Holiday rentals near Saint Marys Square Museum
We found 650 holiday rentals — enter your dates for availability
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:15 Aug - 22 Aug
Image gallery for Waterfront Home on the Chesapeake Bay!
9.89.8 out of 10 rating
Exceptional
(27 reviews)
Waterfront Home on the Chesapeake Bay!
Shady Side, MD
8% off
Price is NZ$7,304
NZ$7,304
NZ$1,043 per night
includes taxes & fees
Image gallery for 4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues
1010 out of 10 rating
Exceptional
(33 reviews)
4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues
Stevensville, MD
8% off
Price is NZ$11,549
NZ$11,549
NZ$1,650 per night
includes taxes & fees
Image gallery for St Michaels Retreat, Log Cabin, Family & Pet-Friendly
9.89.8 out of 10 rating
Exceptional
(6 reviews)
St Michaels Retreat, Log Cabin, Family & Pet-Friendly
St. Michaels, MD
16% off
Price is NZ$10,360
NZ$10,360
NZ$1,480 per night
includes taxes & fees
Image gallery for Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
East New Market, MD
5% off
Price is NZ$12,385
NZ$12,385
NZ$1,769 per night
includes taxes & fees
Image gallery for Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Annapolis, MD
16% off
Price is NZ$10,375
NZ$10,375
NZ$1,482 per night
includes taxes & fees
Image gallery for Annapolis Charm - Waterfront Private Fishing Dock Pier Near Beach - Navy Academy
9.89.8 out of 10 rating
Exceptional
(22 reviews)
Annapolis Charm - Waterfront Private Fishing Dock Pier Near Beach - Navy Academy
Annapolis, MD
8% off
Price is NZ$6,393
NZ$6,393
NZ$913 per night
includes taxes & fees
Image gallery for Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
1010 out of 10 rating
Exceptional
(41 reviews)
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
Stevensville, MD
8% off
Price is NZ$8,459
NZ$8,459
NZ$1,208 per night
includes taxes & fees
Image gallery for Grandma's Summer House @ Beverly Beach
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Grandma's Summer House @ Beverly Beach
Edgewater, MD
7% off
Price is NZ$3,988
NZ$3,988
NZ$570 per night
includes taxes & fees
Image gallery for Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
1010 out of 10 rating
Exceptional
(25 reviews)
Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
Queenstown, MD
17% off
Price is NZ$1,356
NZ$1,356
NZ$194 per night
includes taxes & fees
Image gallery for Chesapeake Bay Waterfront ARTectural Home
1010 out of 10 rating
Exceptional
(27 reviews)
Chesapeake Bay Waterfront ARTectural Home
Stevensville, MD
8% off
Price is NZ$12,999
NZ$12,999
NZ$1,857 per night
includes taxes & fees
Image gallery for Enchanting West River Retreat
1010 out of 10 rating
Exceptional
(8 reviews)
Enchanting West River Retreat
West River, MD
7% off
Price is NZ$5,615
NZ$5,615
NZ$802 per night
includes taxes & fees
Image gallery for Charming 4 Bdr Home Chesapeake Beach
1010 out of 10 rating
Exceptional
(17 reviews)
Charming 4 Bdr Home Chesapeake Beach
Chesapeake Beach, MD
8% off
Price is NZ$3,695
NZ$3,695
NZ$528 per night
includes taxes & fees
Image gallery for "PIER JOY!" - 3BR WATERFRONT HOME W/PRIVATE DOCK
9.89.8 out of 10 rating
Exceptional
(33 reviews)
"PIER JOY!" - 3BR WATERFRONT HOME W/PRIVATE DOCK
Shady Side, MD
8% off
Price is NZ$7,184
NZ$7,184
NZ$1,026 per night
includes taxes & fees
Image gallery for Luxury on the river, steps to downtown &boat ramp!
1010 out of 10 rating
Exceptional
(5 reviews)
Luxury on the river, steps to downtown &boat ramp!
Cambridge, MD
8% off
Price is NZ$4,452
NZ$4,452
NZ$636 per night
includes taxes & fees
Image gallery for Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
1010 out of 10 rating
Exceptional
(38 reviews)
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Stevensville, MD
8% off
Price is NZ$11,549
NZ$11,549
NZ$1,650 per night
includes taxes & fees
Image gallery for Perfect Waterview Cottage - St. Michaels Getaway
9.89.8 out of 10 rating
Exceptional
(111 reviews)
Perfect Waterview Cottage - St. Michaels Getaway
Wittman, MD
8% off
Price is NZ$3,212
NZ$3,212
NZ$459 per night
includes taxes & fees
Image gallery for Kent Island Waterfront Cottage
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Kent Island Waterfront Cottage
Stevensville, MD
16% off
Price is NZ$4,261
NZ$4,261
NZ$609 per night
includes taxes & fees
Image gallery for Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport
1010 out of 10 rating
Exceptional
(49 reviews)
Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport
Annapolis, MD
11% off
Price is NZ$2,944
NZ$2,944
NZ$421 per night
includes taxes & fees
Image gallery for Restful and Charming Home in Eastport
9.89.8 out of 10 rating
Exceptional
(59 reviews)
Restful and Charming Home in Eastport
Annapolis, MD
16% off
Price is NZ$4,419
NZ$4,419
NZ$631 per night
includes taxes & fees
Image gallery for Captain's Retreat! Newly Renovated - few steps from the beach!
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Captain's Retreat! Newly Renovated - few steps from the beach!
Annapolis, MD
15% off
Price is NZ$13,123
NZ$13,123
NZ$1,875 per night
includes taxes & fees
Image gallery for The Cottage
1010 out of 10 rating
Exceptional
(5 reviews)
The Cottage
Shady Side, MD
11% off
Price is NZ$2,722
NZ$2,722
NZ$389 per night
includes taxes & fees
Image gallery for Jellyfish Cottage - Waterfront. Spectacular Sunsets over Chesapeake Bay
9.69.6 out of 10 rating
Exceptional
(23 reviews)
Jellyfish Cottage - Waterfront. Spectacular Sunsets over Chesapeake Bay
Tilghman, MD
12% off
Price is NZ$5,497
NZ$5,497
NZ$785 per night
includes taxes & fees
Image gallery for Water Views - Close to Downtown Annapolis
1010 out of 10 rating
Exceptional
(43 reviews)
Water Views - Close to Downtown Annapolis
Annapolis, MD
11% off
Price is NZ$6,526
NZ$6,526
NZ$932 per night
includes taxes & fees
Image gallery for Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
9.89.8 out of 10 rating
Exceptional
(52 reviews)
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Annapolis, MD
8% off
Price is NZ$3,122
NZ$3,122
NZ$446 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Saint Marys Square Museum
An Afternoon Nap in the Hammock is a Must.
Sleeps 6 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Cass-N-Reel Luxury Houseboat
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
Stay in the HEART of Saint Michaels!
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
347 reviews(347 reviews)
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
Sleeps 9 · 6 bedrooms · 3+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
126 reviews(126 reviews)
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Sleeps 6 · 3 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
St. Michael's Premier In-Town Rental with heated pool-opens 4/11/2025
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
134 reviews(134 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value