Family Adventure at St. Michaels Rentals

“The Town that Fooled the British” is the nickname given to St. Michaels, due to their revolutionary war tactics. Learning that the British were coming and not wishing to be harmed, settlers extinguished all lights in the colony, and it is said the British flew by without realizing the town was there. A relaxing vacation awaits you at St. Michaels rentals in this Maryland town. Seafood, swimming, and fishing are all available when you rent St. Michaels houses.

Self-guided Tours from St. Michaels Vacation Rentals


Touring a city can often be enjoyable, especially with sea breezes wafting through your hair as you walk from your St. Michaels vacation rentals to historical sites in the town. Self-guided tours allow you to walk down the streets viewing 19th century St. Michaels houses, some of which you can rent.

Maritime Education by St. Michaels Houses


St. Michaels houses are near Chesapeake Bay, known for its maritime sites, expensive properties, and beautiful landscape. The Chesapeake Bay Maritime Museum is a quick trip from St. Michaels vacation rentals. The museum holds history within its structure displaying skipjacks, waterfowling boats, and other ship models. If you want, you can rent a boat at your St. Michaels rentals, rather than just learning about historical ships.

Patriot Cruises of St. Michaels Rentals


Accommodations at St. Michaels rentals present you with plenty of opportunities to explore the region. After a visit to the maritime museum, you can stop off at your St. Michaels vacation rentals for lunch or head towards the Patriot Cruise ship. The cruise lasts for 60 or 90 minutes and will enlighten you about the Miles River. They offer sunset cruises along the river daily in summer, and on the weekends, during the off season. You may also enjoy the sunrise from your deck.

Other options for Maryland vacation rentals include Annapolis rentals, Washington DC accommodations, or Ocean City Maryland beach houses.


Vacation Rentals in St. Michaels, Maryland

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One level family vacation home with pool, dock, sheltered cove and lots of living spaces!

— Property 7004789h
St. Michaels house rental - Welcome to Anchorage
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, dock boatslip, DVD
Rates - per house (USD)
$2,448 - $5,568/week
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Expansive 5BR home with great wide water views, pool, beautifully decorated

— Property 7004818h
St. Michaels house rental - A waterfront retreat
5 Bedrooms, Sleeps 10,
House, 3 Bathrooms, dock boatslip, DVD
Rates - per house (USD)
$2,873 - $6,462/week
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Nautical Cottage just outside St. Michaels, great getaway spot

— Property 7007433h
St. Michaels cottage rental - A cute cottage overlooking Long Haul Creek
3 Bedrooms, Sleeps 6,
Cottage, 3 Bathrooms, dock boatslip, DVD
Rates - per cottage (USD)
$1,551 - $2,676/week
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Budget friendly home outside St. Michaels

— Property 7007434h
St. Michaels house rental - A charming vacation spot
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, dock boatslip, DVD
Rates - per house (USD)
$1,513 - $3,385/week
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Contemporary Cottage with pool, tranquil views and great nature watching!

— Property 7014511h
St. Michaels cottage rental - Pool
3 Bedrooms, Sleeps 8,
Cottage, 2 Bathrooms, dock boatslip, DVD
Rates - per cottage (USD)
$1,646 - $3,336/week
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Conveniently located home between Easton and St. Michaels, private with Tred Avon views!

— Property 7015502h
St. Michaels cottage rental - My Blue Heron
3 Bedrooms, Sleeps 6,
Cottage, 2 Bathrooms, dock boatslip, DVD
Rates - per cottage (USD)
$1,375 - $2,275/week
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Cottage with pool, hot tub and great water

— Property 7018652h
St. Michaels house rental - The Orchard
4 Bedrooms, Sleeps 8,
House, 4 Bathrooms, dock boatslip, DVD
Rates - per house (USD)
$1,704 - $3,576/week
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Waterfront Cottage minutes to St. Michaels, hot tub

— Property 7018650h
St. Michaels cottage rental - Pandion
3 Bedrooms, Sleeps 5,
Cottage, 2 Bathrooms, DVD, fireplace
Rates - per cottage (USD)
$1,358 - $2,158/week
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Away from it all! Secluded spot for rest and relaxation, pool, dock, great kayaking!

— Property 7022554h
St. Michaels cottage rental - Your Private Dock with Kayak for your personal use
3 Bedrooms, Sleeps 6,
Cottage, 2 Bathrooms, dock boatslip, DVD
Rates - per cottage (USD)
$1,291 - $2,696/week
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Beautifully appointed vacation home outside St. Michaels

— Property 7022556h
St. Michaels house rental - Welcome to Sycamore Acres
6 Bedrooms, Sleeps 12,
House, 5 Bathrooms, dock boatslip, DVD
Rates - per house (USD)
$3,251 - $5,307/week
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Budget friendly cottage getaway, with rowboat included!

— Property 7022552h
St. Michaels cottage rental - Welcome to Caulk''s Cove
4 Bedrooms, Sleeps 8,
Cottage, 2 Bathrooms, dock boatslip, DVD
Rates - per cottage (USD)
$1,315 - $1,940/week
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Sweeping Chesapeake Bay views with Sandy Beach,dock, pool.

