

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Sleeps 10 · 6 bedrooms · 3+ bathrooms

Top rated rentals - Saint Marys Square Museum

House, pond, property. Private beach and Chesapeake Bay is behind far tree line.

Premier Host

Great place for a family reunion

Our family was gathered in the area for a wedding. Although we only had nine people sleeping here, we accommodated other relatives for meals and a crab feast. The house has several seating areas, including the beach area, where people could sit down and catch up. Had it been warmer weather, we would have also enjoyed the kayaks and paddle boards. Overall, it suited our needs perfectly.

Kathryn A.

Stayed Oct 2023

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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More quality time
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All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
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Holiday rentals near Saint Marys Square Museum

Holiday rentals with weekly discounts - Saint Marys Square Museum

Image gallery for Chesapeake Houseboat Getaway on Kent Island, Maryland

Chesapeake Houseboat Getaway on Kent Island, Maryland

Find spaces that suit your style

Find the best place to stay - Saint Marys Square Museum

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Top rated rentals - Saint Marys Square Museum

Great place for a family reunion

Peace of mind

More quality time

All the privacy of home

More for less

Holiday Rental options near Saint Marys Square Museum

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