— Property 7004795h
St. Michaels house rental - Cabin Cove Manor
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, dock boatslip, DVD
Rates - per house (USD)
$1,913 - $3,998/week
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Fantastic Family Compound 1/2 mile to St. Michaels, Pool, Dock, Hot tub

— Property 7004796h
St. Michaels house rental - Captains Cove Front Exterior
5 Bedrooms, Sleeps 10,
House, 4 Bathrooms, dock boatslip, DVD
Rates - per house (USD)
$2,839 - $6,271/week
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Hideaway on Long Haul Creek, minutes to town

— Property 7004799h
St. Michaels cottage rental - Crabbiest Cottage
3 Bedrooms, Sleeps 6,
Cottage, 3 Bathrooms, dock boatslip, DVD
Rates - per cottage (USD)
$1,295 - $1,920/week
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90 acre farm with wrap around views, 5 minutes to St. Michaels, pool, dock

— Property 7004794h
St. Michaels house rental - Welcome to Bushey Heath Farm
4 Bedrooms, Sleeps 8,
House, 2 Bathrooms, dock boatslip, DVD
Rates - per house (USD)
$1,453 - $3,325/week
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Expansive 4 bedroom home 5 blocks to town of St. Michaels, wide water views.

— Property 7004814h
St. Michaels house rental - Welcome to Swan Harbor
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, dock boatslip, DVD
Rates - per house (USD)
$1,265 - $2,190/week
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Single family getaway! Pool, playgym, dock, and more!

— Property 7004805h
St. Michaels cottage rental - Welcome to Mack''s Landing
3 Bedrooms, Sleeps 6,
Cottage, 1 Bathroom, dock boatslip, DVD
Rates - per cottage (USD)
$1,328 - $2,333/week
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Bungalow in heart of historic district

— Property 7004802h
St. Michaels cottage rental - Harbour Hideaway
2 Bedrooms, Sleeps 4,
Cottage, 2 Bathrooms, DVD, grill
Rates - per cottage (USD)
$1,150 - $1,175/week
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Historic Estate with 5BR's, pool, hot tub, gourmet kitchen and deep water dock.

— Property 7004801h
St. Michaels house rental - The oldest brick structure in Talbot County
5 Bedrooms, Sleeps 14,
House, 4 Bathrooms, dock boatslip, DVD
Rates - per house (USD)
$2,603 - $5,878/week
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Very private 25 acre home with sunset views, deep water dock, pool

— Property 7004811h
St. Michaels house rental - View of the house from the dock
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, dock boatslip, DVD
Rates - per house (USD)
$1,653 - $3,350/week
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Waterfront cottage with pool and hot tub, close to town of St. Michaels

— Property 7004810h
St. Michaels cottage rental - Welcome to Pines at Barrett Cove
3 Bedrooms, Sleeps 6,
Cottage, 3 Bathrooms, dock boatslip, DVD
Rates - per cottage (USD)
$1,401 - $2,976/week
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Restored farmhouse with pool, poolhouse, dock, kayak and more!

— Property 7004804h
St. Michaels house rental - Lee Haven
5 Bedrooms, Sleeps 10,
House, 4 Bathrooms, dock boatslip, DVD
Rates - per house (USD)
$2,895 - $5,407/week
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Classic Bay home with pool, dock, game room, just outside Easton and St. Michaels.

— Property 7004816h
St. Michaels house rental - The Cove
4 Bedrooms, Sleeps 8,
House, 4 Bathrooms, dock boatslip, DVD
Rates - per house (USD)
$4,700/week
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Adorable and Cozy Cape with wide water views, minutes to St. Michaels

— Property 7004820h
St. Michaels cottage rental - Waterfront Cottage with Great Views, Private Dock
3 Bedrooms, Sleeps 7,
Cottage, 3 Bathrooms, dock boatslip, DVD
Rates - per cottage (USD)
$1,350 - $2,250/week
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Charming cottage with great sunsets, cozy fireplaces and patios.

— Property 7004817h
St. Michaels cottage rental - View from the dock
3 Bedrooms, Sleeps 7,
Cottage, 2 Bathrooms, dock boatslip, DVD
Rates - per cottage (USD)
$1,419 - $2,319/week
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Light Filled Contemporary with 4 Queen bedrooms, dock,pool

— Property 7004815h
St. Michaels house rental - Welcome to Swift Haven
4 Bedrooms, Sleeps 9,
House, 2 Bathrooms, dock boatslip, DVD
Rates - per house (USD)
$1,747 - $3,776/week
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Upscale home outside St. Michaels, pool, dock, newly renovated kitchen and baths, a fabulous retreat

— Property 7004819h
St. Michaels house rental - Willows on the Miles
6 Bedrooms, Sleeps 11,
House, 3 Bathrooms, dock boatslip, DVD
Rates - per house (USD)
$2,850 - $5,362/week
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Authentic 1920's Waterman's Cottage

— Property 7007439h
St. Michaels cottage rental - Welcome to Simplicity Cottage
2 Bedrooms, Sleeps 4,
Cottage, 1 Bathroom, dock boatslip, DVD
Rates - per cottage (USD)
$1,490/week
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Fun house outside St. Michaels, pool, dock, hot tub, ping pong

— Property 7007440h
St. Michaels house rental - 4 Bedroom Home Near St. Michaels
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, dock boatslip, DVD
Rates - per house (USD)
$1,473 - $3,345/week
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One level vacation home outside St. Michaels, pool, wide views, great breezes

— Property 7007442h
St. Michaels house rental - Create Wonderful Summer Memories
3 Bedrooms, Sleeps 8,
House, 3 Bathrooms, DVD, fireplace
Rates - per house (USD)
$1,744 - $3,773/week